U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H17FN8O2
Molecular Weight 408.3891
Optical Activity UNSPECIFIED
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

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

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Comparison of soluble guanylate cyclase stimulators and activators in models of cardiovascular disease associated with oxidative stress.
2012
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 May
Renal effects of soluble guanylate cyclase stimulators and activators: a review of the preclinical evidence.
2015 Apr
Patents

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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:59:19 UTC 2019
Edited
by admin
on Mon Oct 21 21:59:19 UTC 2019
Record UNII
M2A18LL56O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NELOCIGUAT
INN   WHO-DD  
INN  
Official Name English
NELOCIGUAT [WHO-DD]
Common 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
BAY 60-4552
Code 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
INN
9477
Created by admin on Mon Oct 21 21:59:19 UTC 2019 , Edited by admin on Mon Oct 21 21:59:19 UTC 2019
PRIMARY
PUBCHEM
11690019
Created by admin on Mon Oct 21 21:59:19 UTC 2019 , Edited by admin on Mon Oct 21 21:59:19 UTC 2019
PRIMARY
CAS
625115-52-8
Created by admin on Mon Oct 21 21:59:19 UTC 2019 , Edited by admin on Mon Oct 21 21:59:19 UTC 2019
PRIMARY
Related Record Type Details
BINDER->LIGAND
The protein binding of M1 is ~97% and is concentration independent.
Related Record Type Details
PARENT -> METABOLITE LESS ACTIVE
MAJOR
FECAL; PLASMA; URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC