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    Chemistry

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    Also known as: 503612-47-3, Eliquis, Bms-562247, Bms-562247-01, Bms 562247-01, 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide
    Molecular Formula
    C25H25N5O4
    Molecular Weight
    459.5  g/mol
    InChI Key
    QNZCBYKSOIHPEH-UHFFFAOYSA-N
    FDA UNII
    3Z9Y7UWC1J
    Apixaban
    Apixaban is an orally active inhibitor of coagulation factor Xa with anticoagulant activity. Apixaban directly inhibits factor Xa, thereby interfering with the conversion of prothrombin to thrombin and preventing formation of cross-linked fibrin clots.
    Apixaban is a Factor Xa Inhibitor. The mechanism of action of apixaban is as a Factor Xa Inhibitor.
    1 2D Structure

    Apixaban

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxamide
    2.1.2 InChI
    InChI=1S/C25H25N5O4/c1-34-19-11-9-18(10-12-19)30-23-20(22(27-30)24(26)32)13-15-29(25(23)33)17-7-5-16(6-8-17)28-14-3-2-4-21(28)31/h5-12H,2-4,13-15H2,1H3,(H2,26,32)
    2.1.3 InChI Key
    QNZCBYKSOIHPEH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC1=CC=C(C=C1)N2C3=C(CCN(C3=O)C4=CC=C(C=C4)N5CCCCC5=O)C(=N2)C(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    3Z9Y7UWC1J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bms 562247

    2. Bms-562247

    3. Bms-562247-01

    4. Bms562247

    5. Eliquis

    2.3.2 Depositor-Supplied Synonyms

    1. 503612-47-3

    2. Eliquis

    3. Bms-562247

    4. Bms-562247-01

    5. Bms 562247-01

    6. 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide

    7. 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide

    8. 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxamide

    9. 3z9y7uwc1j

    10. Chembl231779

    11. Chebi:72296

    12. Bms562247-01

    13. Apixaban-13c,d3

    14. 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-1h,4h,5h,6h,7h-pyrazolo[3,4-c]pyridine-3-carboxamide

    15. 1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxylic Acid Amide

    16. 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydropyrazolo[5,4-c]pyridine-3-carboxamide

    17. Apixaban [usan]

    18. Gg2

    19. Eliquis (tn)

    20. Unii-3z9y7uwc1j

    21. Apixabanum

    22. Apixaban (jan/usan/inn)

    23. Apixaban [usan:inn:jan]

    24. Hsdb 8223

    25. Apixaban- Bio-x

    26. Apixaban(bms-562247-01)

    27. Apixaban-[d3]

    28. Bms 562247

    29. Apixaban [inn]

    30. Apixaban [jan]

    31. Apixaban [mi]

    32. Apixaban [vandf]

    33. Apixaban [mart.]

    34. Apixaban [who-dd]

    35. Apixaban - Adooq Bioscience

    36. Apixaban [ema Epar]

    37. Mls006010026

    38. Schembl118023

    39. Apixaban [orange Book]

    40. Gtpl6390

    41. Apixaban,bms-562247-01

    42. Bdbm19023

    43. Amy1826

    44. Dtxsid80436500

    45. Ex-a048

    46. 2p16

    47. Bcpp000396

    48. Hms3655o07

    49. Bcp02451

    50. 503612-47-3, Eliquis,

    51. Apixaban (bms 562247-01)

    52. Bms562247

    53. Mfcd11977295

    54. Nsc784102

    55. S1593

    56. Zinc11677837

    57. Akos005146204

    58. Bcp9000310

    59. Ccg-229675

    60. Cs-0401

    61. Db06605

    62. Me-0152

    63. Nsc-784102

    64. Pb10976

    65. Ncgc00346555-01

    66. Ncgc00346555-02

    67. Ncgc00346555-05

    68. Ncgc00346555-08

    69. Ac-26301

    70. Bm164185

    71. Hy-50667

    72. Smr004676529

    73. Ft-0686944

    74. Sw220177-1

    75. D03213

    76. Ab01565766_02

    77. 612a473

    78. Ar-270/43507990

    79. Q414462

    80. J-200194

    81. 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyi)-4,5,6,7-tetrahydro-1h-pyrazolo(3,4-c)pyridine-3-carboxamide

    82. 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1h-pyrazolo(3,4c)pyridine-3-carboxamide

