U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
A pharmacokinetic evaluation of HIV protease inhibitors, cyclic ureas, in rats and dogs.
1994 Oct
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
Nonsymmetric P2/P2' cyclic urea HIV protease inhibitors. Structure-activity relationship, bioavailability, and resistance profile of monoindazole-substituted P2 analogues.
1998 Jun 18
Molecular recognition of cyclic urea HIV-1 protease inhibitors.
1998 May 15
In vitro activity of potential anti-poxvirus agents.
2003 Jan
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 UTC 2023
Edited
by admin
on Fri Dec 15 16:06:08 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
Code System Code Type Description
FDA UNII
64OO8946ER
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
PUBCHEM
154044
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID40169822
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
INN
8080
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
CAS
174391-92-5
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
NCI_THESAURUS
C77390
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
SMS_ID
300000037020
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
DRUG BANK
DB02102
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL223824
Created by admin on Fri Dec 15 16:06:08 UTC 2023 , Edited by admin on Fri Dec 15 16:06:08 UTC 2023
PRIMARY
WIKIPEDIA
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
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
Related Record Type Details
ACTIVE MOIETY