efavirenz   Click here for help

GtoPdb Ligand ID: 11287

Synonyms: DMP-266 | DMP266 | EFV | L-743,726 | L-743726 | Stocrin® | Sustiva®
Approved drug PDB Ligand
efavirenz is an approved drug (FDA (1998), EMA (1999))
Compound class: Synthetic organic
Comment: Efavirenz is an antiviral drug that is used in the treatment of HIV. It is a synthetic non-nucleoside inhibitor (NNRTI) that binds to the HIV RNA-dependent DNA polymerase and thereby blocks viral DNA replication [6].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 38.33
Molecular weight 315.03
XLogP 4.63
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES FC([C@@]1(C#CC2CC2)OC(=O)Nc2c1cc(Cl)cc2)(F)F
Isomeric SMILES FC([C@@]1(C#CC2CC2)OC(=O)Nc2c1cc(Cl)cc2)(F)F
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
InChI Key XPOQHMRABVBWPR-ZDUSSCGKSA-N
References
1. Decloedt EH, Rosenkranz B, Maartens G, Joska J. (2015)
Central nervous system penetration of antiretroviral drugs: pharmacokinetic, pharmacodynamic and pharmacogenomic considerations.
Clin Pharmacokinet, 54 (6): 581-98. [PMID:25777740]
2. Fernández-Bargiela N, Rotea-Salvo S, Margusino-Framiñán L, Balboa-Barreiro V, Martín-Herranz I, Castro-Iglesias Á, Mena-De-Cea Á, López-Calvo S, Vázquez-Rodríguez P, Míguez-Rey E et al.. (2022)
Discontinuation due to neuropsychiatric adverse events with efavirenz- and dolutegravir-based antiretroviral therapy: a comparative real-life study.
Eur J Hosp Pharm, 29 (4): 207-211. [PMID:33051194]
3. Hesse LM, von Moltke LL, Shader RI, Greenblatt DJ. (2001)
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.
Drug Metab Dispos, 29 (2): 100-2. [PMID:11159797]
4. von Moltke LL, Greenblatt DJ, Granda BW, Giancarlo GM, Duan SX, Daily JP, Harmatz JS, Shader RI. (2001)
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.
J Clin Pharmacol, 41 (1): 85-91. [PMID:11225565]
5. Wang PF, Neiner A, Kharasch ED. (2019)
Efavirenz Metabolism: Influence of Polymorphic CYP2B6 Variants and Stereochemistry.
Drug Metab Dispos, 47 (10): 1195-1205. [PMID:31324697]
6. Young SD, Britcher SF, Tran LO, Payne LS, Lumma WC, Lyle TA, Huff JR, Anderson PS, Olsen DB, Carroll SS et al.. (1995)
L-743, 726 (DMP-266): a novel, highly potent nonnucleoside inhibitor of the human immunodeficiency virus type 1 reverse transcriptase.
Antimicrob Agents Chemother, 39 (12): 2602-5. [PMID:8592986]