    83. 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo Piperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide

    84. 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1-piperidinyl)phenyl]-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide

    85. 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide?bms-562247; Bms-562247-01

    86. 1h-pyrazolo(3,4-c)pyridine-3-carboxamide, 4,5,6,7-tetrahydro-1-( 4-methoxyphenyl)-7-oxo-6-(4-(2-oxo-1-piperidinyl)phenyl)-

    87. 1h-pyrazolo(3,4-c)pyridine-3-carboxamide,4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxo-1-piperidinyl)phenyl)-

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 459.5 g/mol
    Molecular Formula C25H25N5O4
    XLogP32.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass459.19065430 g/mol
    Monoisotopic Mass459.19065430 g/mol
    Topological Polar Surface Area111 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity777
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameEliquis
    PubMed HealthApixaban (By mouth)
    Drug ClassesAnticoagulant
    Drug LabelELIQUIS (apixaban), a factor Xa (FXa) inhibitor, is chemically described as 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide. Its molecular formula is C25H25N5O4, which correspond...
    Active IngredientApixaban
    Dosage FormTablet
    RouteOral
    Strength2.5mg; 5mg
    Market StatusPrescription
    CompanyBristol Myers Squibb

    2 of 2  
    Drug NameEliquis
    PubMed HealthApixaban (By mouth)
    Drug ClassesAnticoagulant
    Drug LabelELIQUIS (apixaban), a factor Xa (FXa) inhibitor, is chemically described as 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide. Its molecular formula is C25H25N5O4, which correspond...
    Active IngredientApixaban
    Dosage FormTablet
    RouteOral
    Strength2.5mg; 5mg
    Market StatusPrescription
    CompanyBristol Myers Squibb

    4.2 Therapeutic Uses

    Eliquis (apixaban) is indicated to reduce the risk of stroke and systemic embolism in patients with nonvalvular atrial fibrillation. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    Eliquis is indicated for the prophylaxis of deep vein thrombosis (DVT), which may lead to pulmonary embolism (PE), in patients who have undergone hip or knee replacement surgery. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    Eliquis is indicated for the treatment of pulmonary embolism (PE). /Included in US product label/

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    Eliquis is indicated for the treatment of deep vein thrombosis (DVT). /Included in US product label/

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    For more Therapeutic Uses (Complete) data for Apixaban (7 total), please visit the HSDB record page.

    4.3 Drug Warning

    /BOXED WARNING/ WARNING: PREMATURE DISCONTINUATION OF ELIQUIS INCREASES THE RISK OF THROMBOTIC EVENTS. Premature discontinuation of any oral anticoagulant, including Eliquis, increases the risk of thrombotic events. If anticoagulation with Eliquis is discontinued for a reason other than pathological bleeding or completion of a course of therapy, consider coverage with another anticoagulant.

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    /BOXED WARNING/ WARNING: SPINAL/EPIDURAL HEMATOMA. Epidural or spinal hematomas may occur in patients treated with Eliquis who are receiving neuraxial anesthesia or undergoing spinal puncture. These hematomas may result in long-term or permanent paralysis. Consider these risks when scheduling patients for spinal procedures. Factors that can increase the risk of developing epidural or spinal hematomas in these patients include: use of indwelling epidural catheters concomitant use of other drugs that affect hemostasis, such as nonsteroidal anti-inflammatory drugs (NSAIDs), platelet inhibitors, other anticoagulants a history of traumatic or repeated epidural or spinal punctures a history of spinal deformity or spinal surgery optimal timing between the administration of Eliquis and neuraxial procedures is not known. Monitor patients frequently for signs and symptoms of neurological impairment. If neurological compromise is noted, urgent treatment is necessary. Consider the benefits and risks before neuraxial intervention in patients anticoagulated or to be anticoagulated.

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    FDA Pregnancy Risk Category: B /NO EVIDENCE OF RISK IN HUMANS. Adequate, well controlled studies in pregnant women have not shown increased risk of fetal abnormalities despite adverse findings in animals, or, in the absence of adequate human studies, animal studies show no fetal risk. The chance of fetal harm is remote but remains a possibility./

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    It is unknown whether apixaban or its metabolites are excreted in human milk. Rats excrete apixaban in milk (12% of the maternal dose). Women should be instructed either to discontinue breastfeeding or to discontinue Eliquis therapy, taking into account the importance of the drug to the mother.

