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    Chemistry

    Click the arrow to open the dropdown
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    Also known as: 154598-52-4, Sustiva, Stocrin, Dmp-266, Dmp 266, Efv
    Molecular Formula
    C14H9ClF3NO2
    Molecular Weight
    315.67  g/mol
    InChI Key
    XPOQHMRABVBWPR-ZDUSSCGKSA-N
    FDA UNII
    JE6H2O27P8
    Efavirenz
    Efavirenz is a synthetic non-nucleoside reverse transcriptase (RT) inhibitor with antiviral activity. Efavirenz binds directly to the human immunodeficiency virus type 1 (HIV-1) RT, an RNA-dependent DNA polymerase, blocking its function in viral DNA replication. In combination with other antiretroviral drugs, this agent has been shown to significantly reduce HIV viral load, retarding or preventing damage to the immune system and reducing the risk of developing AIDS. Efavirenz induces activity of the cytochrome P450 system, accelerating its own metabolism.
    Efavirenz is a Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of efavirenz is as a Non-Nucleoside Reverse Transcriptase Inhibitor, and Cytochrome P450 3A Inducer, and Cytochrome P450 2B6 Inducer, and Cytochrome P450 2C9 Inhibitor, and Cytochrome P450 2C19 Inhibitor, and Cytochrome P450 3A4 Inhibitor.
    1 2D Structure

    Efavirenz

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
    2.1.2 InChI
    InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1
    2.1.3 InChI Key
    XPOQHMRABVBWPR-ZDUSSCGKSA-N
    2.1.4 Canonical SMILES
    C1CC1C#CC2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F
    2.1.5 Isomeric SMILES
    C1CC1C#C[C@]2(C3=C(C=CC(=C3)Cl)NC(=O)O2)C(F)(F)F
    2.2 Other Identifiers
    2.2.1 UNII
    JE6H2O27P8
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (s)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2h-3,1-benzoxazin-2-one

    2. Dmp 266

    3. Dmp-266

    4. Efavirenz, (r)-isomer

    5. Efavirenz, (s)-isomer

    6. L 743,726

    7. L 743726

    8. L-743,726

    9. L-743726

    10. Stocrin

    11. Sustiva

    2.3.2 Depositor-Supplied Synonyms

    1. 154598-52-4

    2. Sustiva

    3. Stocrin

    4. Dmp-266

    5. Dmp 266

    6. Efv

    7. (4s)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one

    8. (4s)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1h-3,1-benzoxazin-2-one

    9. Viraday

    10. Efavirenz Teva

    11. L-743726

    12. (rac)-efavirenz

    13. L-743,726

    14. (s)-efavirenz

    15. (4s)-6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one

    16. (s)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one

    17. Nsc-742403

    18. (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2h-3,1-benzoxazin-2-one

    19. (4s)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1h-3,1-benzoxazin-2-one

    20. Je6h2o27p8

    21. Chebi:119486

    22. Nsc742403

    23. (4s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2h-3,1-benzoxazin-2-one

    24. (s)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

    25. Dsstox_cid_26029

    26. Dsstox_rid_81298

    27. Dsstox_gsid_46029

    28. (s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2h-benzo[d][1,3]oxazin-2-one

    29. (s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1h-benzo[d][1,3]oxazin-2(4h)-one

    30. 2h-3,1-benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4s)-

    31. 6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4s)-1,4-dihydro-2h-benzo[d][1,3]oxazin-2-one

    32. (-)-efavirenz

    33. (rac)-dmp 266; (rac)-efv; (rac)-l-743726

    34. Eravirenz

    35. Smr000466351

    36. Strocin (tm)

    37. Sustiva (tm)

    38. Sustiva (tn)

    39. Cas-154598-52-4

    40. L 743726

    41. Hsdb 7163

    42. Sr-01000759360

    43. Efavirenz [usp:inn:ban]

    44. Unii-je6h2o27p8

    45. Efavirenzum

    46. Met-sdf-1.beta. & Efavirenz

    47. 1ikv

    48. 1ikw

    49. Efavirenz- Bio-x

    50. Ncgc00159337-02

    51. Efavirenz, (s)

    52. Efavirenz & Plga

    53. Mfcd05662344

    54. Efavirenz & Ifnl1

    55. Efavirenz & Ifnl2

    56. Efavirenz & Ifnl3

    57. Efavirenz & Il-29

    58. Efavirenz [inn]

    59. Efavirenz [jan]

    60. Dmp-266; Efavirenz

    61. Efavirenz & Il-28a

    62. Efavirenz & Il-28b

    63. Efavirenz [mi]

    64. Efavirenz [hsdb]

    65. Efavirenz [usan]

    66. Efv & Interleukin 29

    67. Efavirenz [vandf]

    68. Efv & Interleukin 28a

    69. Efv & Interleukin 28b

    70. Efv & Plga

    71. Efavirenz [mart.]

    72. Efavirenz [usp-rs]

    73. Efavirenz [who-dd]

    74. Efavirenz [who-ip]

    75. Efv & Ifnl1

    76. Efv & Ifnl2

    77. Efv & Ifnl3

    78. Efavirenz (jan/usp/inn)

    79. Efv & Interferon Lambda-1

    80. Efv & Interferon Lambda-2

    81. Efv & Interferon Lambda-3

    82. Efavirenz & Interleukin 29

    83. Schembl37762

    84. Efavirenz [ema Epar]

    85. Efavirenz & Interleukin 28a

    86. Efavirenz & Interleukin 28b

    87. Efavirenz Ready Made Solution

    88. Mls000759465

    89. Mls001424087

    90. Bidd:gt0383

    91. Amy229

    92. Bdbm2483

    93. Chembl223228

    94. Dmp266

    95. Efv & Il-28a

    96. Efv & Il-28b

    97. Efavirenz [orange Book]

    98. Dtxsid9046029

    99. Efavirenz, >=98% (hplc)

    100. Efavirenz & Interferon Lambda-1

    101. Efavirenz & Interferon Lambda-2

    102. Efavirenz & Interferon Lambda-3

    103. Efv & Il-29

    104. Gtpl11287

    105. Telura Component Efavirenz

    106. Efavirenz [usp Monograph]

    107. Atripla Component Efavirenz

    108. Bcpp000245

    109. Hms2051j08

    110. Hms2090n16

    111. Hms3393j08

    112. Hms3713m14

    113. Met-stromal Cell-derived Factor-1.beta. (human) & Efavirenz

    114. Efavirenzum [who-ip Latin]

    115. 2h-3,1-benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4s)-

    116. Bcp27719

    117. Zinc2020233

    118. Tox21_111582

    119. Dl-535

    120. S4685

    121. Efavirenz Component Of Atripla

    122. Akos015894951

    123. Efavirenz & Poly-lactide-co-glycolide

    124. Tox21_111582_1

    125. Ab21723

    126. Bcp9000636

    127. Ccg-101011

    128. Db00625

    129. Ks-5380

    130. Nc00261

    131. Nsc 742403

    132. (s)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2h-3,1-benzoxazin-2-one

    133. Efavirenz 100 Microg/ml In Acetonitrile

    134. Ncgc00159337-04

    135. Ncgc00159337-12

    136. Ncgc00271713-05

    137. Ncgc00271713-08

    138. Ac-25006

    139. Bc164402

    140. Hy-10572

    141. E0997

    142. C08088

    143. D00896

    144. F17329

    145. Ab00639956-06

    146. Ab00639956-08

    147. 598e524

    148. A809555

    149. Q422645

    150. J-520431

    151. Sr-01000759360-4

    152. Sr-01000759360-5

    153. Z2186909878

    154. Efavirenz, United States Pharmacopeia (usp) Reference Standard

    155. Efavirenz Solution, 1.0 Mg/ml In Acetonitrile, Certified Reference Material

    156. (4s)-6-chloranyl-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1h-3,1-benzoxazin-2-one

