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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
Molecular Formula C36H39NO5
Molecular Weight 565.6986
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Bayer
150
Curator's Comment: # Bayer HealthCare

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1447
 15.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.32 μg/L
EXPERIMENT
https://onlinelibrary.wiley.com/doi/10.1093/eurjhf/hsq013
400 μg single, intravenous
dose: 400 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CINACIGUAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11.07 μg × h/L
EXPERIMENT
https://onlinelibrary.wiley.com/doi/10.1093/eurjhf/hsq013
400 μg single, intravenous
dose: 400 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CINACIGUAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.56 h
EXPERIMENT
https://onlinelibrary.wiley.com/doi/10.1093/eurjhf/hsq013
400 μg single, intravenous
dose: 400 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CINACIGUAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.56 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3363258/
400 μg single, intravenous
dose: 400 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CINACIGUAT plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYPs
29
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYPs
35
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00C6VU
https://www.1pchem.com/search?query=1P00C6VU
1PlusChem LLC
1P00EMGY
https://www.1pchem.com/search?query=1P00EMGY
AK Scientific
3550AH
https://aksci.com/item_detail.php?cat=3550AH
ApexBio Technology
A3314
https://www.apexbt.com/catalogsearch/result/?q=A3314
Axon MedChem
2172
https://www.axonmedchem.com/product/2172
BLD Pharm
BD630649
http://www.bldpharm.com/search/Search.html?keyword=BD630649
Cayman Chemical
17468
http://www.caymanchem.com/app/template/Product.vm/catalog/17468
Chem Scene
CS-1169
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1169
Chem Scene
CS-6013
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6013
eMolecules
300733083
https://orderbb.emolecules.com/search/#?query=300733083
eMolecules
44466495
https://orderbb.emolecules.com/search/#?query=44466495
eMolecules
45475576
https://orderbb.emolecules.com/search/#?query=45475576
mcule
MCULE-2336398228
https://mcule.com/MCULE-2336398228/
mcule
MCULE-6139644519
https://mcule.com/MCULE-6139644519/
MedChem Express
HY-14181
https://www.medchemexpress.com/search.html?q=HY-14181A&ft=&fa=&fp=
MedChem Express
HY-14181A
https://www.medchemexpress.com/search.html?q=HY-14181A&ft=&fa=&fp=
Molnova
M14089
https://www.molnova.com/en/serch-list.html?keywords=M14089
MolPort
MolPort-039-139-611
https://www.molport.com/shop/molecule-link/MolPort-039-139-611
MolPort
MolPort-042-665-825
https://www.molport.com/shop/molecule-link/MolPort-042-665-825
MuseChem
I004436
https://www.musechem.com/product/I004436.html
Ryan Scientific
101-94141
https://ryansci.com/products?q=101-94141&list_q=&search_type=exact
Ryan Scientific
KX1-004
https://ryansci.com/products?q=KX1-004&list_q=&search_type=exact
ShangHai Biochempartner
BCP000944
http://www.biochempartner.com/search_BCP000944
ShangHai Biochempartner
BCP07942
http://www.biochempartner.com/search_BCP07942
TargetMol
T1984
https://www.targetmol.com/search?keyword=T1984
PubMed

PubMed

TitleDatePubMed
Direct fusion of subunits of heterodimeric nitric oxide sensitive guanylyl cyclase leads to functional enzymes with preserved biochemical properties: evidence for isoform specific activation by ciguates.
2010-12-01
Cinaciguat, a soluble guanylate cyclase activator for the potential treatment of acute heart failure.
2010-09
Structure of cinaciguat (BAY 58-2667) bound to Nostoc H-NOX domain reveals insights into heme-mimetic activation of the soluble guanylyl cyclase.
2010-07-16
Fluorescent fusion proteins of soluble guanylyl cyclase indicate proximity of the heme nitric oxide domain and catalytic domain.
2010-07-15
Nitric oxide sensitive guanylyl cyclase activity decreases during cerebral postnatal development because of a reduction in heterodimerization.
2010-01
Animal models related to congenital heart disease and clinical research in pulmonary hypertension.
2010
Population pharmacokinetics and pharmacodynamics of cinaciguat, a soluble guanylate cyclase activator, in patients with acute decompensated heart failure.
2010
Role of guanylate cyclase modulators in decompensated heart failure.
2009-12
Gateways to clinical trials.
2009-10
Pharmacological activation of soluble guanylate cyclase protects the heart against ischemic injury.
2009-08-25
Cinaciguat, a soluble guanylate cyclase activator, causes potent and sustained pulmonary vasodilation in the ovine fetus.
2009-08
Cinaciguat (BAY 58-2667) improves cardiopulmonary hemodynamics in patients with acute decompensated heart failure.
2009-06-02
Pharmacokinetics, pharmacodynamics, tolerability, and safety of the soluble guanylate cyclase activator cinaciguat (BAY 58-2667) in healthy male volunteers.
2008-12
Gateways to clinical trials.
2008-05
Residues stabilizing the heme moiety of the nitric oxide sensor soluble guanylate cyclase.
2005-04-18
NO- and haem-independent activation of soluble guanylyl cyclase: molecular basis and cardiovascular implications of a new pharmacological principle.
2002-07
Patents

Patents

US20140328933
1
WO2008154323A1
2
WO2014100733A1
4

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).
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:21:54 GMT 2025
Edited
by admin
on Mon Mar 31 18:21:54 GMT 2025
Record UNII
59K0Y58UAD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BAY 58-2667
Preferred Name English
CINACIGUAT
INN   JAN  
INN  
Official Name English
CINACIGUAT [JAN]
Common Name English
cinaciguat [INN]
Common Name English
Cinaciguat [WHO-DD]
Common Name English
BAY-58-2667
Systematic Name English
4-(((4-CARBOXYBUTYL)(2-(2-((4-(2-PHENYLETHYL)PHENYL)METHOXY)PHENYL)ETHYL)AMINO)METHYL)BENZOIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C87280
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
MESH
C480588
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
FDA UNII
59K0Y58UAD
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
SMS_ID
100000175111
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
CAS
329773-35-5
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
CHEBI
142433
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
PUBCHEM
9808022
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
INN
8856
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID40954614
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
WIKIPEDIA
CINACIGUAT
Created by admin on Mon Mar 31 18:21:54 GMT 2025 , Edited by admin on Mon Mar 31 18:21:54 GMT 2025
PRIMARY
Related Record Type Details
GUANYLATE CYCLASE SOLUBLE .ALPHA.1.BETA.1
TARGET -> ACTIVATOR
Related Record Type Details
Structure of CINACIGUAT
ACTIVE MOIETY
NIH
NCATS
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