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Details

Stereochemistry ACHIRAL
Molecular Formula C36H39NO5
Molecular Weight 565.6986
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINACIGUAT

SMILES

OC(=O)CCCCN(CCC1=CC=CC=C1OCC2=CC=C(CCC3=CC=CC=C3)C=C2)CC4=CC=C(C=C4)C(O)=O

InChI

InChIKey=WPYWMXNXEZFMAK-UHFFFAOYSA-N
InChI=1S/C36H39NO5/c38-35(39)12-6-7-24-37(26-30-19-21-33(22-20-30)36(40)41)25-23-32-10-4-5-11-34(32)42-27-31-17-15-29(16-18-31)14-13-28-8-2-1-3-9-28/h1-5,8-11,15-22H,6-7,12-14,23-27H2,(H,38,39)(H,40,41)

HIDE SMILES / InChI

Description

Cinaciguat acts specifically on oxidized/haem-free soluble guanylyl cyclase by binding to the enzyme's haem pocket and mimicking the nitric-oxide-bound haem group. It is in clinical development for the treatment of acute decompensated heart failure. Cinaciguat had been in phase II clinical trials. However, trials were terminated early because of an excess of hypotension in the cinaciguat arms and subsequent slow enrolment.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
15.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
3.32 μg/L
400 μg single, intravenous
CINACIGUAT plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
11.07 μg × h/L
400 μg single, intravenous
CINACIGUAT plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.56 h
400 μg single, intravenous
CINACIGUAT plasma
Homo sapiens
1.56 h
400 μg single, intravenous
CINACIGUAT plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
25 ug/h, 10 ug/h during 48 h
Route of Administration: Intravenous
In Vitro Use Guide
Cinaciguat (1-50 nM) infused for 60 min starting 5 min before reperfusion significantly reduced infarction from 33.0 +/- 3.2% in control isolated rabbit hearts to 9.5-12.7% (P < 0.05).