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

MedKoo CAT#: 510352

CAS#: 174022-42-5

Description: Bevirimat, also known as MPC-4326 and PA-457, is an anti-HIV drug derived from a betulinic acid-like compound, first isolated from Syzygium claviflorum, a Chinese herb. It is believed to inhibit HIV by a novel mechanism, so-called maturation inhibition. Like protease inhibitors, bevirimat and other maturation inhibitors interfere with protease processing of newly translated HIV polyprotein precursor, called gag. Bevirimat prevents this viral replication by specifically inhibiting cleavage of the capsid protein (CA) from the SP1 spacer protein.


Chemical Structure

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Bevirimat
CAS# 174022-42-5

Theoretical Analysis

MedKoo Cat#: 510352
Name: Bevirimat
CAS#: 174022-42-5
Chemical Formula: C36H56O6
Exact Mass: 584.40769
Molecular Weight: 584.84
Elemental Analysis: C, 73.93; H, 9.65; O, 16.41

Price and Availability

Size Price Availability Quantity
5.0mg USD 325.0 2 weeks
10.0mg USD 650.0 2 weeks
25.0mg USD 1450.0 2 weeks
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Synonym: MPC4326; MPC 4326; MPC-4326; PA457; PA 457; PA-457; FH11327; FH-11327; FH 11327; YK FH312; Bevirimat.

IUPAC/Chemical Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-((3-carboxy-3-methylbutanoyl)oxy)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid

InChi Key: YJEJKUQEXFSVCJ-WRFMNRASSA-N

InChi Code: InChI=1S/C36H56O6/c1-21(2)22-12-17-36(30(40)41)19-18-34(8)23(28(22)36)10-11-25-33(7)15-14-26(42-27(37)20-31(3,4)29(38)39)32(5,6)24(33)13-16-35(25,34)9/h22-26,28H,1,10-20H2,2-9H3,(H,38,39)(H,40,41)/t22-,23+,24-,25+,26-,28+,33-,34+,35+,36-/m0/s1

SMILES Code: CC1(C)[C@@H](OC(CC(C)(C(O)=O)C)=O)CC[C@]2(C)[C@@]3([H])CC[C@]4([H])[C@@]5([H])[C@H](C(C)=C)CC[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H]

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

Preparing Stock Solutions

The following data is based on the product molecular weight 584.84 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

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1: Coric P, Turcaud S, Souquet F, Briant L, Gay B, Royer J, Chazal N, Bouaziz S. Synthesis and biological evaluation of a new derivative of bevirimat that targets the Gag CA-SP1 cleavage site. Eur J Med Chem. 2013 Apr;62:453-65. doi: 10.1016/j.ejmech.2013.01.013. Epub 2013 Jan 19. PubMed PMID: 23399723.

2: Dang Z, Ho P, Zhu L, Qian K, Lee KH, Huang L, Chen CH. New betulinic acid derivatives for bevirimat-resistant human immunodeficiency virus type-1. J Med Chem. 2013 Mar 14;56(5):2029-37. doi: 10.1021/jm3016969. Epub 2013 Feb 20. PubMed PMID: 23379607; PubMed Central PMCID: PMC3600082.

3: Qian K, Bori ID, Chen CH, Huang L, Lee KH. Anti-AIDS agents 90. novel C-28 modified bevirimat analogues as potent HIV maturation inhibitors. J Med Chem. 2012 Sep 27;55(18):8128-36. Epub 2012 Sep 14. PubMed PMID: 22978745; PubMed Central PMCID: PMC3478670.

4: Dang Z, Qian K, Ho P, Zhu L, Lee KH, Huang L, Chen CH. Synthesis of betulinic acid derivatives as entry inhibitors against HIV-1 and bevirimat-resistant HIV-1 variants. Bioorg Med Chem Lett. 2012 Aug 15;22(16):5190-4. doi: 10.1016/j.bmcl.2012.06.080. Epub 2012 Jul 3. PubMed PMID: 22818973; PubMed Central PMCID: PMC3426442.

5: Nguyen AT, Feasley CL, Jackson KW, Nitz TJ, Salzwedel K, Air GM, Sakalian M. The prototype HIV-1 maturation inhibitor, bevirimat, binds to the CA-SP1 cleavage site in immature Gag particles. Retrovirology. 2011 Dec 7;8:101. doi: 10.1186/1742-4690-8-101. PubMed PMID: 22151792; PubMed Central PMCID: PMC3267693.

6: Dybowski JN, Riemenschneider M, Hauke S, Pyka M, Verheyen J, Hoffmann D, Heider D. Improved Bevirimat resistance prediction by combination of structural and sequence-based classifiers. BioData Min. 2011 Nov 14;4:26. doi: 10.1186/1756-0381-4-26. PubMed PMID: 22082002; PubMed Central PMCID: PMC3248369.

7: Fun A, van Maarseveen NM, Pokorná J, Maas RE, Schipper PJ, Konvalinka J, Nijhuis M. HIV-1 protease inhibitor mutations affect the development of HIV-1 resistance to the maturation inhibitor bevirimat. Retrovirology. 2011 Aug 24;8:70. doi: 10.1186/1742-4690-8-70. PubMed PMID: 21864346; PubMed Central PMCID: PMC3184055.

8: Lu W, Salzwedel K, Wang D, Chakravarty S, Freed EO, Wild CT, Li F. A single polymorphism in HIV-1 subtype C SP1 is sufficient to confer natural resistance to the maturation inhibitor bevirimat. Antimicrob Agents Chemother. 2011 Jul;55(7):3324-9. doi: 10.1128/AAC.01435-10. Epub 2011 Apr 18. PubMed PMID: 21502630; PubMed Central PMCID: PMC3122462.

9: Keller PW, Adamson CS, Heymann JB, Freed EO, Steven AC. HIV-1 maturation inhibitor bevirimat stabilizes the immature Gag lattice. J Virol. 2011 Feb;85(4):1420-8. doi: 10.1128/JVI.01926-10. Epub 2010 Nov 24. PubMed PMID: 21106735; PubMed Central PMCID: PMC3028903.

10: Knapp DJ, Harrigan PR, Poon AF, Brumme ZL, Brockman M, Cheung PK. In vitro selection of clinically relevant bevirimat resistance mutations revealed by "deep" sequencing of serially passaged, quasispecies-containing recombinant HIV-1. J Clin Microbiol. 2011 Jan;49(1):201-8. doi: 10.1128/JCM.01868-10. Epub 2010 Nov 17. PubMed PMID: 21084518; PubMed Central PMCID: PMC3020451.



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