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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