Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H9ClF3NO2 |
Molecular Weight | 315.6754 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CC1C#C[C@]2(c3cc(ccc3N=C(O)O2)Cl)C(F)(F)F
InChI
InChIKey=XPOQHMRABVBWPR-ZDUSSCGKSA-N
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00625Curator's Comment:: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB00625
Curator's Comment:: Description was created based on several sources, including
Efavirenz (brand names Sustiva® and Stocrin®) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and is used as part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1. For HIV infection that has not previously been treated, efavirenz and lamivudine in combination with zidovudine or tenofovir is the preferred NNRTI-based regimen. Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regimen to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission.
CNS Activity
Originator
Sources: http://adisinsight.springer.com/drugs/800005773
Curator's Comment:: # Merck & Co
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19469474 |
4.0 nM [EC50] | ||
Target ID: CHEMBL612848 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27249967 |
26.1 µM [IC50] | ||
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20408889 |
52.0 µM [IC50] | ||
Target ID: CHEMBL247 Sources: http://www.drugbank.ca/drugs/DB00625 |
20.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SUSTIVA Approved UseSUSTIVA is a non-nucleoside reverse transcriptase inhibitor indicated in combination with other antiretroviral agents for the treatment of human immunodeficiency virus type 1 infection. Launch Date9.05904E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.9 μM |
600 mg 1 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EFAVIRENZ plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.04 μg/mL |
300 mg 1 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EFAVIRENZ plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
184 μM × h |
600 mg 1 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EFAVIRENZ plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
257.56 μM × h |
300 mg 1 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EFAVIRENZ plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40 h |
600 mg 1 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EFAVIRENZ plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.5% |
600 mg 1 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
EFAVIRENZ plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3 g single, oral Overdose |
unhealthy, 12 years n = 1 Health Status: unhealthy Condition: HIV infection Age Group: 12 years Sex: M Population Size: 1 Sources: |
|
600 mg 1 times / day multiple, oral Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Co-administed with:: abacavir(300 mg q12h) Sources: nelfinavir(1250 mg q12h) |
unhealthy, 33 years n = 1 Health Status: unhealthy Condition: HIV infection Age Group: 33 years Sex: F Population Size: 1 Sources: |
Disc. AE: Mania... AEs leading to discontinuation/dose reduction: Mania (1 patient) Sources: |
25 mg/kg 1 times / day steady, oral Highest studied dose Dose: 25 mg/kg, 1 times / day Route: oral Route: steady Dose: 25 mg/kg, 1 times / day Sources: |
unhealthy, 33.9 months (range: 29.2–40.2 months) n = 52 Health Status: unhealthy Condition: HIV infection Age Group: 33.9 months (range: 29.2–40.2 months) Sex: M+F Population Size: 52 Sources: |
|
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
unhealthy, 37.3 years n = 67 Health Status: unhealthy Condition: tuberculosis Age Group: 37.3 years Sex: M+F Population Size: 67 Sources: |
Disc. AE: Hallucination, Dizziness... AEs leading to discontinuation/dose reduction: Hallucination (1 patient) Sources: Dizziness (1 patient) Insomnia (1 patient) Hepatotoxicity (1 patient) Skin rash (1 patient) Pruritus (1 patient) Rash (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Mania | 1 patient Disc. AE |
600 mg 1 times / day multiple, oral Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Co-administed with:: abacavir(300 mg q12h) Sources: nelfinavir(1250 mg q12h) |
unhealthy, 33 years n = 1 Health Status: unhealthy Condition: HIV infection Age Group: 33 years Sex: F Population Size: 1 Sources: |
Dizziness | 1 patient Disc. AE |
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
unhealthy, 37.3 years n = 67 Health Status: unhealthy Condition: tuberculosis Age Group: 37.3 years Sex: M+F Population Size: 67 Sources: |
Hallucination | 1 patient Disc. AE |
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
unhealthy, 37.3 years n = 67 Health Status: unhealthy Condition: tuberculosis Age Group: 37.3 years Sex: M+F Population Size: 67 Sources: |
Hepatotoxicity | 1 patient Disc. AE |
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
unhealthy, 37.3 years n = 67 Health Status: unhealthy Condition: tuberculosis Age Group: 37.3 years Sex: M+F Population Size: 67 Sources: |
Insomnia | 1 patient Disc. AE |
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
unhealthy, 37.3 years n = 67 Health Status: unhealthy Condition: tuberculosis Age Group: 37.3 years Sex: M+F Population Size: 67 Sources: |
Pruritus | 1 patient Disc. AE |
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
unhealthy, 37.3 years n = 67 Health Status: unhealthy Condition: tuberculosis Age Group: 37.3 years Sex: M+F Population Size: 67 Sources: |
Rash | 1 patient Disc. AE |
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
unhealthy, 37.3 years n = 67 Health Status: unhealthy Condition: tuberculosis Age Group: 37.3 years Sex: M+F Population Size: 67 Sources: |
Skin rash | 1 patient Disc. AE |
800 mg 1 times / day steady, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: steady Dose: 800 mg, 1 times / day Sources: |
