GS-6207, HIV-1 capsid inhibitor.

Lenacapavir, also known as GS-6207, is a HIV-1 capsid inhibitor. Lenacapavir shows anti-HIV activity. Lenacapavir displays a mean EC50 of 50 pM (20-160 pM) against 23 HIV-1 clinical isolates from different subtypes in peripheral blood mononuclear cells (PBMCs).

Product information

CAS Number: 2189684-44-2

Molecular Weight: 968.28

Formula: C39H32ClF10N7O5S2

Synonym:

Lenacapavir

GS 6207

GS6207

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-[(2S, 4R)-5, 5-difluoro-9-(trifluoromethyl)-7, 8-diazatricyclo[4.3.0.0², ⁴]nona-1(6), 8-dien-7-yl]acetamide

Related CAS Number:

2375019-65-9 (Deleted CAS)

2413356-73-5 (Deleted CAS)

Chemical Name: 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-[(2S, 4R)-5, 5-difluoro-9-(trifluoromethyl)-7, 8-diazatricyclo[4.3.0.0, ]nona-1(6), 8-dien-7-yl]acetamide

Smiles: CC(C)(C#CC1=CC=C(C2=CC=C(Cl)C3=C2N(CC(F)(F)F)N=C3NS(C)(=O)=O)C(=N1)[C@H](CC1C=C(F)C=C(F)C=1)NC(=O)CN1N=C(C2[C@H]3C[C@H]3C(F)(F)C1=2)C(F)(F)F)S(C)(=O)=O

InChiKey: BRYXUCLEHAUSDY-WEWMWRJBSA-N

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

Technical Data

Appearance: Solid powder

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

References:

1. Link JO, Rhee MS, Tse WC, Zheng J, Somoza JR, Rowe W, Begley R, Chiu A, Mulato A, Hansen D, Singer E, Tsai LK, Bam RA, Chou CH, Canales E, Brizgys G, Zhang JR, Li J, Graupe M, Morganelli P, Liu Q, Wu Q, Halcomb RL, Saito RD, Schroeder SD, Lazerwith SE, Bondy S, Jin D, Hung M, Novikov N, Liu X, Villaseñor AG, Cannizzaro CE, Hu EY, Anderson RL, Appleby TC, Lu B, Mwangi J, Liclican A, Niedziela-Majka A, Papalia GA, Wong MH, Leavitt SA, Xu Y, Koditek D, Stepan GJ, Yu H, Pagratis N, Clancy S, Ahmadyar S, Cai TZ, Sellers S, Wolckenhauer SA, Ling J, Callebaut C, Margot N, Ram RR, Liu YP, Hyland R, Sinclair GI, Ruane PJ, Crofoot GE, McDonald CK, Brainard DM, Lad L, Swaminathan S, Sundquist WI, Sakowicz R, Chester AE, Lee WE, Daar ES, Yant SR, Cihlar T. Clinical targeting of HIV capsid protein with a long-acting small molecule. Nature. 2020 Aug;584(7822):614-618. doi: 10.1038/s41586-020-2443-1. Epub 2020 Jul 1. PMID: 32612233.
2. Rana AI, Castillo-Mancilla JR, Tashima KT, Landovitz RL. Advances in Long- Acting Agents for the Treatment of HIV Infection. Drugs. 2020 Apr;80(6):535-545. doi: 10.1007/s40265-020-01284-1. PMID: 32180205; PMCID: PMC7206978.
3. Marcelin AG, Charpentier C, Jary A, Perrier M, Margot N, Callebaut C, Calvez V, Descamps D. Frequency of capsid substitutions associated with GS-6207 in vitro resistance in HIV-1 from antiretroviral-naive and -experienced patients. J Antimicrob Chemother. 2020 Jun 1;75(6):1588-1590. doi: 10.1093/jac/dkaa060. PMID: 32154864.
4. Pham HT, Yoo S, Mesplède T. Combination therapies currently under investigation in phase I and phase II clinical trials for HIV-1. Expert Opin Investig Drugs. 2020 Mar;29(3):273-283. doi: 10.1080/13543784.2020.1724281. Epub 2020 Feb 5. PMID: 31994943.
5. McArthur C, Gallazzi F, Quinn TP, Singh K. HIV Capsid Inhibitors Beyond PF74. Diseases. 2019 Oct 30;7(4):56. doi: 10.3390/diseases7040056. PMID: 31671622; PMCID: PMC6956309.
6. Singh K, Gallazzi F, Hill KJ, Burke DH, Lange MJ, Quinn TP, Neogi U, Sönnerborg A. GS-CA Compounds: First-In-Class HIV-1 Capsid Inhibitors Covering Multiple Grounds. Front Microbiol. 2019 Jun 20;10:1227. doi: 10.3389/fmicb.2019.01227. PMID: 31312185; PMCID: PMC6613529.

Products are for research use only. Not for human use.