COBICISTAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C40H53N7O5S2
Molecular Weight	776.023
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(C)C1=NC(CN(C)C(=O)N[C@@H](CCN2CCOCC2)C(=O)N[C@H](CC[C@H](CC3=CC=CC=C3)NC(=O)OCC4=CN=CS4)CC5=CC=CC=C5)=CS1

InChI

InChIKey=ZCIGNRJZKPOIKD-CQXVEOKZSA-N

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

HIDE SMILES / InChI

Molecular Formula	C40H53N7O5S2
Molecular Weight	776.023
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Cobicistat (GS-9350) is a potent, and selective inhibitor of human cytochrome P450 3A (CYP3A) enzymes. Cobicistat is a pharmacokinetic booster of several antiretrovirals. TYBOST (cobicistat) is indicated to increase systemic exposure of atazanavir or darunavir in combination with other antiretroviral agents in the treatment of HIV-1 infection.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 3A 22	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 151	Primary		Approved 8,429	TYBOST

C_max

Value	Dose	Co-administered	Analyte	Population
0.99 μg/mL	150 mg 1 times / day steady-state, oral	Atazanavir	COBICISTAT plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
7.6 mg × h/mL	150 mg 1 times / day steady-state, oral	Atazanavir	COBICISTAT plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.5 h	150 mg 1 times / day steady-state, oral	Atazanavir	COBICISTAT plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
2.5%	150 mg 1 times / day steady-state, oral	Atazanavir	COBICISTAT plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
300 mg 1 times / day steady, oral Highest studied dose	healthy, 27 years (range: 18–45 years) n = 12
400 mg single, oral Highest studied dose	healthy, 27 years (range: 18–45 years) n = 12

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inducer 781	inhibitor 1,767 inducer 389	substrate 1,217 inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 214 CYP1A2 1,524 CYP2B6 810 CYP2C8 911 CYP2C19 1,478 UGT1A1 204 P-gp 1,461 BCRP 699 OAT1 599 OAT3 642 MRP4 204 OCT2 647 OATP1B1 788 OATP1B3 706	P-gp 1,537 BCRP 561	CYP2C19 293 CYP1A2 701 CYP2B6 547 CYP2C8 168 UGT1A1 69 P-gp 257

Drug as perpetrator

Show entries

Target	Modality	Activity
OATP1B3 715	inhibitor 3,277	likely [IC50 1.88 uM]
OATP1B1 803	inhibitor 3,277	likely [IC50 3.5 uM]
CYP1A2 1,692	inducer 1,573	no
CYP2B6 1,001	inducer 1,573	no
CYP2C19 1,553	inducer 1,573	no

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Drug as victim

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Target	Modality	Activity
BCRP 561	substrate 3,367	yes
CYP2D6 1,217	substrate 3,367	yes
CYP3A4 1,737	substrate 3,367	yes
P-gp 1,537	substrate 3,367	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:72291	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:72291
ChemicalBook	CB62627692	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB62627692
MolPort	MolPort-035-395-741	https://www.molport.com/shop/molecule-link/MolPort-035-395-741
Selleck Chemicals	cobicistat-gs-9350	http://www.selleckchem.com/products/cobicistat-gs-9350.html
ZINC	ZINC000085537014	http://zinc15.docking.org/substances/ZINC000085537014

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PubMed

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Title	Date	PubMed
Cobicistat boosts the intestinal absorption of transport substrates, including HIV protease inhibitors and GS-7340, in vitro.	2012 Oct	22850510

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Patents

Sample Use Guides

In Vivo Use Guide

TYBOST (cobicistat) (150 mg orally once daily) must be coadministered with atazanavir (300 mg orally once daily) or darunavir (800 mg orally once daily) at the same time, with food, and in combination with other HIV-1 antiretroviral agents

Route of Administration: Oral

In Vitro Use Guide

HIV infected monocytic (U1) cellss were treated with 2 uM Cobicistat as a booster drug for 5 uM elvitegravir.

Substance Class	Chemical
Record UNII	LW2E03M5PG
Record Status	`Validated (UNII)`
Record Version

Related Record	Type
No data available in table

Show entries

Name

Type

Language

COBICISTAT

Official Name

English

COBICISTAT [JAN]

Common Name

English

COBICISTAT COMPONENT OF SYMTUZA

Brand Name

English

STRIBILD COMPONENT COBICISTAT

Brand Name

English

(1,3-THIAZOL-5-YL)METHYL (5S,8R,11R)-8,11-DIBENZYL-2-METHYL-5-(2-(MORPHOLIN-4-YL)ETHYL)-1-(2-(PROPAN-2-YL)-1,3-THIAZOL-4-YL)-3,6-DIOXO-2,4,7,12-TETRAAZATRIDECAN-13-OATE

Common Name

English

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Code System

Code