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Details

Stereochemistry RACEMIC
Molecular Formula C22H30N2O.ClH
Molecular Weight 374.947
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRMENOL HYDROCHLORIDE

SMILES

Cl.C[C@H]1CCC[C@@H](C)N1CCC[C@@](O)(C2=CC=CC=C2)C3=CC=CC=N3

InChI

InChIKey=HFIHPVIVQSWZBV-UBKAUKJESA-N
InChI=1S/C22H30N2O.ClH/c1-18-10-8-11-19(2)24(18)17-9-15-22(25,20-12-4-3-5-13-20)21-14-6-7-16-23-21;/h3-7,12-14,16,18-19,25H,8-11,15,17H2,1-2H3;1H/t18-,19+,22-;/m1./s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: DOI: 10.1111/j.1527-3466.1983.tb00446.x | https://www.ncbi.nlm.nih.gov/pubmed/3241147 | https://www.ncbi.nlm.nih.gov/pubmed/1381764

Pirmenol is an antiarrhythmic agent, which exhibits effects on the fast action potential similar to other class 1 membrane active antiarrhythmic agents. Pirmenol depresses not only the fast Na+ channel, but also others, such as the slow Ca2+ and K+ channels. Pirmenol had sevenfold lower affinity for glandular-type muscarinic receptors (M3) than for cardiac-type muscarinic receptors (M2). This medicine regulates disturbed pulse by acting on the cardiac muscle. Usually, used for treatment of tachyarrhythmia (ventricular). The most commonly reported adverse reactions include constipation, discomfort in stomach, difficulty in urination (urinary retention), headache, insomnia, bitterness in the mouth, nausea, dry mouth and palpitation. Lidocaine, procainamide and quinidine a greater degree of arrhythmia conversion occurred when dosed 15 min after pirmenol than when these agents were dosed alone.

Originator

Curator's Comment: http://www.chemdrug.com/article/8/3284/16419223.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PIMENOL

Approved Use

Drug is used for the treatment of tachyarrhythmia (ventricular).
PubMed

PubMed

TitleDatePubMed
A patient responding to combined therapy with pirmenol and midodrine for refractory neurally mediated syncope complicated by prostatic hypertrophy.
2004 Sep
Progressive facilitation of antegrade conduction via an accessory pathway in a patient with Wolff-Parkinson-White syndrome and permanent atrial fibrillation.
2005 Dec
Patents

Sample Use Guides

1 capsule (100 mg of pirmenol) twice a day
Route of Administration: Oral
In Vitro Use Guide
The IC50 of pirmenol for acetylcholine- and adenosine-induced current was about 1 and 8 microM in a single atrial myocytes
Name Type Language
PIRMENOL HYDROCHLORIDE
MART.   USAN   WHO-DD  
USAN  
Official Name English
PIRMENOL HYDROCHLORIDE [USAN]
Common Name English
PIRMAVAR
Brand Name English
(±)-CIS-2,6-DIMETHYL-.ALPHA.-PHENYL-.ALPHA.-2-PYRIDYL-1-PIPERIDINEBUTANOL MONOHYDROCHLORIDE
Systematic Name English
PIRMENOL MONOHYDROCHLORIDE [MI]
Common Name English
CI-845
Code English
Pirmenol hydrochloride [WHO-DD]
Common Name English
CL-845 HYDROCHLORIDE
Code English
2-PYRIDINEMETHANOL, .ALPHA.-(3-(2,6-DIMETHYL-1-PIPERIDINYL)PROPYL)-.ALPHA.-PHENYL-, MONOHYDROCHLORIDE, CIS-, (±)-
Systematic Name English
PIRMENOL HYDROCHLORIDE [MART.]
Common Name English
PIRMENOL HCL
Common Name English
CL-845
Code English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
Code System Code Type Description
CAS
61477-94-9
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID6021169
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PRIMARY
MESH
C024318
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
PRIMARY
MERCK INDEX
m8884
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL432103
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
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PUBCHEM
76962233
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
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NCI_THESAURUS
C81547
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
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EVMPD
SUB03874MIG
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
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FDA UNII
JA79OMG4QT
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
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SMS_ID
100000085333
Created by admin on Fri Dec 15 15:25:37 GMT 2023 , Edited by admin on Fri Dec 15 15:25:37 GMT 2023
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