EFAVIRENZ

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H9ClF3NO2
Molecular Weight	315.675
Optical Activity	( - )
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

FC(F)(F)[C@]1(OC(=O)NC2=CC=C(Cl)C=C12)C#CC3CC3

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

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Description

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Human immunodeficiency virus 1 34	Inhibitor 8,504	4.0 nM [EC50]
Leishmania infantum 3	Inhibitor 8,504	26.1 µM [IC50]
Estrogen receptor alpha 134	Modulator 846	52.0 µM [IC50]
Human immunodeficiency virus type 1 reverse transcriptase 70	Inhibitor 8,504	20.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156	Primary		Approved 8,583	SUSTIVA

C_max

Value	Dose	Analyte	Population
1.6 μM	100 mg single, oral	EFAVIRENZ plasma	Homo sapiens
9.1 μM	1600 mg single, oral	EFAVIRENZ plasma	Homo sapiens
12.9 μM	600 mg 1 times / day steady-state, oral	EFAVIRENZ plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
184 μM × h	600 mg 1 times / day steady-state, oral		EFAVIRENZ plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
40 h	600 mg 1 times / day steady-state, oral		EFAVIRENZ plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.5%	600 mg 1 times / day steady-state, oral		EFAVIRENZ plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
3 g single, oral Overdose	unhealthy, 12 years
600 mg 1 times / day multiple, oral Recommended	unhealthy, 33 years	Disc. AE: Mania...
25 mg/kg 1 times / day steady, oral Highest studied dose	unhealthy, 33.9 months (range: 29.2–40.2 months)
800 mg 1 times / day steady, oral Highest studied dose	unhealthy, 37.3 years	Disc. AE: Hallucination, Dizziness...

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AEs

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AE	Significance	Dose	Population
Mania	1 patient Disc. AE	600 mg 1 times / day multiple, oral Recommended	unhealthy, 33 years
Dizziness	1 patient Disc. AE	800 mg 1 times / day steady, oral Highest studied dose	unhealthy, 37.3 years
Hallucination	1 patient Disc. AE	800 mg 1 times / day steady, oral Highest studied dose	unhealthy, 37.3 years
Hepatotoxicity	1 patient Disc. AE	800 mg 1 times / day steady, oral Highest studied dose	unhealthy, 37.3 years
Insomnia	1 patient Disc. AE	800 mg 1 times / day steady, oral Highest studied dose	unhealthy, 37.3 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1,087 inhibitor 2,252 substrate 1,946	inhibitor 2,438 substrate 1,193	inhibitor 2,507 substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT 45 CYP2C19 2,057 CYP1A2 2,153 CYP2E1 1,060 BCRP 910 MATE1 415 MRP2 499 MATE2-K 77 MRP1 116 OCT1 620 P-gp 1,741 MRP3 246 OCT2 779	CYP2B6 776 CYP2C8 810 UGT1A3 470 UGT1A7 249 UGT2B4 278 UGT1A6 343 CYP2C19 1,119 UGT1A8 323 CYP2E1 729 UGT1A1 479 UGT1A4 399 UGT1A10 331 UGT2B7 456 UGT2B17 237 UGT2B15 236 UGT1A9 423 CYP2A6 626 CYP1A2 1,197 P-gp 2,052 MRP1 113 MRP2 252	CYP2B6 669 UGT1A1 78 MRP1 74 MRP2 146 P-gp 301

Drug as perpetrator

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Target	Modality	Activity
MATE2-K 77	inhibitor 4,027	likely
CYP2E1 1,146	inhibitor 4,027	no
MRP1 232	inducer 1,966	no
MRP2 625	inducer 1,966	no
P-gp 1,932	inducer 1,966	no

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Drug as victim

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Target	Modality	Activity
CYP2B6 776	substrate 4,014	major
CYP3A4 1,946	substrate 4,014	major
CYP1A2 1,197	substrate 4,014	minor
CYP2A6 626	substrate 4,014	minor
CYP2C19 1,119	substrate 4,014	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:119486	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:119486
ChemicalBook	CB7181559	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7181559
eMolecules	2735350	https://www.emolecules.com/cgi-bin/more?vid=2735350
MolPort	MolPort-003-983-924	https://www.molport.com/shop/molecule-link/MolPort-003-983-924
ZINC	ZINC000002020233	http://zinc15.docking.org/substances/ZINC000002020233

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PubMed

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Title	Date	PubMed
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	10843527
Synthesis and evaluation of analogs of Efavirenz (SUSTIVA) as HIV-1 reverse transcriptase inhibitors.	1999 Oct 4	10522695
Persistent dyslipidemia in HIV-infected individuals switched from a protease inhibitor-containing to an efavirenz-containing regimen.	2001 Apr 1	11317084
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	11472208
Trifluoromethyl-containing 3-alkoxymethyl- and 3-aryloxymethyl-2-pyridinones are potent inhibitors of HIV-1 non-nucleoside reverse transcriptase.	2001 Feb 12	11212098

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Patents

Sample Use Guides

In Vivo Use Guide

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

10 pM efavirenz completely inhibited 0.5 U HIV RT.

Show entries

Name

Type

Language

EFAVIRENZ

Official Name

English

TELURA COMPONENT EFAVIRENZ

Preferred Name