Compound Detail

CHEMBL223228

EFAVIRENZ

💊 Approved Drug

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💊 Approved Drug

O=C1Nc2ccc(Cl)cc2[C@@](C#CC2CC2)(C(F)(F)F)O1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL223228
Name	EFAVIRENZ
Phase	Approved
Structure Type	MOL
InChI Key	XPOQHMRABVBWPR-ZDUSSCGKSA-N
Therapeutic	✓ Yes

Known Names

(-)-efavirenz DMP-266 Efavirenz Efavirenz component of atripla Efavirenz component of symfi Efavirenz component of telura Efavirenz teva Efavirenzum L-743726 NSC-742403 Stocrin Sustiva +2 more

Targets

1,410

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

315.7

MW (Da)

4.07

ALogP

HBA

HBD

38.3

PSA (Å²)

0.73

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1998
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral

USAN Stem

ef-; -vir-

Extended Properties

Molecular Formula	C14H9ClF3NO2
MW	315.68
Aromatic Rings	1
Heavy Atoms	21
NP-Likeness	0.07

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Human immunodeficiency virus type 1 reverse transcriptase inhibitor	INHIBITOR	Human immunodeficiency virus type 1 reverse transcriptase	✓	✓

Indications

Autoimmune Diseases HIV Infections HIV Infections Infections Virus Diseases Acquired Immunodeficiency Syndrome Tuberculosis Pancreatic Neoplasms Prostatic Neoplasms, Castration-Resistant Triple Negative Breast Neoplasms Diabetes Mellitus, Type 2 Hepatitis C Lymphoma, Non-Hodgkin Malaria Neoplasms