    157. 2h-3, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4s)-

    158. (s)-6-chloro-4-(cyclopropyl-ethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazine-2-one

    159. (s)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-(s)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one

    160. (s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2h-3,1-ben Zoxazin-2-one

    161. (s)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2h-3,1-benzoxazin-2-one

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 315.67 g/mol
    Molecular Formula C14H9ClF3NO2
    XLogP34
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count1
    Exact Mass315.0273907 g/mol
    Monoisotopic Mass315.0273907 g/mol
    Topological Polar Surface Area38.3 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity519
    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 4  
    Drug NameEfavirenz
    PubMed HealthEfavirenz (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelSUSTIVA (efavirenz) is an HIV-1 specific, non-nucleoside, reverse transcriptase inhibitor (NNRTI). Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formu...
    Active IngredientEfavirenz
    Dosage FormTablet; Capsule
    Routeoral
    Strength200mg; 100mg; 50mg; 600mg
    Market StatusTentative Approval
    CompanyMatrix Labs; Macleods Pharms; Hetero Drugs; Strides; Aurobindo; Par Formulations Private; Emcure Pharma; Aurobindo Pharma; Cipla; Micro Labs

    2 of 4  
    Drug NameSustiva
    PubMed HealthEfavirenz (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelSUSTIVA (efavirenz) is an HIV-1 specific, non-nucleoside, reverse transcriptase inhibitor (NNRTI). Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formu...
    Active IngredientEfavirenz
    Dosage FormTablet; Capsule
    RouteOral
    Strength200mg; 600mg; 50mg
    Market StatusPrescription
    CompanyBristol Myers Squibb

    3 of 4  
    Drug NameEfavirenz
    PubMed HealthEfavirenz (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelSUSTIVA (efavirenz) is an HIV-1 specific, non-nucleoside, reverse transcriptase inhibitor (NNRTI). Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formu...
    Active IngredientEfavirenz
    Dosage FormTablet; Capsule
    Routeoral
    Strength200mg; 100mg; 50mg; 600mg
    Market StatusTentative Approval
    CompanyMatrix Labs; Macleods Pharms; Hetero Drugs; Strides; Aurobindo; Par Formulations Private; Emcure Pharma; Aurobindo Pharma; Cipla; Micro Labs

    4 of 4  
    Drug NameSustiva
    PubMed HealthEfavirenz (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelSUSTIVA (efavirenz) is an HIV-1 specific, non-nucleoside, reverse transcriptase inhibitor (NNRTI). Efavirenz is chemically described as (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one. Its empirical formu...
    Active IngredientEfavirenz
    Dosage FormTablet; Capsule
    RouteOral
    Strength200mg; 600mg; 50mg
    Market StatusPrescription
    CompanyBristol Myers Squibb

    4.2 Therapeutic Uses

    Anti-HIV Agents; Reverse Transcriptase Inhibitors

    National Library of Medicine's Medical Subject Headings. Efavirenz. Online file (MeSH, 2014). Available from, as of November 19, 2013: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html

