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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 of TROVIRDINE

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

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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
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
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
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
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
Patents

Sample Use Guides

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
  • Download
Name Type Language
TROVIRDINE
INN  
INN  
Official Name English
LY-300046
Code English
trovirdine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C97453
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
Code System Code Type Description
INN
7350
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
ChEMBL
CHEMBL39999
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
NCI_THESAURUS
C76931
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
MESH
C095511
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
FDA UNII
ZE3K6J8614
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
PUBCHEM
3000870
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
SMS_ID
100000076963
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
CAS
149488-17-5
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
EVMPD
SUB11351MIG
Created by admin on Fri Dec 15 16:09:57 GMT 2023 , Edited by admin on Fri Dec 15 16:09:57 GMT 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY