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Details

Stereochemistry ACHIRAL
Molecular Formula C19H35NO2
Molecular Weight 309.4874
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
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BENTYL

Approved Use

Dicyclomine hydrochloride oral solution is indicated for the treatment of functional bowel/irritable bowel syndrome.

Launch Date

466646400000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
50.47 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICYCLOMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
47.98 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICYCLOMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
202.67 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICYCLOMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
207.88 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICYCLOMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.66 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICYCLOMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.09 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICYCLOMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.8 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICYCLOMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
600 mg single, oral
Highest recorded dose
unhealthy, 10 months
Health Status: unhealthy
Age Group: 10 months
Sex: unknown
Sources:
1500 mg single, oral
Highest recorded dose
unhealthy, adult
40 mg 4 times / day multiple, oral
Recommended
Dose: 40 mg, 4 times / day
Route: oral
Route: multiple
Dose: 40 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Dry mouth, Dizziness...
Other AEs:
Dry mouth (33%)
Dizziness (40%)
Vision blurred (27%)
Nausea (14%)
Somnolence (9%)
Asthenia (7%)
Nervousness (6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea 14%
40 mg 4 times / day multiple, oral
Recommended
Dose: 40 mg, 4 times / day
Route: oral
Route: multiple
Dose: 40 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Vision blurred 27%
40 mg 4 times / day multiple, oral
Recommended
Dose: 40 mg, 4 times / day
Route: oral
Route: multiple
Dose: 40 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Dry mouth 33%
40 mg 4 times / day multiple, oral
Recommended
Dose: 40 mg, 4 times / day
Route: oral
Route: multiple
Dose: 40 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Dizziness 40%
40 mg 4 times / day multiple, oral
Recommended
Dose: 40 mg, 4 times / day
Route: oral
Route: multiple
Dose: 40 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Nervousness 6%
40 mg 4 times / day multiple, oral
Recommended
Dose: 40 mg, 4 times / day
Route: oral
Route: multiple
Dose: 40 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Asthenia 7%
40 mg 4 times / day multiple, oral
Recommended
Dose: 40 mg, 4 times / day
Route: oral
Route: multiple
Dose: 40 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Somnolence 9%
40 mg 4 times / day multiple, oral
Recommended
Dose: 40 mg, 4 times / day
Route: oral
Route: multiple
Dose: 40 mg, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

PubMed

PubMed

TitleDatePubMed
Dicyclomine: worrying symptoms associated with its use in some small babies.
1984 Mar 24
Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells.
1989 Apr
Antinociceptive and antiamnesic properties of the presynaptic cholinergic amplifier PG-9.
1998 Mar
Infantile colic.
2002 Jun
Medical, social, and legal implications of treating nausea and vomiting of pregnancy.
2002 May
Prenatal prescription of macrolide antibiotics and infantile hypertrophic pyloric stenosis.
2003 Apr
Bendectin and birth defects. II: Ecological analyses.
2003 Feb
Antibacterial potential of an antispasmodic drug dicyclomine hydrochloride.
2003 Nov
Infantile colic.
2004
Dicycloverine for persistent crying in babies: dicycloverine is contraindicated in infants.
2004 Apr 17
Experimental analysis of antimicrobial action of dicyclomine hydrochloride.
2004 Dec
Infantile colic.
2004 Jun
The negative impact of litigation on women's health care.
2005 Dec
Quantitative determination of pharmaceuticals using nano-electrospray ionization mass spectrometry after reversed phase mini-solid phase extraction.
2005 Feb 23
Infantile colic.
2005 Jun
Pharmacodynamic effects of darifenacin, a muscarinic M selective receptor antagonist for the treatment of overactive bladder, in healthy volunteers.
2005 Nov
Current gut-directed therapies for irritable bowel syndrome.
2006 Jul
Clinical inquiries. What is the best treatment for infants with colic?
2006 Jul
Role of muscarinic M1 receptors in inhibitory avoidance and contextual fear conditioning.
2006 Sep
American Gastroenterological Association institute medical position statement on the use of gastrointestinal medication in pregnancy.
2007 Feb
Antagonism of muscarinic M1 receptors by dicyclomine inhibits the consolidation of morphine-associated contextual memory.
2008 Jul 1
Blockade of M1 muscarinic acetylcholine receptors modulates the methamphetamine-induced psychomotor stimulant effect.
2008 Jun 2
Fustin flavonoid attenuates beta-amyloid (1-42)-induced learning impairment.
2009 Dec
Antispasmodic and bronchodilator activities of Artemisia vulgaris are mediated through dual blockade of muscarinic receptors and calcium influx.
2009 Dec 10
Oxybutynin extended release for the management of overactive bladder: a clinical review.
2009 Sep 21
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

Sample Use Guides

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.
Route of Administration: Other
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.
Name Type Language
DICYCLOMINE
HSDB   MI   VANDF  
Common Name English
DICYCLOMINE [MI]
Common Name English
DICYCLOMINE [HSDB]
Common Name English
DICYCLOVERINE [INN]
Common Name English
DICYCLOVERINE
INN   WHO-DD  
INN  
Official Name English
DICYCLOMINE [VANDF]
Common Name English
DICYMINE
Brand Name English
DICYCLOVERINE [WHO-DD]
Common Name English
(BICYCLOHEXYL)-1-CARBOXYLIC ACID, 2-(DIETHYLAMINO)ETHYL ESTER
Common Name English
2-(DIETHYLAMINO)ETHYL (BICYCLOHEXYL)-1-CARBOXYLATE
Systematic Name English
KOLANTYL
Brand Name English
Classification Tree Code System Code
WHO-VATC QA03AA07
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
LIVERTOX 299
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
NDF-RT N0000175370
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
WHO-ATC A03AA07
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
NDF-RT N0000175574
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
Code System Code Type Description
INN
619
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
NCI_THESAURUS
C61720
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
MERCK INDEX
M4378
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
DICYCLOVERINE
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL1123
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
DRUG CENTRAL
868
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
EVMPD
SUB07103MIG
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
IUPHAR
355
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
MESH
D004025
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
HSDB
3058
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
DRUG BANK
DB00804
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
CAS
77-19-0
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
RXCUI
3361
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY RxNorm
LACTMED
Dicyclomine
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
EPA CompTox
77-19-0
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-009-4
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
FDA UNII
4KV4X8IF6V
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY
PUBCHEM
3042
Created by admin on Sat Jun 26 14:42:49 UTC 2021 , Edited by admin on Sat Jun 26 14:42:49 UTC 2021
PRIMARY