WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H124943
CAS#: 2023798-97-0 (HCl hydrate)
Description: GSK3532795, also known as BMS-955176, is a potent, orally active, second-generation HIV-1 maturation inhibitor (MI) that advanced through phase IIb clinical trials. GSK3532795 combines broad coverage of polymorphic viruses (EC50 <15 nM toward a panel of common polymorphisms representative of 96.5% HIV-1 subtype B virus) with a favorable pharmacokinetic profile in preclinical species.
Hodoodo Cat#: H124943
Name: BMS-955176 HCl hydrate
CAS#: 2023798-97-0 (HCl hydrate)
Chemical Formula: C42H65ClN2O5S
Exact Mass: 744.43
Molecular Weight: 745.500
Elemental Analysis: C, 67.67; H, 8.79; Cl, 4.76; N, 3.76; O, 10.73; S, 4.30
This product is not in stock, which may be available by custom synthesis.
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Related CAS #: 1392312-45-6 (free base) 2023808-13-9 (HCl) 2023798-97-0 (HCl hydrate) 2097784-79-5 (oxalate) 2097784-79-5 (TFA)
Synonym: VF90GZ0UQI; UNII-VF90GZ0UQI; BMS-955176 hydrochloride monohydrate; 2023798-97-0;
IUPAC/Chemical Name: 4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[2-(1,1-dioxo-1,4-thiazinan-4-yl)ethylamino]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid;hydrate;hydrochloride
InChi Key: YBXZLRMEOIDFCT-JMNTVBGTSA-N
InChi Code: InChI=1S/C42H62N2O4S.ClH.H2O/c1-28(2)31-14-19-42(43-22-23-44-24-26-49(47,48)27-25-44)21-20-40(6)33(36(31)42)12-13-35-39(5)17-15-32(29-8-10-30(11-9-29)37(45)46)38(3,4)34(39)16-18-41(35,40)7;;/h8-11,15,31,33-36,43H,1,12-14,16-27H2,2-7H3,(H,45,46);1H;1H2/t31-,33+,34-,35+,36+,39-,40+,41+,42-;;/m0../s1
SMILES Code: O=C(O)C1=CC=C(C2=CC[C@@]3(C)[C@@](C2(C)C)([H])CC[C@@]4(C)[C@]5(C)CC[C@](CC[C@H]6C(C)=C)(NCCN(CC7)CCS7(=O)=O)[C@@]6([H])[C@@]5([H])CC[C@]34[H])C=C1.[H]O[H].[H]Cl
Appearance: To be determined
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 745.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Ortiz A, Soumeillant M, Savage SA, Strotman NA, Haley M, Benkovics T, Nye J, Xu Z, Tan Y, Ayers S, Gao Q, Kiau S. Synthesis of HIV-Maturation Inhibitor BMS-955176 from Betulin by an Enabling Oxidation Strategy. J Org Chem. 2017 May 5;82(9):4958-4963. doi: 10.1021/acs.joc.7b00438. Epub 2017 Apr 19. PubMed PMID: 28406018.
2: Strotman NA, Ortiz A, Savage SA, Wilbert CR, Ayers S, Kiau S. Revisiting a Classic Transformation: A Lossen Rearrangement Initiated by Nitriles and "Pseudo-Catalytic" in Isocyanate. J Org Chem. 2017 Apr 21;82(8):4044-4049. doi: 10.1021/acs.joc.7b00450. Epub 2017 Apr 12. PubMed PMID: 28394130.
3: Lin Z, Cantone J, Lu H, Nowicka-Sans B, Protack T, Yuan T, Yang H, Liu Z, Drexler D, Regueiro-Ren A, Meanwell NA, Cockett M, Krystal M, Lataillade M, Dicker IB. Mechanistic Studies and Modeling Reveal the Origin of Differential Inhibition of Gag Polymorphic Viruses by HIV-1 Maturation Inhibitors. PLoS Pathog. 2016 Nov 28;12(11):e1005990. doi: 10.1371/journal.ppat.1005990. eCollection 2016 Nov. PubMed PMID: 27893830; PubMed Central PMCID: PMC5125710.
4: Regueiro-Ren A, Liu Z, Chen Y, Sin N, Sit SY, Swidorski JJ, Chen J, Venables BL, Zhu J, Nowicka-Sans B, Protack T, Lin Z, Terry B, Samanta H, Zhang S, Li Z, Beno BR, Huang XS, Rahematpura S, Parker DD, Haskell R, Jenkins S, Santone KS, Cockett MI, Krystal M, Meanwell NA, Hanumegowda U, Dicker IB. Discovery of BMS-955176, a Second Generation HIV-1 Maturation Inhibitor with Broad Spectrum Antiviral Activity. ACS Med Chem Lett. 2016 Apr 22;7(6):568-72. doi: 10.1021/acsmedchemlett.6b00010. eCollection 2016 Jun 9. PubMed PMID: 27326328; PubMed Central PMCID: PMC4904268.
5: Nowicka-Sans B, Protack T, Lin Z, Li Z, Zhang S, Sun Y, Samanta H, Terry B, Liu Z, Chen Y, Sin N, Sit SY, Swidorski JJ, Chen J, Venables BL, Healy M, Meanwell NA, Cockett M, Hanumegowda U, Regueiro-Ren A, Krystal M, Dicker IB. Identification and Characterization of BMS-955176, a Second-Generation HIV-1 Maturation Inhibitor with Improved Potency, Antiviral Spectrum, and Gag Polymorphic Coverage. Antimicrob Agents Chemother. 2016 Jun 20;60(7):3956-69. doi: 10.1128/AAC.02560-15. Print 2016 Jul. PubMed PMID: 27090171; PubMed Central PMCID: PMC4914680.
6: Gulick RM. Choosing Initial Antiretroviral Therapy: Current Recommendations for Initial Therapy and Newer or Investigational Agents. Top Antivir Med. 2015 Oct-Nov;23(4):128-31. Review. PubMed PMID: 26713502.
7: Olender SA, Taylor BS, Wong M, Wilkin TJ. CROI 2015: Advances in Antiretroviral Therapy. Top Antivir Med. 2015 Mar-Apr;23(1):28-45. PubMed PMID: 25965310.
