DROXINAVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H51N5O4
Molecular Weight	533.7463
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNCC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CCC(C)C)C(=O)NC(C)(C)C)C(C)(C)C

InChI

InChIKey=ICOKEKQSBZSLIB-JBRSBNLGSA-N

InChI=1S/C29H51N5O4/c1-20(2)15-16-34(27(38)33-29(6,7)8)19-23(35)22(17-21-13-11-10-12-14-21)31-26(37)25(28(3,4)5)32-24(36)18-30-9/h10-14,20,22-23,25,30,35H,15-19H2,1-9H3,(H,31,37)(H,32,36)(H,33,38)/t22-,23+,25+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H51N5O4
Molecular Weight	533.7463
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9055985 | https://www.ncbi.nlm.nih.gov/pubmed/9527815 | https://adisinsight.springer.com/drugs/800004768

Droxinavir is hydroxyethylurea human immunodeficiency virus type 1 (HIV-1) protease inhibitor. Position 88 of HIV-1 protease gene plays a key role in the interaction between droxinavir and the protease molecule. A mutation in this position, located outside the active site, confers resistance to the hydroxyethylurea inhibitor droxinavir. The V82A and N88S substitutions conferred droxinavir resistance on HIV-1 recombinant variants. Positions 82 and 88 are reported to be variable in natural populations isolated from patients who have not been treated with protease inhibitors. Droxinavir had been in preclinical phase for the treatment of HIV-1 infection. However, this study was discontinued.

Approval Year

PubMed

Title	Date	PubMed
Protease inhibitors: where are they now?	1995 Jan	11367375
A mutation in human immunodeficiency virus type 1 protease at position 88, located outside the active site, confers resistance to the hydroxyethylurea inhibitor SC-55389A.	1997 Mar	9055985
Estimate of the frequency of human immunodeficiency virus type 1 protease inhibitor resistance within unselected virus populations in vitro.	1998 Feb	9527815

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:01:45 UTC 2023` Edited by `admin` on `Sat Dec 16 17:01:45 UTC 2023`
Record UNII	3CF21QCB9J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DROXINAVIR

Official Name

English

3-TERT-BUTYL-1-((2R,3S)-3-((2S)-3,3-DIMETHYL-2-(2-(METHYLAMINO)ACETAMIDO)BUTYRAMIDO)-2-HYDROXY-4-PHENYLBUTYL)-1-ISOPENTYLUREA

Systematic Name

English

L-VALINAMIDE, N-METHYLGLYCYL-N-(3-((((1,1-DIMETHYLETHYL)AMINO)CARBONYL)(3-METHYLBUTYL)AMINO)-2-HYDROXY-1-(PHENYLMETHYL)PROPYL)-3-METHYL

Common Name

English

droxinavir [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97366