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Bevirimat

Names

[ CAS No. ]:
174022-42-5

[ Name ]:
Bevirimat

[Synonym ]:
DSB
UNII-S125DW66N8
3-O-(3',3'-dimethylsuccinyl)betulinic acid
YK FH312
YK-FH312
PA-457
BVM
(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-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Bevirimat
Butanedioic acid, 2,2-dimethyl-, 4-[(3β)-28-hydroxy-28-oxolup-20(29)-en-3-yl] ester
(3β)-3-[(3-Carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid

Biological Activity

[Description]:

Bevirimat(YK FH312; FH11327; MPC-4326) is an anti-HIV drug derived from a betulinic acid-like compound; is believed to inhibit HIV by a novel mechanism, so-called maturation inhibition.IC50 value:Target: Anti-HIVLike 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.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV
Research Areas >> Infection
Natural Products >> Terpenoids and Glycosides

[References]

[1]. Smith PF, et al. Phase I and II study of the safety, virologic effect, and pharmacokinetics/pharmacodynamics of single-dose 3-o-(3',3'-dimethylsuccinyl)betulinic acid (bevirimat) against human immunodeficiency virus infection. Antimicrob Agents Chemother. 2007 Oct;51(10):3574-81.

[2]. Salzwedel K, et al. Maturation inhibitors: a new therapeutic class targets the virus structure. AIDS Rev. 2007 Jul-Sep;9(3):162-72.

[3]. Martin DE, et al. Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection. Antivir Chem Chemother. 2008;19(3):107-13.


[Related Small Molecules]

Cenicriviroc | Ebselen | Triciribine | Raltegravir (potassium salt) | Tipranavir | DELAVIRDINE MESYLATE | Bictegravir | TAK-779 | Betulinic acid | Nelfinavir mesylate | Cabotegravir | nevirapine | Zidovudine | Celgosivir (hydrochloride)

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
662.7±40.0 °C at 760 mmHg

[ Molecular Formula ]:
C36H56O6

[ Molecular Weight ]:
584.826

[ Flash Point ]:
197.7±20.8 °C

[ Exact Mass ]:
584.407715

[ PSA ]:
100.90000

[ LogP ]:
10.15

[ Vapour Pressure ]:
0.0±4.3 mmHg at 25°C

[ Index of Refraction ]:
1.548

[ Storage condition ]:
-20°C

Synthetic Route

Click to get detail synthetic route