WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H510352
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.
Hodoodo Cat#: H510352
Name: Bevirimat
CAS#: 174022-42-5
Chemical Formula: C36H56O6
Exact Mass: 584.41
Molecular Weight: 584.840
Elemental Analysis: C, 73.93; H, 9.65; O, 16.41
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
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
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.
| 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: Martin DE, Salzwedel K, Allaway GP. Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection. Antivir Chem Chemother. 2008;19(3):107-13. doi: 10.1177/095632020801900301. PMID: 19024627.
2: Kleinpeter AB, Freed EO. HIV-1 Maturation: Lessons Learned from Inhibitors. Viruses. 2020 Aug 26;12(9):940. doi: 10.3390/v12090940. PMID: 32858867; PMCID: PMC7552077.
3: Martin DE, Blum R, Doto J, Galbraith H, Ballow C. Multiple-dose pharmacokinetics and safety of bevirimat, a novel inhibitor of HIV maturation, in healthy volunteers. Clin Pharmacokinet. 2007;46(7):589-98. doi: 10.2165/00003088-200746070-00004. PMID: 17596104.
4: Verheyen J, Verhofstede C, Knops E, Vandekerckhove L, Fun A, Brunen D, Dauwe K, Wensing AM, Pfister H, Kaiser R, Nijhuis M. High prevalence of bevirimat resistance mutations in protease inhibitor-resistant HIV isolates. AIDS. 2010 Mar 13;24(5):669-73. doi: 10.1097/QAD.0b013e32833160fa. PMID: 19926962.
5: Heider D, Verheyen J, Hoffmann D. Predicting Bevirimat resistance of HIV-1 from genotype. BMC Bioinformatics. 2010 Jan 20;11:37. doi: 10.1186/1471-2105-11-37. PMID: 20089140; PMCID: PMC3224585.
6: 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. PMID: 22151792; PMCID: PMC3267693.
7: Wainberg MA, Albert J. Can the further clinical development of bevirimat be justified? AIDS. 2010 Mar 13;24(5):773-4. doi: 10.1097/QAD.0b013e328331c83b. PMID: 20154583.
8: Bullock P, Larsen D, Press R, Wehrman T, Martin DE. The absorption, distribution, metabolism and elimination of bevirimat in rats. Biopharm Drug Dispos. 2008 Oct;29(7):396-405. doi: 10.1002/bdd.625. PMID: 18615840.
9: 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. PMID: 22082002; PMCID: PMC3248369.
10: Stoddart CA, Joshi P, Sloan B, Bare JC, Smith PC, Allaway GP, Wild CT, Martin DE. Potent activity of the HIV-1 maturation inhibitor bevirimat in SCID- hu Thy/Liv mice. PLoS One. 2007 Nov 28;2(11):e1251. doi: 10.1371/journal.pone.0001251. PMID: 18043758; PMCID: PMC2080775.
11: Martin DE, Galbraith H, Schettler J, Ellis C, Doto J. Pharmacokinetic properties and tolerability of bevirimat and atazanavir in healthy volunteers: an open-label, parallel-group study. Clin Ther. 2008 Oct;30(10):1794-805. doi: 10.1016/j.clinthera.2008.10.006. PMID: 19014835.
12: Pak AJ, Purdy MD, Yeager M, Voth GA. Preservation of HIV-1 Gag Helical Bundle Symmetry by Bevirimat Is Central to Maturation Inhibition. J Am Chem Soc. 2021 Nov 17;143(45):19137-19148. doi: 10.1021/jacs.1c08922. Epub 2021 Nov 5. PMID: 34739240; PMCID: PMC8610020.
13: 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. PMID: 22818973; PMCID: PMC3426442.
14: Urano E, Ablan SD, Mandt R, Pauly GT, Sigano DM, Schneider JP, Martin DE, Nitz TJ, Wild CT, Freed EO. Alkyl Amine Bevirimat Derivatives Are Potent and Broadly Active HIV-1 Maturation Inhibitors. Antimicrob Agents Chemother. 2015 Oct 19;60(1):190-7. doi: 10.1128/AAC.02121-15. PMID: 26482309; PMCID: PMC4704169.
15: Zhao Y, Gu Q, Morris-Natschke SL, Chen CH, Lee KH. Incorporation of Privileged Structures into Bevirimat Can Improve Activity against Wild-Type and Bevirimat-Resistant HIV-1. J Med Chem. 2016 Oct 13;59(19):9262-9268. doi: 10.1021/acs.jmedchem.6b00461. Epub 2016 Sep 22. PMID: 27676157; PMCID: PMC5151175.
16: Neyret A, Gay B, Cransac A, Briant L, Coric P, Turcaud S, Laugâa P, Bouaziz S, Chazal N. Insight into the mechanism of action of EP-39, a bevirimat derivative that inhibits HIV-1 maturation. Antiviral Res. 2019 Apr;164:162-175. doi: 10.1016/j.antiviral.2019.02.014. Epub 2019 Feb 27. PMID: 30825471.
17: 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. PMID: 23379607; PMCID: PMC3600082.
18: 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. PMID: 23399723.
19: Chrobak E, Marciniec K, Dąbrowska A, Pęcak P, Bębenek E, Kadela-Tomanek M, Bak A, Jastrzębska M, Boryczka S. New Phosphorus Analogs of Bevirimat: Synthesis, Evaluation of Anti-HIV-1 Activity and Molecular Docking Study. Int J Mol Sci. 2019 Oct 21;20(20):5209. doi: 10.3390/ijms20205209. PMID: 31640137; PMCID: PMC6829466.
20: Temesgen Z, Feinberg JE. Drug evaluation: bevirimat--HIV Gag protein and viral maturation inhibitor. Curr Opin Investig Drugs. 2006 Aug;7(8):759-65. PMID: 16955688.
