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    Chemistry

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    Also known as: 129618-40-2, Viramune, Bi-rg-587, Nevirapine anhydrous, Birg 0587, 11-cyclopropyl-4-methyl-5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
    Molecular Formula
    C15H14N4O
    Molecular Weight
    266.30  g/mol
    InChI Key
    NQDJXKOVJZTUJA-UHFFFAOYSA-N
    FDA UNII
    99DK7FVK1H
    Nevirapine
    A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.
    Nevirapine is a Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of nevirapine is as a Non-Nucleoside Reverse Transcriptase Inhibitor, and Cytochrome P450 3A Inducer, and Cytochrome P450 2B6 Inducer.
    1 2D Structure

    Nevirapine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-cyclopropyl-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
    2.1.2 InChI
    InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)
    2.1.3 InChI Key
    NQDJXKOVJZTUJA-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C2C(=NC=C1)N(C3=C(C=CC=N3)C(=O)N2)C4CC4
    2.2 Other Identifiers
    2.2.1 UNII
    99DK7FVK1H
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bi Rg 587

    2. Bi-rg-587

    3. Birg587

    4. Hemihydrate, Nevirapine

    5. Nevirapine Hemihydrate

    6. Viramune

    2.3.2 Depositor-Supplied Synonyms

    1. 129618-40-2

    2. Viramune

    3. Bi-rg-587

    4. Nevirapine Anhydrous

    5. Birg 0587

    6. 11-cyclopropyl-4-methyl-5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

    7. Nvp

    8. Viramune Xr

    9. Bi-rg 587

    10. 11-cyclopropyl-5,11-dihydro-4-methyl-6h-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one

    11. Nevirapine, Anhydrous

    12. 11-cyclopropyl-5,11-dihydro-4-methyl-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

    13. Nevirapine Teva

    14. Birg-0587

    15. Nsc 641530

    16. Nevirapine (viramune)

    17. Chembl57

    18. 11-cyclopropyl-4-methyl-5,11-dihydro-6h-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one

    19. 11-cyclopropyl-4-methyl-5h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11h)-one

    20. Mfcd00866928

    21. Nev

    22. Nsc-641530

    23. 99dk7fvk1h

    24. 6h-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one, 11-cyclopropyl-5,11-dihydro-4-methyl-

    25. Mls000084585

    26. Chebi:63613

    27. Nsc641530

    28. Ncgc00065890-02

    29. Smr000048458

    30. Dsstox_cid_10787

    31. Dsstox_rid_78889

    32. Dsstox_gsid_31797

    33. 2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

    34. Birg587

    35. Viramune(tm)

    36. Viramune (tn)

    37. Cas-129618-40-2

    38. Hsdb 7164

    39. Nevirapine & Cd4-igg

    40. Nevirapine & Pro 140

    41. Unii-99dk7fvk1h

    42. Nevirapine (jan/usp/inn)

    43. Nevirapine)

    44. 11-cyclopropyl-4-methyl-5h-dipyrido[[?],[?]][1,4]diazepin-6-one

    45. Birg 587

    46. Birg-587

    47. Non-nucleoside Rt Inhibitor Nevirapine

    48. 11-cyclopropyl-4-methyl-5h-dipyrido[2,3-b:3',2'-e][1,4]diazepin-6-one

    49. Viramune Ir

    50. 1vrt

    51. 2hny

    52. Nevirapine,(s)

    53. Nevirapine [usan:usp:inn:ban]

    54. Bi-rg-587 & Cd4-igg

    55. 6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one, 11-cyclopropyl-5,11-dihydro-4-methyl-

    56. Nevirapinum Anhydrous

    57. Nevirapine (anhydrous)

    58. Nevirapine [mi]

    59. Opera_id_934

    60. Nevirapine [inn]

    61. Nevirapine [jan]

    62. Nevirapine [hsdb]

    63. Nevirapine [usan]

    64. Nevirapine [vandf]

    65. Nevirapine [mart.]

    66. Schembl3318

    67. Nevirapine [who-dd]

    68. Mls000759409

    69. Mls001055309

    70. Mls001201730

    71. Mls001424058

    72. Mls006011423

    73. Bidd:gt0326

    74. Nevirapine [ema Epar]

    75. Bdbm1434

    76. Zinc4778

    77. Dtxsid7031797

    78. Nevirapine [orange Book]

    79. Nevirapine [ep Monograph]

    80. Nevirapine [usp Impurity]

    81. Nevirapine For Peak Identification

    82. Hms2051j09

    83. Hms2231o23

    84. Hms3264d21

    85. Hms3371e03

    86. Hms3393j09

    87. Hms3655i08

    88. Hms3715b10

    89. Nevirapine [usp Monograph]

    90. Pharmakon1600-01503842

    91. Albb-027264

    92. Bcp05587

    93. Tox21 110982

    94. Tox21_110982

    95. Tox21_200770

    96. Ac-643

    97. Ac1280

    98. Bbl010768

    99. Nsc759902

    100. Stk580320

    101. Nevirapine Anhydrous [usp-rs]

    102. Nevirapine Anhydrous [who-ip]

    103. Akos005504351

    104. Tox21_110982_1

    105. Ab07544

    106. Ccg-100939

    107. Db00238

    108. Ks-5019

    109. Nc00189

    110. Nsc-759902

    111. Ncgc00065890-03

    112. Ncgc00065890-04

    113. Ncgc00065890-05

    114. Ncgc00065890-07

    115. Ncgc00065890-14

    116. Ncgc00258324-01

    117. 11-cyclopropyl-4-methyl-5,11-dihydro-6h-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one & Pro 140 (anti-ccr5 Monoclonal Antibody)

    118. 2-cyclopropyl-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

    119. Hy-10570

    120. N11-cyclopropyl-4-methyl-5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e]-[1,4]diazepin-6-one & Cd4-immunoadhesin

    121. Nevirapine 100 Microg/ml In Acetonitrile

    122. Sy009679

    123. Bi-rg 587;nsc 641530;nvp

    124. Db-041930

    125. Ft-0607215

    126. Ft-0672686

    127. N0922

    128. Nevirapinum Anhydrous [who-ip Latin]

    129. S1742

    130. Sw197569-2

    131. C07263

    132. D00435

    133. Ab00393001-13

    134. Ab00393001-15

    135. Ab00393001_16

    136. Ab00393001_17

    137. 618n402

    138. Q263713

    139. F2173-0607

    140. Z1695906730

    141. Bi-rg-587; Birg 0587; Birg587; Hsdb 7164; Nsc 641530; Nvp

    142. Nevirapine (anhydrous), European Pharmacopoeia (ep) Reference Standard

    143. Nevirapine Anhydrous, United States Pharmacopeia (usp) Reference Standard

    144. Nevirapine Solution, 1.0 Mg/ml In Methanol, Certified Reference Material

    145. Nevirapine, Pharmaceutical Secondary Standard; Certified Reference Material

    146. 11-cyclopropyl-5,11-dihydro-4-methyl-6h-dipyrido-[3,2-b:2',3'-e][1,4]diazepin-6-one

    147. 11-cyclopropyl-5,11-dihydro-4-methyl-6h-dipyrido[3,2-b :2',3'-e][1,4 ]diazepin-6-one

    148. 11-cyclopropyl-5,11-dihydro-4-methyl-6h-dipyrido[3,2-b:2 ,3 -e][1,4]diazepin-6-one

    149. 11-cyclopropyl-5,11-dihydro-4-methyl-6h-dipyrido[3,2-b:2', 3'-e][1,4]diazepin-6-one

    150. 6h-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one, 11-cyclopropyl-5,11-dihydro-4-methyl-

    151. Nevirapine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    152. 11-cyclopropyl-4-methyl-5,11-dihydro-6h-dipyrido[3,2-b:2 Inverted Exclamation Mark ,3 Inverted Exclamation Mark -e][1,4]diazepin-6-one

    153. 2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-10-one

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 266.30 g/mol
    Molecular Formula C15H14N4O
    XLogP32
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count1
    Exact Mass266.11676108 g/mol
    Monoisotopic Mass266.11676108 g/mol
    Topological Polar Surface Area58.1 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity397
    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 6  
    Drug NameNevirapine
    PubMed HealthNevirapine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelVIRAMUNE XR is the brand name for nevirapine extended-release tablets. Nevirapine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Nevirapine is structurally a member of th...
    Active IngredientNevirapine
    Dosage FormTablet, extended release; Tablet, for suspension; Tablet; Suspension
    Routeoral; Oral
    Strength200mg; 50mg/5ml; 400mg; 100mg; 50mg
    Market StatusTentative Approval; Prescription
    CompanyMylan Pharms; Ranbaxy; Macleods Pharma; Apotex; Aurobindo; Hetero Labs Ltd Iii; Mylan Labs; Sciegen Pharms; Sandoz; Prinston; Cipla; Strides Pharma; Emcure Pharma; Micro Labs

