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
Molecular Formula | C33H36N4O3 |
Molecular Weight | 536.6639 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|
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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Cyclic HIV protease inhibitors: synthesis, conformational analysis, P2/P2' structure-activity relationship, and molecular recognition of cyclic ureas. | 1996 Aug 30 |
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Genetic correlates of in vivo viral resistance to indinavir, a human immunodeficiency virus type 1 protease inhibitor. | 1996 Dec |
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Nonsymmetrically substituted cyclic urea HIV protease inhibitors. | 1997 Dec 5 |
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Molecular basis of HIV-1 protease drug resistance: structural analysis of mutant proteases complexed with cyclic urea inhibitors. | 1997 Feb 18 |
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Improved P1/P1' substituents for cyclic urea based HIV-1 protease inhibitors: synthesis, structure-activity relationship, and X-ray crystal structure analysis. | 1997 May 9 |
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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 |
|
In vitro activity of potential anti-poxvirus agents. | 2003 Jan |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:06:08 UTC 2023
by
admin
on
Fri Dec 15 16:06:08 UTC 2023
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Record UNII |
64OO8946ER
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Record Status |
Validated (UNII)
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Record Version |
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Official Name | English | ||
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Common Name | English |
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NCI_THESAURUS |
C97366
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64OO8946ER
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154044
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DTXSID40169822
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8080
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174391-92-5
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C77390
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300000037020
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DB02102
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CHEMBL223824
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Mozenavir
Created by
admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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