EFAVIRENZ

Search structure
Trade Names:
Synonyms:
Status: Approved (1998)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J05AG03
UNII: JE6H2O27P8

Structure
InChI Key XPOQHMRABVBWPR-ZDUSSCGKSA-N
Smile O=C1Nc2ccc(Cl)cc2[C@@](C#CC2CC2)(C(F)(F)F)O1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H9ClF3NO2
Molecular Weight 315.68
AlogP 4.07
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 38.33
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 21.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
- - - - 95
Enzyme Hydrolase
1-514 0-2100 - 0-3000 18-98
Enzyme Oxidoreductase
- - 800-10200 - -
Enzyme
1-514 0-2100 800-10200 0-3000 18-98
Surface antigen
- 4 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 18
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 37

Indications

Mesh Heading Maximum Phase Mesh ID Reference
HIV Infections 4 D015658 ClinicalTrials
HIV Infections 4 D015658 ClinicalTrials
Acquired Immunodeficiency Syndrome 3 D000163 ClinicalTrials
Tuberculosis 3 D014376 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Lymphoma, Non-Hodgkin 1 D008228 ClinicalTrials

Related Entries

Scaffolds

Mixture
Mixture
Mixture
Mixture
Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Skin and subcutaneous tissue disorders Dermatitis 46.0
Skin and subcutaneous tissue disorders Rash 46.0
Skin and subcutaneous tissue disorders Dermatitis 45.6
Skin and subcutaneous tissue disorders Rash 45.6
Skin and subcutaneous tissue disorders Dermatitis 40.3
Skin and subcutaneous tissue disorders Rash 40.3
Skin and subcutaneous tissue disorders Dermatitis 40.0
Skin and subcutaneous tissue disorders Rash 40.0
Gastrointestinal disorders Diarrhoea 39.0
Skin and subcutaneous tissue disorders Dermatitis 31.6
Skin and subcutaneous tissue disorders Rash 31.6
Skin and subcutaneous tissue disorders Dermatitis 27.3
Skin and subcutaneous tissue disorders Rash 27.3
Skin and subcutaneous tissue disorders Dermatitis 26.3
Skin and subcutaneous tissue disorders Rash 26.3
Investigations Body temperature increased 26.0
Respiratory, thoracic and mediastinal disorders Cough 25.0
Gastrointestinal disorders Nausea 25.0
Skin and subcutaneous tissue disorders Dermatitis 24.5
Skin and subcutaneous tissue disorders Rash 24.5
Gastrointestinal disorders Nausea 24.0
Investigations Body temperature increased 21.0
Skin and subcutaneous tissue disorders Dermatitis 17.5
Skin and subcutaneous tissue disorders Rash 17.5
Skin and subcutaneous tissue disorders Dermatitis 17.3
Skin and subcutaneous tissue disorders Rash 17.3
General disorders and administration site conditions Pain 17.0
Skin and subcutaneous tissue disorders Dermatitis 16.7
Skin and subcutaneous tissue disorders Rash 16.7
Respiratory, thoracic and mediastinal disorders Cough 16.0
Skin and subcutaneous tissue disorders Dermatitis 16.0
Cardiac disorders Dizziness 16.0
Nervous system disorders Loss of consciousness 16.0
Skin and subcutaneous tissue disorders Rash 16.0
Vascular disorders Shock 16.0
Cardiac disorders Syncope 16.0
Gastrointestinal disorders Vomiting 16.0
Skin and subcutaneous tissue disorders Dermatitis 14.7
Skin and subcutaneous tissue disorders Rash 14.7
Gastrointestinal disorders Diarrhoea 14.0
General disorders and administration site conditions Discomfort 14.0
Gastrointestinal disorders Vomiting 14.0
Skin and subcutaneous tissue disorders Dermatitis 13.0
General disorders and administration site conditions Pain 13.0
Skin and subcutaneous tissue disorders Rash 13.0
Gastrointestinal disorders Nausea 12.0
Gastrointestinal disorders Vomiting 12.0
Skin and subcutaneous tissue disorders Dermatitis 11.6
Skin and subcutaneous tissue disorders Rash 11.6
Skin and subcutaneous tissue disorders Dermatitis 11.0
Nervous system disorders Headache 11.0
Skin and subcutaneous tissue disorders Rash 11.0
Skin and subcutaneous tissue disorders Dermatitis 10.7
Skin and subcutaneous tissue disorders Rash 10.7
General disorders and administration site conditions Asthenia 10.0
Cardiac disorders Dizziness 10.0
General disorders and administration site conditions Fatigue 10.0
Gastrointestinal disorders Nausea 10.0
Skin and subcutaneous tissue disorders Dermatitis 9.9
Skin and subcutaneous tissue disorders Rash 9.9
Skin and subcutaneous tissue disorders Dermatitis 9.8
Skin and subcutaneous tissue disorders Erythema 9.8