    2 of 6  
    Drug NameViramune
    PubMed HealthNevirapine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelVIRAMUNE XR is the brand name for nevirapine extended-release tablets. Nevirapine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Nevirapine is structurally a member of th...
    Active IngredientNevirapine
    Dosage FormTablet; Suspension
    RouteOral
    Strength200mg; 50mg/5ml
    Market StatusPrescription
    CompanyBoehringer Ingelheim

    3 of 6  
    Drug NameViramune xr
    Active IngredientNevirapine
    Dosage FormTablet, extended release
    RouteOral
    Strength400mg; 100mg
    Market StatusPrescription
    CompanyBoehringer Ingelheim

    4 of 6  
    Drug NameNevirapine
    PubMed HealthNevirapine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelVIRAMUNE XR is the brand name for nevirapine extended-release tablets. Nevirapine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Nevirapine is structurally a member of th...
    Active IngredientNevirapine
    Dosage FormTablet, extended release; Tablet, for suspension; Tablet; Suspension
    Routeoral; Oral
    Strength200mg; 50mg/5ml; 400mg; 100mg; 50mg
    Market StatusTentative Approval; Prescription
    CompanyMylan Pharms; Ranbaxy; Macleods Pharma; Apotex; Aurobindo; Hetero Labs Ltd Iii; Mylan Labs; Sciegen Pharms; Sandoz; Prinston; Cipla; Strides Pharma; Emcure Pharma; Micro Labs

    5 of 6  
    Drug NameViramune
    PubMed HealthNevirapine (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelVIRAMUNE XR is the brand name for nevirapine extended-release tablets. Nevirapine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Nevirapine is structurally a member of th...
    Active IngredientNevirapine
    Dosage FormTablet; Suspension
    RouteOral
    Strength200mg; 50mg/5ml
    Market StatusPrescription
    CompanyBoehringer Ingelheim

    6 of 6  
    Drug NameViramune xr
    Active IngredientNevirapine
    Dosage FormTablet, extended release
    RouteOral
    Strength400mg; 100mg
    Market StatusPrescription
    CompanyBoehringer Ingelheim

    4.2 Therapeutic Uses

    Nevirapine is indicated, in combination with other antiretroviral agents, for the treatment of HIV-1 infection. Drug-resistant HIV emerges rapidly and uniformly when nevirapine is administered as monotherapy. Therefore, nevirapine should always be administered in combination with at least two other antiretroviral agents when it is used for the treatment of HIV-1 infection. /Included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1997

    Nevirapine is indicated for the prevention of mother-to-child transmission of HIV-1 infection. /NOT included in US product labeling/

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1997

    Nevirapine has been evaluated in pregnant HIV-infected women. In a landmark study performed in Uganda, a single, oral intrapartum dose of nevirapine followed by a single dose to the newborn was superior to more complicated zidovudine therapy in preventing vertical transmission. of HIV. Only 13% of nevirapine-treated women transmitted HIV compared to 21.5% of zidovudine-treated women.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1361

    4.3 Drug Warning

    Severe, life-threatening, and in some cases fatal hepatotoxicity, including fulminant and cholestatic hepatitis (e.g., transaminase elevations with or without hyperbilirubinemia, prolonged partial thromboplastin time, or eosinophilia), hepatic necrosis, and hepatic failure, have been reported in patients receiving nevirapine. Although clinical presentation varied, frequently occurring features included nonspecific prodromal signs and symptoms of fatigue, malaise, anorexia, nausea, jaundice, liver tenderness, and/or hepatomegaly, with or without initially abnormal serum transaminase concentrations; a diagnosis of hepatotoxicity should be considered even if liver function tests are initially normal or alternative diagnoses are possible. Manifestations progressed over several days to hepatic failure with transaminase elevation, with or without hyperbilirubinemia, prolonged partial thromboplastin time, and/or eosinophilia. ... If nevirapine is discontinued because of hepatitis, it should be permanently discontinued and not reinitiated.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 683

