Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H36N4O3 |
Molecular Weight | 536.6639 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC=CC(CN2[C@H](CC3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H](CC4=CC=CC=C4)N(CC5=CC(N)=CC=C5)C2=O)=C1
InChI
InChIKey=KYRSNWPSSXSNEP-ZRTHHSRSSA-N
InChI=1S/C33H36N4O3/c34-27-15-7-13-25(17-27)21-36-29(19-23-9-3-1-4-10-23)31(38)32(39)30(20-24-11-5-2-6-12-24)37(33(36)40)22-26-14-8-16-28(35)18-26/h1-18,29-32,38-39H,19-22,34-35H2/t29-,30-,31+,32+/m1/s1
Mozenavir is a non-peptidomimetic, water soluble, cyclic urea that is a selective inhibitor of HIV-1 protease. Mozenavir is active against the virus with the signature D30N nelfinavir resistance-associated mutation and the L90M mutants with decreased susceptibility to a number of other protease inhibitors. In a dose-ranging study assessing Mozenavir, in doses of 750 mg 3 times a day, 1250 mg twice daily, or 1250 mg 3 times a day, compared with standard doses of indinavir, both in combination with lamivudine and stavudine, plasma HIV-1 RNA levels were reduced to below 50 copies/mL in 75% to 80% of patients receiving Mozenavir-based treatment and in 70% of those receiving indinavir-based treatment. Mozenavir-based regimens were generally well tolerated. However, the virus was able to mount considerable resistance against this compound, which was not further developed, also because of poor oral bioavailability in humans and highly variable blood levels.
Approval Year
PubMed
Title | Date | PubMed |
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A pharmacokinetic evaluation of HIV protease inhibitors, cyclic ureas, in rats and dogs. | 1994 Oct |
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Improved cyclic urea inhibitors of the HIV-1 protease: synthesis, potency, resistance profile, human pharmacokinetics and X-ray crystal structure of DMP 450. | 1996 Apr |
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Nonpeptide cyclic cyanoguanidines as HIV-1 protease inhibitors: synthesis, structure-activity relationships, and X-ray crystal structure studies. | 1998 Apr 23 |
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Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues. | 1998 Jun 18 |
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Cyclic HIV protease inhibitors: design and synthesis of orally bioavailable, pyrazole P2/P2' cyclic ureas with improved potency. | 1998 Jun 4 |
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Design and selection of DMP 850 and DMP 851: the next generation of cyclic urea HIV protease inhibitors. | 1998 Oct |
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In vitro activity of potential anti-poxvirus agents. | 2003 Jan |
Patents
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Common Name | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C97366
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64OO8946ER
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C77390
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CHEMBL223824
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Mozenavir
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)