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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
Structure of MOZENAVIR

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

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
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
Genetic correlates of in vivo viral resistance to indinavir, a human immunodeficiency virus type 1 protease inhibitor.
1996 Dec
Nonsymmetrically substituted cyclic urea HIV protease inhibitors.
1997 Dec 5
Molecular basis of HIV-1 protease drug resistance: structural analysis of mutant proteases complexed with cyclic urea inhibitors.
1997 Feb 18
Cyclic urea amides: HIV-1 protease inhibitors with low nanomolar potency against both wild type and protease inhibitor resistant mutants of HIV.
1997 Jan 17
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
Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
1998 Jun 18
Cyclic HIV protease inhibitors: design and synthesis of orally bioavailable, pyrazole P2/P2' cyclic ureas with improved potency.
1998 Jun 4
Molecular recognition of cyclic urea HIV-1 protease inhibitors.
1998 May 15
Design and selection of DMP 850 and DMP 851: the next generation of cyclic urea HIV protease inhibitors.
1998 Oct
Patents

Sample Use Guides

750 mg 3 times a day, 1250 mg twice daily, or 1250 mg 3 times a day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:06:08 GMT 2023
Edited
by admin
on Fri Dec 15 16:06:08 GMT 2023
Record UNII
64OO8946ER
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MOZENAVIR
INN  
INN  
Official Name English
mozenavir [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C97366
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
Code System Code Type Description
FDA UNII
64OO8946ER
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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PUBCHEM
154044
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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EPA CompTox
DTXSID40169822
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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INN
8080
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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CAS
174391-92-5
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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NCI_THESAURUS
C77390
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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SMS_ID
300000037020
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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DRUG BANK
DB02102
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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ChEMBL
CHEMBL223824
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
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WIKIPEDIA
Mozenavir
Created by admin on Fri Dec 15 16:06:08 GMT 2023 , Edited by admin on Fri Dec 15 16:06:08 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
Related Record Type Details
ACTIVE MOIETY