    Hepatotoxicity has been also reported in a small number of individuals receiving nevirapine as part of a combination regimen for post-exposure prophylaxis of nosocomial or sexual HIV exposure.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1999

    Serious hepatotoxicity has been reported in individuals not infected with HIV who received multiple doses of nevirapine as part of a 2- or 3-drug regimen for postexposure prophylaxis following occupational or nonoccupational exposure to HIV. Adverse hepatic effects in these individuals have included end-stage liver failure requiring transplantation, clinical hepatitis (e.g., jaundice, fever, nausea, vomiting, abdominal pain, and/or hepatomegaly), and elevated serum ALT and AST concentrations without clinical hepatitis. ...

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 683

    Severe and life-threatening skin reactions (e.g., Stevens-Johnson syndrome; toxic epidermal necrolysis; hypersensitivity reactions characterized by rash, constitutional findings, and organ dysfunction), including some fatalities, have occurred in patients receiving nevirapine. ...

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 684

    For more Drug Warnings (Complete) data for NEVIRAPINE (15 total), please visit the HSDB record page.

    4.4 Drug Indication

    For use in combination with other antiretroviral drugs in the ongoing treatment of HIV-1 infection.

    FDA Label

    * Tablets and oral suspension:

    Viramune is indicated in combination with other antiretroviral medicinal products for the treatment of HIV-1-infected adults, adolescents, and children of any age.

    Most of the experience with Viramune is in combination with nucleoside reverse-transcriptase inhibitors (NRTIs). The choice of a subsequent therapy after Viramune should be based on clinical experience and resistance testing.

    * 50- and 100-mg prolonged-release tablets:

    Viramune is indicated in combination with other antiretroviral medicinal products for the treatment of HIV-1-infected adolescents and children three years and above and able to swallow tablets.

    Prolonged-release tablets are not suitable for the 14-day lead-in phase for patients starting nevirapine. Other nevirapine formulations, such as immediate-release tablets or oral suspension should be used.

    Most of the experience with Viramune is in combination with nucleoside reverse-transcriptase inhibitors (NRTIs). The choice of a subsequent therapy after Viramune should be based on clinical experience and resistance testing.

    * 400-mg prolonged-release tablets:

    Viramune is indicated in combination with other antiretroviral medicinal products for the treatment of HIV-1-infected adults, adolescents and children three years and above and able to swallow tablets.

    Prolonged-release tablets are not suitable for the 14-day lead-in phase for patients starting nevirapine. Other nevirapine formulations, such as immediate-release tablets or oral suspension should be used.

    Most of the experience with Viramune is in combination with nucleoside reverse-transcriptase inhibitors (NRTIs). The choice of a subsequent therapy after Viramune should be based on clinical experience and resistance testing.

    Nevirapine Teva is indicated in combination with other anti-retroviral medicinal products for the treatment of HIV 1 infected adults, adolescents, and children of any age.

    Most of the experience with nevirapine is in combination with nucleoside reverse transcriptase inhibitors (NRTIs). The choice of a subsequent therapy after nevirapine should be based on clinical experience and resistance testing.

    Treatment of human immunodeficiency virus (HIV-1) infection

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Nevirapine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by nevirapine. Nevirapine is, in general, only prescribed after the immune system has declined and infections have become evident. It is always taken with at least one other HIV medication such as Retrovir or Videx. The virus can develop resistance to nevirapine if the drug is taken alone, although even if used properly, nevirapine is effective for only a limited time.

    5.2 MeSH Pharmacological Classification

    Anti-HIV Agents

    Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

    Cytochrome P-450 CYP3A Inducers

    Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inducers.)

    Reverse Transcriptase Inhibitors

    Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    NEVIRAPINE
    5.3.2 FDA UNII
    99DK7FVK1H
    5.3.3 Pharmacological Classes
    Cytochrome P450 3A Inducers [MoA]; Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]; Non-Nucleoside Analog [EXT]; Non-Nucleoside Reverse Transcriptase Inhibitors [MoA]; Cytochrome P450 2B6 Inducers [MoA]
    5.4 ATC Code

    J05AG01

    J05AG01

    J05AG01

    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

    J - Antiinfectives for systemic use

    J05 - Antivirals for systemic use

    J05A - Direct acting antivirals

    J05AG - Non-nucleoside reverse transcriptase inhibitors

    J05AG01 - Nevirapine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Nevirapine is readily absorbed (greater than 90%) after oral administration in healthy subjects and adults with HIV-1 infection. The absolute bioavailability in healthy adults following a single dose administration is 93 9% (mean SD) for a 50 mg tablet and 91 8% for an oral solution. Peak plasma nevirapine concentrations of 2 0.4 mcg/mL (7.5 micromolar) were attained by 4 hours following a single 200 mg dose. Nevirapine tablets and suspension have been shown to be comparably bioavailable and interchangeable at doses up to 200 mg. When the oral tablet is given with a high-fat meal, the extent of absorption is compared to that of the fasted-state.

    Route of Elimination

    Thus cytochrome P450 metabolism, glucuronide conjugation, and urinary excretion of glucuronidated metabolites represent the primary route of nevirapine biotransformation and elimination in humans. Only a small fraction (<5%) of the radioactivity in urine (representing <3% of the total dose) was made up of parent compound; therefore, renal excretion plays a minor role in elimination of the parent compound.

    Volume of Distribution

    1.21 0.09 L/kg [apparent volume of distribution, healthy adults, IV] Nevirapine is capable of crossing the placenta and is found in breast milk.

    Nevirapine readily crosses the placenta and has been found in breast milk. The CSF-plasma ratio for nevirapine is approximately 0.45.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1360

    Nevirapine is readily (more than 90%) absorbed following oral administration in healthy or HIV-infected adults. Absolute bioavailability of nevirapine in 12 healthy adults was 93% following administration of a single 30 mg tablet or 91% following administration of an oral solution of the drug. Peak plasma nevirapine concentrations average 2 ug/ml and are attained within 4 hours after a single 200 mg dose of the dose in adults. Following multiple doses, peak plasma nevirapine concentrations appear to increase linearly in the dosage range of 200-400 mg daily. Nevirapine dosage of 400 mg daily resulted in steady-state trough plasma concentrations of 4.5 ug/ml.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 687

    Widely distributed. Nevirapine is highly lipophilic and essentially is nonionized at physiologic pH. Nevirapine readily crosses the placenta and is distributed into breast milk. Nevirapine concentrations in the cerebrospinal fluid were 45% of the concentrations in plasma, which is a ratio that is approximately equal to the fraction not bound to plasma protein.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1998

    Nevirapine crosses the placenta in humans. In a limited number of HIV-infected pregnant women who received a single 100- or 200-mg oral dose of nevirapine 0.9-10.5 hours prior to delivery, cord blood concentrations of nevirapine were 74-123% of maternal serum concentrations and peak serum concentrations of the drug in the neonates of these women averaged 862 ng/mL (range: 257-1031 ng/mL) or 925 ng/mL (range: 62-2030 ng/mL), respectively. In pregnant HIV-infected women who received a regimen of nevirapine (200 mg once daily for 2 weeks followed by 200 mg twice daily), zidovudine, and lamivudine during the second and third trimester, cord blood concentrations (at delivery) and neonatal serum concentrations (24 hours after birth) of nevirapine were 76 and 60%, respectively, of maternal serum concentrations (at delivery). These neonatal concentrations were lower than those reported in neonates whose mothers received a single nevirapine dose during labor, possibly as the result of hepatic enzyme induction in the neonate after placental transfer.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 687

    Nevirapine is distributed into human milk. Following administration of a single 100- or 200-mg dose of nevirapine to pregnant women several hours before delivery, postpartum, concentrations of the drug in milk were 25-122% of maternal serum concentrations.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 687

    5.6 Metabolism/Metabolites

    Hepatic. In vivo studies in humans and in vitro studies with human liver microsomes have shown that nevirapine is extensively biotransformed via cytochrome P450 3A4 metabolism to several hydroxylated metabolites.