    Due to ongoing neuropsychiatric adverse events in some efavirenz (EFV)-treated patients, a switch to an alternative non-nucleoside reverse transcriptase inhibitor may be considered. Rilpivirine (RPV) has been coformulated as a single-tablet regimen (STR) with emtricitabine/tenofovir disoproxil fumarate (FTC/TDF), and the components have demonstrated noninferior efficacy to EFV+FTC/TDF, good tolerability profile, and high adherence. After discontinuation, EFV has an extended inductive effect on cytochrome P450 (CYP) 3A4 that, after switching, may reduce RPV exposures and adversely impact clinical outcomes. This study examines the clinical implications of reduced RPV exposures with concomitant FTC/TDF and declining EFV exposures when patients, intolerant to EFV, switch from EFV/FTC/TDF to RPV/FTC/TDF. This 48-week, phase 2b, open-label, multicenter study evaluated the efficacy and safety of switching from EFV/FTC/TDF (>/= 3 months duration) to RPV/FTC/TDF. Virologic suppression (HIV-1 RNA <50 copies/mL), safety, and EFV and RPV pharmacokinetics were assessed. At weeks 12 and 24, all 49 dosed subjects remained suppressed on RPV/FTC/TDF. At week 48, 46 (93.9%) subjects remained suppressed and virologic failure occurred in 2/49 (4.1%) subjects with no emergence of resistance. EFV concentrations were above the 90th percentile for inhibitory concentration (IC90) for several weeks after EFV discontinuation, and RPV exposures were in the range observed in phase 3 studies by approximately 2 weeks post switch. No subjects discontinued the study due to an adverse event. Switching from EFV/FTC/TDF to RPV/FTC/ TDF was a safe, efficacious option for virologically suppressed HIV-infected patients with EFV intolerance wishing to remain on an STR.

    PMID:24144898 Mills AM et al; HIV Clin Trials 14 (5): 216-23 (2013)

    Efavirenz is indicated in combination with other antiretroviral agents 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. 1184

    4.3 Drug Warning

    To report a case of acquired long QT syndrome that, after exclusion of all other possible causes, was probably related to therapy with efavirenz, a novel nonnucleoside reverse transcriptase inhibitor.

    PMID:12022902 Castillo R et al; Ann Pharmacother 36 (6): 1006-8 (2002)

    About 53% of adults receiving efavirenz (600 mg once daily) in controlled clinical studies reported adverse CNS effects such as abnormal dreams, abnormal thinking, agitation, amnesia, confusion, depersonalization, dizziness, euphoria, hallucinations, impaired concentration, insomnia, somnolence, and stupor; these adverse effects were reported in 25% of adults in the control groups not receiving efavirenz. These effects were described as mild (do not interfere with daily activities) in 33.3%, moderate (may interfere with daily activities) in 17.4%, or severe (interrupt usual daily activities) in 2% of patients receiving efavirenz and required discontinuance of the drug in 2.1%. Dizziness was reported in 28.1% and insomnia was reported in 16.3% of patients receiving the drug. Impaired concentration, somnolence, or abnormal dreams were reported in 6.2-8.3% and hallucinations were reported in 1.2% of patients.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 660

    Serious adverse psychiatric symptoms have been reported rarely in adults receiving efavirenz. Severe depression, suicidal ideation, nonfatal suicide attempts, aggressive behavior, paranoid reactions, or manic reactions have been reported in 0.4-1.6% of patients receiving efavirenz in controlled clinical studies; these psychiatric symptoms were reported in up to 0.6% of those in the control groups not receiving the drug. The incidence of each of these psychiatric symptoms ranges from 0.3% (for manic reactions) to 2% (for severe depression or suicidal ideation) in patients with a prior history of psychiatric disorders, and these individuals appear to be at greater risk of such symptoms than other individuals. Other psychiatric symptoms reported in controlled clinical studies in adults receiving efavirenz include depression (15.8%), anxiety (11.1%), and nervousness (6.3%); these symptoms were reported in 13.1, 7.6, or 2%, respectively, of those in the control groups not receiving the drug. Although a causal relationship with efavirenz has not been established, there have been occasional postmarketing reports of death by suicide, delusions, or psychosis-like behavior in patients receiving efavirenz. In addition, aggressive reactions, agitation, emotional lability, mania, neurosis,and paranoia have been reported during postmarketing surveillance. There is no evidence that patients who develop adverse CNS effects (e.g., dizziness, insomnia, impaired concentration, abnormal dreams) during efavirenz therapy are at greater risk of developing psychiatric symptoms.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 661

    Fatigue has been reported in up to 7% of adults receiving efavirenz in clinical studies. Other adverse nervous system effects reported during postmarketing surveillance include abnormal coordination, ataxia, seizures, hypoesthesia, paresthesia, neuropathy, and tremor. Adverse CNS effects occurred in 18% of children receiving efavirenz in clinical studies.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 661

    For more Drug Warnings (Complete) data for EFAVIRENZ (21 total), please visit the HSDB record page.

    4.4 Drug Indication

    For use in combination treatment of HIV infection (AIDS)

    FDA Label

    Stocrin is indicated in antiviral combination treatment of human-immunodeficiency-virus-1 (HIV-1)-infected adults, adolescents and children three years of age and older.

    Stocrin has not been adequately studied in patients with advanced HIV disease, namely in patients with CD4 counts < 50 cells/mm3, or after failure of protease-inhibitor (PI)-containing regimens. Although cross-resistance of efavirenz with PIs has not been documented, there are at present insufficient data on the efficacy of subsequent use of PI-based combination therapy after failure of regimens containing Stocrin.

    Efavirenz is indicated in antiviral combination treatment of human-immunodeficiency-virus-1 (HIV-1)-infected adults, adolescents and children 3 years of age and older.

    Efavirenz has not been adequately studied in patients with advanced HIV disease, namely in patients with CD4 counts < 50 cells/mm3, or after failure of protease inhibitor (PI)-containing regimens. Although cross-resistance of efavirenz with protease inhibitors (PIs) has not been documented, there are at present insufficient data on the efficacy of subsequent use of PI-based combination therapy after failure of regimens containing efavirenz.

    Sustiva is indicated in antiviral combination treatment of human-immunodeficiency-virus-1 (HIV-1)-infected adults, adolescents and children three years of age and older.

    Sustiva has not been adequately studied in patients with advanced HIV disease, namely in patients with CD4 counts < 50 cells/mm3, or after failure of protease-inhibitor (PI)-containing regimens. Although cross-resistance of efavirenz with PIs has not been documented, there are at present insufficient data on the efficacy of subsequent use of PI-based combination therapy after failure of regimens containing Sustiva.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Efavirenz (dideoxyinosine, ddI) is an oral non-nucleoside reverse transcriptase inhibitor (NNRTI). It is a synthetic purine derivative and, similar to zidovudine, zalcitabine, and stavudine. Efavirenz was originally approved specifically for the treatment of HIV infections in patients who failed therapy with zidovudine. Currently, the CDC recommends that Efavirenz be given as part of a three-drug regimen that includes another nucleoside reverse transcriptase inhibitor (e.g., lamivudine, stavudine, zidovudine) and a protease inhibitor or efavirenz when treating HIV infection.

    5.2 MeSH Pharmacological Classification

    Cytochrome P-450 CYP2C19 Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2C19. (See all compounds classified as Cytochrome P-450 CYP2C19 Inhibitors.)

    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.)

    Cytochrome P-450 CYP2B6 Inducers

    Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP2B6. (See all compounds classified as Cytochrome P-450 CYP2B6 Inducers.)

    Cytochrome P-450 CYP2C9 Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2C9. (See all compounds classified as Cytochrome P-450 CYP2C9 Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    EFAVIRENZ
    5.3.2 FDA UNII
    JE6H2O27P8
    5.3.3 Pharmacological Classes
    Cytochrome P450 2C19 Inhibitors [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]; Cytochrome P450 3A Inducers [MoA]; Cytochrome P450 3A4 Inhibitors [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

    J05AG03

    J05AG03

    J05AG03

    J05AG03

    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

    J05AG03 - Efavirenz

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    Nearly all of the urinary excretion of the radiolabeled drug was in the form of metabolites.

    Oral bioavailability of efavirenz may be affected by administration with food. Administration of a single 600-mg dose of efavirenz as capsules with a high-fat, high-calorie meal (894 kcal, 54 g fat, 54% of calories from fat) or a reduced-fat, normal-calorie meal (440 kcal, 2 g fat, 4% of calories from fat) increases peak plasma concentrations of the drug by 39 or 51%, respectively, and AUC by 22 or 17%, respectively, compared with administration in the fasting state. Administration of a single 600-mg dose of efavirenz as tablets with a high-fat, high-calorie meal (approximately 1000 kcal, 500-600 kcal from fat) increases peak plasma concentrations and AUC of the drug by 79 and 28%, respectively, compared with administration in the fasting state.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 667

    Efavirenz is excreted principally in the feces, both as unchanged drug and metabolites. Excretion of efavirenz has been evaluated in individuals receiving 400 mg daily for 1 month. Following oral administration of 400 mg of radiolabeled efavirenz on day 8, 14-34% of the dose was excreted in urine (less than 1% as unchanged drug), and 16-61% was excreted in feces (predominantly as unchanged drug).

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 667

    Efavirenz is about 99.5-99.75% bound to plasma proteins, principally albumin.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 667

    In HIV-infected adults receiving efavirenz 200, 400, or 600 mg once daily, peak plasma concentrations of the drug generally occur in 3-5 hours and steady-state plasma concentrations are achieved in 6-10 days. Following continued administration of efavirenz, plasma concentrations are lower than expected from single-dose studies, presumably because of increased clearance of the drug. In one study in individuals receiving efavirenz 200-400 mg once daily for 10 days, plasma concentrations of the drug were 22-42% lower than those predicted from single-dose studies. Following oral administration of efavirenz 600 mg once daily in HIV-infected adults, peak plasma concentration, trough plasma concentration, and AUC of the drug at steady-state averaged 4.1 mcg/mL, 1.8 mcg/mL, and 58. mcg*hour/mL, respectively.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 666

    For more Absorption, Distribution and Excretion (Complete) data for EFAVIRENZ (8 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Efavirenz is principally metabolized by the cytochrome P450 system to hydroxylated metabolites with subsequent glucuronidation of these hydroxylated metabolites. These metabolites are essentially inactive against HIV-1.

    Efavirenz was metabolized extensively by all the species as evidenced by the excretion of none or trace quantities of parent compound in urine. Significant species differences in the metabolism of efavirenz were observed. The major metabolite excreted in the urine of all species was the O-glucuronide conjugate (M1) of the 8-hydroxylated metabolite. Efavirenz was also metabolized by direct conjugation with glucuronic acid, forming the N-glucuronide (M2) in all five species. The sulfate conjugate of 8-OH efavirenz (M3) was found in the urine of rats and cynomolgus monkeys but not in humans. In addition to the aromatic ring-hydroxylated products, metabolites with a hydroxylated cyclopropane ring (at C14) were also isolated. GSH-related products of efavirenz were identified in rats and guinea pigs. The cysteinylglycine adduct (M10), formed from the GSH adduct (M9), was found in significant quantities in only rat and guinea pig urine and was not detected in other species. In vitro metabolism studies were conducted to show that the GSH adduct was produced from the cyclopropanol intermediate (M11) in the presence of only rat liver and kidney subcellular fractions and was not formed by similar preparations from humans or cynomolgus monkeys. These studies indicated the existence of a specific glutathione-S-transferase in rats capable of metabolizing the cyclopropanol metabolite (M11) to the GSH adduct, M9.

    PMID:10534318 Mutlib AE et al; Drug Metab Dispos 27 (11): 1319-33 (1999)

    Efavirenz is a substrate for cytochrome p450 isoforms, particularly CYP3A4 and CYP2B6. The 8-hydroxy metabolite is excreted in the urine, and the glucuronide conjugate of 8-hydroxy-efavirenz is present in plasma and urine. Sixty percent of the dose is excreted in urine as the glucuronide conjugate.

    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. 1363

    Efavirenz has known human metabolites that include 8-hydroxyefavirenz.

