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MedKoo Cat#: 524481 | Name: BMS-488043

Description:

WARNING: This product is for research use only, not for human or veterinary use.

BMS-488043 is a novel and unique oral small-molecule inhibitor of the attachment of human immunodeficiency virus type 1 (HIV-1) to CD4(+) lymphocytes.

Chemical Structure

BMS-488043
BMS-488043
CAS#452296-83-2

Theoretical Analysis

MedKoo Cat#: 524481

Name: BMS-488043

CAS#: 452296-83-2

Chemical Formula: C22H22N4O5

Exact Mass: 422.1590

Molecular Weight: 422.44

Elemental Analysis: C, 62.55; H, 5.25; N, 13.26; O, 18.94

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
BMS-488043; BMS488043; BMS 488043; UNII-MKS21EJ435; CHEMBL238103; BMS 043.
IUPAC/Chemical Name
1-(4-benzoylpiperazin-1-yl)-2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione
InChi Key
FCBQJNCAKZSIAH-NDEPHWFRSA-N
InChi Code
InChI=1S/C21H23FN2O3S/c22-17-3-1-15(2-4-17)13-16-7-9-24(10-8-16)11-12-28(26)18-5-6-19-20(14-18)27-21(25)23-19/h1-6,14,16H,7-13H2,(H,23,25)/t28-/m0/s1
SMILES Code
c1(ncc(c2c1[nH]cc2C(=O)C(=O)N1CCN(CC1)C(=O)c1ccccc1)OC)OC
Appearance
Solid powder
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
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 422.44 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.

Recalculate based on batch purity %
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
1: Habgood M, Sugden IJ, Kazantsev AV, Adjiman CS, Pantelides CC. Efficient Handling of Molecular Flexibility in Ab Initio Generation of Crystal Structures. J Chem Theory Comput. 2015 Apr 14;11(4):1957-69. doi: 10.1021/ct500621v. PubMed PMID: 26574397. 2: Patel RV, Park SW. Pyrroloaryls and pyrroloheteroaryls: Inhibitors of the HIV fusion/attachment, reverse transcriptase and integrase. Bioorg Med Chem. 2015 Sep 1;23(17):5247-63. doi: 10.1016/j.bmc.2015.06.016. Epub 2015 Jun 14. Review. PubMed PMID: 26116177. 3: Sato S, Inokuma T, Otsubo N, Burton DR, Barbas CF 3rd. Chemically Programmed Antibodies AS HIV-1 Attachment Inhibitors. ACS Med Chem Lett. 2013 May 9;4(5):460-465. PubMed PMID: 23750312; PubMed Central PMCID: PMC3673733. 4: Regueiro-Ren A, Xue QM, Swidorski JJ, Gong YF, Mathew M, Parker DD, Yang Z, Eggers B, D'Arienzo C, Sun Y, Malinowski J, Gao Q, Wu D, Langley DR, Colonno RJ, Chien C, Grasela DM, Zheng M, Lin PF, Meanwell NA, Kadow JF. Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment. 12. Structure-activity relationships associated with 4-fluoro-6-azaindole derivatives leading to the identification of 1-(4-benzoylpiperazin-1-yl)-2-(4-fluoro-7-[1,2,3]triazol-1-yl-1h-pyrrolo[2,3-c]py ridin-3-yl)ethane-1,2-dione (BMS-585248). J Med Chem. 2013 Feb 28;56(4):1656-69. doi: 10.1021/jm3016377. Epub 2013 Feb 7. PubMed PMID: 23360431. 5: Bender JA, Yang Z, Eggers B, Gong YF, Lin PF, Parker DD, Rahematpura S, Zheng M, Meanwell NA, Kadow JF. Inhibitors of HIV-1 attachment. Part 11: the discovery and structure-activity relationships associated with 4,6-diazaindole cores. Bioorg Med Chem Lett. 2013 Jan 1;23(1):218-22. doi: 10.1016/j.bmcl.2012.10.118. Epub 2012 Nov 5. PubMed PMID: 23206859. 6: Li L, Chen H, Zhao RN, Han JG. The investigations on HIV-1 gp120 bound with BMS-488043 by using docking and molecular dynamics simulations. J Mol Model. 2013 Feb;19(2):905-17. doi: 10.1007/s00894-012-1619-5. Epub 2012 Oct 20. PubMed PMID: 23086459. 7: Kadow JF, Ueda Y, Meanwell NA, Connolly TP, Wang T, Chen CP, Yeung KS, Zhu J, Bender JA, Yang Z, Parker D, Lin PF, Colonno RJ, Mathew M, Morgan D, Zheng M, Chien C, Grasela D. Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment 6. Preclinical and human pharmacokinetic profiling of BMS-663749, a phosphonooxymethyl prodrug of the HIV-1 attachment inhibitor 2-(4-benzoyl-1-piperazinyl)-1-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxo ethanone (BMS-488043). J Med Chem. 2012 Mar 8;55(5):2048-56. doi: 10.1021/jm201218m. Epub 2012 Feb 22. PubMed PMID: 22356441. 8: Da LT, Quan JM, Wu YD. Understanding the binding mode and function of BMS-488043 against HIV-1 viral entry. Proteins. 2011 Jun;79(6):1810-9. doi: 10.1002/prot.23005. Epub 2011 Apr 4. PubMed PMID: 21465559. 9: Hanna GJ, Lalezari J, Hellinger JA, Wohl DA, Nettles R, Persson A, Krystal M, Lin P, Colonno R, Grasela DM. Antiviral activity, pharmacokinetics, and safety of BMS-488043, a novel oral small-molecule HIV-1 attachment inhibitor, in HIV-1-infected subjects. Antimicrob Agents Chemother. 2011 Feb;55(2):722-8. doi: 10.1128/AAC.00759-10. Epub 2010 Nov 15. PubMed PMID: 21078951; PubMed Central PMCID: PMC3028796. 10: Zhou N, Nowicka-Sans B, Zhang S, Fan L, Fang J, Fang H, Gong YF, Eggers B, Langley DR, Wang T, Kadow J, Grasela D, Hanna GJ, Alexander L, Colonno R, Krystal M, Lin PF. In vivo patterns of resistance to the HIV attachment inhibitor BMS-488043. Antimicrob Agents Chemother. 2011 Feb;55(2):729-37. doi: 10.1128/AAC.01173-10. Epub 2010 Nov 15. PubMed PMID: 21078948; PubMed Central PMCID: PMC3028813. 11: Zhou N, Fan L, Ho HT, Nowicka-Sans B, Sun Y, Zhu Y, Hu Y, McAuliffe B, Rose B, Fang H, Wang T, Kadow J, Krystal M, Alexander L, Colonno R, Lin PF. Increased sensitivity of HIV variants selected by attachment inhibitors to broadly neutralizing antibodies. Virology. 2010 Jul 5;402(2):256-61. doi: 10.1016/j.virol.2010.03.033. Epub 2010 Apr 18. PubMed PMID: 20400170. 12: Zhang S, Alexander L, Wang T, Agler M, Zhou N, Fang H, Kadow J, Clapham P, Lin PF. Protection against HIV-envelope-induced neuronal cell destruction by HIV attachment inhibitors. Arch Virol. 2010 May;155(5):777-81. doi: 10.1007/s00705-010-0644-x. Epub 2010 Mar 19. PubMed PMID: 20300783. 13: Yang Z, Zadjura LM, Marino AM, D'Arienzo CJ, Malinowski J, Gesenberg C, Lin PF, Colonno RJ, Wang T, Kadow JF, Meanwell NA, Hansel SB. Utilization of in vitro Caco-2 permeability and liver microsomal half-life screens in discovering BMS-488043, a novel HIV-1 attachment inhibitor with improved pharmacokinetic properties. J Pharm Sci. 2010 Apr;99(4):2135-52. doi: 10.1002/jps.21948. PubMed PMID: 19780144. 14: Wang T, Yin Z, Zhang Z, Bender JA, Yang Z, Johnson G, Yang Z, Zadjura LM, D'Arienzo CJ, DiGiugno Parker D, Gesenberg C, Yamanaka GA, Gong YF, Ho HT, Fang H, Zhou N, McAuliffe BV, Eggers BJ, Fan L, Nowicka-Sans B, Dicker IB, Gao Q, Colonno RJ, Lin PF, Meanwell NA, Kadow JF. Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment. 5. An evolution from indole to azaindoles leading to the discovery of 1-(4-benzoylpiperazin-1-yl)-2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane -1,2-dione (BMS-488043), a drug candidate that demonstrates antiviral activity in HIV-1-infected subjects. J Med Chem. 2009 Dec 10;52(23):7778-87. doi: 10.1021/jm900843g. PubMed PMID: 19769332. 15: Tobyn M, Brown J, Dennis AB, Fakes M, Gao Q, Gamble J, Khimyak YZ, McGeorge G, Patel C, Sinclair W, Timmins P, Yin S. Amorphous drug-PVP dispersions: application of theoretical, thermal and spectroscopic analytical techniques to the study of a molecule with intermolecular bonds in both the crystalline and pure amorphous state. J Pharm Sci. 2009 Sep;98(9):3456-68. doi: 10.1002/jps.21738. PubMed PMID: 19603506. 16: Fakes MG, Vakkalagadda BJ, Qian F, Desikan S, Gandhi RB, Lai C, Hsieh A, Franchini MK, Toale H, Brown J. Enhancement of oral bioavailability of an HIV-attachment inhibitor by nanosizing and amorphous formulation approaches. Int J Pharm. 2009 Mar 31;370(1-2):167-74. doi: 10.1016/j.ijpharm.2008.11.018. Epub 2008 Nov 28. PubMed PMID: 19100319. 17: Kadow J, Wang HG, Lin PF. Small-molecule HIV-1 gp120 inhibitors to prevent HIV-1 entry: an emerging opportunity for drug development. Curr Opin Investig Drugs. 2006 Aug;7(8):721-6. Review. PubMed PMID: 16955683. 18: Ho HT, Fan L, Nowicka-Sans B, McAuliffe B, Li CB, Yamanaka G, Zhou N, Fang H, Dicker I, Dalterio R, Gong YF, Wang T, Yin Z, Ueda Y, Matiskella J, Kadow J, Clapham P, Robinson J, Colonno R, Lin PF. Envelope conformational changes induced by human immunodeficiency virus type 1 attachment inhibitors prevent CD4 binding and downstream entry events. J Virol. 2006 Apr;80(8):4017-25. PubMed PMID: 16571818; PubMed Central PMCID: PMC1440438. 19: McNicholl IR, McNicholl JJ. On the horizon: promising investigational antiretroviral agents. Curr Pharm Des. 2006;12(9):1091-103. Review. PubMed PMID: 16515488. 20: De Clercq E. Emerging anti-HIV drugs. Expert Opin Emerg Drugs. 2005 May;10(2):241-73. Review. PubMed PMID: 15934866.