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

Details

Stereochemistry ABSOLUTE
Molecular Formula C40H53N7O5S2
Molecular Weight 776.0264
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COBICISTAT

SMILES

CC(C)c1nc(CN(C)C(=N[C@@]([H])(CCN2CCOCC2)C(=N[C@]([H])(CC[C@]([H])(Cc3ccccc3)N=C(O)OCc4cncs4)Cc5ccccc5)O)O)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 776.0264
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1411516800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.99 μg/mL
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Atazanavir
COBICISTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7.6 mg × h/mL
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Atazanavir
COBICISTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: Atazanavir
COBICISTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2.5%
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: 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:
healthy, 27 years (range: 18–45 years)
Health Status: healthy
Age Group: 27 years (range: 18–45 years)
Sex: M+F
Sources:
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
healthy, 27 years (range: 18–45 years)
Health Status: healthy
Age Group: 27 years (range: 18–45 years)
Sex: M+F
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely [IC50 1.88 uM]
likely [IC50 3.5 uM]
no
no
no
no
no
no
no
not expected [IC50 2.8 uM]
not expected [IC50 30.1 uM]
not expected [IC50 8.24 uM]
not expected [IC50 >100 uM]
not expected [IC50 >100 uM]
not expected [IC50 >25 uM]
not expected [IC50 >25 uM]
not expected [IC50 >25 uM]
weak [IC50 22.5 uM]
weak (co-administration study)
Comment: increased Cmax of digoxin by 41%, increased AUC0-inf by 8%
Page: 61,63
weak [IC50 59 uM]
weak
yes [IC50 0.03 uM]
yes [IC50 16.3 uM]
yes [IC50 20.7 uM]
yes [IC50 9.2 uM]
Drug as victimTox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Cobicistat (GS-9350): A Potent and Selective Inhibitor of Human CYP3A as a Novel Pharmacoenhancer.
2010 Aug 12
Cobicistat boosts the intestinal absorption of transport substrates, including HIV protease inhibitors and GS-7340, in vitro.
2012 Oct
Pharmacokinetic enhancers in HIV therapeutics.
2014 Oct
Patents

Sample Use Guides

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
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 Fri Jun 25 23:00:06 UTC 2021
Edited
by admin
on Fri Jun 25 23:00:06 UTC 2021
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 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 [VANDF]
Common Name English
COBICISTAT [MI]
Common Name English
COBICISTAT [USAN]
Common Name English
EVOTAZ COMPONENT COBICISTAT
Brand Name English
COBICISTAT [WHO-DD]
Common 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 Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
WHO-ATC J05AR15
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
WHO-ATC V03AX03
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
NDF-RT N0000191001
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
FDA ORPHAN DRUG 577917
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
EMA ASSESSMENT REPORTS GENVOYA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
LIVERTOX 231
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
NCI_THESAURUS C471
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
WHO-VATC QV03AX03
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
WHO-ATC J05AR18
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
EMA ASSESSMENT REPORTS EVOTAZ (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
WHO-ATC J05AR14
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
EMA ASSESSMENT REPORTS STRIBILD (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
EMA ASSESSMENT REPORTS REZOLSTA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
WHO-VATC QJ05AR09
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
Code System Code Type Description
DRUG BANK
DB09065
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
NDF-RT
N0000190107
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]
RXCUI
1306284
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL2095208
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
NCI_THESAURUS
C97360
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
EPA CompTox
1004316-88-4
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
NDF-RT
N0000182137
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY Cytochrome P450 2D6 Inhibitors [MoA]
NDF-RT
N0000185503
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY P-Glycoprotein Inhibitors [MoA]
NDF-RT
N0000190113
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
PUBCHEM
25151504
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
MERCK INDEX
M3706
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY Merck Index
INN
9266
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
WIKIPEDIA
COBICISTAT
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
FDA UNII
LW2E03M5PG
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
NDF-RT
N0000190114
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
NDF-RT
N0000190108
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]
CAS
1004316-88-4
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
EVMPD
SUB33760
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
IUPHAR
7535
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
DRUG CENTRAL
4299
Created by admin on Fri Jun 25 23:00:06 UTC 2021 , Edited by admin on Fri Jun 25 23:00:06 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
IC50
METABOLIC ENZYME -> NON-INHIBITOR
IC50
TRANSPORTER -> NON-INHIBITOR
IC50
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
IC50
METABOLIC ENZYME -> INHIBITOR
INHIBITOR
IC50
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
IC50
TRANSPORTER -> NON-INHIBITOR
IC50
TRANSPORTER -> INHIBITOR
IC50
METABOLIC ENZYME -> INHIBITOR
IC50
SUB_CONCEPT->SUBSTANCE
TRANSPORTER -> INHIBITOR
INHIBITOR
IC50
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
k(inactivation)
METABOLIC ENZYME -> NON-INHIBITOR
IC50
METABOLIC ENZYME -> INHIBITOR
TIME-DEPENDENT INHIBITION
IC50
METABOLIC ENZYME -> NON-INHIBITOR
IC50
METABOLIC ENZYME -> NON-INHIBITOR
INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC