Identification

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Name
Cobicistat
Accession Number
DB09065
Type
Small Molecule
Groups
Approved
Description

Cobicistat, marketed under the name Tybost (formerly GS-9350), indicated for treating infection with human immunodeficiency virus (HIV). Although it does not have any anti-HIV activity, cobicistat acts as a pharmacokinetic enhancer by inhibiting cytochrome P450 3A isoforms (CYP3A) and therefore increases the systemic exposure of coadministered agents that are metabolized by CYP3A enzymes. More specifically, cobicistat is 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. Increasing systemic exposure of anti-retrovirals (ARVs) without increasing dosage allows for better treatment outcomes and a decreased side effect profile.

Structure
Thumb
Synonyms
  • 1,3-thiazol-5-ylmethyl [(2R,5R)-5-{[(2S)-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-4-(morpholin-4-yl)butanoyl]amino}-1,6-diphenylhexan-2-yl]carbamate
  • Cobicistat
External IDs
GS 9350 / GS-9350 / GS9350
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TybostTablet, film coated150 mg/1OralGilead Sciences, Inc.2014-09-24Not applicableUs
TybostTablet, film coated150 mgOralGilead Sciences Ireland Uc2013-09-19Not applicableEu
TybostTablet, film coated150 mgOralGilead Sciences Ireland Uc2013-09-19Not applicableEu
TybostTablet150 mgOralGilead Sciences2015-04-10Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
EvotazCobicistat (150 mg/1) + Atazanavir sulfate (300 mg/1)TabletOralA-S Medication Solutions2015-01-29Not applicableUs
EvotazCobicistat (150 mg/1) + Atazanavir sulfate (300 mg/1)TabletOralE.R. Squibb & Sons, L.L.C.2015-01-29Not applicableUs
EvotazCobicistat (150 mg/1) + Atazanavir sulfate (300 mg/1)TabletOralA-S Medication Solutions2015-01-29Not applicableUs
EvotazCobicistat (150 mg) + Atazanavir (300 mg)TabletOralBristol Myers Squibb2016-02-112017-09-22Canada
GenvoyaCobicistat (150 mg/1) + Elvitegravir (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir alafenamide fumarate (10 mg/1)TabletOralGilead Sciences, Inc.2015-11-05Not applicableUs
GenvoyaCobicistat (150 mg/1) + Elvitegravir (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir alafenamide fumarate (10 mg/1)TabletOralA-S Medication Solutions2015-11-05Not applicableUs
GenvoyaCobicistat (150 mg) + Elvitegravir (150 mg) + Emtricitabine (200 mg) + Tenofovir alafenamide (10 mg)Tablet, film coatedOralGilead Sciences Ireland Uc2015-11-19Not applicableEu
GenvoyaCobicistat (150 mg) + Elvitegravir (150 mg) + Emtricitabine (200 mg) + Tenofovir alafenamide (10 mg)TabletOralGilead Sciences2016-02-03Not applicableCanada
GenvoyaCobicistat (150 mg) + Elvitegravir (150 mg) + Emtricitabine (200 mg) + Tenofovir alafenamide (10 mg)Tablet, film coatedOralGilead Sciences Ireland Uc2015-11-19Not applicableEu
GenvoyaCobicistat (150 mg/1) + Elvitegravir (150 mg/1) + Emtricitabine (200 mg/1) + Tenofovir alafenamide fumarate (10 mg/1)TabletOralREMEDYREPACK INC.2017-06-06Not applicableUs
Categories
UNII
LW2E03M5PG
CAS number
1004316-88-4
Weight
Average: 776.03
Monoisotopic: 775.354960183
Chemical Formula
C40H53N7O5S2
InChI Key
ZCIGNRJZKPOIKD-CQXVEOKZSA-N
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
IUPAC Name
(1,3-thiazol-5-yl)methyl N-[(2R,5R)-5-[(2S)-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}-4-(morpholin-4-yl)butanamido]-1,6-diphenylhexan-2-yl]carbamate
SMILES
CC(C)C1=NC(CN(C)C(=O)N[C@@H](CCN2CCOCC2)C(=O)N[C@H](CC[C@H](CC2=CC=CC=C2)NC(=O)OCC2=CN=CS2)CC2=CC=CC=C2)=CS1

Pharmacology

Indication

Cobicistat is a CYP3A inhibitor 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. It is not interchangeable with ritonavir to increase systemic exposure of darunavir 600 mg twice daily, fosamprenavir, saquinavir, or tipranavir due to lack of exposure data. The use of cobicistat is not recommended with darunavir 600 mg twice daily, fosamprenavir, saquinavir or tipranavir. Complex or unknown mechanisms of drug interactions preclude extrapolation of ritonavir drug interactions to certain cobicistat interactions. Cobicistat and ritonavir when administered with either atazanavir or darunavir may result in different drug interactions when used with concomitant medications.