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    For more Drug Warnings (Complete) data for Apixaban (17 total), please visit the HSDB record page.

    4.4 Drug Indication

    Apixaban is indicated for reducing the risk of stroke and systemic embolism in patients who have nonvalvular atrial fibrillation, prophylaxis of deep vein thrombosis(DVT) leading to pulmonary embolism(PE) in patients after a hip or knee replacement surgery, and treatment of DVT and PE to reduce the risk of recurrence.

    FDA Label

    For

    * Eliquis 2. 5 mg film-coated tablets: :

    - Prevention of venous thromboembolic events (VTE) in adult patients who have undergone elective hip or knee replacement surgery.

    - Prevention of stroke and systemic embolism in adult patients with non-valvular atrial fibrillation (NVAF), with one or more risk factors, such as prior stroke or transient ischaemic attack (TIA); age 75 years; hypertension; diabetes mellitus; symptomatic heart failure (NYHA Class II).

    - Treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE), and prevention of recurrent DVT and PE in adults (see section 4. 4 for haemodynamically unstable PE patients).

    For

    * Eliquis 5 mg film-coated tablets: :

    - Prevention of stroke and systemic embolism in adult patients with non-valvular atrial fibrillation (NVAF), with one or more risk factors, such as prior stroke or transient ischaemic attack (TIA); age 75 years; hypertension; diabetes mellitus; symptomatic heart failure (NYHA Class II).

    - Treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE), and prevention of recurrent DVT and PE in adults (see section 4. 4 for haemodynamically unstable PE patients).

    Prevention of venous thromboembolic events (VTE) in adult patients who have undergone elective hip or knee replacement surgery.

    Prevention of stroke and systemic embolism in adult patients with non-valvular atrial fibrillation (NVAF), with one or more risk factors, such as prior stroke or transient ischaemic attack (TIA); age 75 years; hypertension; diabetes mellitus; symptomatic heart failure (NYHA Class II).

    Treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE), and prevention of recurrent DVT and PE in adults (see section 4. 4 for haemodynamically unstable PE patients).

    Prevention of stroke and systemic embolism in adult patients with non-valvular atrial fibrillation (NVAF), with one or more risk factors, such as prior stroke or transient ischaemic attack (TIA); age 75 years; hypertension; diabetes mellitus; symptomatic heart failure (NYHA Class II).

    Treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE), and prevention of recurrent DVT and PE in adults (see section 4. 4 for haemodynamically unstable PE patients).

    Treatment of venous thromboembolism

    Prevention of arterial thromboembolism, Prevention of venous thromboembolism

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Apixaban selectively inhibits factor Xa in its free and bound forms, independant of antithrombin III. Apixaban also inhibits prothrominase. These effects prevent the formation of a thrombus.

    5.2 MeSH Pharmacological Classification

    Factor Xa Inhibitors

    Endogenous factors and drugs that inhibit or block the activity of FACTOR XA. (See all compounds classified as Factor Xa Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    APIXABAN
    5.3.2 FDA UNII
    3Z9Y7UWC1J
    5.3.3 Pharmacological Classes
    Factor Xa Inhibitors [MoA]; Factor Xa Inhibitor [EPC]
    5.4 ATC Code

    B01AF02

    B01AF02

    B01AF02

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    B - Blood and blood forming organs

    B01 - Antithrombotic agents

    B01A - Antithrombotic agents

    B01AF - Direct factor xa inhibitors

    B01AF02 - Apixaban

    5.5 Absorption, Distribution and Excretion

    Absorption

    Apixaban is approximately 50% bioavailable though other studies report 43-46% oral bioavailability.

    Route of Elimination

    56% of an orally administered dose is recovered in the feces and 24.5-28.8% of the dose is recovered in the urine. 83-88% of the dose recovered in the urine was the unchanged parent compound.

    Volume of Distribution

    Approximately 21L.

    Clearance

    3.3L/h though other studies report 4876mL/h.

