U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of COBICISTAT

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

Description
Curator's Comment: Description was created based on several sources, including http://www.gilead.com/~/media/Files/pdfs/medicines/hiv/tybost/tybost_pi.pdf | https://www.ncbi.nlm.nih.gov/pubmed/23471741

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

2012
595
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
TYBOST

Approved Use

TYBOST (cobicistat) indicated to increase systemic exposure of atazanavir or darunavir (once daily dosing regimen) in combination with other antiretroviral agents in the treatment of HIV-1 infection.

Launch Date

2014
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.99 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/203094s008lbl.pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Atazanavir
Atazanavir
 COBICISTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7.6 mg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/203094s008lbl.pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Atazanavir
Atazanavir
 COBICISTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/203094s008lbl.pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Atazanavir
Atazanavir
 COBICISTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2.5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/203094s008lbl.pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Atazanavir
Atazanavir
 COBICISTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day steady, oral
Highest studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20043009
healthy, 27 years (range: 18–45 years)
n = 12
Health Status: healthy
Age Group: 27 years (range: 18–45 years)
Sex: M+F
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/20043009
Sources:
https://pubmed.ncbi.nlm.nih.gov/20043009
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/20043009
healthy, 27 years (range: 18–45 years)
n = 12
Health Status: healthy
Age Group: 27 years (range: 18–45 years)
Sex: M+F
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/20043009
Sources:
https://pubmed.ncbi.nlm.nih.gov/20043009
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inducer
781
inhibitor
1767

inducer
389
substrate
1217

inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP3A
214

CYP1A2
1524

CYP2B6
810

CYP2C8
911

CYP2C19
1478

UGT1A1
204

P-gp
1461

BCRP
699

OAT1
599

OAT3
642

MRP4
204

OCT2
647

OATP1B1
788

OATP1B3
706
P-gp
1537

BCRP
561
CYP2C19
293

CYP1A2
701

CYP2B6
547

CYP2C8
168

UGT1A1
69

P-gp
257
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OATP1B3
715
 likely [IC50 1.88 uM]
OATP1B1
803
 likely [IC50 3.5 uM]
CYP1A2
1692
 no
CYP2B6
1001
 no
CYP2C19
1553
 no
CYP2C8
965
 no
CYP2C9
1819
 no
P-gp
1650
 no
UGT1A1
254
 no
CYP2B6
1001
 not expected [IC50 2.8 uM]
CYP2C8
965
 not expected [IC50 30.1 uM]
OCT2
648
 not expected [IC50 8.24 uM]
OAT1
603
 not expected [IC50 >100 uM]
OAT3
644
 not expected [IC50 >100 uM]
CYP1A2
1692
 not expected [IC50 >25 uM]
CYP2C19
1553
 not expected [IC50 >25 uM]
CYP2C9
1819
 not expected [IC50 >25 uM]
P-gp
1650
 weak [IC50 22.5 uM]
weak (co-administration study)
Comment: increased Cmax of digoxin by 41%, increased AUC0-inf by 8%
Page: 61,63
BCRP
773
 weak [IC50 59 uM]
CYP3A4
1925
 weak
CYP3A
298
 yes [IC50 0.03 uM]
UGT1A1
254
 yes [IC50 16.3 uM]
MRP4
238
 yes [IC50 20.7 uM]
CYP2D6
1891
 yes [IC50 9.2 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
561
 yes
CYP2D6
1217
 yes
CYP3A4
1737
 yes
P-gp
1537
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
PubMed

PubMed

TitleDatePubMed
Pharmacokinetic enhancers in HIV therapeutics.
2014 Oct
Patents

Patents

20080108617
1
20080207620
1
20090093467
1
20090093482
1
20090181902
1
20090291952
1

