Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H44N4O6S |
Molecular Weight | 624.791 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)N[C@@H](C(C1=CC=CC=C1)C2=CC=CC=C2)C(=O)NCCCC[C@@H](CO)N(CC(C)C)S(=O)(=O)C3=CC=C(N)C=C3
InChI
InChIKey=QAHLFXYLXBBCPS-IZEXYCQBSA-N
InChI=1S/C33H44N4O6S/c1-24(2)22-37(44(41,42)29-19-17-27(34)18-20-29)28(23-38)16-10-11-21-35-32(39)31(36-33(40)43-3)30(25-12-6-4-7-13-25)26-14-8-5-9-15-26/h4-9,12-15,17-20,24,28,30-31,38H,10-11,16,21-23,34H2,1-3H3,(H,35,39)(H,36,40)/t28-,31-/m0/s1
MX-100 (also known as PL-100) is a benzenesulfonamide derivative patented by Pharmacor Inc as HIV aspartyl protease inhibitor. MX-100 retained excellent antiviral activity against almost all of these protease inhibitor-resistant viruses and that its performance in this regard was superior to those of atazanavir, amprenavir, indinavir, lopinavir, nelfinavir, and saquinavir. In almost every case, the increase in the EC50 for MX-100 observed with viruses containing multiple mutations in protease was far less than that obtained with the other drugs. Preclinical studies showed that MX-100 possessed suboptimal solubility and pharmacokinetic, (PK) properties, possibly hindering further development. MX-100 successfully completed preclinical and clinical development (phase I in healthy volunteers) and have been licensed to Merck in 2006
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Lysine sulfonamides as novel HIV-protease inhibitors: Nepsilon-acyl aromatic alpha-amino acids. | 2006 Jul 1 |
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Epsilon substituted lysinol derivatives as HIV-1 protease inhibitors. | 2010 Jul 15 |
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Assessment of the susceptibility of mutant HIV-1 to antiviral agents. | 2010 May |
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In vitro and structural evaluation of PL-100 as a potential second-generation HIV-1 protease inhibitor. | 2013 Jan |
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ACTIVE MOIETY