TREQUINSIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H27N3O3
Molecular Weight	405.4895
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C=C1OC)C3=CC(=NC4=C(C)C=C(C)C=C4C)N(C)C(=O)N3CC2

InChI

InChIKey=MCMSJVMUSBZUCN-UHFFFAOYSA-N

InChI=1S/C24H27N3O3/c1-14-9-15(2)23(16(3)10-14)25-22-13-19-18-12-21(30-6)20(29-5)11-17(18)7-8-27(19)24(28)26(22)4/h9-13H,7-8H2,1-6H3

HIDE SMILES / InChI

Molecular Formula	C24H27N3O3
Molecular Weight	405.4895
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6294426
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12016266 | https://www.ncbi.nlm.nih.gov/pubmed/2544722 | https://www.ncbi.nlm.nih.gov/pubmed/3526628

Trequinsin is a potent PDE3 inhibitor that inhibits PDE4 and PDE2 at higher concentrations. Trequinsin can block platelet aggregation and also inhibit tissue factor expression in human endothelial cells. Trequinsin can enhance cellular cAMP content, forskolin-induced cAMP synthesis, and renin release in cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Phosphodiesterase 4 54 Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2544722	Inhibitor 8504	400.0 nM [IC50]
Phosphodiesterase 5A 31 Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2544722	Inhibitor 8504	5000.0 nM [IC50]
Phosphodiesterase 3 61 Target ID: CHEMBL2094125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12016266	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Female sexual dysfunction 5 Sources: https://www.google.co.in/patents/US20040014761	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Rat (male Sprague-Dawley, 80 g) JG cells were isolated as for mouse JG cells by enzymatic digestion of renal cortex with collagenase A (Roche Diagnostics, Denmark) and trypsin (Sigma, Denmark), followed by filtration and wash. JG-cell suspensions were seeded in 1-mL aliquots and incubated with agents (1 and 10 mkmol/L of the Trequinsin) for 10 minutes. The cells were harvested in cold ethanol with 20 mmol/L HCl. After evaporation, cAMP was measured by RIA (Amersham-Biotrak RPA509).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:25:35 GMT 2025` Edited by `admin` on `Mon Mar 31 21:25:35 GMT 2025`
Record UNII	739I2958C1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TREQUINSIN

Official Name

English

trequinsin [INN]

Preferred Name

English

2,3,6,7-TETRAHYDRO-2-(MESITYLIMINO)-9,10-DIMETHOXY-3-METHYL-4H-PYRIMIDO(6,1-A)ISOQUINOLIN-4-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744