    Distribution in pregnant rats/fetuses: Cmax in amnion was high. Significant concentrations were found in placenta and fetal blood, kidney and liver. Toxicokinetic data collected in the reproductive and developmental toxicity studies in rats, mice and rabbits showed that generally fetal plasma concentrations of apixaban were lower than those in the dams.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Eliquis (Apixaban) p.13 (2011). Available from, as of March 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002148/WC500107726.pdf

    Two single dose radiolabel distribution studies were provided in rats. The data show a wide distribution, with the highest values in excretory organs (liver, kidney, urinary bladder (and contents), bile) and intestinal tract (and contents). After a dose of 20 mg/kg in male Long-Evans rats also relatively high Cmax and AUC were found in adrenals, lungs, thyroid gland, but after a dose of 5 mg/kg in Sprague Dawley rats (both sexes) these organs showed Cmax similar to most other organs and tissues. There was no qualitative difference in distribution between male and female rats, but the female rats showed higher Cmax values in the intestinal tract.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Eliquis (Apixaban) p.13 (2011). Available from, as of March 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002148/WC500107726.pdf

    Protein binding differs between the species. The unbound fraction at concentrations of 1-10 uM is about 13% in human vs about 4% in rats and 8% in dogs. At the tested concentrations there was no effect of concentration or gender. In mice protein binding is much lower, with 44-6 % unbound, dependent on the tested concentration (range 100-2000 ng apixaban/mL).

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Eliquis (Apixaban) p.13 (2011). Available from, as of March 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002148/WC500107726.pdf

    Plasma to blood ratios of about one in dog and human blood indicate uniform distribution between plasma and red blood cells and thus no specific distribution to red blood cells.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Eliquis (Apixaban) p.13 (2011). Available from, as of March 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002148/WC500107726.pdf

    For more Absorption, Distribution and Excretion (Complete) data for Apixaban (12 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    50% of the orally administered dose is excreted as the unchanged parent compound, however 25% of the dose is excreted as O-demethyl apixaban sulfate. All apixaban metabolites account for approximately 32% of the excreted dose though the structure of all metabolites are not well defined. Apixaban is mainly metabolized by cytochrome p450(CYP)3A4 and to a lesser extent by CYP1A2, CYP2C8, CYP2C9, CYP2C19, and CYP2J2.

    Approximately 25% of an orally administered apixaban dose is recovered in urine and feces as metabolites. Apixaban is metabolized mainly via CYP3A4 with minor contributions from CYP1A2, 2C8, 2C9, 2C19, and 2J2. O-demethylation and hydroxylation at the 3-oxopiperidinyl moiety are the major sites of biotransformation. Unchanged apixaban is the major drug-related component in human plasma; there are no active circulating metabolites.

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of December 31, 2014: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    Apixaban is mainly metabolized by CYP3A4/5 with conjugation via SULT1A1, but several other CYP and SULT isozymes are also involved. No apixaban metabolites were found to have pharmacological activity and there were no unique human metabolites.

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Eliquis (Apixaban) p.13 (2011). Available from, as of March 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002148/WC500107726.pdf

    The metabolism and disposition of (14)C-apixaban, an orally bioavailable, highly selective, and direct acting/reversible factor Xa inhibitor, was investigated in 10 healthy male subjects without (group 1, n=6) and with bile collection (group 2, n=4) after a single 20-mg oral dose. Urine, blood, and feces samples were collected from all subjects. Bile samples were also collected for 3 to 8 hr after dosing from group 2 subjects. There were no serious adverse events or discontinuations due to adverse effects. In plasma, apixaban was the major circulating component and O-demethyl apixaban sulfate, a stable and water-soluble metabolite, was the significant metabolite. The exposure of apixaban (C(max) and area under the plasma concentration versus time curve) in subjects with bile collection was generally similar to that in subjects without bile collection. The administered dose was recovered in feces (group 1, 56.0%; group 2, 46.7%) and urine (group 1, 24.5%; group 2, 28.8%), with the parent drug representing approximately half of the recovered dose. Biliary excretion represented a minor elimination pathway (2.44% of the administered dose) from group 2 subjects within the limited collection period. Metabolic pathways identified for apixaban included O-demethylation, hydroxylation, and sulfation of hydroxylated O-demethyl apixaban. Thus, apixaban is an orally bioavailable inhibitor of factor Xa with elimination pathways that include metabolism and renal excretion.

    PMID:18832478 Raghavan N et al; Drug Metab Dispos 37 (1): 74-81 (2009)

    The metabolism and disposition of (14)C-apixaban, a potent, reversible, and direct inhibitor of coagulation factor Xa, were investigated in mice, rats, rabbits, dogs, and humans after a single oral administration and in incubations with hepatocytes. In plasma, the parent compound was the major circulating component in mice, rats, dogs, and humans. O-Demethyl apixaban sulfate (M1) represented approximately 25% of the parent area under the time curve in human plasma. This sulfate metabolite was present, but in lower amounts relative to the parent, in plasma from mice, rats, and dogs. Rabbits showed a plasma metabolite profile distinct from that of other species with apixaban as a minor component and M2 (O-demethyl apixaban) and M14 (O-demethyl apixaban glucuronide) as prominent components. The fecal route was a major elimination pathway, accounting for >54% of the dose in animals and >46% in humans. The urinary route accounted for <15% of the dose in animals and 25 to 28% in humans. Apixaban was the major component in feces of every species and in urine of all species except rabbit. M1 and M2 were common prominent metabolites in urine and feces of all species as well as in bile of rats and humans. In vivo metabolite profiles showed quantitative differences between species and from in vitro metabolite profiles, but all human metabolites were found in animal species. After intravenous administration of (14)C-apixaban to bile duct-cannulated rats, the significant portion (approximately 22%) of the dose was recovered as parent drug in the feces, suggesting direct excretion of the drug from gastrointestinal tracts of rats. Overall, apixaban was effectively eliminated via multiple elimination pathways in animals and humans, including oxidative metabolism, and direct renal and intestinal excretion.

    PMID:19420130 Zhang D et al; Drug Metab Dispos 37 (8): 1738-48 (2009)

    ... The O-demethyl apixaban sulfate is a major circulating metabolite in humans but circulates at lower concentrations relative to parent in animals. The aim of this study was to identify the sulfotransferases (SULTs) responsible for the sulfation reaction. Apixaban undergoes O-demethylation catalyzed by cytochrome P450 enzymes to O-demethyl apixaban, and then is conjugated by SULTs to form O-demethyl apixaban sulfate. Of the five human cDNA-expressed SULTs tested, SULT1A1 and SULT1A2 exhibited significant levels of catalytic activity for formation of O-demethyl apixaban sulfate, and SULT1A3, SULT1E1, and SULT2A1 showed much lower catalytic activities. In human liver S9, quercetin, a highly selective inhibitor of SULT1A1 and SULT1E1, inhibited O-demethyl apixaban sulfate formation by 99%; 2,6-dichloro-4-nitrophenol, another inhibitor of SULT1A1, also inhibited this reaction by >90%; estrone, a competitive inhibitor for SULT1E1, had no effect on this reaction. The comparable K(m) values for formation of O-demethyl apixaban sulfate were 41.4 microM (human liver S9), 36.8 microM (SULT1A1), and 70.8 microM (SULT1A2). Because of the high level of expression of SULT1A1 in liver and its higher level of catalytic activity for formation of O-demethyl apixaban sulfate, SULT1A1 might play a major role in humans for formation of O-demethyl apixaban sulfate. O-Demethyl apixaban was also investigated in liver S9 of mice, rats, rabbits, dogs, monkeys, and humans. The results indicated that liver S9 samples from dogs, monkeys, and humans had higher activities for formation of O-demethyl apixaban sulfate than those of mice, rats, and rabbits.

    PMID:19131519 Wang L et al; Drug Metab Dispos 37 (4): 802-8 (2009)

    5.7 Biological Half-Life

    12.78.55h.

    Apixaban has ... an apparent half-life of approximately 12 hours following oral administration.

    NIH; DailyMed. Current Medication Information for Eliquis (Apixaban) Tablet, Film Coated (Revised: August 2014). Available from, as of March 26, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9481622-7cc6-418a-acb6-c5450daae9b0

    In a comparative study elimination half-life in rats (2-3 hrs) was shorter than in dogs (5-6 hrs) and chimpanzees (5-7 hrs). Distribution volume is relatively low in rats (0.31 L/kg), dogs (0.30 L/kg) and chimpanzees (0.17 L/kg).

    European Medicines Agency (EMA), Committee for Medicinal Products for Human Use (CHMP), European Public Assessment Report (EPAR): Eliquis (Apixaban) p.13 (2011). Available from, as of March 26, 2015: https://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002148/WC500107726.pdf

    ... After a single oral administration ... the elimination half life of radioactivity in blood was 1.7 to 4.2 hr.

    PMID:2107152 Wang L et al; Drug Metab Dispos 39 (2): 256-64 (2011)

    5.8 Mechanism of Action

    Apixaban selectively inhibits factor Xa in its free and bound forms, independant of antithrombin III. Apixaban also inhibits prothrominase. These effects prevent the formation of a thrombus.

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D6 D8, SY.NO. 234\/2,234\/3,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1714415400,"product":"APIXABAN","address":"H.NO. 8-2-337,BESIDE TV9 OFFICE","city":"HYDERABAD ANDHRA PRADESH","supplier":"ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD","supplierCountry":"CHINA","foreign_port":"HANGCHOW (HANGZHOU)","customer":"DRREDDY\\'S LABORATORIES LTD","customerCountry":"INDIA","quantity":"1.50","actualQuantity":"1.5","unit":"KGS","unitRateFc":"3000","totalValueFC":"4548.1","currency":"USD","unitRateINR":"253200","date":"30-Apr-2024","totalValueINR":"379800","totalValueInUsd":"4548.1","indian_port":"Hyderabad Air","hs_no":"29337990","bill_no":"3268130","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HANGCHOW (HANGZHOU)","supplierAddress":"XUNQIAO, LINHAI, ZHEJIANG, 317024,CHINA China ChinaSDNF China","customerAddress":"H.NO. 8-2-337,BESIDE TV9 OFFICE"}]
    03-Jan-2022
    25-Apr-2025
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    01

    Brand Name : Eliquis

    Apixaban

    arrow
    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Bristol Myers Squibb

    Apixaban

    Main Therapeutic Indication : Cardiovascular Diseases

    Currency : USD

    2020 Revenue in Millions : 9,168

    2019 Revenue in Millions : 7,929

    Growth (%) : 16

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    02

    Brand Name : Eliquis

    Apixaban

    arrow
    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Pfizer Inc.

    Apixaban

    Main Therapeutic Indication : Cardiovascular Diseases

    Currency : USD

    2020 Revenue in Millions : 4,949

    2019 Revenue in Millions : 4,220

    Growth (%) : 17

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    03

    Brand Name : Eliquis

    Apixaban

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    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Bristol Myers Squibb

    Apixaban

    Main Therapeutic Indication : Cardiovascular Diseases

    Currency : USD

    2021 Revenue in Millions : 10,762

    2020 Revenue in Millions : 9,168

    Growth (%) : 17

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    04

    Brand Name : Eliquis

    Apixaban

    arrow
    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Pfizer Inc.

    Apixaban

    Main Therapeutic Indication : Cardiovascular Diseases

    Currency : USD

    2021 Revenue in Millions : 5,970

    2020 Revenue in Millions : 4,949

    Growth (%) : 21

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    05

    Brand Name : Eliquis

    Apixaban

    arrow
    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Bristol Myers Squibb

    Apixaban

    Main Therapeutic Indication : Cardiology/Vascular Diseases

    Currency : USD

    2022 Revenue in Millions : 11,789

    2021 Revenue in Millions : 10,762

    Growth (%) : 10

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    06

    Brand Name : Eliquis

    Apixaban

    arrow
    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Pfizer Inc.

    Apixaban

    Main Therapeutic Indication : Cardiology/Vascular Diseases

    Currency : USD

    2022 Revenue in Millions : 6,480

    2021 Revenue in Millions : 5,970

    Growth (%) : 9

    blank

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    07

    Brand Name : Eliquis

    Apixaban

    arrow
    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Bristol Myers Squibb

    Apixaban

    Main Therapeutic Indication : Cardiology/Vascular Diseases

    Currency : USD

    2023 Revenue in Millions : 12,206

    2022 Revenue in Millions : 11,789

    Growth (%) : 4

    blank

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    08

    Brand Name : Eliquis

    Apixaban

    arrow
    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Pfizer Inc.

    Apixaban

    Main Therapeutic Indication : Cardiology/Vascular Diseases

    Currency : USD

    2023 Revenue in Millions : 6,747

    2022 Revenue in Millions : 6,480

    Growth (%) : 4

    blank

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    09

    Brand Name : Eliquis

    Apixaban

    arrow
    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Bristol-Myers Squibb

    Apixaban

    Main Therapeutic Indication : Anticoagulants

    Currency : USD

    2014 Revenue in Millions : 430.10%

    2013 Revenue in Millions :

    Growth (%) :

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    10

    Brand Name : Eliquis

    Apixaban

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    Peptide Forum
    Not Confirmed