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

    5.7 Biological Half-Life

    40-55 hours

    The terminal elimination half-life of efavirenz is prolonged in patients with chronic liver disease. Following oral administration of a single 400-mg dose of efavirenz, an elimination half-life of 152 or 118 hours was reported in individuals with or without chronic liver disease, respectively.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 667

    The terminal elimination half-life of efavirenz reported in single-dose studies is longer than that reported in multiple-dose studies and has averaged 52-76 hours after a single oral dose and 40-55 hours following administration of 200-400 mg daily for 10 days.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 667

    5.8 Mechanism of Action

    Similar to zidovudine, efavirenz inhibits the activity of viral RNA-directed DNA polymerase (i.e., reverse transcriptase). Antiviral activity of efavirenz is dependent on intracellular conversion to the active triphosphorylated form. The rate of efavirenz phosphorylation varies, depending on cell type. It is believed that inhibition of reverse transcriptase interferes with the generation of DNA copies of viral RNA, which, in turn, are necessary for synthesis of new virions. Intracellular enzymes subsequently eliminate the HIV particle that previously had been uncoated, and left unprotected, during entry into the host cell. Thus, reverse transcriptase inhibitors are virustatic and do not eliminate HIV from the body. Even though human DNA polymerase is less susceptible to the pharmacologic effects of triphosphorylated efavirenz, this action may nevertheless account for some of the drug's toxicity.

    Efavirenz diffuses into the cell where it binds adjacent to the active site of reverse transcriptase. This produces a conformational change in the enzyme that inhibits function.

    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. 1363

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    04-Jan-2021
    28-Mar-2025
    KGS
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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - 400MG;300MG;300MG

    USFDA APPLICATION NUMBER - 208255

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    DOSAGE - CAPSULE;ORAL - 100MG **Federal Regis...DOSAGE - CAPSULE;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20972

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    DOSAGE - CAPSULE;ORAL - 200MG **Federal Regis...DOSAGE - CAPSULE;ORAL - 200MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20972

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    DOSAGE - CAPSULE;ORAL - 50MG **Federal Regist...DOSAGE - CAPSULE;ORAL - 50MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20972

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    DOSAGE - TABLET;ORAL - 300MG **Federal Regist...DOSAGE - TABLET;ORAL - 300MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 21360

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    DOSAGE - TABLET;ORAL - 600MG

    USFDA APPLICATION NUMBER - 21360

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    DOSAGE - TABLET;ORAL - 600MG;200MG;300MG

    USFDA APPLICATION NUMBER - 21937

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    ABOUT THIS PAGE

    Looking for 154598-52-4 / Efavirenz API manufacturers, exporters & distributors?

    Efavirenz manufacturers, exporters & distributors 1

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

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

    API | Excipient name

    Efavirenz

    Synonyms

    154598-52-4, Sustiva, Stocrin, Dmp-266, Dmp 266, Efv

    Cas Number

    154598-52-4

    Unique Ingredient Identifier (UNII)

    JE6H2O27P8

    About Efavirenz

    Efavirenz is a synthetic non-nucleoside reverse transcriptase (RT) inhibitor with antiviral activity. Efavirenz binds directly to the human immunodeficiency virus type 1 (HIV-1) RT, an RNA-dependent DNA polymerase, blocking its function in viral DNA replication. In combination with other antiretroviral drugs, this agent has been shown to significantly reduce HIV viral load, retarding or preventing damage to the immune system and reducing the risk of developing AIDS. Efavirenz induces activity of the cytochrome P450 system, accelerating its own metabolism.

    Efavirenz Manufacturers

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

    Efavirenz Suppliers

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

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

    Efavirenz USDMF

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

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

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

    Efavirenz KDMF

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

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

    After submitting a Efavirenz 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 Efavirenz API can apply through the Korea Drug Master File (KDMF).

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

    Efavirenz WC

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

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

    Efavirenz 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 Efavirenz as an active pharmaceutical ingredient (API).

    Finished drug products

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

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

    Efavirenz GMP

    Efavirenz 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 Efavirenz 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 Efavirenz GMP manufacturer or Efavirenz GMP API supplier for your needs.

    Efavirenz CoA

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

    Efavirenz CoA mostly includes findings from lab analyses of a specific batch. For each Efavirenz 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.

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