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    Also known as: 102767-28-2, Keppra, (s)-2-(2-oxopyrrolidin-1-yl)butanamide, Keppra xr, (2s)-2-(2-oxopyrrolidin-1-yl)butanamide, Ucb l059
    Molecular Formula
    C8H14N2O2
    Molecular Weight
    170.21  g/mol
    InChI Key
    HPHUVLMMVZITSG-LURJTMIESA-N
    FDA UNII
    44YRR34555
    Levetiracetam
    A pyrrolidinone and acetamide derivative that is used primarily for the treatment of SEIZURES and some movement disorders, and as a nootropic agent.
    The physiologic effect of levetiracetam is by means of Decreased Central Nervous System Disorganized Electrical Activity.
    1 2D Structure

    Levetiracetam

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-(2-oxopyrrolidin-1-yl)butanamide
    2.1.2 InChI
    InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1
    2.1.3 InChI Key
    HPHUVLMMVZITSG-LURJTMIESA-N
    2.1.4 Canonical SMILES
    CCC(C(=O)N)N1CCCC1=O
    2.1.5 Isomeric SMILES
    CC[C@@H](C(=O)N)N1CCCC1=O
    2.2 Other Identifiers
    2.2.1 UNII
    44YRR34555
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Alpha Ethyl 2 Oxo 1 Pyrrolidineacetamide