unhealthy, 37.3 years n = 67 Health Status: unhealthy Condition: tuberculosis Age Group: 37.3 years Sex: M+F Population Size: 67 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Four new antiretroviral medications will soon offer more options to HIV patients. | 1998 Jul-Aug |
|
Expanded-spectrum nonnucleoside reverse transcriptase inhibitors inhibit clinically relevant mutant variants of human immunodeficiency virus type 1. | 1999 Dec |
|
A novel genotype encoding a single amino acid insertion and five other substitutions between residues 64 and 74 of the HIV-1 reverse transcriptase confers high-level cross-resistance to nucleoside reverse transcriptase inhibitors. Abacavir CNA2007 International Study Group. | 1999 Oct 1 |
|
Synthesis and evaluation of analogs of Efavirenz (SUSTIVA) as HIV-1 reverse transcriptase inhibitors. | 1999 Oct 4 |
|
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues. | 2000 Aug |
|
Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors. | 2000 May 18 |
|
The tolerability of efavirenz after nevirapine-related adverse events. | 2000 Sep |
|
A single amino acid change at Leu-188 in the reverse transcriptase of HIV-2 and SIV renders them sensitive to non-nucleoside reverse transcriptase inhibitors. | 2001 |
|
Efavirenz: a pharmacoeconomic review of its use in HIV infection. | 2001 |
|
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy. | 2001 |
|
Retinal toxicity due to Efavirenz. | 2001 Apr |
|
Amino acid deletion at codon 67 and Thr-to-Gly change at codon 69 of human immunodeficiency virus type 1 reverse transcriptase confer novel drug resistance profiles. | 2001 Apr |
|
Persistent dyslipidemia in HIV-infected individuals switched from a protease inhibitor-containing to an efavirenz-containing regimen. | 2001 Apr 1 |
|
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography. | 2001 Apr 13 |
|
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire. | 2001 Apr 15 |
|
A pilot study of the use of mycophenolate mofetil as a component of therapy for multidrug-resistant HIV-1 infection. | 2001 Apr 15 |
|
[Progress in HIV therapy. Effective and simple therapy with efavirenz]. | 2001 Apr 2 |
|
Antiretrovirals: simultaneous determination of five protease inhibitors and three nonnucleoside transcriptase inhibitors in human plasma by a rapid high-performance liquid chromatography--mass spectrometry assay. | 2001 Aug |
|
Antiviral drugs: current state of the art. | 2001 Aug |
|
Structure-based design, synthesis, and biological evaluation of conformationally restricted novel 2-alkylthio-6-[1-(2,6-difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H)-ones as non-nucleoside inhibitors of HIV-1 reverse transcriptase. | 2001 Aug 2 |
|
Antiretroviral therapy for previously treated patients. | 2001 Aug 9 |
|
Nelfinavir, efavirenz, or both after the failure of nucleoside treatment of HIV infection. | 2001 Aug 9 |
|
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion. | 2001 Feb |
|
Quinoxalinylethylpyridylthioureas (QXPTs) as potent non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors. Further SAR studies and identification of a novel orally bioavailable hydrazine-based antiviral agent. | 2001 Feb 1 |
|
3,3a-Dihydropyrano[4,3,2-de]quinazolin-2(1H)-ones are potent non-nucleoside reverse transcriptase inhibitors. | 2001 Jan 22 |
|
Efavirenz-associated breast hypertrophy in HIV-infection patients. | 2001 Jan 5 |
|
Protease-sparing regimen in a real-life practice with naïve patients: an equal opportunity approach? | 2001 Jan-Feb |
|
New developments in anti-HIV chemotherapy. | 2001 Jan-Feb |
|
Gynecomastia without lipodystrophy syndrome in HIV-infected men treated with efavirenz. | 2001 Jul 27 |
|
In vitro anti-HIV-1 synergy between non-nucleoside reverse transcriptase inhibitors nevirapine and efavirenz. | 2001 Jun |
|
Phenotypic hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in treatment-experienced HIV-infected patients: impact on virological response to efavirenz-based therapy. | 2001 Jun 15 |
|
4,1-Benzoxazepinone analogues of efavirenz (Sustiva) as HIV-1 reverse transcriptase inhibitors. | 2001 Jun 4 |
|
Sequencing antiretroviral drugs. | 2001 Mar 30 |
|
Efavirenz-induced photoallergic dermatitis in HIV. | 2001 May 25 |
|
[Apropos of atypical melancholia with Sustiva (efavirenz)]. | 2001 May-Jun |
|
[Drug interactions with antiretroviral agents]. | 2001 May-Jun |
|
Other issues: penetration into sanctuary sites, immune reconstitution and NNRTI sequencing. | 2001 Nov |
|
Factors affecting adherence and convenience in antiretroviral therapy. | 2001 Nov |
|
Comparison of NNRTIs in antiretroviral-experienced patients. | 2001 Nov |
|
Comparison of NNRTIs in antiretroviral-naïve patients. | 2001 Nov |
|
The role of NNRTIs in antiretroviral combination therapy: an introduction. | 2001 Nov |
|
New developments in anti-HIV chemotherapy. | 2001 Nov |
|
The stereoselective targeting of a specific enzyme-substrate complex is the molecular mechanism for the synergic inhibition of HIV-1 reverse transcriptase by (R)-(-)-PPO464: a novel generation of nonnucleoside inhibitors. | 2001 Nov 30 |
|
Thiosugars. VIII. Preparation of new 4'-thio-L-lyxo pyrimidine nucleoside analogues. | 2001 Sep |
|
Efavirenz-induced psychosis. | 2001 Sep 28 |
|
Response to first protease inhibitor- and efavirenz-containing antiretroviral combination therapy. The Swiss HIV Cohort Study. | 2001 Sep 28 |
|
Structural mechanisms of drug resistance for mutations at codons 181 and 188 in HIV-1 reverse transcriptase and the improved resilience of second generation non-nucleoside inhibitors. | 2001 Sep 28 |
|
Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues. | 2001 Sep 3 |
|
Switching from protease inhibitors to the non-nuke efavirenz. | 2001 Spring |
Sample Use Guides
SUSTIVA should be taken orally once daily on an empty stomach, preferably at bedtime.
• Recommended adult dose: 600 mg.
• With voriconazole, increase voriconazole maintenance dose to 400 mg every 12 hours and decrease SUSTIVA dose to 300 mg once daily using the capsule formulation.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24068579
10 pM efavirenz completely inhibited 0.5 U HIV RT.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000009948
Created by
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LIVERTOX |
341
Created by
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WHO-ATC |
J05AR11
Created by
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NDF-RT |
N0000175460
Created by
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EMA ASSESSMENT REPORTS |
SUSTIVA (AUTHORIZED: HIV INFECTIONS)
Created by
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EMA ASSESSMENT REPORTS |
ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by
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NDF-RT |
N0000175463
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.3 (EFV/FTC/TEN)
Created by
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WHO-VATC |
QJ05AR11
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WHO-ATC |
J05AR06
Created by
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WHO-VATC |
QJ05AR06
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.2
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NCI_THESAURUS |
C97453
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WHO-VATC |
QJ05AG03
Created by
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WHO-ATC |
J05AG03
Created by
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EMA ASSESSMENT REPORTS |
STOCRIN (AUTHORIZED: HIV INFECTIONS)
Created by
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EMA ASSESSMENT REPORTS |
EFAVIRENZ TEVA (AUTHORIZED: HIV INFECTIONS)
Created by
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Code System | Code | Type | Description | ||
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N0000182140
Created by
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PRIMARY | Cytochrome P450 2C19 Inhibitors [MoA] | ||
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CHEMBL223228
Created by
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PRIMARY | |||
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1234103
Created by
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PRIMARY | USP-RS | ||
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154598-52-4
Created by
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PRIMARY | |||
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989
Created by
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PRIMARY | |||
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EFAVIRENZ
Created by
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PRIMARY | Description: White to slightly pink powder.Solubility: Practically insoluble in water, freely soluble in methanol.Category. Antiretroviral (Non-nucleoside Reverse Transcriptase Inhibitor).Storage. Efavirenz should be kept in a well-closed container, protected from light.Additional information: Efavirenz may exhibit polymorphism.Requirements: Definition: Efavirenz contains not less than 97.0% and not more than 103.0% of C14H9ClF3NO2, calculated with reference to thedried substance.Manufacture: The production method is validated to ensure that the substance is the (4S)-enantiomer. | ||
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SUB06463MIG
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PRIMARY | |||
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64139
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PRIMARY | |||
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C098320
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PRIMARY | |||
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195085
Created by
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PRIMARY | RxNorm | ||
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N0000182141
Created by
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PRIMARY | Cytochrome P450 3A4 Inhibitors [MoA] | ||
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Efavirenz
Created by
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PRIMARY | |||
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M4839
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PRIMARY | Merck Index | ||
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7163
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PRIMARY | |||
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7718
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PRIMARY | |||
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JE6H2O27P8
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PRIMARY | |||
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C29027
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PRIMARY | |||
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EFAVIRENZ
Created by
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PRIMARY | |||
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N0000185504
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PRIMARY | Cytochrome P450 2C9 Inhibitors [MoA] | ||
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N0000187064
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PRIMARY | Cytochrome P450 2B6 Inducers [MoA] | ||
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154598-52-4
Created by
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PRIMARY | |||
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DB00625
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PRIMARY | |||
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N0000190118
Created by
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PRIMARY | Cytochrome P450 3A Inducers [MoA] |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)