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Chemistry

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Also known as: 1004316-88-4, Cobicistat (gs-9350), Gs-9350, Tybost, Gs 9350, Cobicistat,gs-9350
Molecular Formula
C40H53N7O5S2
Molecular Weight
776.0  g/mol
InChI Key
ZCIGNRJZKPOIKD-CQXVEOKZSA-N
FDA UNII
LW2E03M5PG

Cobicistat
A carbamate and thiazole derivative that functions as a CYTOCHROME P450 CYP3A INHIBITOR to enhance the concentration of ANTI-HIV AGENTS, with which it is used in combination, for the treatment of HIV INFECTIONS.
Cobicistat is a Cytochrome P450 3A Inhibitor. The mechanism of action of cobicistat is as a Cytochrome P450 3A Inhibitor, and P-Glycoprotein Inhibitor, and Cytochrome P450 2D6 Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and Multidrug and Toxin Extrusion Transporter 1 Inhibitor.
1 2D Structure

Cobicistat

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,3-thiazol-5-ylmethyl N-[(2R,5R)-5-[[(2S)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate
2.1.2 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
2.1.3 InChI Key
ZCIGNRJZKPOIKD-CQXVEOKZSA-N
2.1.4 Canonical SMILES
CC(C)C1=NC(=CS1)CN(C)C(=O)NC(CCN2CCOCC2)C(=O)NC(CCC(CC3=CC=CC=C3)NC(=O)OCC4=CN=CS4)CC5=CC=CC=C5
2.1.5 Isomeric SMILES
CC(C)C1=NC(=CS1)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
2.2 Other Identifiers
2.2.1 UNII
LW2E03M5PG
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 9350, Gs

2. Gs 9350

3. Gs-9350

4. Gs9350

5. Tybost

2.3.2 Depositor-Supplied Synonyms

1. 1004316-88-4

2. Cobicistat (gs-9350)

3. Gs-9350

4. Tybost

5. Gs 9350

6. Cobicistat,gs-9350

7. Unii-lw2e03m5pg

8. Chebi:72291

9. Lw2e03m5pg

10. 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

11. 1,3-thiazol-5-ylmethyl N-[(2r,5r)-5-[[(2s)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate

12. Thiazol-5-ylmethyl ((2r,5r)-5-((s)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-4-morpholinobutanamido)-1,6-diphenylhexan-2-yl)carbamate

13. 1,3-thiazol-5-ylmethyl 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

14. 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)-

15. Cobicistat [usan]

16. Cobicistat [usan:inn]

17. Cobicistatum

18. 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)-

19. Thiazol-5-ylmethyl (2r,5r)-5-((s)-2-(3-((2-isopropylthiazol-4-yl)methyl)-3-methylureido)-4-morpholinobutanamido)-1,6-diphenylhexan-2-ylcarbamate

20. Tybost (tn)

21. Cobicistat [mi]

22. Cobicistat [inn]

23. Cobicistat [jan]

24. Cobicistat; Gs-9350

25. Cobicistat [vandf]

26. Cobicistat [who-dd]

27. Cobicistat On Silicon Dioxide

28. Cobicistat (jan/usan/inn)

29. Gtpl7535

30. Schembl2736227

31. Chembl2095208

32. Cobicistat [orange Book]

33. Cobicistat, (r,r,s)-

34. Dtxsid00143269

35. Evotaz Component Cobicistat

36. Genvoya Component Cobicistat

37. Symtuza Component Cobicistat

38. Bcp06630

39. Ex-a2578

40. Rezolsta Component Cobicistat

41. Stribild Component Cobicistat

42. Bdbm50447471

43. Mfcd18251449

44. Prezcobix Component Cobicistat

45. S2900

46. Zinc85537014

47. Cobicistat Component Of Evotaz

48. Akos025404908

49. Cobicistat Component Of Genvoya

50. Cobicistat Component Of Symtuza

51. Ccg-270459

52. Cobicistat Component Of Stribild

53. Cs-0742

54. Db09065

55. Cobicistat Component Of Prezcobix

56. Ncgc00386235-04

57. Ncgc00386235-06

58. Ac-28961

59. As-17061

60. Hy-10493

61. Sw219553-1

62. D09881

63. Ab01566899_01

64. Q5138908

65. (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

66. 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

67. Thiazol-5-ylmethyl ((1r,4r)-1-benzyl-4-({(2s)-2-((methyl{(2-(1-methylethyl)thiazol-4-yl)methyl}carbamoyl)amino)-4-(morpholin-4-yl)butanoyl}amino)-5-phenylpentyl)carbamate

68. Thiazol-5-ylmethyl N-[(1r,4r)-1-benzyl-4-[[(2s)-2-[[(2-isopropylthiazol-4-yl)methyl-methyl-carbamoyl]amino]-4-morpholino-butanoyl]amino]-5-phenyl-pentyl]carbamate

2.4 Create Date
2009-02-23
3 Chemical and Physical Properties
Molecular Weight 776.0 g/mol
Molecular Formula C40H53N7O5S2
XLogP35.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count10
Rotatable Bond Count20
Exact Mass775.35496016 g/mol
Monoisotopic Mass775.35496016 g/mol
Topological Polar Surface Area195 Ų
Heavy Atom Count54
Formal Charge0
Complexity1120
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug 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.


FDA Label


Tybost is indicated as a pharmacokinetic enhancer of atazanavir 300 mg once daily or darunavir 800 mg once daily as part of antiretroviral combination therapy in human immunodeficiency virus-1 (HIV-1) infected adults and adolescents aged 12 years and older:

- weighing at least 35 kg coadministered with atazanavir or

- weighing at least 40 kg coadministered with darunavir.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)


Cytochrome P-450 CYP3A Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
COBICISTAT
5.2.2 FDA UNII
LW2E03M5PG
5.2.3 Pharmacological Classes
Cytochrome P450 2D6 Inhibitors [MoA]; Cytochrome P450 3A Inhibitor [EPC]; Cytochrome P450 3A Inhibitors [MoA]; Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]; Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Breast Cancer Resistance Protein Inhibitors [MoA]
5.3 ATC Code

V03AX03


J05AR14

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


V - Various

V03 - All other therapeutic products

V03A - All other therapeutic products

V03AX - Other therapeutic products

V03AX03 - Cobicistat


5.4 Absorption, Distribution and Excretion

Absorption

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


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.


5.5 Metabolism/Metabolites

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


5.6 Biological Half-Life

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


5.7 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.


DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;300M...DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;300MG

USFDA APPLICATION NUMBER - 203100

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DOSAGE - TABLET;ORAL - 150MG;800MG

USFDA APPLICATION NUMBER - 205395

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DOSAGE - TABLET;ORAL - EQ 300MG BASE;150MG

USFDA APPLICATION NUMBER - 206353

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DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;EQ 1...DOSAGE - TABLET;ORAL - 150MG;150MG;200MG;EQ 10MG BASE

USFDA APPLICATION NUMBER - 207561

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