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Technical details about Elvitegravir, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: 697761-98-1, Gs-9137, Jtk-303, Vitekta, Gs 9137, Elvitegravir (gs-9137)
Molecular Formula
C23H23ClFNO5
Molecular Weight
447.9  g/mol
InChI Key
JUZYLCPPVHEVSV-LJQANCHMSA-N
FDA UNII
4GDQ854U53

Elvitegravir is a modified quinolone antibiotic with activity against human immunodeficiency virus 1. Elvitegravir is an inhibitor of viral integrase and retains activity against integrase mutants that are resistant to Raltegravir.
Elvitegravir is a Human Immunodeficiency Virus Integrase Strand Transfer Inhibitor. The mechanism of action of elvitegravir is as a HIV Integrase Inhibitor, and Cytochrome P450 2C9 Inducer.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-[(3-chloro-2-fluorophenyl)methyl]-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxoquinoline-3-carboxylic acid
2.1.2 InChI
InChI=1S/C23H23ClFNO5/c1-12(2)19(11-27)26-10-16(23(29)30)22(28)15-8-14(20(31-3)9-18(15)26)7-13-5-4-6-17(24)21(13)25/h4-6,8-10,12,19,27H,7,11H2,1-3H3,(H,29,30)/t19-/m1/s1
2.1.3 InChI Key
JUZYLCPPVHEVSV-LJQANCHMSA-N
2.1.4 Canonical SMILES
CC(C)C(CO)N1C=C(C(=O)C2=C1C=C(C(=C2)CC3=C(C(=CC=C3)Cl)F)OC)C(=O)O
2.1.5 Isomeric SMILES
CC(C)[C@@H](CO)N1C=C(C(=O)C2=C1C=C(C(=C2)CC3=C(C(=CC=C3)Cl)F)OC)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
4GDQ854U53
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gs 9137

2. Gs-9137

3. Gs9137

4. Jtk 303

5. Jtk-303

6. Jtk303

7. Vitekta

2.3.2 Depositor-Supplied Synonyms

1. 697761-98-1

2. Gs-9137

3. Jtk-303

4. Vitekta

5. Gs 9137

6. Elvitegravir (gs-9137)

7. Evg

8. Unii-4gdq854u53

9. (s)-6-(3-chloro-2-fluorobenzyl)-1-(1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

10. 6-(3-chloro-2-fluorobenzyl)-1-[1(s)-(hydroxymethyl)-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

11. Chebi:72289

12. 6-[(3-chloro-2-fluorophenyl)methyl]-1-[(2s)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxoquinoline-3-carboxylic Acid

13. Chembl204656

14. 4gdq854u53

15. D06677

16. 6-(3-chloro-2-fluorobenzyl)-1-((2s)-1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

17. 6-(3-chloro-2-fluorobenzyl)-1-[(2s)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

18. Jtk 303

19. 3-quinolinecarboxylic Acid, 6-((3-chloro-2-fluorophenyl)methyl)-1,4-dihydro-1-((1s)-1-(hydroxymethyl)-2-methylpropyl)-7-methoxy-4-oxo-

20. 6-(3-chloro-2-fluorobenzyl)-1-[(1s)-1-(hydroxymethyl)-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

21. Jtk303

22. Elvitegravir [usan]

23. Gs9137

24. Elvitegravir [usan:inn]

25. Elvitegravirum

26. 6-(3-chloro-2-fluorobenzyl)-1-((1s)-1-(hydroxymethyl)-2-methylpropyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

27. 6-[(3-chloro-2-fluoro-phenyl)methyl]-1-[(1s)-1-(hydroxymethyl)-2-methyl-propyl]-7-methoxy-4-oxo-quinoline-3-carboxylic Acid

28. Elv

29. Vitekta (tn)

30. Elvitegravir [mi]

31. Elvitegravir (jan/usan)

32. Elvitegravir [inn]

33. Elvitegravir [jan]

34. Elvitegravir (jtk-303)

35. Elvitegravir [vandf]

36. Elvitegravir [mart.]

37. Mls006011136

38. Elvitegravir [who-dd]

39. Schembl726252

40. Gtpl11574

41. Bcpp000242

42. Dtxsid101021650

43. Elvitegravir [orange Book]

44. Ex-a1542

45. Bdbm50183273

46. Mfcd11846134

47. S2001

48. Vitekta Component Elvitegravir

49. Zinc13682481

50. Elvitegravir; Gs9137; Jtk 303

51. Stribild Component Elvitegravir

52. Akos025396642

53. Bcp9000642

54. Ccg-269208

55. Compound 2 [pmid: 18281931]

56. Cs-0439

57. Db09101

58. Elvitegravir (gs-9137, Jtk-303)

59. Elvitegravir Component Of Genvoya

60. Elvitegravir Component Of Vitekta

61. Elvitegravir Component Of Stribild

62. Ncgc00346565-01

63. Ncgc00346565-04

64. Ncgc00346565-08

65. Ac-29947

66. As-16986

67. Hy-14740

68. Smr004702914

69. Elvitegravir 100 Microg/ml In Acetonitrile

70. A4070

71. Sw219721-1

72. Ec-000.2332

73. Ab01274749-01

74. Ab01274749_02

75. J-518006

76. Q2740966

77. Brd-k54472332-001-01-8

78. 3-quinolinecarboxylic Acid, 6-[(3-chloro-2-fluorophenyl)methyl]-1,4-dihydro-1-[(1s)-1-isopropyl-2-hydroxyethyl]-7-methoxy-4-oxo-

79. 6-(3-chloro-2-fluorobenzyl)-1-[(s)-1-hydroxymethyl-2-methylpropyl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

2.4 Create Date
2005-10-07
3 Chemical and Physical Properties
Molecular Weight 447.9 g/mol
Molecular Formula C23H23ClFNO5
XLogP35.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count7
Exact Mass447.1248787 g/mol
Monoisotopic Mass447.1248787 g/mol
Topological Polar Surface Area87.1 Ų
Heavy Atom Count31
Formal Charge0
Complexity702
Isotope Atom Count0
Defined Atom Stereocenter Count1
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

Elvitegravir in combination with an HIV protease inhibitor coadministered with ritonavir and with other antiretroviral drug(s) is indicated for the treatment of HIV-1 infection in antiretroviral treatment-experienced adults.


FDA Label


Vitekta co-administered with a ritonavir-boosted protease inhibitor and with other antiretroviral agents, is indicated for the treatment of human-immunodeficiency-virus-1 (HIV-1) infection in adults who are infected with HIV-1 without known mutations associated with resistance to elvitegravir.


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.)


Anti-Retroviral Agents

Agents used to treat RETROVIRIDAE INFECTIONS. (See all compounds classified as Anti-Retroviral Agents.)


Integrase Inhibitors

Compounds which inhibit or antagonize biosynthesis or actions of integrase. (See all compounds classified as Integrase Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
ELVITEGRAVIR
5.2.2 FDA UNII
4GDQ854U53
5.2.3 Pharmacological Classes
Mechanisms of Action [MoA] - Cytochrome P450 2C9 Inducers
5.3 ATC Code

J05AX11


J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AJ - Integrase inhibitors

J05AJ02 - Elvitegravir


5.4 Absorption, Distribution and Excretion

Absorption

Following oral administration of elvitegravir and ritonavir with food, in HIV-1 infected subjects, peak elvitegravir plasma concentrations were observed approximately 4 hours post-dose.


Route of Elimination

Following oral administration of [14C]elvitegravir/ritonavir, 94.8% of the dose was recovered in feces, while 6.7% was recovered in urine as metabolites.


5.5 Metabolism/Metabolites

Elvitegravir undergoes primarily oxidative metabolism via CYP3A, and is secondarily glucuronidated via UGT1A1/3 enzymes. Metabolites are found in the plasma at very low concentrations, displayed considerably lower anti-HIV activity, and did not contribute to the overall antiviral activity of elvitegravir.


5.6 Biological Half-Life

The median terminal plasma half-life following administration of elvitegravir and ritonavir was approximately 8.7 hours.


5.7 Mechanism of Action

Elvitegravir is an HIV-1 integrase strand transfer inhibitor (INSTI). Integrase is an HIV-1 encoded enzyme that is required for viral replication. Inhibition of integrase prevents the integration of HIV-1 DNA into host genomic DNA, blocking the formation of the HIV-1 provirus and propagation of the viral infection. Elvitegravir does not inhibit human topoisomerases I or II.


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