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Details

Stereochemistry RACEMIC
Molecular Formula C22H30N2O
Molecular Weight 338.4864
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRMENOL

SMILES

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

InChI

InChIKey=APUDBKTWDCXQJA-XQBPLPMBSA-N
InChI=1S/C22H30N2O/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/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
Pirmenol, a new antiarrhythmic agent: initial study of efficacy, safety and pharmacokinetics.
1982 Feb
Pharmacodynamics and pharmacokinetics of oral pirmenol.
1987 Oct
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
INN   MI   WHO-DD  
INN  
Official Name English
2-PYRIDINEMETHANOL, .ALPHA.-(3-(2,6-DIMETHYL-1-PIPERIDINYL)PROPYL)-.ALPHA.-PHENYL-, CIS-, (±)-
Common Name English
(±)-CIS-2,6-DIMETHYL-.ALPHA.-PHENYL-.ALPHA.-2-PYRIDYL-1-PIPERIDINEBUTANOL
Systematic Name English
pirmenol [INN]
Common Name English
PIRMENOL [MI]
Common Name English
Pirmenol [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 16:11:40 GMT 2023 , Edited by admin on Fri Dec 15 16:11:40 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL432103
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PRIMARY
INN
4685
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PRIMARY
MERCK INDEX
m8884
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PRIMARY Merck Index
EVMPD
SUB09925MIG
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PRIMARY
EPA CompTox
DTXSID1043839
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PRIMARY
CAS
68252-19-7
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FDA UNII
VZ3B6ACV72
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PRIMARY
MESH
C024318
Created by admin on Fri Dec 15 16:11:40 GMT 2023 , Edited by admin on Fri Dec 15 16:11:40 GMT 2023
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PUBCHEM
76962234
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PRIMARY
DRUG CENTRAL
2207
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PRIMARY
NCI_THESAURUS
C81434
Created by admin on Fri Dec 15 16:11:40 GMT 2023 , Edited by admin on Fri Dec 15 16:11:40 GMT 2023
PRIMARY
SMS_ID
100000081693
Created by admin on Fri Dec 15 16:11:40 GMT 2023 , Edited by admin on Fri Dec 15 16:11:40 GMT 2023
PRIMARY