TELINAVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C33H44N6O5
Molecular Weight	604.7397
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(N)=O)NC(=O)C2=NC3=CC=CC=C3C=C2)C(=O)NC(C)(C)C

InChI

InChIKey=ZILOOGIOHVCEKS-HZFUHODCSA-N

InChI=1S/C33H44N6O5/c1-21(2)19-39(32(44)38-33(3,4)5)20-28(40)26(17-22-11-7-6-8-12-22)36-31(43)27(18-29(34)41)37-30(42)25-16-15-23-13-9-10-14-24(23)35-25/h6-16,21,26-28,40H,17-20H2,1-5H3,(H2,34,41)(H,36,43)(H,37,42)(H,38,44)/t26-,27-,28+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C33H44N6O5
Molecular Weight	604.7397
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/9215651 | https://www.ncbi.nlm.nih.gov/pubmed/8619573

Telinavir (previously known as SC-52151) was developed as an anti-HIV aspartyl protease inhibitor for the treatment of HIV Infections. Telinavir participated in Phase I/II clinical study. In spite of the drug was well tolerated no antiviral activity was produced and further development of the drug was discontinued.

Approval Year

PubMed

Title	Date	PubMed
Discovery of a novel class of potent HIV-1 protease inhibitors containing the (R)-(hydroxyethyl)urea isostere.	1993 Jan 22	8423599
Aminodiol HIV protease inhibitors. 1. Design, synthesis, and preliminary SAR.	1994 Jun 10	8021916
Characterization of a human immunodeficiency virus type 1 variant with reduced sensitivity to an aminodiol protease inhibitor.	1995 Apr	7884862
In vivo emergence of HIV-1 variants resistant to multiple protease inhibitors.	1995 Apr 6	7700387
SC-52151, a novel inhibitor of the human immunodeficiency virus protease.	1995 Oct	8619573
Genetic correlates of in vivo viral resistance to indinavir, a human immunodeficiency virus type 1 protease inhibitor.	1996 Dec	8970946
Human immunodeficiency virus type 1 viral background plays a major role in development of resistance to protease inhibitors.	1996 Feb 20	8643685
Design, synthesis, and resistance patterns of MP-134 and MP-167, two novel inhibitors of HIV type 1 protease.	1996 Jan 1	8825619
Evaluation of reverse transcriptase and protease inhibitors in two-drug combinations against human immunodeficiency virus replication.	1996 Jun	8725999
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
In vitro effect of alpha1-acid glycoprotein on the anti-human immunodeficiency virus (HIV) activity of the protease inhibitor CGP 61755: a comparative study with other relevant HIV protease inhibitors.	1997 May	9129067

Sample Use Guides

In Vivo Use Guide

Forty-nine patients received the elixir or self-emulsifying drug delivery system at a dosage of 750 mg three times daily or 1125 mg twice daily for 14 days

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:16:58 UTC 2023` Edited by `admin` on `Fri Dec 15 16:16:58 UTC 2023`
Record UNII	IZF55EH3CG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TELINAVIR

Official Name

English

SC-52151

Code

English

telinavir [INN]

Common Name

English

NSC-670881

Code

English

(2S)-N-[(1S,2R)-1-Benzyl-3-(3-tert-butyl-1-isobutylureido)-2-hydroxypropyl]-2-quinaldamidosuccinamide

Systematic Name

English

N-(3-((((1,1-DIMETHYLETHYL)AMINO)CARBONYL)(2-METHYLPROPYL)-AMINO)-2R-HYDROXY-1S-(PHENYLMETHYL)PROPYL)-2S-((2-QUINOLINYLCARBONYL)AMINO)BUTANEDIAMIDE

Systematic Name

English

BUTANEDIAMIDE, N1-((1S,2R)-3-((((1,1-DIMETHYLETHYL)AMINO)CARBONYL)(2-METHYLPROPYL)AMINO)-2-HYDROXY-1-(PHENYLMETHYL)PROPYL)-2-((2-QUINOLINYLCARBONYL)AMINO)-, (2S)-

Systematic Name

English

TELINAVIR [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97366