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Details

Stereochemistry RACEMIC
Molecular Formula C22H30N2O.ClH.H2O
Molecular Weight 392.963
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRMENOL HYDROCHLORIDE MONOHYDRATE

SMILES

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

InChI

InChIKey=GYTCSFJBULWQKM-XUKLEHFWSA-N
InChI=1S/C22H30N2O.ClH.H2O/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;1H2/t18-,19+,22-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C22H30N2O
Molecular Weight 338.4864
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:32:40 GMT 2023
Edited
by admin
on Sat Dec 16 07:32:40 GMT 2023
Record UNII
98737Y0095
Record Status Validated (UNII)
Record Version
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Name Type Language
PIRMENOL HYDROCHLORIDE MONOHYDRATE
Common Name English
PIRMENOL HYDROCHLORIDE HYDRATE [JAN]
Common Name English
PIRMENOL HYDROCHLORIDE HYDRATE
JAN  
Common Name English
(±)-CIS-2,6-DIMETHYL-.ALPHA.-PHENYL-.ALPHA.-2-PYRIDYL-1-PIPERIDINEBUTANOL MONOHYDROCHLORIDE MONOHYDRATE
Systematic Name English
Code System Code Type Description
FDA UNII
98737Y0095
Created by admin on Sat Dec 16 07:32:40 GMT 2023 , Edited by admin on Sat Dec 16 07:32:40 GMT 2023
PRIMARY
PUBCHEM
76965981
Created by admin on Sat Dec 16 07:32:40 GMT 2023 , Edited by admin on Sat Dec 16 07:32:40 GMT 2023
PRIMARY
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ACTIVE MOIETY