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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24900196Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900196
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900196 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TYBOST Approved UseTYBOST (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 Date2014 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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) n = 12 Health Status: healthy Age Group: 27 years (range: 18–45 years) Sex: M+F Population Size: 12 Sources: |
|
400 mg single, oral Highest studied dose |
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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203100Orig1s000ClinPharmR.pdf=60 Page: 60.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203100Orig1s000ClinPharmR.pdf#page=56 Page: 53.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203100Orig1s000ClinPharmR.pdf#page=56 Page: 53.0 |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203100Orig1s000ClinPharmR.pdf=60 Page: 60.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Cobicistat (GS-9350): A Potent and Selective Inhibitor of Human CYP3A as a Novel Pharmacoenhancer. | 2010 Aug 12 |
|
Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. | 2010 Mar |
|
Pharmacokinetics and bioavailability of an integrase and novel pharmacoenhancer-containing single-tablet fixed-dose combination regimen for the treatment of HIV. | 2010 Nov |
|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28231276
HIV infected monocytic (U1) cellss were treated with 2 uM Cobicistat as a booster drug for 5 uM elvitegravir.
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 16:02:00 GMT 2023
by
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on
Sat Dec 16 16:02:00 GMT 2023
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Record UNII |
LW2E03M5PG
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
J05AR09
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FDA ORPHAN DRUG |
577917
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WHO-ATC |
J05AR15
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WHO-ATC |
V03AX03
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NDF-RT |
N0000191001
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EMA ASSESSMENT REPORTS |
GENVOYA (AUTHORIZED: HIV INFECTIONS)
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LIVERTOX |
NBK547911
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NCI_THESAURUS |
C471
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WHO-VATC |
QV03AX03
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WHO-ATC |
J05AR18
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EMA ASSESSMENT REPORTS |
EVOTAZ (AUTHORIZED: HIV INFECTIONS)
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WHO-ATC |
J05AR14
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EMA ASSESSMENT REPORTS |
STRIBILD (AUTHORIZED: HIV INFECTIONS)
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EMA ASSESSMENT REPORTS |
REZOLSTA (AUTHORIZED: HIV INFECTIONS)
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WHO-VATC |
QJ05AR09
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DB09065
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PRIMARY | |||
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N0000190107
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PRIMARY | Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA] | ||
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1306284
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PRIMARY | RxNorm | ||
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CHEMBL2095208
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LW2E03M5PG
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PRIMARY | |||
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C97360
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PRIMARY | |||
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DTXSID00143269
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PRIMARY | |||
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N0000182137
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PRIMARY | Cytochrome P450 2D6 Inhibitors [MoA] | ||
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N0000185503
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PRIMARY | P-Glycoprotein Inhibitors [MoA] | ||
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N0000190113
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PRIMARY | Breast Cancer Resistance Protein Inhibitors [MoA] | ||
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100000127699
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PRIMARY | |||
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25151504
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m3706
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PRIMARY | Merck Index | ||
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9266
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COBICISTAT
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72291
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LW2E03M5PG
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N0000190114
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PRIMARY | Cytochrome P450 3A Inhibitors [MoA] | ||
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N0000190108
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PRIMARY | Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA] | ||
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1004316-88-4
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SUB33760
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7535
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4299
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WW-13
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR |
IC50
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METABOLIC ENZYME -> NON-INHIBITOR |
IC50
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TRANSPORTER -> NON-INHIBITOR |
IC50
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METABOLIC ENZYME -> INHIBITOR |
TIME-DEPENDENT INHIBITION
IC50
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METABOLIC ENZYME -> INHIBITOR |
INHIBITOR
IC50
|
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR |
IC50
|
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TRANSPORTER -> NON-INHIBITOR |
IC50
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TRANSPORTER -> INHIBITOR |
IC50
|
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METABOLIC ENZYME -> INHIBITOR |
IC50
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SUB_CONCEPT->SUBSTANCE | |||
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TRANSPORTER -> INHIBITOR |
INHIBITOR
IC50
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METABOLIC ENZYME -> INHIBITOR |
TIME-DEPENDENT INHIBITION
k(inactivation)
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METABOLIC ENZYME -> NON-INHIBITOR |
IC50
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METABOLIC ENZYME -> INHIBITOR |
TIME-DEPENDENT INHIBITION
IC50
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METABOLIC ENZYME -> NON-INHIBITOR |
IC50
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METABOLIC ENZYME -> NON-INHIBITOR |
INHIBITOR
IC50
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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