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
Created
by admin
on Sat Dec 16 16:02:00 GMT 2023
Edited
by admin
on Sat Dec 16 16:02:00 GMT 2023
Record UNII
LW2E03M5PG
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
COBICISTAT
DASH   INN   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
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
COBICISTAT COMPONENT OF GENVOYA
Brand Name English
REZOLSTA COMPONENT COBICISTAT
Brand Name English
2,7,10,12-TETRAAZATRIDECANOIC ACID, 12-METHYL-13-(2-(1-METHYLETHYL)-4-THIAZOLYL)-9-(2-(4-MORPHOLINYL)ETHYL)-8,11-DIOXO-3,6-BIS(PHENYLMETHYL)-, 5-THIAZOLYLMETHYL ESTER, (3R,6R,9S)-
Common Name English
COBICISTAT, (R,R,S)-
Common Name English
COBICISTAT COMPONENT OF PREZCOBIX
Brand Name English
SYMTUZA COMPONENT COBICISTAT
Brand Name English
COBICISTAT [ORANGE BOOK]
Common Name English
GENVOYA COMPONENT COBICISTAT
Brand Name English
Cobicistat [WHO-DD]
Common Name English
COBICISTAT [VANDF]
Common Name English
COBICISTAT [MI]
Common Name English
COBICISTAT [USAN]
Common Name English
EVOTAZ COMPONENT COBICISTAT
Brand Name English
COBICISTAT COMPONENT OF STRIBILD
Brand Name English
GS-9350
Code English
PREZCOBIX COMPONENT COBICISTAT
Brand Name English
1,3-THIAZOL-5-YLMETHYL ((2R,5R)-5-(((2S)-2-((METHYL((2-(PROPAN-2-YL)-1,3-THIAZOL-4-YL)METHYL)CARBAMOYL)AMINO)-4-(MORPHOLIN-4-YL)BUTANOYL)AMINO)-1,6-DIPHENYLHEXAN-2-YL)CARBAMATE
Common Name English
cobicistat [INN]
Common Name English
COBICISTAT COMPONENT OF EVOTAZ
Brand Name English
Classification Tree Code System Code
WHO-ATC J05AR09
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
FDA ORPHAN DRUG 577917
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
WHO-ATC J05AR15
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
WHO-ATC V03AX03
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
NDF-RT N0000191001
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
EMA ASSESSMENT REPORTS GENVOYA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
LIVERTOX NBK547911
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
NCI_THESAURUS C471
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
WHO-VATC QV03AX03
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
WHO-ATC J05AR18
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
EMA ASSESSMENT REPORTS EVOTAZ (AUTHORIZED: HIV INFECTIONS)
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
WHO-ATC J05AR14
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
EMA ASSESSMENT REPORTS STRIBILD (AUTHORIZED: HIV INFECTIONS)
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
EMA ASSESSMENT REPORTS REZOLSTA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
WHO-VATC QJ05AR09
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
Code System Code Type Description
DRUG BANK
DB09065
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
NDF-RT
N0000190107
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]
RXCUI
1306284
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL2095208
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
DAILYMED
LW2E03M5PG
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
NCI_THESAURUS
C97360
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID00143269
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
NDF-RT
N0000182137
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY Cytochrome P450 2D6 Inhibitors [MoA]
NDF-RT
N0000185503
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY P-Glycoprotein Inhibitors [MoA]
NDF-RT
N0000190113
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
SMS_ID
100000127699
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
PUBCHEM
25151504
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
MERCK INDEX
m3706
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY Merck Index
INN
9266
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
WIKIPEDIA
COBICISTAT
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
CHEBI
72291
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
FDA UNII
LW2E03M5PG
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
NDF-RT
N0000190114
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
NDF-RT
N0000190108
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]
CAS
1004316-88-4
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
EVMPD
SUB33760
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
IUPHAR
7535
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
DRUG CENTRAL
4299
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
USAN
WW-13
Created by admin on Sat Dec 16 16:02:02 GMT 2023 , Edited by admin on Sat Dec 16 16:02:02 GMT 2023
PRIMARY
Related Record Type Details
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
CYTOCHROME P450 1A2
METABOLIC ENZYME -> NON-INHIBITOR
IC50
OAT-2
TRANSPORTER -> NON-INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
IC50
CYTOCHROME P450 2B6
METABOLIC ENZYME -> INHIBITOR
INHIBITOR
IC50
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
OCT-2
TRANSPORTER -> INHIBITOR
IC50
OCT-3
TRANSPORTER -> NON-INHIBITOR
IC50
MATE-2
TRANSPORTER -> INHIBITOR
IC50
CYTOCHROME P450 2D6
METABOLIC ENZYME -> INHIBITOR
IC50
COBICISTAT ON SILICON DIOXIDE
SUB_CONCEPT->SUBSTANCE
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> INHIBITOR
INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
k(inactivation)
CYTOCHROME P450 2C9
METABOLIC ENZYME -> NON-INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
IC50
CYTOCHROME P450 2C19
METABOLIC ENZYME -> NON-INHIBITOR
IC50
CYTOCHROME P450 2C8
METABOLIC ENZYME -> NON-INHIBITOR
INHIBITOR
IC50
Related Record Type Details
Structure of BIS(THIAZOL-5-YLMETHYL)CARBONATE
IMPURITY -> PARENT
Structure of HYDROXY COBICISTAT
IMPURITY -> PARENT
Structure of 5-THIAZOLYLMETHYL N-((1R,4R)-4-(((2S)-2-AMINO-4-(4-MORPHOLINYL)-1-OXOBUTYL)AMINO)-5-PHENYL-1-(PHENYLMETHYL)PENTYL)CARBAMATE
IMPURITY -> PARENT
Structure of C,C′-Bis(5-thiazolylmethyl) N,N′-[(1R,4R)-1,4-bis(phenylmethyl)-1,4-butanediyl]bis[carbamate]
IMPURITY -> PARENT
Structure of 5-THIAZOLYLMETHYL N-((1R,4R)-4-AMINO-5-PHENYL-1-(PHENYLMETHYL)PENTYL)CARBAMATE
IMPURITY -> PARENT
Structure of N-METHYL-N-((2-(1-METHYLETHYL)-4-THIAZOLYL)METHYL)-N'-((3S)-TETRAHYDRO-2-OXO-3-FURANYL)UREA
IMPURITY -> PARENT
Structure of (2S)-2-((METHYL(((2-(PROPAN-2-YL)-1,3-THIAZOL-4-YL)METHYL))CARBAMOYL)AMINO)-4-(MORPHOLIN-4-YL)BUTANOIC ACID
IMPURITY -> PARENT
Related Record Type Details
Structure of COBICISTAT
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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DISCLAIMER
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