Skin and subcutaneous tissue disorders Pruritus 9.8
Skin and subcutaneous tissue disorders Rash 9.8
Skin and subcutaneous tissue disorders Dermatitis 9.4
Skin and subcutaneous tissue disorders Rash 9.4
General disorders and administration site conditions Asthenia 9.0
Skin and subcutaneous tissue disorders Dermatitis 9.0
Gastrointestinal disorders Diarrhoea 9.0
Nervous system disorders Disturbance in attention 9.0
Cardiac disorders Dizziness 9.0
General disorders and administration site conditions Fatigue 9.0
Social circumstances Mental disability 9.0
Skin and subcutaneous tissue disorders Pruritus 9.0
Skin and subcutaneous tissue disorders Rash 9.0
Skin and subcutaneous tissue disorders Dermatitis 8.8
Skin and subcutaneous tissue disorders Erythema 8.8
Skin and subcutaneous tissue disorders Pruritus 8.8
Skin and subcutaneous tissue disorders Rash 8.8
Cardiac disorders Dizziness 8.5
General disorders and administration site conditions Asthenia 8.0
Skin and subcutaneous tissue disorders Dermatitis 8.0
Gastrointestinal disorders Diarrhoea 8.0
Cardiac disorders Dizziness 8.0
General disorders and administration site conditions Fatigue 8.0
Nervous system disorders Headache 8.0
Gastrointestinal disorders Nausea 8.0
General disorders and administration site conditions Pain 8.0
Skin and subcutaneous tissue disorders Rash 8.0
Skin and subcutaneous tissue disorders Dermatitis 7.4
Skin and subcutaneous tissue disorders Rash 7.4
General disorders and administration site conditions Asthenia 7.0
Skin and subcutaneous tissue disorders Dermatitis 7.0
General disorders and administration site conditions Fatigue 7.0
Nervous system disorders Headache 7.0
Nervous system disorders Insomnia 7.0
Skin and subcutaneous tissue disorders Rash 7.0
Gastrointestinal disorders Vomiting 7.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
Gastrointestinal disorders Diarrhoea 6.0
Cardiac disorders Dizziness 6.0
Gastrointestinal disorders Dyspepsia 6.0
Nervous system disorders Headache 6.0
Nervous system disorders Insomnia 6.0
Gastrointestinal disorders Nausea 6.0
General disorders and administration site conditions Pain 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Gastrointestinal disorders Vomiting 6.0
Nervous system disorders Headache 5.7
General disorders and administration site conditions Asthenia 5.5
General disorders and administration site conditions Fatigue 5.5
Gastrointestinal disorders Abdominal pain 5.0
General disorders and administration site conditions Asthenia 5.0
Psychiatric disorders Depression 5.0
Skin and subcutaneous tissue disorders Dermatitis 5.0
Gastrointestinal disorders Diarrhoea 5.0
Nervous system disorders Disturbance in attention 5.0
Cardiac disorders Dizziness 5.0
Gastrointestinal disorders Dyspepsia 5.0
General disorders and administration site conditions Fatigue 5.0
Gastrointestinal disorders Gastrointestinal pain 5.0
Nervous system disorders Headache 5.0
Social circumstances Mental disability 5.0
General disorders and administration site conditions Pain 5.0
Skin and subcutaneous tissue disorders Pruritus 5.0
Skin and subcutaneous tissue disorders Rash 5.0
Gastrointestinal disorders Abdominal pain 4.0
Nervous system disorders Abnormal dreams 4.0
Psychiatric disorders Anxiety 4.0
Psychiatric disorders Depression 4.0
Gastrointestinal disorders Dyspepsia 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Renal and urinary disorders Haematuria 4.0
Nervous system disorders Headache 4.0
Renal and urinary disorders Nephrolithiasis 4.0
Nervous system disorders Somnolence 4.0
Nervous system disorders Disturbance in attention 3.6
Skin and subcutaneous tissue disorders Dermatitis 3.5
Immune system disorders Dermatitis exfoliative 3.5
Immune system disorders Erythema multiforme 3.5
General disorders and administration site conditions Necrosis 3.5
Skin and subcutaneous tissue disorders Rash 3.5
Immune system disorders Stevens-Johnson syndrome 3.5
Immune system disorders Toxic epidermal necrolysis 3.5
Gastrointestinal disorders Abdominal pain 3.0
Nervous system disorders Abnormal dreams 3.0
General disorders and administration site conditions Asthenia 3.0
Psychiatric disorders Depression 3.0
Gastrointestinal disorders Diarrhoea 3.0
Nervous system disorders Disturbance in attention 3.0
Cardiac disorders Dizziness 3.0
Gastrointestinal disorders Dyspepsia 3.0
General disorders and administration site conditions Fatigue 3.0
Gastrointestinal disorders Gastrointestinal pain 3.0
Nervous system disorders Headache 3.0
Nervous system disorders Insomnia 3.0
Social circumstances Mental disability 3.0
Gastrointestinal disorders Nausea 3.0
Renal and urinary disorders Nephrolithiasis 3.0
Nervous system disorders Somnolence 3.0
Gastrointestinal disorders Vomiting 3.0
Gastrointestinal disorders Abdominal pain 2.0
Psychiatric disorders Anxiety 2.0
General disorders and administration site conditions Asthenia 2.0
General disorders and administration site conditions Decreased appetite 2.0
Psychiatric disorders Depression 2.0
Gastrointestinal disorders Diarrhoea 2.0
Cardiac disorders Dizziness 2.0
Gastrointestinal disorders Dyspepsia 2.0
General disorders and administration site conditions Fatigue 2.0
Gastrointestinal disorders Flatulence 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Nervous system disorders Headache 2.0
General disorders and administration site conditions Hyperhidrosis 2.0
Nervous system disorders Hypoaesthesia 2.0
Nervous system disorders Insomnia 2.0
Gastrointestinal disorders Nausea 2.0
Psychiatric disorders Nervousness 2.0
General disorders and administration site conditions Pain 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Nervous system disorders Somnolence 2.0
Psychiatric disorders Tension 2.0
Skin and subcutaneous tissue disorders Dermatitis 1.8
Skin and subcutaneous tissue disorders Rash 1.8
Skin and subcutaneous tissue disorders Dermatitis 1.7
Skin and subcutaneous tissue disorders Rash 1.7
Gastrointestinal disorders Abdominal pain 1.0
Nervous system disorders Abnormal dreams 1.0
Psychiatric disorders Anxiety 1.0
General disorders and administration site conditions Asthenia 1.0
General disorders and administration site conditions Decreased appetite 1.0
Psychiatric disorders Depression 1.0
Nervous system disorders Disturbance in attention 1.0
Cardiac disorders Dizziness 1.0
Gastrointestinal disorders Dyspepsia 1.0
General disorders and administration site conditions Fatigue 1.0
Gastrointestinal disorders Flatulence 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Renal and urinary disorders Haematuria 1.0
General disorders and administration site conditions Hyperhidrosis 1.0
Nervous system disorders Hypoaesthesia 1.0
Nervous system disorders Insomnia 1.0
Social circumstances Mental disability 1.0
General disorders and administration site conditions Pain 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Nervous system disorders Somnolence 1.0
Skin and subcutaneous tissue disorders Dermatitis 0.8
Skin and subcutaneous tissue disorders Rash 0.8
Skin and subcutaneous tissue disorders Dermatitis 0.7
Skin and subcutaneous tissue disorders Rash 0.7
Psychiatric disorders Suicidal ideation 0.6
Psychiatric disorders Aggression 0.4
Psychiatric disorders Suicide attempt 0.4
Psychiatric disorders Aggression 0.3
Skin and subcutaneous tissue disorders Dermatitis 0.3
Skin and subcutaneous tissue disorders Rash 0.3
Psychiatric disorders Suicidal ideation 0.3
Skin and subcutaneous tissue disorders Dermatitis 0.1
Skin and subcutaneous tissue disorders Rash 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Pregnancy, puerperium and perinatal conditions
20.19
Injury, poisoning and procedural complications
14.29
General disorders and administration site conditions
9.13
Nervous system disorders
6.31
Infections and infestations
4.85
Congenital, familial and genetic disorders
4.01
Psychiatric disorders
3.94
Metabolism and nutrition disorders
3.59
Hepatobiliary disorders
3.14
Gastrointestinal disorders
2.85
Investigations
2.84
Vascular disorders
2.72
Surgical and medical procedures
2.71
Skin and subcutaneous tissue disorders
2.68
Musculoskeletal and connective tissue disorders
2.39
Renal and urinary disorders
2.35
Respiratory, thoracic and mediastinal disorders
2.28
Cardiac disorders
2.16
Immune system disorders
2.15

Cross References

Resources Reference
CAS NUMBER 154598-52-4
ChEBI 119486
ChEMBL CHEMBL223228
DrugBank DB00625
DrugCentral 989
EPA CompTox DTXSID9046029
FDA SRS JE6H2O27P8
Human Metabolome Database HMDB0014763
Guide to Pharmacology 11287
KEGG C08088
PDB EFZ
PharmGKB PA449441
PubChem 64139
SureChEMBL SCHEMBL37762
ZINC ZINC000002020233
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