NELOCIGUAT

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 Search

SMILES

COC(=O)NC1=C(N)N=C(N=C1N)C2=NN(CC3=C(F)C=CC=C3)C4=NC=CC=C24

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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/984381c0f2f6388d272227375ac5c373.html | http://www.probechem.com/products_Nelociguat.aspx | https://www.ncbi.nlm.nih.gov/pubmed/26507720

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

Primary Target	Pharmacology	Condition	Potency
Soluble guanylate cyclase 22 Target ID: CHEMBL2111348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27784018	Inhibitor 8146

PubMed

Title	Date	PubMed
Comparison of soluble guanylate cyclase stimulators and activators in models of cardiovascular disease associated with oxidative stress.	2012	22783192
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	23421435
Renal effects of soluble guanylate cyclase stimulators and activators: a review of the preclinical evidence.	2015 Apr	25645316

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 `Sat Dec 17 05:30:32 UTC 2022` Edited by `admin` on `Sat Dec 17 05:30:32 UTC 2022`
Record UNII	M2A18LL56O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NELOCIGUAT

Official 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

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

FDA UNII

M2A18LL56O