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Amprenavir

CAT: 0804-HY-17430-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-17430-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Amprenavir (VX-478) is a HIV protease inhibitor (Ki=0.6 nM) used to treat HIV infection. Amprenavir is also a SARS-CoV 3CLpro inhibitor with an IC50 of 1.09 μM.
CAS Number
161814-49-9
Product Name Alternative
VX-478
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
HIV; HIV Protease; SARS-CoV
Type
Reference compound
Related Pathways
Anti-infection; Metabolic Enzyme/Protease
Applications
COVID-19-anti-virus
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/Amprenavir.html
Purity
99.55
Solubility
DMSO : ≥ 100 mg/mL
Smiles
O=C(O[C@@H]1COCC1)N[C@@H](CC2=CC=CC=C2)[C@H](O)CN(S(=O)(C3=CC=C(N)C=C3)=O)CC(C)C
Molecular Formula
C25H35N3O6S
Molecular Weight
505.63
Precautions
H302, H315, H319, H335
References & Citations
[1]Sadler BM, Stein DS. Clinical pharmacology and pharmacokinetics of amprenavir. Ann Pharmacother. 2002 Jan;36 (1) :102-18.|[2]Esposito V, Verdina A, Manente L, Amprenavir inhibits the migration in human hepatocarcinoma cell and the growth of xenografts. J Cell Physiol. 2013 Mar;228 (3) :640-5.|[3]Helsley RN, Sui Y, Ai N, Pregnane X Receptor Mediates Dyslipidemia Induced by the HIV Protease Inhibitor Amprenavir in Mice. Mol Pharmacol. 2013 Jun;83 (6) :1190-9.|[4]Qi Sun, et al. Bardoxolone and bardoxolone methyl, two Nrf2 activators in clinical trials, inhibit SARS-CoV-2 replication and its 3C-like protease. Signal Transduct Target Ther. 2021 May 29;6 (1) :212.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Amprenavir

Amprenavir is a carbamate ester, a sulfonamide and a tetrahydrofuryl ester. It has a role as a HIV protease inhibitor and an antiviral drug.

CAS Number161814-49-9
PubChem CID65016
IUPAC Name[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
Molecular FormulaC25H35N3O6S
Molecular Weight505.6
XLogP2.9
Topological Polar Surface Area140
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count12
Heavy Atom Count35
Formal Charge0
Complexity745
SMILES
CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
InChI
InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1
InChIKey
YMARZQAQMVYCKC-OEMFJLHTSA-N
Chemical Structure
2D Structure
2D structure of Amprenavir
CAS: 161814-49-9
CID: 65016
Formula: C25H35N3O6S
MW: 505.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight505.6
XLogP32.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count12
Exact Mass505.22465702
Monoisotopic Mass505.22465702
Topological Polar Surface Area140 Ų
Heavy Atom Count35
Formal Charge0
Complexity745
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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