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Lenacapavir

Lenacapavir

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

2 NDC API

2 NDC API

DEVELOPMENTS

23 Drug(s) in Development

23 Drug(s) in Development

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1 Suppliers

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2 Dossiers, 2 FDA Orange Book

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8 US Patents, 2 US Exclusivities

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Also known as: Gs-6207, 2189684-44-2, Gs-hiv, Gs-ca2, Gs-ca-2, Lenacapavir [usan]

Molecular Formula

C₃₉H₃₂ClF₁₀N₇O₅S₂

Molecular Weight

968.3 g/mol

InChI Key

BRYXUCLEHAUSDY-WEWMWRJBSA-N

FDA UNII

A9A0O6FB4H

Lenacapavir is under investigation in clinical trial NCT04150068 (Study to Evaluate the Safety and Efficacy of Lenacapavir in Combination With an Optimized Background Regimen in Heavily Treatment Experienced Participants Living With HIV-1 Infection With Multidrug Resistance).

1 2D Structure

Lenacapavir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(1S)-1-[3-[4-chloro-3-(methanesulfonamido)-1-(2,2,2-trifluoroethyl)indazol-7-yl]-6-(3-methyl-3-methylsulfonylbut-1-ynyl)pyridin-2-yl]-2-(3,5-difluorophenyl)ethyl]-2-[(2S,4R)-5,5-difluoro-9-(trifluoromethyl)-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-dien-7-yl]acetamide

2.1.2 InChI

InChI=1S/C39H32ClF10N7O5S2/c1-36(2,63(3,59)60)10-9-21-5-6-22(23-7-8-26(40)30-32(23)57(17-37(43,44)45)54-35(30)55-64(4,61)62)31(51-21)27(13-18-11-19(41)14-20(42)12-18)52-28(58)16-56-34-29(33(53-56)39(48,49)50)24-15-25(24)38(34,46)47/h5-8,11-12,14,24-25,27H,13,15-17H2,1-4H3,(H,52,58)(H,54,55)/t24-,25+,27-/m0/s1

2.1.3 InChI Key

BRYXUCLEHAUSDY-WEWMWRJBSA-N

2.1.4 Canonical SMILES

CC(C)(C#CC1=NC(=C(C=C1)C2=C3C(=C(C=C2)Cl)C(=NN3CC(F)(F)F)NS(=O)(=O)C)C(CC4=CC(=CC(=C4)F)F)NC(=O)CN5C6=C(C7CC7C6(F)F)C(=N5)C(F)(F)F)S(=O)(=O)C

2.1.5 Isomeric SMILES

CC(C)(C#CC1=NC(=C(C=C1)C2=C3C(=C(C=C2)Cl)C(=NN3CC(F)(F)F)NS(=O)(=O)C)[C@H](CC4=CC(=CC(=C4)F)F)NC(=O)CN5C6=C([C@H]7C[C@H]7C6(F)F)C(=N5)C(F)(F)F)S(=O)(=O)C

2.2 Other Identifiers

2.2.1 UNII

A9A0O6FB4H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Gs-ca1

2.3.2 Depositor-Supplied Synonyms

1. Gs-6207

2. 2189684-44-2

3. Gs-hiv

4. Gs-ca2

5. Gs-ca-2

6. Lenacapavir [usan]

7. Gs-ca1

8. A9a0o6fb4h

9. Gs-714207

10. Gs6207

11. N-[(1s)-1-[3-[4-chloro-3-(methanesulfonamido)-1-(2,2,2-trifluoroethyl)indazol-7-yl]-6-(3-methyl-3-methylsulfonylbut-1-ynyl)pyridin-2-yl]-2-(3,5-difluorophenyl)ethyl]-2-[(2s,4r)-5,5-difluoro-9-(trifluoromethyl)-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-dien-7-yl]acetamide

12. N-((s)-1-(3-(4-chloro-3-(methylsulfonamido)-1-(2,2,2-trifluoroethyl)-1h-indazol-7-yl)-6-(3-methyl-3-(methylsulfonyl)but-1-yn-1-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-((3bs,4ar)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1h-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide

13. N-[(1s)-1-(3-{4-chloro-3-[(methylsulfonyl)amino]-1-(2,2,2-trifluoroethyl)-1h-indazol-7-yl}-6-[3-methyl-3-(methylsulfonyl)but-1-yn-1-yl]pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl]-2-[(3bs,4ar)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1h-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl]acetamide

14. Qng

15. Lenacapavir [inn]

16. Unii-a9a0o6fb4h

17. Lenacapavir [who-dd]

18. Chembl4594438

19. Schembl19875642

20. Gtpl11446

21. Ex-a5518

22. Who 11108

23. At20076

24. Hy-111964

25. Cs-0094695

26. 1h-cyclopropa(3,4)cyclopenta(1,2-c)pyrazole, N-((1s)-1-(3-(4-chloro-3-((methylsulfonyl)amino)-1-(2,2,2-trifluoroethyl)-1h-indazol-7-yl)-6-(3-methyl-3-(methylsulfonyl)-1-butyn-1-yl)-2-pyridinyl)-2-(3,5-difluorophenyl)ethyl)-5,5-difluoro-3b,4,4a,5-tetrahydro-3-(trifluoromethyl)-, (3bs,4ar)-

27. N-((1s)-1-(3-(4-chloro-3-(methanesulfonamido)-1-(2,2,2-trifluoroethyl)-1h-indazol-7-yl)-6-(3-(methanesulfonyl)-3-methylbut-1-yn-1-yl)pyridin-2-yl)-2-(3,5- Difluorophenyl)ethyl)-2-((3bs,4ar)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1h-cyclopropa(3,4)cyclopenta(1,2-c)pyrazol-1-yl)acetamide

28. N-[(1s)-1-[3-[4-chloro-3-(methanesulfonamido)-1-(2,2,2-trifluoroethyl)indazol-7-yl]-6-(3-methyl-3-methylsulfonyl-but-1-ynyl)-2-pyridyl]-2-(3,5-difluorophenyl)ethyl]-2-[difluoro(trifluoromethyl)[?]yl]acetamide

2.4 Create Date

2018-05-16

3 Chemical and Physical Properties

Molecular Formula	C₃₉H₃₂ClF₁₀N₇O₅S₂
Molecular Weight	968.3 g/mol
XLogP3	6.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	13
Exact Mass	967.1435188 g/mol
Monoisotopic Mass	967.1435188 g/mol
Topological Polar Surface Area	175 Å²
Heavy Atom Count	64
Formal Charge	0
Complexity	2040
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Treatment of human immunodeficiency virus (HIV-1) infection

* Sunlenca injection: , in combination with other antiretroviral(s), is indicated for the treatment of adults with multidrug resistant HIV 1 infection for whom it is otherwise not possible to construct a suppressive anti viral regimen (see sections 4. 2 and 5. 1).

* Sunlenca tablet: , in combination with other antiretroviral(s), is indicated for the treatment of adults with multidrug resistant HIV 1 infection for whom it is otherwise not possible to construct a suppressive anti viral regimen, for oral loading prior to administration of long-acting lenacapavir injection (see sections 4. 2 and 5. 1).

5 Pharmacology and Biochemistry

5.1 ATC Code

J05AX

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AX - Other antivirals

J05AX31 - Lenacapavir