TROVIRDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H13BrN4S
Molecular Weight	337.238
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

BrC1=CN=C(NC(=S)NCCC2=CC=CC=N2)C=C1

InChI

InChIKey=HOCFDYZWQYGULA-UHFFFAOYSA-N

InChI=1S/C13H13BrN4S/c14-10-4-5-12(17-9-10)18-13(19)16-8-6-11-3-1-2-7-15-11/h1-5,7,9H,6,8H2,(H2,16,17,18,19)

HIDE SMILES / InChI

Molecular Formula	C13H13BrN4S
Molecular Weight	337.238
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800002628 | https://www.ncbi.nlm.nih.gov/pubmed/8669892 | https://www.ncbi.nlm.nih.gov/pubmed/7574525

Trovirdine [LY 300046, LY 300082, PETT 1] is a NNRT inhibitor of HIV-1 RT, which progressed through Phase II trials for the treatment of HIV infection. Trovirdine inhibits HIV-1 RT with an IC50 of 7 nM. Cell culture experiments demonstrated that LY300046 was a potent inhibitor of the replication of HIV-1 in human T-cell lines and human PBL, including spread of the virus from infected to uninfected T cells. It was potent against patient isolates as well as laboratory isolates of HIV-1 but was not active against HIV-2 or simian immunodeficiency virus.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Reverse transcriptase 8 Target ID: CHEMBL2366516 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8669892	Inhibitor 8297		7.0 nM [IC50]

PubMed

Title	Date	PubMed
Inhibition of human immunodeficiency virus type 1 wild-type and mutant reverse transcriptases by the phenyl ethyl thiazolyl thiourea derivatives trovirdine and MSC-127.	1995 Dec	8669892
Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure-activity relationship studies of PETT analogs.	1995 Dec 8	8523406
Phenethylthiazolylthiourea (PETT) compounds as a new class of HIV-1 reverse transcriptase inhibitors. 2. Synthesis and further structure-activity relationship studies of PETT analogs.	1996 Oct 11	8863804
Structure-based design of N-[2-(1-piperidinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea as potent non-nucleoside inhibitors of HIV-1 reverse transcriptase.	1998 Aug 18	9873515
Synthesis and anti-HIV activities of urea-PETT analogs belonging to a new class of potent non-nucleoside HIV-1 reverse transcriptase inhibitors.	1998 Jun 16	9873380
N'-[2-(2-thiophene)ethyl]-N'-[2-(5-bromopyridyl)] thiourea as a potent inhibitor of NNI-resistant and multidrug-resistant human immunodeficiency virus-1.	1999 Dec 20	10617082
Novel derivatives of phenethyl-5-bromopyridylthiourea and dihydroalkoxybenzyloxopyrimidine are dual-function spermicides with potent anti-human immunodeficiency virus activity.	1999 Jun	10330101
Rational design of N-[2-(2,5-dimethoxyphenylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea (HI-236) as a potent non-nucleoside inhibitor of drug-resistant human immunodeficiency virus.	1999 Jun 7	10386942
Structure-based design of non-nucleoside reverse transcriptase inhibitors of drug-resistant human immunodeficiency virus.	1999 Sep	10574178
N-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea and N'-[2-(1-cyclohexenyl)ethyl]-N'-[2-(5-chloropyridyl)]-thiourea as potent inhibitors of multidrug-resistant human immunodeficiency virus-1.	1999 Sep 20	10509923
Prophylactic contraceptives for HIV/AIDS.	1999 Sep-Oct	10582788
Novel thiourea compounds as dual-function microbicides.	2000 Jul	10859260
N-[2-(4-methylphenyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea as a potent inhibitor of NNRTI-resistant and multidrug-resistant human immunodeficiency virus type 1.	2000 Mar	10819437
Stereochemistry of halopyridyl and thiazolyl thiourea compounds is a major determinant of their potency as nonnucleoside inhibitors of HIV-1 reverse transcriptase.	2000 Sep 18	10999473
Structural requirements for potent anti-human immunodeficiency virus (HIV) and sperm-immobilizing activities of cyclohexenyl thiourea and urea non-nucleoside inhibitors of HIV-1 reverse transcriptase.	2002 Dec	12444075
Effect of stereochemistry on the anti-HIV activity of chiral thiourea compounds.	2004 Aug 1	15246104
Effect of stereo and regiochemistry towards wild and multidrug resistant HIV-1 virus: viral potency of chiral PETT derivatives.	2004 May 15	15130770
Structure-based design, parallel synthesis, structure-activity relationship, and molecular modeling studies of thiocarbamates, new potent non-nucleoside HIV-1 reverse transcriptase inhibitor isosteres of phenethylthiazolylthiourea derivatives.	2005 Jun 2	15916438

Patents

Sample Use Guides

In Vivo Use Guide

Rats were administered a single 20-mg/kg oral dose of Trovirdine [LY 300046].

Route of Administration: Oral

In Vitro Use Guide

Trovirdine inhibits HIV-1 RT with an IC50 of 7 nM when employing heteropolymeric primer/template (oligo-DNA/ribosomal RNA)and dGTP as substrate.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:09:57 GMT 2023` Edited by `admin` on `Fri Dec 15 16:09:57 GMT 2023`
Record UNII	ZE3K6J8614
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TROVIRDINE

Official Name

English

LY-300046

Code

English

trovirdine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97453