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Details

Stereochemistry ACHIRAL
Molecular Formula C13H13BrN4S.ClH
Molecular Weight 373.699
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROVIRDINE HYDROCHLORIDE

SMILES

Cl.BrC1=CC=C(NC(=S)NCCC2=CC=CC=N2)N=C1

InChI

InChIKey=IUQKLSJRANLIKE-UHFFFAOYSA-N
InChI=1S/C13H13BrN4S.ClH/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);1H

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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

CNS Penetrant
2554
Curator's Comment: Concentrations of LY300046 in the brain were similar to those in plasma at all of the time points examined, indicating that LY300046 readily crosses the blood-brain barrier in rats.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 7.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
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
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
The PETT series, a new class of potent nonnucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase.
1995 Jun
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
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
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
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
Novel derivatives of phenethyl-5-bromopyridylthiourea and dihydroalkoxybenzyloxopyrimidine are dual-function spermicides with potent anti-human immunodeficiency virus activity.
1999 Jun
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
Structure-based design of non-nucleoside reverse transcriptase inhibitors of drug-resistant human immunodeficiency virus.
1999 Sep
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
Prophylactic contraceptives for HIV/AIDS.
1999 Sep-Oct
Novel thiourea compounds as dual-function microbicides.
2000 Jul
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
Piperidinylethyl, phenoxyethyl and fluoroethyl bromopyridyl thiourea compounds with potent anti-HIV activity.
2000 Sep
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
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
Design, synthesis, SAR, and molecular modeling studies of acylthiocarbamates: a novel series of potent non-nucleoside HIV-1 reverse transcriptase inhibitors structurally related to phenethylthiazolylthiourea derivatives.
2003 Feb 27
Effect of stereochemistry on the anti-HIV activity of chiral thiourea compounds.
2004 Aug 1
PHI-443: a novel noncontraceptive broad-spectrum anti-human immunodeficiency virus microbicide.
2004 Dec
Effect of stereo and regiochemistry towards wild and multidrug resistant HIV-1 virus: viral potency of chiral PETT derivatives.
2004 May 15
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
Novel broad-spectrum thiourea non-nucleoside inhibitors for the prevention of mucosal HIV transmission.
2006 Jul
N2-benzyloxycarbonylguan-9-yl acetic acid derivatives as HIV-1 reverse transcriptase non-nucleoside inhibitors with decreased loss of potency against common drug-resistance mutations.
2007 Oct
Novel modifications in the series of O-(2-phthalimidoethyl)-N-substituted thiocarbamates and their ring-opened congeners as non-nucleoside HIV-1 reverse transcriptase inhibitors.
2009 Apr
Patents

Patents

EP1466628A1
8
EP2912070A1
2

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 17:35:14 GMT 2023
Edited
by admin
on Fri Dec 15 17:35:14 GMT 2023
Record UNII
70714531RJ
Record Status Validated (UNII)
Record Version
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Name Type Language
TROVIRDINE HYDROCHLORIDE
Common Name English
TROVIRDINE HCL
Common Name English
THIOUREA, N-(5-BROMO-2-PYRIDINYL)-N'-(2-(2-PYRIDINYL)ETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
LY-300046 HYDROCHLORIDE
Code English
Code System Code Type Description
PUBCHEM
5327620
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
FDA UNII
70714531RJ
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
CAS
148311-89-1
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
Related Record Type Details
Structure of TROVIRDINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of TROVIRDINE
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