cobicistat   Click here for help

GtoPdb Ligand ID: 7535

Synonyms: GS-9350
Approved drug PDB Ligand
cobicistat is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: This compound is approved as a component of the so-called 'Quad pill' (Stribild®), an anti-HIV therapy which contains cobicistat, elvitegravir, emtricitabine, and tenofovir.

cobicistat is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 12
Hydrogen bond donors 3
Rotatable bonds 24
Topological polar surface area 194.5
Molecular weight 775.35
XLogP 3.7
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C(NC(Cc1ccccc1)CCC(Cc1ccccc1)NC(=O)C(NC(=O)N(Cc1csc(n1)C(C)C)C)CCN1CCOCC1)OCc1cncs1
Isomeric SMILES O=C(N[C@@H](Cc1ccccc1)CC[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)N(Cc1csc(n1)C(C)C)C)CCN1CCOCC1)OCc1cncs1
InChI InChI=1S/C40H53N7O5S2/c1-29(2)38-43-34(27-53-38)25-46(3)39(49)45-36(16-17-47-18-20-51-21-19-47)37(48)42-32(22-30-10-6-4-7-11-30)14-15-33(23-31-12-8-5-9-13-31)44-40(50)52-26-35-24-41-28-54-35/h4-13,24,27-29,32-33,36H,14-23,25-26H2,1-3H3,(H,42,48)(H,44,50)(H,45,49)/t32-,33-,36+/m1/s1
InChI Key ZCIGNRJZKPOIKD-CQXVEOKZSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Lepist EI, Phan TK, Roy A, Tong L, Maclennan K, Murray B, Ray AS. (2012)
Cobicistat boosts the intestinal absorption of transport substrates, including HIV protease inhibitors and GS-7340, in vitro.
Antimicrob Agents Chemother, 56 (10): 5409-13. [PMID:22850510]
2. Mathias AA, German P, Murray BP, Wei L, Jain A, West S, Warren D, Hui J, Kearney BP. (2010)
Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity.
Clin Pharmacol Ther, 87 (3): 322-9. [PMID:20043009]
3. Xu L, Liu H, Murray BP, Callebaut C, Lee MS, Hong A, Strickley RG, Tsai LK, Stray KM, Wang Y et al.. (2010)
Cobicistat (GS-9350): A Potent and Selective Inhibitor of Human CYP3A as a Novel Pharmacoenhancer.
ACS Med Chem Lett, 1 (5): 209-13. [PMID:24900196]