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Details

Stereochemistry ACHIRAL
Molecular Formula C19H17FN8O2
Molecular Weight 408.3891
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Nelociguat

SMILES

COC(=O)NC1=C(N)N=C(N=C1N)C2=NN(CC3=C(F)C=CC=C3)C4=C2C=CC=N4

InChI

InChIKey=FTQHGWIXJSSWOY-UHFFFAOYSA-N
InChI=1S/C19H17FN8O2/c1-30-19(29)24-14-15(21)25-17(26-16(14)22)13-11-6-4-8-23-18(11)28(27-13)9-10-5-2-3-7-12(10)20/h2-8H,9H2,1H3,(H,24,29)(H4,21,22,25,26)

HIDE SMILES / InChI

Description

Nelociguat, a soluble guanylate cyclase (sGC) activator, has been in phase II clinical trials by Bayer for the treatment of erectile dysfunction and heart failure. However, no recent development has been reported. Nelociguat is a direct soluble guanylate cyclase (sGC) stimulator that acts independently of nitric oxide (NO); has an EC50 of 353 nM on P-VASP formation in rat aortic smooth muscle cells. BAY 60-4552 is pharmacologically active major metabolite of Riociguat.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
PubMed

PubMed

TitleDatePubMed
Renal effects of soluble guanylate cyclase stimulators and activators: a review of the preclinical evidence.
2015-04
Synergistic effects of BAY 60-4552 and vardenafil on relaxation of corpus cavernosum tissue of patients with erectile dysfunction and clinical phosphodiesterase type 5 inhibitor failure.
2013-05
Comparison of soluble guanylate cyclase stimulators and activators in models of cardiovascular disease associated with oxidative stress.
2012
Patents

Patents

07173037
3
08492544
1
08501945
1
20060052397
2
20070225299
2

Sample Use Guides

In Vivo Use Guide
Heart Failure: Single dose escalation planned at dose of 1 mg, 2.5 mg, 5 mg, 7.5 mg, and 10 mg
Route of Administration: Oral
In Vitro Use Guide
Nelociguat has an EC50 of 353 nM on P-VASP formation in rat aortic smooth muscle cells.
Name Type Language
Nelociguat
INN   WHO-DD  
INN  
Official Name English
BAY 60-4552
Preferred Name English
nelociguat [INN]
Common Name English
CARBAMIC ACID, N-(4,6-DIAMINO-2-(1-((2-FLUOROPHENYL)METHYL)-1H-PYRAZOLO(3,4-B)PYRIDIN-3-YL)-5-PYRIMIDINYL)-, METHYL ESTER
Common Name English
Nelociguat [WHO-DD]
Common Name English
BAY-60-4552
Code English
RIOCIGUAT METABOLITE M1
Common Name English
CARBAMIC ACID, (4,6-DIAMINO-2-(1-((2-FLUOROPHENYL)METHYL)-1H-PYRAZOLO(3,4-B)PYRIDIN-3-YL)-5-PYRIMIDINYL)-, METHYL ESTER
Common Name English
METHYL (4,6-DIAMINO-2-(1-((2-FLUOROPHENYL)METHYL)-1H-PYRAZOLO(3,4-B)PYRIDIN-3-YL)PYRIMIDIN-5-YL)CARBAMATE
Systematic Name English
Code System Code Type Description
SMS_ID
300000034301
Created by admin on Mon Mar 31 20:13:09 GMT 2025 , Edited by admin on Mon Mar 31 20:13:09 GMT 2025
PRIMARY
FDA UNII
M2A18LL56O
Created by admin on Mon Mar 31 20:13:09 GMT 2025 , Edited by admin on Mon Mar 31 20:13:09 GMT 2025
PRIMARY
INN
9477
Created by admin on Mon Mar 31 20:13:09 GMT 2025 , Edited by admin on Mon Mar 31 20:13:09 GMT 2025
PRIMARY
PUBCHEM
11690019
Created by admin on Mon Mar 31 20:13:09 GMT 2025 , Edited by admin on Mon Mar 31 20:13:09 GMT 2025
PRIMARY
CHEBI
149785
Created by admin on Mon Mar 31 20:13:09 GMT 2025 , Edited by admin on Mon Mar 31 20:13:09 GMT 2025
PRIMARY
CAS
625115-52-8
Created by admin on Mon Mar 31 20:13:09 GMT 2025 , Edited by admin on Mon Mar 31 20:13:09 GMT 2025
PRIMARY
NCI_THESAURUS
C174685
Created by admin on Mon Mar 31 20:13:09 GMT 2025 , Edited by admin on Mon Mar 31 20:13:09 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of Nelociguat
PARENT (METABOLITE LESS ACTIVE)
Structure of RIOCIGUAT
NIH
NCATS
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