    2. Alpha-ethyl-2-oxo-1-pyrrolidineacetamide

    3. Etiracetam

    4. Etiracetam, (r)-

    5. Etiracetam, R Isomer

    6. Etiracetam, R-isomer

    7. Etiracetam, S Isomer

    8. Etiracetam, S-isomer

    9. Keppra

    10. R-isomer Etiracetam

    11. S-isomer Etiracetam

    12. Ucb 6474

    13. Ucb L059

    14. Ucb L060

    15. Ucb-6474

    16. Ucb-l059

    17. Ucb-l060

    18. Ucb6474

    19. Ucbl060

    2.3.2 Depositor-Supplied Synonyms

    1. 102767-28-2

    2. Keppra

    3. (s)-2-(2-oxopyrrolidin-1-yl)butanamide

    4. Keppra Xr

    5. (2s)-2-(2-oxopyrrolidin-1-yl)butanamide

    6. Ucb L059

    7. Ucb-l 059

    8. Matever

    9. Ucb-l059

    10. Levetiracetame

    11. Levetiracetamum

    12. Spritam

    13. (s)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide

    14. Sib-s1

    15. Elepsia

    16. Levetiracetam Sun

    17. (-)-(s)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide

    18. Levetiracetam Teva

    19. Ucb-22059

    20. Levetiracetam Accord

    21. Levetiracetam [inn]

    22. Levetiracetam Actavis

    23. Levetiracetam Hospira

    24. N03ax14

    25. Ucb 22059

    26. Levetiracetamum [inn-latin]

    27. Nsc-760119

    28. 1-pyrrolidineacetamide, Alpha-ethyl-2-oxo-, (alphas)-

    29. Chebi:6437

    30. Levetiracetam In Sodium Chloride

    31. Agb-101

    32. 44yrr34555

    33. Levroxa

    34. (s)-(-)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide

    35. Leviteracetam

    36. Levipil

    37. Torleva

    38. Elepsia Xr

    39. (s)-levetiracetam

    40. Smr000466303

    41. Keppra (tn)

    42. Levesam 500

    43. Etiracetam Levo-isomer

    44. Sr-01000759400

    45. Mfcd03265610

    46. Unii-44yrr34555

    47. E Keppra

    48. Hsdb 7528

    49. Levetiracetam [usan:usp:inn:ban]

    50. E Keppra (tn)

    51. Levetiracetam Solution

    52. Levetiracetam- Bio-x

    53. (s)-2-(2-oxo-1-pyrrolidinyl)butyramide

    54. L-059

    55. Levetiracetam [mi]

    56. Levetiracetam [jan]

    57. Chembl1286

    58. Levetiracetam [hsdb]

    59. Levetiracetam [usan]

    60. Levetiracetam [vandf]

    61. 1-pyrrolidineacetamide, Alpha-ethyl-2-oxo-, (s)-

    62. Mls000759403

    63. Mls001424069

    64. Mls006010215

    65. Bidd:gt0242

    66. Levetiracetam [mart.]

    67. Schembl118843

    68. Levetiracetam Ratiopharm

    69. Levetiracetam [usp-rs]

    70. Levetiracetam [who-dd]

    71. Gtpl6826

    72. Levetiracetam (jan/usp/inn)

    73. Dtxsid9023207

    74. Levetiracetam [ema Epar]

    75. Levetiracetam Actavis Group

    76. Levetiracetam, >=98% (hplc)

    77. Levetiracetam, Analytical Standard

    78. Hms2051d07

    79. Hms2089l20

    80. Hms2235i18

    81. Hms3262h11

    82. Hms3713p16

    83. Hms3884o11

    84. Pharmakon1600-01502265

    85. Levetiracetam [ep Impurity]

    86. Levetiracetam [orange Book]

    87. Act02712

    88. Albb-027275

    89. Bcp11856

    90. Hy-b0106

    91. Zinc1547851

    92. Levetiracetam [ep Monograph]

    93. Levetiracetam [usp Impurity]

    94. Tox21_500835

    95. Bdbm50422542

    96. Levetiracetam [usp Monograph]

    97. Nsc760119

    98. S1356

    99. Stl388027

    100. Levetiracetam 1.0 Mg/ml In Methanol

    101. Akos015841981

    102. Ac-1479

    103. Ccg-100928

    104. Cs-1854

    105. Db01202

    106. Ks-1176

    107. Lp00835

    108. Nc00178

    109. Nsc 760119

    110. Sdccgsbi-0633760.p001

    111. (2s)-(2-oxopyrrolidin-1-yl)butyramide

    112. Ncgc00186028-01

    113. Ncgc00186028-13

    114. Ncgc00261520-01

    115. (s)-2-(2-oxopyrrolidin-1-yl)butyramide

    116. Bl164623

    117. (s)-2-(2-oxopyrrolidin-1-yl) Butyramide

    118. Am20070676

    119. L0234

    120. Sw197558-3

    121. C07841

    122. D00709

    123. Ab00639945-06

    124. Ab00639945_07

    125. Ab00639945_08

    126. 767l282

    127. A800616

    128. (s)-2-(2-oxo-pyrrolidin-1-yl)-butyramide

    129. Q-201292

    130. Sr-01000759400-4

    131. Sr-01000759400-5

    132. (2s)-2-(2-oxopyrrolidin-1-yl)butanamide;levetiracetam

    133. (-)-(s)-.alpha.-ethyl-2-oxo-1-pyrrolidineacetamide

    134. 1-pyrrolidineacetamide, .alpha.-ethyl-2-oxo-, (.alpha.s)-

    135. Levetiracetam, European Pharmacopoeia (ep) Reference Standard

    136. Levetiracetam, United States Pharmacopeia (usp) Reference Standard

    137. (-)-(s)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide (2s)-2-(2-oxo-pyrrolidin-1-yl)butanamide

    138. Levetiracetam Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    139. Levitiracetam, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-11-20
    3 Chemical and Physical Properties
    Molecular Weight 170.21 g/mol
    Molecular Formula C8H14N2O2
    XLogP3-0.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count3
    Exact Mass170.105527694 g/mol
    Monoisotopic Mass170.105527694 g/mol
    Topological Polar Surface Area63.4 Ų
    Heavy Atom Count12
    Formal Charge0
    Complexity203
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    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 6  
    Drug NameKeppra
    PubMed HealthLevetiracetam (By mouth)
    Drug ClassesAnticonvulsant
    Drug LabelKEPPRA is an antiepileptic drug available as 250 mg (blue), 500 mg (yellow), 750 mg (orange), and 1000 mg (white) tablets and as a clear, colorless, grape-flavored liquid (100 mg/mL) for oral administration.The chemical name of levetiracetam, a singl...
    Active IngredientLevetiracetam
    Dosage FormTablet; Injectable; Solution
    RouteIv (infusion); Oral
    Strength250mg; 500mg; 500mg/5ml (100mg/ml); 100mg/ml; 750mg; 1gm
    Market StatusPrescription
    CompanyUcb

    2 of 6  
    Drug NameKeppra xr
    PubMed HealthLevetiracetam
    Drug ClassesAnticonvulsant
    Drug LabelKEPPRA XR is an antiepileptic drug available as 500 mg and 750 mg (white) extended-release tablets for oral administration.The chemical name of levetiracetam, a single enantiomer, is (-)-(S)--ethyl-2-oxo-1-pyrrolidine acetamide, its molecular formu...
    Active IngredientLevetiracetam
    Dosage FormTablet, extended release
    RouteOral
    Strength500mg; 750mg
    Market StatusPrescription
    CompanyUcb

    3 of 6  
    Drug NameLevetiracetam
    PubMed HealthLevetiracetam
    Drug ClassesAnticonvulsant
    Drug LabelLevetiracetam is an antiepileptic drug available as 250 mg (blue), 500 mg (yellow) and 750 mg (orange) tablets.The chemical name of levetiracetam, a single enantiomer, is (-)-(S)-acetamide, its molecular formula is C8H14N2O2 and its molecular weight...
    Active IngredientLevetiracetam
    Dosage FormTablet, extended release; Tablet; Injectable; Solution
    Routeoral; Iv (infusion); Oral
    Strength250mg; 500mg/5ml(100mg/ml); 1000mg; 500mg; 500mg/ml (100mg/ml); 500mg/5ml (100mg/ml); 100mg/ml; 750mg; 1gm
    Market StatusTentative Approval; Prescription
    CompanyVintage Pharms; Mylan Pharms; Anchen Pharms; Amneal Pharms; Wockhardt; Silarx; Hospira; Breckenridge Pharm; Actavis Labs Fl; X Gen Pharms; Methapharm; Apotex; Lotus Pharm; Accord Hlthcare; Hetero Labs Ltd Iii; Hikma Farmaceutica; Sun Pharm Inds; Aurobindo

    4 of 6  
    Drug NameKeppra
    PubMed HealthLevetiracetam (By mouth)
    Drug ClassesAnticonvulsant
    Drug LabelKEPPRA is an antiepileptic drug available as 250 mg (blue), 500 mg (yellow), 750 mg (orange), and 1000 mg (white) tablets and as a clear, colorless, grape-flavored liquid (100 mg/mL) for oral administration.The chemical name of levetiracetam, a singl...
    Active IngredientLevetiracetam
    Dosage FormTablet; Injectable; Solution
    RouteIv (infusion); Oral
    Strength250mg; 500mg; 500mg/5ml (100mg/ml); 100mg/ml; 750mg; 1gm
    Market StatusPrescription
    CompanyUcb

    5 of 6  
    Drug NameKeppra xr
    PubMed HealthLevetiracetam
    Drug ClassesAnticonvulsant
    Drug LabelKEPPRA XR is an antiepileptic drug available as 500 mg and 750 mg (white) extended-release tablets for oral administration.The chemical name of levetiracetam, a single enantiomer, is (-)-(S)--ethyl-2-oxo-1-pyrrolidine acetamide, its molecular formu...
    Active IngredientLevetiracetam
    Dosage FormTablet, extended release
    RouteOral
    Strength500mg; 750mg
    Market StatusPrescription
    CompanyUcb

    6 of 6  
    Drug NameLevetiracetam
    PubMed HealthLevetiracetam
    Drug ClassesAnticonvulsant
    Drug LabelLevetiracetam is an antiepileptic drug available as 250 mg (blue), 500 mg (yellow) and 750 mg (orange) tablets.The chemical name of levetiracetam, a single enantiomer, is (-)-(S)-acetamide, its molecular formula is C8H14N2O2 and its molecular weight...
    Active IngredientLevetiracetam
    Dosage FormTablet, extended release; Tablet; Injectable; Solution
    Routeoral; Iv (infusion); Oral
    Strength250mg; 500mg/5ml(100mg/ml); 1000mg; 500mg; 500mg/ml (100mg/ml); 500mg/5ml (100mg/ml); 100mg/ml; 750mg; 1gm
    Market StatusTentative Approval; Prescription
    CompanyVintage Pharms; Mylan Pharms; Anchen Pharms; Amneal Pharms; Wockhardt; Silarx; Hospira; Breckenridge Pharm; Actavis Labs Fl; X Gen Pharms; Methapharm; Apotex; Lotus Pharm; Accord Hlthcare; Hetero Labs Ltd Iii; Hikma Farmaceutica; Sun Pharm Inds; Aurobindo

    4.2 Therapeutic Uses

    Levetiracetam is indicated as adjunctive therapy in the treatment of partial onset seizures in adults and children 4 years of age and older with epilepsy. /included in US product labe/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1815

    4.3 Drug Warning

    Adverse neuropsychiatric effects reported during levetiracetam treatment are classified into 3 categories: somnolence and fatigue, coordination difficulties, and behavioral changes. In controlled studies, 14.8% of patients who received levetiracetam experienced somnolence compared with 8.4% of placebo-treated patients, and about 3% of levetiracetam-treated patients discontinued treatment due to somnolence. About 14.7% of patients who received levetiracetam experienced asthenia compared with 9.1% of placebo-treated patients, and 0.8% of levetiracetam-treated patients discontinued treatment due to asthenia. Coordination difficulties were experienced by 3.4% of levetiracetam patients compared with 1.6% of placebo-treated patients. Somnolence, asthenia, and coordination difficulties occurred most frequently within the first 4 weeks of treatment. Psychotic manifestations and hallucinations were reported rarely in patients receiving levetiracetam in clinical studies. Other behavioral symptoms (e.g., agitation, hostility, anxiety, apathy, emotional lability, depersonalization, depression, aggression, anger, irritability) occurred in 13.3% of levetiracetam-treated patients in clinical studies compared with 6.2% of placebo patients, and 1.7% of levetiracetam-treated patients discontinued treatment because of these events.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2240

    Because of the possibility of increased seizure frequency, anticonvulsant drugs, including levetiracetam, should not be discontinued suddenly. Levetiracetam should be withdrawn gradually by reducing the dosage by 1g daily at 2-week intervals.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2240

    Adverse effects occurring in 1% or more of patients receiving levetiracetam and more frequently than placebo include somnolence, asthenia, headache, infection, dizziness, pain, pharyngitis, depression, nervousness, rhinitis, anorexia, ataxia, vertigo, amnesia, anxiety, emotional lability, hostility, paresthesia, increased cough, sinusitis, and diplopia and were reported in clinical studies in which levetiracetam was administered in conjunction with other anticonvulsants. Asthenia, somnolence, and dizziness occurred predominantly during the initial 4 weeks of treatment.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2240

    Minor decreases in total mean erythrocyte count, mean hemoglobin, and mean hematocrit have been reported. Leukopenia, neutropenia, pancytopenia (with myelosuppression in some cases), and thrombocytopenia also have been observed, although a causal relationship to the drug has not been established.

    McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2240

    For more Drug Warnings (Complete) data for LEVETIRACETAM (12 total), please visit the HSDB record page.

    4.4 Drug Indication

    Levetiracetam is indicated as an adjunctive therapy in the treatment of partial onset seizures in epileptic patients who are one month of age and older. Additionally, it is indicated as an adjunct in the treatment of myoclonic seizures in patients with juvenile myoclonic epilepsy who are 12 years of age and older, and in primary generalized tonic-clonic seizures in patients with idiopathic generalized epilepsy who are 6 years of age and older. Levetiracetam is also available as an orally dissolvable tablet that is indicated as an adjunct in the treatment of partial onset seizures in patients with epilepsy who are 4 years of age and older and weigh more than 20kg.

    Levetiracetam Actavis is indicated as monotherapy in the treatment of partial-onset seizures with or without secondary generalisation in patients from 16 years of age with newly diagnosed epilepsy.

    Levetiracetam Actavis is indicated as adjunctive therapy:

    - in the treatment of partial-onset seizures with or without secondary generalisation in adults, children and infants from one month of age with epilepsy;

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with juvenile myoclonic epilepsy;

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with idiopathic generalised epilepsy.

    Levetiracetam Actavis Group is indicated as monotherapy in the treatment of partial-onset seizures with or without secondary generalisation in patients from 16 years of age with newly diagnosed epilepsy.

    Levetiracetam Actavis Group is indicated as adjunctive therapy:

    - in the treatment of partial-onset seizures with or without secondary generalisation in adults, children and infants from 1 month of age with epilepsy;

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with juvenile myoclonic epilepsy;

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with idiopathic generalised epilepsy.

