NIAPRAZINE

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H25FN4O
Molecular Weight	356.4371
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of NIAPRAZINE

Structure Search

SMILES

CC(CCN1CCN(CC1)C2=CC=C(F)C=C2)NC(=O)C3=CN=CC=C3

InChI

InChIKey=RSKQGBFMNPDPLR-UHFFFAOYSA-N

InChI=1S/C20H25FN4O/c1-16(23-20(26)17-3-2-9-22-15-17)8-10-24-11-13-25(14-12-24)19-6-4-18(21)5-7-19/h2-7,9,15-16H,8,10-14H2,1H3,(H,23,26)

HIDE SMILES / InChI

Molecular Formula	C20H25FN4O
Molecular Weight	356.4371
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16700077 | https://www.ncbi.nlm.nih.gov/pubmed/1354861 | https://www.ncbi.nlm.nih.gov/pubmed/2853885

Niaprazine is a potent and selective antagonist of 5-HT2A and alpha-1 adrenergic receptors. It was used for the treatment of sleep disturbances in children and was investigated for the treatment of sleep disorders in patients with attention-deficit hyperactivity disorder and autistic disorder.

Approval Year

Targets

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10456769\|https://www.drugs.com/international/niaprazine.html	Antagonist 2778
Serotonin 2 (5-HT2) receptor 87 Target ID: CHEMBL2093870 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2853885	Antagonist 2778		25.0 nM [Ki]
Adrenergic receptor alpha-1 169 Target ID: CHEMBL1907610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2853885	Antagonist 2778		77.0 nM [Ki]

PubMed

PubMed

Title	Date	PubMed
Drug use in children: cohort study in three European countries.	2008 Nov 24	19029175

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:04:39 GMT 2023` Edited by `admin` on `Fri Dec 15 18:04:39 GMT 2023`
Record UNII	R2H3YN6E3L
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NIAPRAZINE

Official Name

English

N-(3-(4-(4-FLUOROPHENYL)-1-PIPERAZINYL)-1-METHYLPROPYL)-3-PYRIDINECARBOXAMIDE

Systematic Name

English

Niaprazine [WHO-DD]

Common Name

English

1709 CERM

Code

English

NIAPRAZINE [MI]

Common Name

English

1709CERM

Code

English

1709-CERM

Code

English

NOPRON

Brand Name

English

NIAPRAZINE [MART.]

Common Name

English

J10.716F

Code

English

niaprazine [INN]

Common Name

English

NICOTINAMIDE, N-(3-(4-(P-FLUOROPHENYL)-1-PIPERAZINYL)-1-METHYLPROPYL)-

Common Name

English

3-PYRIDINECARBOXAMIDE, N-(3-(4-(4-FLUOROPHENYL)-1-PIPERAZINYL)-1-METHYLPROPYL)-

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QN05CM16

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

WHO-ATC

N05CM16

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

NCI_THESAURUS

C29756

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

Code System Code Type Description

MERCK INDEX

m7847

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

Merck Index

MESH

C021062

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

ChEMBL

CHEMBL2105141

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

INN

2817

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

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DRUG BANK

DB13687

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

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DRUG CENTRAL

1908

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

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PUBCHEM

71919

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

ECHA (EC/EINECS)

248-431-5

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

EPA CompTox

DTXSID10865369

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

CAS

27367-90-4

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

WIKIPEDIA

Niaprazine

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

RXCUI

31722

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

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RxNorm

EVMPD

SUB09218MIG

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

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NCI_THESAURUS

C76943

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

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SMS_ID

100000084183

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

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FDA UNII

R2H3YN6E3L

Created by admin on Fri Dec 15 18:04:39 GMT 2023 , Edited by admin on Fri Dec 15 18:04:39 GMT 2023

PRIMARY

Related Record Type Details


					XF51TNX3MK

NIAPRAZINE TRIHYDROCHLORIDE

SALT/SOLVATE -> PARENT


					5QKW305N9F

NIAPRAZINE, (-)-

ENANTIOMER -> RACEMATE


					3T7136LE8K

ALPHA-1A ADRENERGIC RECEPTOR

TARGET -> INHIBITOR

Qualification:

Ki

Amount:


					NQI5D806LC

5-HYDROXYTRYPTAMINE RECEPTOR 2A

TARGET -> INHIBITOR

Qualification:

Ki

Amount:


					1346Q758L9

NIAPRAZINE, (+)-

ENANTIOMER -> RACEMATE

Related Record Type Details


					VML61BE244

4-FLUORO-PHENYLPIPERAZINE

METABOLITE ACTIVE -> PARENT

Comments:

Identified in the urine specimens from rat (5 mg/kg, po), dog (5 mg/kg, po) and man (1 mg/kg, po).

Interaction Type:

IN-VIVO

Qualification:

URINE

Related Record Type Details


					R2H3YN6E3L

ACTIVE MOIETY