    Oxidative metabolism of nevirapine in the liver by cytochrome p450 isoforms CYP34A4 and CYP2B6 produces several metabolites including 2-, 3-, 8-, and 12-hydroxynevirapine.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1360

    In vivo studies in humans and in vitro studies with human liver microsomes have shown that nevirapine is extensively biotransformed via cytochrome p450 oxidative metabolism to several hydroxylated metabolites. In vitro studies with human liver microsomes suggest that oxidative metabolism of nevirapine is mediated primarily by cytochrome p450 isozymes from the CYP3A family, although other isozymes may have a secondary role.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1998

    Nevirapine has known human metabolites that include 12-hydroxy-nevirapine, 2-Hydroxynevirapine, 3-Hydroxynevirapine, and 8-Hydroxynevirapine.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    45 hours

    Approximately 45 hours after a single dose, and 25 to 30 hours following multiple dosing with 200 to 400 mg per day.

    MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1998

    5.8 Mechanism of Action

    Nevirapine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of nevirapine does not compete with template or nucleoside triphosphates.

    The binding site for nevirapine on HIV-1 reverse transcriptase is near, but not at the proposed site of active polymerization, in a deep pocket lying between the beta sheets of the palm and at the base of the thumb subdomains of the enzyme's p66 subunit. In the absence of nevirapine, the binding of deoxynucleoside triphosphate to the reverse transcriptase-template complex results in a change in the conformation of reverse transcriptase. This conformational change is followed by a magnesium-dependent chemical reaction in which deoxynucleoside triphosphate is incorporated into the newly forming viral DNA; the conformational change appears to be the rate-limiting step of the reverse transcriptase catalysis of viral DNA formation. Nevirapine appears to have no appreciable effect on the rate of or equilibrium constant for the conformational change but may slow the chemical reaction, which then becomes the rate-limiting step in the catalytic sequence. When nevirapine binds to the reverse transcriptase-template complex, changes may occur in the position of aspartic acid carboxyl groups in reverse transcriptase so that magnesium ions are not in proper alignment for the chemical reaction to occur efficiently, and the reaction is slowed. Therefore, although the nevirapine-reverse transcriptase-template complex may continue to bind deoxynucleoside triphosphate and to catalyze its incorporation into the newly forming viral DNA, it appears to do so at a slower rate.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 686

    The mechanism of action of nevirapine differs from that of nucleoside reverse transcriptase inhibitors (e.g., abacavir, didanosine, lamivudine, stavudine, zalcitabine, zidovudine). Nucleoside antiretroviral agents require intracellular conversion to triphosphate metabolites, which then compete with naturally occurring deoxynucleoside triphosphates for incorporation into viral DNA by reverse transcriptase and cause premature viral DNA chain termination by preventing further 5 to 3 phosphodiester linkages. Nevirapine, however, is noncompetitive with respect to primer-template or nucleoside triphosphate binding and is specific for HIV-1 reverse transcriptase. The drug binds directly to heterodimeric HIV-1 reverse transcriptase and appears to inhibit viral RNA- and DNA-dependent DNA polymerase activities by disrupting the catalytic site of the enzyme.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 686

    Nevirapine diffuses into the cell and binds to reverse transcriptase adjacent to the catalytic site. This induces conformational changes that inactivate the enzyme. Resistance develops rapidly in cells exposed to nevirapine. High-level resistance is associated with mutations at reverse transcriptase codons 101, 103, 106,108, 135, 181, 188, and 190. A single mutation at either codon 103 or 181 decreases susceptibility more than 100 fold. Cross-resistance may extend to all FDA-approved nonnucleoside reverse transcriptase inhibitors, especially with the codon 103 mutation.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1360

    Nevirapine is a highly specific inhibitor of HIV-1 reverse transcriptase, and results of in vitro studies indicate that nevirapine does not appear to inhibit cellular DNA polymerases, including human alpha-, beta-, Gamma-, or Delta-polymerases.

    McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 686

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    05-Jan-2021
    03-Feb-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 100M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 100MG

    USFDA APPLICATION NUMBER - 201152

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    DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 400M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 400MG

    USFDA APPLICATION NUMBER - 201152

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    DOSAGE - TABLET;ORAL - 150MG;200MG;300MG

    USFDA APPLICATION NUMBER - 205626

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    DOSAGE - TABLET;ORAL - 200MG

    USFDA APPLICATION NUMBER - 20636

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    DOSAGE - SUSPENSION;ORAL - 50MG/5ML

    USFDA APPLICATION NUMBER - 20933

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