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action

Cobicistat is a mechanism-based inhibitor of cytochrome P450 3A (CYP3A) isoforms. Inhibition of CYP3A-mediated metabolism by cobicistat increases the systemic exposure of CYP3A substrates atazanavir and darunavir and therefore enables increased anti-viral activity at a lower dosage. Cobicistat does not have any anti-HIV activity on its own.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Median peak plasma concentrations were observed at 3.5 hours post-dose.

Volume of distribution
Not Available
Protein binding

97-98% bound to human plasma proteins.

Metabolism

Cobicistat is metabolized by CYP3A and to a minor extent by CYP2D6 enzymes and does not undergo glucuronidation.

Route of elimination

With single dose administration of [14C] cobicistat after multiple dosing of cobicistat for six days, the mean percent of the administered dose excreted in feces and urine was 86.2% and 8.2%, respectively.

Half life

The terminal plasma half-life of cobicistat is approximately 3 to 4 hours.

Clearance
Not Available
Toxicity

The most common adverse reactions reported during clinical trials were jaundice (13%), ocular icterus (15%), and nausea (12%).

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Cobicistat.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Cobicistat.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Cobicistat.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Cobicistat.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Cobicistat.
AbataceptThe metabolism of Cobicistat can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Cobicistat.
AcalabrutinibThe metabolism of Cobicistat can be decreased when combined with Acalabrutinib.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Cobicistat.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Cobicistat.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. German P, Warren D, West S, Hui J, Kearney BP: Pharmacokinetics and bioavailability of an integrase and novel pharmacoenhancer-containing single-tablet fixed-dose combination regimen for the treatment of HIV. J Acquir Immune Defic Syndr. 2010 Nov;55(3):323-9. doi: 10.1097/QAI.0b013e3181eb376b. [PubMed:20683270]
  2. Mathias AA, German P, Murray BP, Wei L, Jain A, West S, Warren D, Hui J, Kearney BP: Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. Clin Pharmacol Ther. 2010 Mar;87(3):322-9. doi: 10.1038/clpt.2009.228. Epub 2009 Dec 30. [PubMed:20043009]
  3. Larson KB, Wang K, Delille C, Otofokun I, Acosta EP: Pharmacokinetic enhancers in HIV therapeutics. Clin Pharmacokinet. 2014 Oct;53(10):865-72. doi: 10.1007/s40262-014-0167-9. [PubMed:25164142]
  4. Lepist EI, Phan TK, Roy A, Tong L, Maclennan K, Murray B, Ray AS: Cobicistat boosts the intestinal absorption of transport substrates, including HIV protease inhibitors and GS-7340, in vitro. Antimicrob Agents Chemother. 2012 Oct;56(10):5409-13. doi: 10.1128/AAC.01089-12. Epub 2012 Jul 30. [PubMed:22850510]
External Links
KEGG Drug
D09881
PubChem Compound
25151504
PubChem Substance
310264999
ChemSpider
25084912
BindingDB
50447471
ChEBI
72291
ChEMBL
CHEMBL2095208
PharmGKB
PA166165092
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Cobicistat
ATC Codes
J05AR09 — Emtricitabine, tenofovir disoproxil, elvitegravir and cobicistatJ05AR15 — Atazanavir and cobicistatJ05AR14 — Darunavir and cobicistatJ05AR22 — Emtricitabine, tenofovir alafenamide, darunavir and cobicistatV03AX03 — CobicistatJ05AR18 — Emtricitabine, tenofovir alafenamide, elvitegravir and cobicistat
AHFS Codes
  • 92:92.00 — Other Miscellaneous Therapeutic Agents
FDA label
Download (467 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
1Active Not RecruitingOtherHIV (Adult) / HIV in Adults1
1CompletedNot AvailableHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV)2
1CompletedNot AvailableHuman Immunodeficiency Virus Type 1 (HIV-1)1
1CompletedBasic ScienceHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
1CompletedOtherHIV-DDI1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentDrug-drug Interaction Study / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHealthy Volunteers5
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)3
1CompletedTreatmentInsulin Resistance1
1CompletedTreatmentPlasmodium Infections1
1RecruitingBasic ScienceHealthy Volunteers1
1RecruitingOtherHealthy Volunteers1
1RecruitingOtherPlasmodium Infections1
1RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
1RecruitingPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1RecruitingTreatmentInsulin Resistance1
1TerminatedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2, 3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2, 3WithdrawnTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
3Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection3
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections6
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHBV / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentHIV Risk1
3CompletedTreatmentHepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections6
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Pregnancy1
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection5
3RecruitingTreatmentHIV-1-infection1
3RecruitingTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4Active Not RecruitingOtherHealthy Volunteers1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
4CompletedOtherHealthy Volunteers1
4CompletedOtherHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4CompletedPreventionHuman Immunodeficiency Virus (HIV)2
4CompletedTreatment2- HIV Infection1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Sleep disorders and disturbances1
4CompletedTreatmentHepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4Not Yet RecruitingTreatmentHIV test positive1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingOtherHuman Immunodeficiency Virus (HIV)1
4RecruitingSupportive CareHuman Immunodeficiency Virus (HIV)1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentBone Diseases, Metabolic / Chronic Hepatitis C Virus (HCV) Infection / Co-Infection / HIV-1-infection / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Intravenous Drug Usage / Methadone Dependence / Opioid Dependence / Substance Abuse1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Severe Immunosuppression1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Neurocognitive Dysfunction1
4RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4TerminatedTreatmentAIDS-Related Dementia Complex1
Not AvailableActive Not RecruitingNot AvailableBone Diseases / Chronic Hepatitis B in HIV Patient / Kidney Injury1
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedOtherHuman Immunodeficiency Virus (HIV) / Sexually Transmitted Infections (STIs)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV)1
Not AvailableNot Yet RecruitingTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableRecruitingNot AvailableAcquired Immune Deficiency Syndrome (AIDS)1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV)2
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) / Illicit Drug User1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Tablet, film coatedOral
TabletOral150 mg
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral150 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7800788No2010-09-212022-02-02Us
US5914331Yes1999-06-222018-01-02Us
US6043230Yes2000-03-282018-01-25Us
US5814639Yes1998-09-292017-03-29Us
US6642245Yes2003-11-042021-05-04Us
US6703396Yes2004-03-092021-09-09Us
US5922695Yes1999-07-132018-01-25Us
US5935946Yes1999-08-102018-01-25Us
US5977089Yes1999-11-022018-01-25Us
US8592397No2013-11-262024-01-13Us
US8716264No2014-05-062024-01-13Us
US5843946Yes1998-12-012016-06-01Us
US7470506Yes2008-12-302019-12-23Us
USRE43802Yes2012-11-132017-04-19Us
US8597876Yes2013-12-032019-12-23Us
US7700645Yes2010-04-202027-06-26Us
USRE42889Yes2011-11-012017-04-19Us
US8518987Yes2013-08-272024-08-16Us
USRE43596Yes2012-08-212017-11-09Us
US5849911Yes1998-12-152017-12-20Us
US6087383Yes2000-07-112019-06-21Us
US8148374No2012-04-032029-09-03Us
US7635704No2009-12-222026-10-26Us
US7176220No2007-02-132023-11-20Us
US8981103No2015-03-172026-10-26Us
US8633219No2014-01-212030-04-24Us
US9296769No2016-03-292032-08-15Us
US7803788No2010-09-282022-02-02Us
US8754065No2014-06-172032-08-15Us
US7390791No2008-06-242022-05-07Us
US9457036No2016-10-042024-01-13Us
US9744181No2017-08-292024-01-13Us
US9891239No2018-02-132029-09-03Us
US9889115Yes2018-02-132019-12-23Us
US10039718No2018-08-072032-10-04Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility0.1 mg/mLFDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.00125 mg/mLALOGPS
logP4.36ALOGPS
logP4.99ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)14.18ChemAxon
pKa (Strongest Basic)6.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area138.02 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity211.49 m3·mol-1ChemAxon
Polarizability83.42 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an carbamoyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-carbamoyl-alpha amino acids and derivatives
Alternative Parents
Alpha amino acid amides / Amphetamines and derivatives / 2,4-disubstituted thiazoles / N-acyl amines / Morpholines / Heteroaromatic compounds / Carbamate esters / Ureas / Trialkylamines / Secondary carboxylic acid amides
show 7 more
Substituents
N-carbamoyl-alpha-amino acid or derivatives / Alpha-amino acid amide / Amphetamine or derivatives / 2,4-disubstituted 1,3-thiazole / Monocyclic benzene moiety / Fatty amide / Morpholine / N-acyl-amine / Oxazinane / Benzenoid
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
carbamate ester, ureas, monocarboxylic acid amide, 1,3-thiazole, morpholines (CHEBI:72291)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Mathias AA, German P, Murray BP, Wei L, Jain A, West S, Warren D, Hui J, Kearney BP: Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. Clin Pharmacol Ther. 2010 Mar;87(3):322-9. doi: 10.1038/clpt.2009.228. Epub 2009 Dec 30. [PubMed:20043009]
  2. Cobicistat versus ritonavir boosting and differences in the drug–drug interaction profiles with co-medications [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Mathias AA, German P, Murray BP, Wei L, Jain A, West S, Warren D, Hui J, Kearney BP: Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. Clin Pharmacol Ther. 2010 Mar;87(3):322-9. doi: 10.1038/clpt.2009.228. Epub 2009 Dec 30. [PubMed:20043009]
  2. Nanda K, Stuart GS, Robinson J, Gray AL, Tepper NK, Gaffield ME: Drug interactions between hormonal contraceptives and antiretrovirals. AIDS. 2017 Apr 24;31(7):917-952. doi: 10.1097/QAD.0000000000001392. [PubMed:28060009]
  3. Wang P, Shehu AI, Liu K, Lu J, Ma X: Biotransformation of Cobicistat: Metabolic Pathways and Enzymes. Drug Metab Lett. 2016;10(2):111-23. [PubMed:26935921]
  4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  5. Cobicistat FDA Label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Mathias AA, German P, Murray BP, Wei L, Jain A, West S, Warren D, Hui J, Kearney BP: Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. Clin Pharmacol Ther. 2010 Mar;87(3):322-9. doi: 10.1038/clpt.2009.228. Epub 2009 Dec 30. [PubMed:20043009]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Mathias AA, German P, Murray BP, Wei L, Jain A, West S, Warren D, Hui J, Kearney BP: Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. Clin Pharmacol Ther. 2010 Mar;87(3):322-9. doi: 10.1038/clpt.2009.228. Epub 2009 Dec 30. [PubMed:20043009]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
Inhibitor
General Function
Monooxygenase activity
Specific Function
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name
CYP3A43
Uniprot ID
Q9HB55
Uniprot Name
Cytochrome P450 3A43
Molecular Weight
57669.21 Da
References
  1. Mathias AA, German P, Murray BP, Wei L, Jain A, West S, Warren D, Hui J, Kearney BP: Pharmacokinetics and pharmacodynamics of GS-9350: a novel pharmacokinetic enhancer without anti-HIV activity. Clin Pharmacol Ther. 2010 Mar;87(3):322-9. doi: 10.1038/clpt.2009.228. Epub 2009 Dec 30. [PubMed:20043009]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Lepist EI, Phan TK, Roy A, Tong L, Maclennan K, Murray B, Ray AS: Cobicistat boosts the intestinal absorption of transport substrates, including HIV protease inhibitors and GS-7340, in vitro. Antimicrob Agents Chemother. 2012 Oct;56(10):5409-13. doi: 10.1128/AAC.01089-12. Epub 2012 Jul 30. [PubMed:22850510]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Lepist EI, Phan TK, Roy A, Tong L, Maclennan K, Murray B, Ray AS: Cobicistat boosts the intestinal absorption of transport substrates, including HIV protease inhibitors and GS-7340, in vitro. Antimicrob Agents Chemother. 2012 Oct;56(10):5409-13. doi: 10.1128/AAC.01089-12. Epub 2012 Jul 30. [PubMed:22850510]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da

Drug created on May 11, 2015 16:33 / Updated on November 21, 2019 12:27