    Levetiracetam Hospira is indicated as monotherapy in the treatment of partial onset seizures with or without secondary generalisation in adults and adolescents from 16 years of age with newly diagnosed epilepsy.

    Levetiracetam Hospira is indicated as adjunctive therapy

    - in the treatment of partial onset seizures with or without secondary generalisation in adults, adolescents and children from 4 years of age with epilepsy.

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with Juvenile Myoclonic Epilepsy .

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with Idiopathic Generalised Epilepsy .

    Levetiracetam Hospira concentrate is an alternative for patients when oral administration is temporarily not feasible.

    Levetiracetam ratiopharm is indicated as monotherapy in the treatment of partial onset seizures with or without secondary generalisation in patients from 16 years of age with newly diagnosed epilepsy.

    Levetiracetam ratiopharm is indicated as adjunctive therapy:

    - in the treatment of partial onset seizures with or without secondary generalisation in adults, children and infants from 1 month of age with epilepsy;

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with juvenile myoclonic epilepsy;

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with idiopathic generalised epilepsy.

    Levetiracetam is indicated as monotherapy in the treatment of partial-onset seizures with or without secondary generalisation in patients from 16 years of age with newly diagnosed epilepsy.

    Levetiracetam is indicated as adjunctive therapy:

    - in the treatment of partial-onset seizures with or without secondary generalisation in adults, children and infants from one month of age with epilepsy;

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with juvenile myoclonic epilepsy;

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with idiopathic generalised epilepsy.

    Levetiracetam Teva is indicated as monotherapy in the treatment of partial onset seizures with or without secondary generalisation in adults and adolescents from 16 years of age with newly diagnosed epilepsy.

    Levetiracetam Teva is indicated as adjunctive therapy:

    - in the treatment of partial onset seizures with or without secondary generalisation in adults, adolescents, children and infants from 1 month of age with epilepsy;

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with juvenile myoclonic epilepsy;

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with idiopathic generalised epilepsy.

    Keppra is indicated as monotherapy in the treatment of partial-onset seizures with or without secondary generalisation in patients from 16 years of age with newly diagnosed epilepsy.

    Keppra is indicated as adjunctive therapy:

    - in the treatment of partial-onset seizures with or without secondary generalisation in adults, children and infants from one month of age with epilepsy;

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with juvenile myoclonic epilepsy;

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with idiopathic generalised epilepsy.

    Matever is indicated as monotherapy in the treatment of partial-onset seizures with or without secondary generalisation in patients from 16 years of age with newly diagnosed epilepsy.

    Matever is indicated as adjunctive therapy:

    - in the treatment of partial-onset seizures with or without secondary generalisation in adults, children and infants from one month of age with epilepsy;

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with juvenile myoclonic epilepsy;

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with idiopathic generalised epilepsy.

    Levetiracetam Sun is indicated as monotherapy in the treatment of partial-onset seizures with or without secondary generalisation in patients from 16 years of age with newly diagnosed epilepsy.

    Levetiracetam Sun is indicated as adjunctive therapy:

    - in the treatment of partial-onset seizures with or without secondary generalisation in adults and children from four years of age with epilepsy;

    - in the treatment of myoclonic seizures in adults and adolescents from 12 years of age with juvenile myoclonic epilepsy;

    - in the treatment of primary generalised tonic-clonic seizures in adults and adolescents from 12 years of age with idiopathic generalised epilepsy.

    Levetiracetam Sun concentrate is an alternative for patients when oral administration is temporarily not feasible.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Levetiracetam appears to prevent seizure activity via the selective inhibition of hypersynchronized epileptiform burst firing without affecting normal neuronal transmission, though the exact mechanism through which this occurs is unclear. The therapeutic index of levetiracetam is wide, making it relatively unique amongst other anti-epileptic medications. Anti-epileptic drugs, including levetiracetam, may increase the risk of suicidal ideation or behaviour - patients taking levetiracetam should be monitored for the emergence or worsening of depressive symptoms, suicidal ideation, and behavioural abnormalities.

    5.2 MeSH Pharmacological Classification

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    Nootropic Agents

    Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    LEVETIRACETAM
    5.3.2 FDA UNII
    44YRR34555
    5.3.3 Pharmacological Classes
    Decreased Central Nervous System Disorganized Electrical Activity [PE]
    5.4 ATC Code

    N03AX14

    N03AX14

    N03AX14

    N03AX14

    N03AX14

    N03AX14

    N03AX14

    N03AX14

    N03AX14

    N03AX14

    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

    N - Nervous system

    N03 - Antiepileptics

    N03A - Antiepileptics

    N03AX - Other antiepileptics

    N03AX14 - Levetiracetam

    5.5 Absorption, Distribution and Excretion

    Absorption

    Levetiracetam is rapidly and nearly completely absorbed following oral administration, with a reported absolute oral bioavailability of essentially 100%. Tmax is approximately 1.3 hours after dosing, and Cmax is 31 g/mL following a single 1000mg dose and 43 g/mL following repeated dosing. Co-administration of levetiracetam with food delays Tmax by approximately 1.5 hours and decreases Cmax by 20%.

    Route of Elimination

    Approximately 66% of the administered dose of levetiracetam is excreted in the urine as unchanged drug, while only 0.3% of the total dose is excreted via the feces. The primary inactive metabolite of levetiracetam, L057, is also found in the urine as approximately 24% of the administered dose.

    Volume of Distribution

    The volume of distribution of levetiracetam is approximately 0.5 to 0.7 L/kg.

    Clearance

    The total plasma clearance of levetiracetam is 0.96 mL/min/kg, with renal clearance comprising 0.6 mL/min/kg. The primary inactive metabolite of levetiracetam, L057, has a renal clearance of 4 mL/min/kg. Given the relatively high proportion of drug undergoing renal clearance, overall clearance of levetiracetam is reduced in patients with renal impairment.

    Absorption of levetiracetam is rapid, with peak plasma concentrations occurring in about an hour following oral administration in fasted subjects. The oral bioavailability of levetiracetam tablets is 100% and the tablets and oral solution are bioequivalent in rate and extent of absorption. Food does not affect the extent of absorption of levetiracetam but it decreases C max by 20% and delays T max by 1.5 hours.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3315

    The pharmacokinetics of levetiracetam are linear over the dose range of 500-5000 mg. Steady state is achieved after 2 days of multiple twice-daily dosing.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3315

    Levetiracetam is not significantly protein-bound (<10% bound) and its volume of distribution is close to the volume of intracellular and extracellular water.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3315

    Levetiracetam C max and AUC were 20% higher in women (N=11) compared to men (N=12). However, clearances adjusted for body weight were comparable.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3315

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

    5.6 Metabolism/Metabolites

    Levetiracetam is minimally metabolized within the body - the major metabolic pathway appears to be the enzymatic hydrolysis of its acetamide group which produces an inactive carboxylic acid metabolite, L057, which accounts for approximately 24% of the total administered dose. The specific enzyme(s) responsible for this reaction are unclear, but this pathway is known to be independent of hepatic CYP enzymes and has been proposed to be driven primarily by type B esterases in the blood and other tissues. Two minor metabolites involving modifications to the pyrrolidone ring have been identified, one involving hydroxylation of the ring (constituting 1.6% of the total dose) and the other involving opening of the ring structure (constituting 0.9% of the total dose).

    Levetiracetam is not extensively metabolized in humans. The major metabolic pathway is the enzymatic hydrolysis of the acetamide group, which produces the carboxylic acid metabolite, ucb L057 (24% of dose) and is not dependent on any liver cytochrome P450 isoenzymes. The major metabolite is inactive in animal seizure models. Two minor metabolites were identified as the product of hydroxylation of the 2-oxo-pyrrolidine ring (2% of dose) and opening of the 2-oxo-pyrrolidine ring in position 5 (1% of dose). There is no enantiomeric interconversion of levetiracetam or its major metabolite.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3315

    5.7 Biological Half-Life

    The plasma half-life of levetiracetam is 6-8 hours and is not affected by dose or repeat administration. Half-life is increased in the elderly (by about 40%) and those with renal impairment.

    ... The plasma elimination half-life of the unchanged drug varied between 7.4 hr and 7.9 hr. ...

