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Details

Stereochemistry ACHIRAL
Molecular Formula C19H35NO2
Molecular Weight 309.4867
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DICYCLOMINE

SMILES

CCN(CC)CCOC(=O)C1(CCCCC1)C2CCCCC2

InChI

InChIKey=CURUTKGFNZGFSE-UHFFFAOYSA-N
InChI=1S/C19H35NO2/c1-3-20(4-2)15-16-22-18(21)19(13-9-6-10-14-19)17-11-7-5-8-12-17/h17H,3-16H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C19H35NO2
Molecular Weight 309.4867
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Dicyclomine is an anticholinergic tertiary amine used frequently by oral and parenteral route as an effective anti-spasmodic agent. Dicyclomine hydrochloride salt is approved under brand name bentyl for the treatment of functional bowel/irritable bowel syndrome. In addition is known, that dicyclomine is also used in morning and motion sickness, dysmenorrheal, intestinal hypermotility. It was shown, that Dicyclomine is a selective M1 and M3 muscarinic receptors antagonist, but os shown pharmacological activity via the M1 receptor.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BENTYL

Cmax

ValueDoseCo-administeredAnalytePopulation
50.47 ng/mL
20 mg single, oral
DICYCLOMINE plasma
Homo sapiens
47.98 ng/mL
20 mg single, oral
DICYCLOMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
202.67 ng × h/mL
20 mg single, oral
DICYCLOMINE plasma
Homo sapiens
207.88 ng × h/mL
20 mg single, oral
DICYCLOMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.66 h
20 mg single, oral
DICYCLOMINE plasma
Homo sapiens
6.09 h
20 mg single, oral
DICYCLOMINE plasma
Homo sapiens
1.8 h
20 mg single, oral
DICYCLOMINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Adults-Oral. The only oral dose clearly shown to be effective is 160 mg per day (in 4 equally divided doses). Since this dose is associated with a significant incidence of side effects, it is prudent to begin with 80 mg per day (in 4 equally divided doses). Depending upon the patient’s response during the first week of therapy, the dose should be increased to 160 mg per day unless side effects limit dosage escalation. If efficacy is not achieved within 2 weeks or side effects require doses below 80 mg per day, the drug should be discontinued. Documented safety data are not available for doses above 80 mg daily for periods longer than 2 weeks. Adults-Intramuscular Injection. NOT FOR INTRAVENOUS USE. The intramuscular dosage form is to be used temporarily when the patient cannot take oral medication. Intramuscular injection is about twice as bioavailable as oral dosage forms; consequently, the recommended intramuscular dose is 80 mg daily (in 4 equally divided doses). Oral dicyclomine hydrochloride should be started as soon as possible and the intramuscular form should not be used for periods longer than 1 or 2 days.
Route of Administration: Other
In Vitro Use Guide
Dicyclomine showed inhibitory action against several pathogenic bacteria. Dicyclomine inhibited most of the bacterial isolates tested at 25-100 microg/ml concentration, and a few were sensitive even at a lower concentration (10 microg/ml). Dicyclomine was found to be bacteriostatic in nature against Shigella dysenteriae 7, and bactericidal against S. aureus NCTC 6571, 8530, and 8531.
Substance Class Chemical
Record UNII
4KV4X8IF6V
Record Status Validated (UNII)
Record Version