ATC Classification

J05AG03

efavirenz

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 920 meas. best 10.3

IC50 442 meas. best 10.05

Ki 45 meas. best 9.4

Kd 3 meas. best 6.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Human immunodeficiency virus 1 CHEMBL378	EC50	10.3	7.7414	0.1	807
Human immunodeficiency virus 1 CHEMBL378	IC50	10.05	7.8669	0.1	166
Human immunodeficiency virus type 1 reverse transcriptase CHEMBL247	IC50	10.04	7.4639	0.1	180
Human immunodeficiency virus type 1 reverse transcriptase CHEMBL247	Ki	9.4	7.2794	0.4	33
HeLa CHEMBL399	EC50	9.4	8.1667	0.4	3
Vesicular stomatitis virus CHEMBL613739	EC50	9.37	9.37	0.4	1
Human immunodeficiency virus CHEMBL613758	IC50	9.3	7.9113	0.5	16
Human immunodeficiency virus CHEMBL613758	EC50	9.3	8.325	0.5	18
HeLa CHEMBL399	IC50	9.3	8.1496	0.5	26
NON-PROTEIN TARGET CHEMBL3879801	EC50	9.15	7.4736	0.7	11
Human immunodeficiency virus type 1 reverse transcriptase CHEMBL247	EC50	9.0	7.5342	1.0	43
Unchecked CHEMBL612545	EC50	9.0	7.745	1.0	8
MT4 CHEMBL388	EC50	9.0	7.7713	1.0	16
MT4 CHEMBL388	IC50	9.0	7.8922	1.0	9
NON-PROTEIN TARGET CHEMBL3879801	IC50	8.98	7.1318	1.0	11
Unchecked CHEMBL612545	IC50	8.7	7.2014	2.0	22
Envelope glycoprotein gp160 CHEMBL1293311	IC50	8.46	8.46	3.5	1
Human immunodeficiency virus 2 CHEMBL380	EC50	7.7	6.155	20.0	2
Unchecked CHEMBL612545	Ki	7.52	6.978	30.0	10
Cholesterol 24-hydroxylase CHEMBL4523510	Kd	6.1	5.4633	800.0	3
ADMET CHEMBL612558	EC50	5.82	5.82	1500.0	1
Leishmania infantum CHEMBL612848	IC50	5.13	5.13	7400.0	1
Trypanosoma cruzi CHEMBL368	IC50	5.07	5.07	8560.0	1
MT2 CHEMBL614184	EC50	4.82	4.82	15000.0	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	4.71	4.71	19600.0	1
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	4.69	4.69	20600.0	1
ADMET CHEMBL612558	IC50	4.59	4.59	25840.0	1
Trypanosoma brucei brucei CHEMBL612851	IC50	4.52	4.52	30200.0	1
HEK293 CHEMBL614818	IC50	4.39	4.39	40600.0	1
Plasmodium falciparum CHEMBL364	IC50	4.36	4.36	43820.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	60000.0	ng.hr.mL-1	Homo sapiens
AUC	63600.0	ng.hr.mL-1	Homo sapiens
AUC	65200.0	ng.hr.mL-1	Homo sapiens
AUC	47.72	-	Homo sapiens
AUC	97.46	-	Homo sapiens
CL	8.51	uL.min-1.(10^6cells)-1	Homo sapiens
CL	0.0024	mL.min-1.g-1	Homo sapiens
CL	0.0064	mL.min-1.g-1	Homo sapiens
CL	0.0145	mL.min-1.g-1	Homo sapiens
CL	0.17	uL/min	Homo sapiens
CL	0.3	uL/min	Homo sapiens
CL	0.19	uL/min	Homo sapiens
CL	0.39	uL/min	Homo sapiens
Cmax	12956.16	nM	Homo sapiens
Cmax	17486.06	nM	Homo sapiens
Cmax	11752.41	nM	Homo sapiens
Cmax	11904.46	nM	Homo sapiens
Cmax	8663.84	nM	Homo sapiens
F	-	%	Canis lupus familiaris
F	-	%	Canis lupus familiaris
Fu	0.0052	-	Homo sapiens
Fu	0.0047	-	Homo sapiens
t1/2	-	-	Rattus norvegicus
t1/2	-	-	Homo sapiens
t1/2	-	-	Homo sapiens
T1/2	1.633	hr	Homo sapiens
t1/2	-	-	Canis lupus familiaris
t1/2	-	-	Canis lupus familiaris
T1/2	33.0	hr	Homo sapiens
T1/2	78.7	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Human immunodeficiency virus 1	EC50	=	0.05	nM	10.3	Antiviral activity against HIV1 NL4-3 infected in human MT2 cells assessed as in...	20660667
Human immunodeficiency virus 1	IC50	=	0.09	nM	10.05	Antiviral activity against HIV1	19112024
Human immunodeficiency virus type 1 reverse transcriptase	IC50	=	0.091	nM	10.04	Inhibition of HIV-1BH10 reverse transcriptase expressed in Escherichia coli asse...	31771827
Human immunodeficiency virus type 1 reverse transcriptase	IC50	=	0.091	nM	10.04	Inhibition of wild type HIV-1 NL4-3 reverse transcriptase using random mRNA as t...	33933756
Human immunodeficiency virus 1	EC50	=	0.1	nM	10.0	Antiviral activity against HIV1 infected in human HeLa cells expressing CD4-LTR ...	17967909
Human immunodeficiency virus 1	EC50	=	0.1	nM	10.0	Antiviral activity against HIV1 subtype B-3B infected in 1 hr-pretreated human M...	18316521
Human immunodeficiency virus 1	EC50	=	0.12	nM	9.92	Antiviral activity against Human immunodeficiency virus 1 subtype G isolate G3 i...	19933797
Human immunodeficiency virus 1	EC50	=	0.15	nM	9.82	Antiviral activity against Human immunodeficiency virus 1 subtype F isolate 93BR...	19933797
Human immunodeficiency virus 1	EC50	=	0.16	nM	9.8	Antiviral activity against Human immunodeficiency virus 1 subtype B isolate WEJO...	19933797
Human immunodeficiency virus type 1 reverse transcriptase	IC50	=	0.166	nM	9.78	Inhibition of HIV1 recombinant reverse transcriptase assessed as incorporation o...	-
Human immunodeficiency virus 1	EC50	=	0.17	nM	9.77	Antiviral activity against wild type HIV1	17116677
Human immunodeficiency virus 1	EC50	=	0.19	nM	9.72	Antiviral activity against Human immunodeficiency virus 1 subtype C isolate 93MW...	19933797
Human immunodeficiency virus 1	EC50	=	0.2	nM	9.7	Antiviral activity against HIV1 subtype B-LAI infected in 1 hr-pretreated human ...	18316521
Human immunodeficiency virus 1	EC50	=	0.2	nM	9.7	Antiviral activity against 0.005 MOI wild type HIV1 NL4-3 infected in human MT2 ...	18316521
Human immunodeficiency virus 1	EC50	=	0.2	nM	9.7	Antiviral activity against 0.005 MOI HIV1 NL4-3 harboring wild type RT infected ...	18316521
Human immunodeficiency virus 1	EC50	=	0.2	nM	9.7	Antiviral activity against 0.005 MOI HIV1 NL4-3 harboring M184V mutant RT infect...	18316521
Human immunodeficiency virus 1	EC50	=	0.27	nM	9.57	Antiviral activity against HIV1 isolate with RT V106I mutation	17116677
Human immunodeficiency virus 1	EC50	=	0.3	nM	9.52	Antiviral activity against HIV1 subtype B-HXB2 infected in 1 hr-pretreated human...	18316521
Human immunodeficiency virus 1	EC50	=	0.3	nM	9.52	Antiviral activity against 0.01 MOI wild type HIV1 NL4-3 infected in human MT2 c...	18316521
Human immunodeficiency virus 1	EC50	=	0.3	nM	9.52	Antiviral activity against HIV1 subtype B-92US076 infected in 1 hr-pretreated PB...	18316521

Literature References

PubMed	DOI	Target Context	# Activities
17116677	10.1128/aac.01032-06	Human immunodeficiency virus 1	138
19933797	10.1128/aac.00986-09	Human immunodeficiency virus 1	92
21115794	10.1128/aac.01209-10	Human immunodeficiency virus 1	52
18316521	10.1128/aac.01313-07	Human immunodeficiency virus 1	42
19029331	10.1128/aac.01156-08	Human immunodeficiency virus 1	42
19104010	10.1128/aac.00984-08	Human immunodeficiency virus 1	37
19883100	10.1021/jm901230r	Human immunodeficiency virus	34
14971897	10.1021/jm030255y	Human immunodeficiency virus 1	27
18665583	10.1021/jm8004493	Human immunodeficiency virus 1	25
20194692	10.1128/aac.00870-09	Human immunodeficiency virus 1	24
19289522	10.1128/aac.01559-08	Human immunodeficiency virus 1	23
22232427	10.1124/dmd.111.042416	ADMET	21
20008779	10.1128/aac.01335-09	Human immunodeficiency virus 1	20
24805780	10.1021/jm500139a	Human immunodeficiency virus 1	20
15481987	10.1021/jm0407658	Human immunodeficiency virus 1	17
15771439	10.1021/jm0408621	Human immunodeficiency virus 1	17
19007201	10.1021/jm800527x	Human immunodeficiency virus	16
20660679	10.1128/aac.00283-10	Homo sapiens	16
25072874	10.1016/j.ejmech.2014.07.072	Human immunodeficiency virus 1	16
19645483	10.1021/jm900802y	Human immunodeficiency virus 1	16

Data from ChEMBL 36 via Core Engine