    PMID:14530892 Strolin-Benedetti M et al; Eur J Clin Pharmacol 59 (8-9): 621-30 (2003)

    Levetiracetam plasma half-life in adults is 7 +/-1 hour and is unaffected by either dose or repeated administration.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3315

    5.8 Mechanism of Action

    The exact mechanism through which levetiracetam exerts its anti-epileptic effects is unclear, but is thought to be unique amongst other anti-epileptic medications. Current knowledge suggests that levetiracetams binding to synaptic vesicle protein 2A (SV2A) is a key driver of its action. SV2A is a membrane-bound protein that is found on synaptic vesicles and is ubiquitous throughout the CNS - it appears to play a role in vesicle exocytosis and in the modulation of synaptic transmission by increasing the available amount of secretory vesicles available for neurotransmission. Stimulation of pre-synaptic SV2A by levetiracetam may inhibit neurotransmitter release, but this action does not appear to affect normal neurotransmission. This has led to the suggestion that levetiracetam exclusively modulates the function of SV2A only under pathophysiological conditions. Levetiracetam and related analogues showed a correlation between affinity for SV2A and anti-epileptic potency, further suggesting that action at this site contributes to the anti-epileptic activity of the drug. Levetiracetam has also been shown to indirectly affect GABAergic neurotransmission (despite having no direct effect on GABAergic or glutamatergic receptors) and modulate ionic currents. Similarly, levetiracetam has been shown in vitro to inhibit N-type calcium channels. How, or even if, these actions are implicated in its anti-epileptic action have yet to be elucidated.

    The precise mechanism by which levetiracetam exerts its antiepileptic effect is unknown. The antiepileptic activity of levetiracetam was assessed in a number of animal models of epileptic seizures. Levetiracetam did not inhibit single seizures induced by maximal stimulation with electrical current or different chemoconvulsants and showed only minimal activity in submaximal stimulation and in threshold tests. Protection was observed, however, against secondarily generalized activity from focal seizures induced by pilocarpine and kainic acid, two chemoconvulsants that induce seizures that mimic some features of human complex partial seizures with secondary generalization. Levetiracetam also displayed inhibitory properties in the kindling model in rats, another model of human complex partial seizures, both during kindling development and in the fully kindled state. The predictive value of these animal models for specific types of human epilepsy is uncertain.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3314

    In vitro and in vivo recordings of epileptiform activity from the hippocampus have shown that levetiracetam inhibits burst firing without affecting normal neuronal excitability, suggesting that levetiracetam may selectively prevent hypersynchronization of epileptiform burst firing and propagation of seizure activity.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3314

    Levetiracetam at concentrations of up to 10 muM did not demonstrate binding affinity for a variety of known receptors, such as those associated with benzodiazepines, GABA (gammaaminobutyric acid), glycine, NMDA (N-methyl-D-aspartate), re-uptake sites, and second messenger systems. Furthermore, in vitro studies have failed to find an effect of levetiracetam on neuronal voltage-gated sodium or T-type calcium currents and levetiracetam does not appear to directly facilitate GABAergic neurotransmission. However, in vitro studies have demonstrated that levetiractem opposes the activity of negative modulators of GABA- and glycine-gated currents and partially inhibits N-type calcium currents in neuronal cells.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3314

    A saturable and stereoselective neuronal binding site in rat brain tissue has been described for levetiracetam. Experimental data indicate that this binding site is the synaptic vesicle protein SV2A, thought to be involved in the regulation of vesicle exocytosis. Although the molecular significance of levetiracetam binding to synaptic vesicle protein SV2A is not understood, levetiracetam and related analogs showed a rank order of affinity for SV2A which correlated with the potency of their antiseizure activity in audiogenic seizure-prone mice. These findings suggest that the interaction of levetiracetam with the SV2A protein may contribute to the antiepileptic mechanism of action of the drug.

    Physicians Desk Reference 61st ed, Thomson PDR, Montvale, NJ 2007., p. 3315

    For more Mechanism of Action (Complete) data for LEVETIRACETAM (6 total), please visit the HSDB record page.

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    DOSAGE - TABLET;ORAL - 1GM

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    DOSAGE - INJECTABLE;INTRAVENOUS - 500MG/5ML (...DOSAGE - INJECTABLE;INTRAVENOUS - 500MG/5ML (100MG/ML)

    USFDA APPLICATION NUMBER - 21872

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 500M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 500MG

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 750M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 750MG

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    ABOUT THIS PAGE

    Looking for 102767-28-2 / Levetiracetam API manufacturers, exporters & distributors?

    Levetiracetam manufacturers, exporters & distributors 1

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    PharmaCompass offers a list of Levetiracetam 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 Levetiracetam manufacturer or Levetiracetam supplier for your needs.

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

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

    API | Excipient name

    Levetiracetam

    Synonyms

    102767-28-2, Keppra, (s)-2-(2-oxopyrrolidin-1-yl)butanamide, Keppra xr, (2s)-2-(2-oxopyrrolidin-1-yl)butanamide, Ucb l059

    Cas Number

    102767-28-2

    Unique Ingredient Identifier (UNII)

    44YRR34555

    About Levetiracetam

    A pyrrolidinone and acetamide derivative that is used primarily for the treatment of SEIZURES and some movement disorders, and as a nootropic agent.

    Etiracetam levo-isomer Manufacturers

    A Etiracetam levo-isomer manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Etiracetam levo-isomer, including repackagers and relabelers. The FDA regulates Etiracetam levo-isomer manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Etiracetam levo-isomer 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 Etiracetam levo-isomer manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Etiracetam levo-isomer Suppliers

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

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

    Etiracetam levo-isomer USDMF

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

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

    click here to find a list of Etiracetam levo-isomer suppliers with USDMF on PharmaCompass.

    Etiracetam levo-isomer 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 Etiracetam levo-isomer Drug Master File in Japan (Etiracetam levo-isomer JDMF) empowers Etiracetam levo-isomer 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 Etiracetam levo-isomer JDMF during the approval evaluation for pharmaceutical products. At the time of Etiracetam levo-isomer 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 Etiracetam levo-isomer suppliers with JDMF on PharmaCompass.

    Etiracetam levo-isomer KDMF

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

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

    After submitting a Etiracetam levo-isomer 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 Etiracetam levo-isomer API can apply through the Korea Drug Master File (KDMF).

    click here to find a list of Etiracetam levo-isomer suppliers with KDMF on PharmaCompass.

    Etiracetam levo-isomer CEP

    A Etiracetam levo-isomer CEP of the European Pharmacopoeia monograph is often referred to as a Etiracetam levo-isomer Certificate of Suitability (COS). The purpose of a Etiracetam levo-isomer CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Etiracetam levo-isomer EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Etiracetam levo-isomer to their clients by showing that a Etiracetam levo-isomer CEP has been issued for it. The manufacturer submits a Etiracetam levo-isomer CEP (COS) as part of the market authorization procedure, and it takes on the role of a Etiracetam levo-isomer CEP holder for the record. Additionally, the data presented in the Etiracetam levo-isomer CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Etiracetam levo-isomer DMF.

    A Etiracetam levo-isomer CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Etiracetam levo-isomer CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

    click here to find a list of Etiracetam levo-isomer suppliers with CEP (COS) on PharmaCompass.

    Etiracetam levo-isomer WC

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

    click here to find a list of Etiracetam levo-isomer suppliers with Written Confirmation (WC) on PharmaCompass.

    Etiracetam levo-isomer 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 Etiracetam levo-isomer as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Etiracetam levo-isomer 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 Etiracetam levo-isomer 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 Etiracetam levo-isomer and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Etiracetam levo-isomer NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Etiracetam levo-isomer suppliers with NDC on PharmaCompass.

    Etiracetam levo-isomer GMP

    Etiracetam levo-isomer 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 Etiracetam levo-isomer 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 Etiracetam levo-isomer GMP manufacturer or Etiracetam levo-isomer GMP API supplier for your needs.

    Etiracetam levo-isomer CoA

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

    Etiracetam levo-isomer CoA mostly includes findings from lab analyses of a specific batch. For each Etiracetam levo-isomer 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.

    Etiracetam levo-isomer may be tested according to a variety of international standards, such as European Pharmacopoeia (Etiracetam levo-isomer EP), Etiracetam levo-isomer JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Etiracetam levo-isomer 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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