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Details

Stereochemistry RACEMIC
Molecular Formula C15H21N3O
Molecular Weight 259.3467
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIZOLIRTINE

SMILES

CN(C)CCOC(C1=CC=NN1C)C2=CC=CC=C2

InChI

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

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 ( + / - )

Description
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

Curator's Comment: Known to be CNS penetrant in rat. Human data not available.

Approval Year

PubMed

PubMed

TitleDatePubMed
Evidence for adenosine- and serotonin-mediated antihyperalgesic effects of cizolirtine in rats suffering from diabetic neuropathy.
2007 Feb
Cizolirtine citrate, an effective treatment for symptomatic patients with urinary incontinence secondary to overactive bladder: a pilot dose-finding study.
2009 Jul
Cizolirtine citrate is safe and effective for treating urinary incontinence secondary to overactive bladder: a phase 2 proof-of-concept study.
2010 Jan
Methylxanthines and pain.
2011
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
Patents

Sample Use Guides

800 mg per day during 12 weeks
Route of Administration: Oral
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 17:42:59 GMT 2023
Edited
by admin
on Fri Dec 15 17:42:59 GMT 2023
Record UNII
SMP167WV5D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIZOLIRTINE
INN   MI   WHO-DD  
INN  
Official Name English
cizolirtine [INN]
Common Name English
Cizolirtine [WHO-DD]
Common Name English
(±)-5-(.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)BENZYL)-1-METHYLPYRAZOLE
Systematic Name English
CIZOLIRTINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
Code System Code Type Description
MESH
C075798
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID10869923
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
FDA UNII
SMP167WV5D
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
PUBCHEM
132412
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
CAS
142155-43-9
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
NCI_THESAURUS
C77311
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
SMS_ID
100000084616
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
INN
7483
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
MERCK INDEX
m3605
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY Merck Index
EVMPD
SUB06634MIG
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL92501
Created by admin on Fri Dec 15 17:42:59 GMT 2023 , Edited by admin on Fri Dec 15 17:42:59 GMT 2023
PRIMARY
Related Record Type Details
TARGET->INHIBITOR OF RELEASE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
TARGET->INHIBITOR OF RELEASE
Related Record Type Details
ACTIVE MOIETY