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Safety Information

SML2057

Sigma-Aldrich

Bevirimat

≥98% (HPLC)

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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
Empirical Formula (Hill Notation):
C36H56O6
CAS Number:
174022-42-5
Molecular Weight:
584.83
MDL number:
MFCD00954243
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

Regulatory Information

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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
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)

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