Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

SML2057

Sigma-Aldrich

Bevirimat

≥98% (HPLC)

Synonym(s):

(3b)-3-(3-Carboxy-3-methyl-1-oxobutoxy)lup-20(29)-en-28-oic acid, 3-0-(3′-3′-Dimethylsuccinyl)betulinic acid, BVM, MPC-4326, O-(3,3-Dimethylsuccinyl)betulinic acid, PA-457

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C36H56O6
CAS Number:
174022-42-5
Molecular Weight:
584.83
MDL number:
MFCD00954243
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

CC([C@H]1[C@]2([H])[C@@]3([H])CC[C@@]4([H])[C@](CC[C@]5([H])[C@]4(C)CC[C@H](OC(CC(C)(C(O)=O)C)=O)C5(C)C)(C)[C@]3(C)CC[C@@]2(C(O)=O)CC1)=C

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

InChI key

YJEJKUQEXFSVCJ-WRFMNRASSA-N

Biochem/physiol Actions

Bevirimat is the first in class HIV maturation inhibitor. It acts by inhibiting the processing of the Gag capsid (CA)/spacer peptide 1 (SP1), which causes accumulation of CA/SP1 (p25) precursor proteins and blocks maturation of the viral core particle.
It also causes defective core condensation and releases the non-infectious virus particles from cells infected with human immunodeficiency virus (HIV). Thus, bevirimat blocks the spread of HIV infection to other cells.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Albert T Nguyen et al.
Retrovirology, 8, 101-101 (2011-12-14)
Bevirimat, the prototype Human Immunodeficiency Virus type 1 (HIV-1) maturation inhibitor, is highly potent in cell culture and efficacious in HIV-1 infected patients. In contrast to inhibitors that target the active site of the viral protease, bevirimat specifically inhibits a
Safety and pharmacokinetics of Bevirimat (PA-457), a novel inhibitor of human immunodeficiency virus maturation, in healthy volunteers.
Martin DE, et al.
Antimicrobial Agents and Chemotherapy, 51(9), 3063-3066 (2007)
Zeyu Lin et al.
PLoS pathogens, 12(11), e1005990-e1005990 (2016-11-29)
HIV-1 maturation inhibitors (MIs) disrupt the final step in the HIV-1 protease-mediated cleavage of the Gag polyprotein between capsid p24 capsid (CA) and spacer peptide 1 (SP1), leading to the production of infectious virus. BMS-955176 is a second generation MI
Patrick F Smith et al.
Antimicrobial agents and chemotherapy, 51(10), 3574-3581 (2007-07-20)
Bevirimat [3-O-(3',3'-dimethylsuccinyl)betulinic acid] is the first in a new class of anti-human immunodeficiency virus (HIV) drugs that inhibit viral maturation by specifically blocking cleavage of the Gag capsid (CA) precursor, CA-SP1, to mature CA protein, resulting in defective core condensation

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service