    Brand Name : Eliquis

    U.S.A
    arrow
    Peptide Forum
    Not Confirmed

    Bristol-Myers Squibb

    Apixaban

    Main Therapeutic Indication : Anticoagulants

    Currency : USD

    2015 Revenue in Millions : 774

    2014 Revenue in Millions : 1,860

    Growth (%) : 140%

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    turkeypng-1602828403png-1622460951png-1622462103.png
    Apixaban API needed in Turkey [ENA19549]
    A Group of companies that focuses on manufacturing, development & distribution of various finished formulations is looking for suppliers of Apixaban API for development purposes. The suppliers must support this enquiry with CEP, DMF and CoA.
    21 May 2024

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    21 May 2024

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    21 May 2024

    Canada.png
    Apixaban (25 kg) API needed in Canada [ENA18844]
    A company that focuses on distribution of various pharmaceutical products is looking for suppliers of Apixaban (25 kg) API for commercial purposes. The suppliers must support this enquiry with USDMF & CoA.
    01 Jan 2024

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    01 Jan 2024

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    Reply Comment (15)

    01 Jan 2024

    SaudiArabia.png
    Apixaban (100 kg) API needed in Saudi Arabia [ENA18820]
    A company that focuses on research, development and manufacturing of active pharmaceutical ingredients is looking for suppliers of Apixaban (100 kg) API for commercial purposes. The suppliers must support this enquiry with CoA.
    26 Dec 2023

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    26 Dec 2023

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    Reply Comment (19)

    26 Dec 2023

    india-flag.png
    Apixaban (1 kg - 5 kg) API needed in India [ENA17221]
    A company that focuses on research, development and manufacturing of tablets, capsules & injectables is looking for suppliers of Apixaban (1 kg - 5 kg) API for development purposes. The suppliers must support this enquiry with USDMF & CoA.
    02 Jun 2023

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    02 Jun 2023

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    Reply Comment (7)

    02 Jun 2023

    india-flag.png
    Apixaban (1 kg) API needed in India [ENA16736]
    A company that deals in various pharmaceutical products is looking for suppliers of Apixaban (1 kg) API for commercial purposes. The suppliers must support this enquiry with CoA.
    28 Mar 2023

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    28 Mar 2023

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    Reply Comment (6)

    28 Mar 2023

    india-flag.png
    Apixaban (1 kg) API needed in India [ENA16308]
    A company that deals in the distribution of various pharmaceutical products is looking for suppliers of Apixaban (1 kg) API for commercial purposes. The suppliers must support this enquiry with CoA.
    06 Feb 2023

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    06 Feb 2023

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    Reply Comment (11)

    06 Feb 2023

    india-flag.png
    Various APIs needed in India [ENA16281]
    A company that focuses on the manufacturing of tablets, creams & ointments, injectables, and ophthalmic is looking for suppliers of Various APIs for commercial purposes. The required quantity is MOQ for each. The suppliers must support this enquiry with open part DMF, GMP & CoA. 1. Apixaban API 2. Losartan API 3. Bisoprolol API 4. Labetalol API 5. Warfarin Sodium API 6. Betahistine Dihydrochloride API
    02 Feb 2023

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    02 Feb 2023

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    Reply Comment (8)

    02 Feb 2023

    india-flag.png
    Various APIs needed in India [ENA15821]
    A CRO that specializes in formulation and analytical development services for OSDs, parenteral and liquid orals is looking for suppliers of Various APIs for development purposes. The suppliers must support this enquiry with CoA. 1. Lurasidone HCl (5 kg) API 2. Apixaban (100 g) API 3. Empagliflozin (100 g) API
    14 Dec 2022

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    14 Dec 2022

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    Reply Comment (7)

    14 Dec 2022

    Latvia.png
    Micronized Apixaban (500 kg) API needed in Latvia [ENA15765]
    A leading company that focuses on manufacturing a wide range of FDFs including neurology, cardiology, infectology and allergology is looking for suppliers of Micronized Apixaban (500 kg) API for commercial purposes. The suppliers must support this enquiry with CoA.
    08 Dec 2022

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    08 Dec 2022

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    Reply Comment (16)

    08 Dec 2022

    korearepublicofnew.png
    Various APIs needed in South Korea [ENA14553]
    A company that focuses in development, manufacturing & marketing a wide range of finished formulations is looking for suppliers of Various APIs for commercial purpose. The suppliers must support this enquiry with KDMF. 1. Apixaban API 2. Edoxaban API
    02 Aug 2022

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    02 Aug 2022

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    02 Aug 2022

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    ABOUT THIS PAGE

    Looking for 503612-47-3 / Apixaban API manufacturers, exporters & distributors?

    Apixaban manufacturers, exporters & distributors 1

    15

    PharmaCompass offers a list of Apixaban API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Apixaban manufacturer or Apixaban supplier for your needs.

    Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Apixaban manufacturer or Apixaban supplier.

    PharmaCompass also assists you with knowing the Apixaban API Price utilized in the formulation of products. Apixaban API Price is not always fixed or binding as the Apixaban Price is obtained through a variety of data sources. The Apixaban Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

    API | Excipient name

    Apixaban

    Synonyms

    503612-47-3, Eliquis, Bms-562247, Bms-562247-01, Bms 562247-01, 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide

    Cas Number

    503612-47-3

    Unique Ingredient Identifier (UNII)

    3Z9Y7UWC1J

    About Apixaban

    Apixaban is an orally active inhibitor of coagulation factor Xa with anticoagulant activity. Apixaban directly inhibits factor Xa, thereby interfering with the conversion of prothrombin to thrombin and preventing formation of cross-linked fibrin clots.

    apixabanum Manufacturers

    A apixabanum manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of apixabanum, including repackagers and relabelers. The FDA regulates apixabanum manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. apixabanum API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of apixabanum manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    apixabanum Suppliers

    A apixabanum supplier is an individual or a company that provides apixabanum active pharmaceutical ingredient (API) or apixabanum finished formulations upon request. The apixabanum suppliers may include apixabanum API manufacturers, exporters, distributors and traders.

    click here to find a list of apixabanum suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    apixabanum USDMF

    A apixabanum DMF (Drug Master File) is a document detailing the whole manufacturing process of apixabanum active pharmaceutical ingredient (API) in detail. Different forms of apixabanum DMFs exist exist since differing nations have different regulations, such as apixabanum USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A apixabanum DMF submitted to regulatory agencies in the US is known as a USDMF. apixabanum USDMF includes data on apixabanum's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The apixabanum USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of apixabanum suppliers with USDMF on PharmaCompass.

    apixabanum JDMF

    The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

    The apixabanum Drug Master File in Japan (apixabanum JDMF) empowers apixabanum API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

    PMDA reviews the apixabanum JDMF during the approval evaluation for pharmaceutical products. At the time of apixabanum JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

    click here to find a list of apixabanum suppliers with JDMF on PharmaCompass.

    apixabanum KDMF

    In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

    Pharmaceutical companies submit a apixabanum Drug Master File in Korea (apixabanum KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of apixabanum. The MFDS reviews the apixabanum KDMF as part of the drug registration process and uses the information provided in the apixabanum KDMF to evaluate the safety and efficacy of the drug.

    After submitting a apixabanum KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their apixabanum API can apply through the Korea Drug Master File (KDMF).

    click here to find a list of apixabanum suppliers with KDMF on PharmaCompass.

    apixabanum WC

    A apixabanum written confirmation (apixabanum WC) is an official document issued by a regulatory agency to a apixabanum manufacturer, verifying that the manufacturing facility of a apixabanum active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting apixabanum APIs or apixabanum finished pharmaceutical products to another nation, regulatory agencies frequently require a apixabanum WC (written confirmation) as part of the regulatory process.

    click here to find a list of apixabanum suppliers with Written Confirmation (WC) on PharmaCompass.

    apixabanum NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing apixabanum as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for apixabanum API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture apixabanum as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain apixabanum and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a apixabanum NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of apixabanum suppliers with NDC on PharmaCompass.

    apixabanum GMP

    apixabanum Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of apixabanum GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right apixabanum GMP manufacturer or apixabanum GMP API supplier for your needs.

    apixabanum CoA

    A apixabanum CoA (Certificate of Analysis) is a formal document that attests to apixabanum's compliance with apixabanum specifications and serves as a tool for batch-level quality control.

    apixabanum CoA mostly includes findings from lab analyses of a specific batch. For each apixabanum CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    apixabanum may be tested according to a variety of international standards, such as European Pharmacopoeia (apixabanum EP), apixabanum JP (Japanese Pharmacopeia) and the US Pharmacopoeia (apixabanum USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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