CIZOLIRTINE CITRATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C15H21N3O.C6H8O7
Molecular Weight	451.4703
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CN(C)CCOC(C1=CC=NN1C)C2=CC=CC=C2

InChI

InChIKey=JLKUMSHHQYQLSG-UHFFFAOYSA-N

InChI=1S/C15H21N3O.C6H8O7/c1-17(2)11-12-19-15(13-7-5-4-6-8-13)14-9-10-16-18(14)3;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-10,15H,11-12H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula	C15H21N3O
Molecular Weight	259.3467
Charge	0
Count

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

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10939032
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/11249967 | https://www.ncbi.nlm.nih.gov/pubmed/16409165 | http://adisinsight.springer.com/drugs/800003782

Cizolirtine is a potent analgesic in mice and rats, with an efficacy superior to that of aspirin and other nonsteroid anti-inflammatory drugs. Recent studies have shown that the analgesic effect of cizolirtine could be related, at least partially, to an inhibition of spinal substance P and calcitonin gene-related peptide release. Cizolirtine has been in clinical trials for the treatment of pain and overactive bladder. Reported adverse events are: dry mouth, dizziness, nausea, vomiting, blurred vision.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
substance P secretion 2 Target ID: GO:1990772 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10939032 \| https://www.ncbi.nlm.nih.gov/pubmed/11249967	Inhibitor 8297
Calcitonin gene-related peptide (CGRP) release 2 Target ID: Calcitonin gene-related peptide (CGRP) release Sources: https://www.ncbi.nlm.nih.gov/pubmed/11249967	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Overactive bladder 38 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19446951 https://www.ncbi.nlm.nih.gov/pubmed/18485575	Primary		Phase II 1132	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15336471 https://www.ncbi.nlm.nih.gov/pubmed/11922399 https://www.ncbi.nlm.nih.gov/pubmed/10893654	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L30XJ
BOC Sciences	142155-43-9	https://www.bocsci.com/cizolirtine-cas-142155-43-9-item-58554.html
THE BioTek	bt-364262	https://www.thebiotek.com/product/others/bt-364262
iChemical	EBD3323772	http://www.ichemical.com/products/142155-43-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Cizolirtine citrate, an effective treatment for symptomatic patients with urinary incontinence secondary to overactive bladder: a pilot dose-finding study.	2009 Jul	18485575
Cizolirtine citrate is safe and effective for treating urinary incontinence secondary to overactive bladder: a phase 2 proof-of-concept study.	2010 Jan	19446951
Methylxanthines and pain.	2011	20859801
Conventional Chiralpak ID vs. capillary Chiralpak ID-3 amylose tris-(3-chlorophenylcarbamate)-based chiral stationary phase columns for the enantioselective HPLC separation of pharmaceutical racemates.	2014 Nov	25271972

Patents

Sample Use Guides

In Vivo Use Guide

800 mg per day during 12 weeks

Route of Administration: Oral

In Vitro Use Guide

The K+ - evoked release of substance P- like material was significantly reduced by cizolirtine at a concentration as low as 0.1 uM. This effect increased to a maximum (-27%, P<0.001) at 10 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:48:44 UTC 2023` Edited by `admin` on `Fri Dec 15 15:48:44 UTC 2023`
Record UNII	8U8XC5Q8QC
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CIZOLIRTINE CITRATE

Common Name

English

(±)-5-(.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)BENZYL)-1-METHYL-1H-PYRAZOLE CITRATE

Systematic Name

English

CIZOLIRTINE CITRATE [MI]

Common Name

English

ETHANAMINE, N,N-DIMETHYL-2-((1-METHYL-1H-PYRAZOL-5-YL)PHENYLMETHOXY)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE

Systematic Name

English

E-4018

Code

English

E4018

Code

English

ETHANAMINE, N,N-DIMETHYL-2-((1-METHYL-1H-PYRAZOL-5-YL)PHENYLMETHOXY)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)

Systematic Name

English

Code System Code Type Description

PUBCHEM

132411