U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H35NO2.ClH
Molecular Weight 345.948
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DICYCLOMINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=GUBNMFJOJGDCEL-UHFFFAOYSA-N
InChI=1S/C19H35NO2.ClH/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;1H

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

4.66646401E11
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
n = 1
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: 10 months
Sex: unknown
Population Size: 1
Sources:
1500 mg single, oral
Highest recorded dose
unhealthy, adult
n = 1
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 1
Sources:
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
n = 100
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 100
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
n = 100
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 100
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
n = 100
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 100
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
n = 100
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 100
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
n = 100
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 100
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
n = 100
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 100
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
n = 100
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 100
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
n = 100
Health Status: unhealthy
Condition: functional bowel/irritable bowel syndrome
Age Group: adult
Sex: unknown
Population Size: 100
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
The effect of M1 muscarinic blockade on behavior and physiological responses following traumatic brain injury in the rat.
1990 Mar 12
Antinociceptive and antiamnesic properties of the presynaptic cholinergic amplifier PG-9.
1998 Mar
Alternative therapies of morning sickness.
2001 Dec
Infantile colic.
2002 Dec
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
Infantile colic.
2003 Dec
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.
2003 Mar
Infantile colic.
2004 Jun
The negative impact of litigation on women's health care.
2005 Dec
Infantile colic.
2005 Jun
Muscarinic M2 and M4 receptors in anterior cingulate cortex: relation to neuropsychiatric symptoms in dementia with Lewy bodies.
2005 Jun 20
Pharmacodynamic effects of darifenacin, a muscarinic M selective receptor antagonist for the treatment of overactive bladder, in healthy volunteers.
2005 Nov
Interaction between M1-muscarinic and glutamatergic NMDA receptors on an inhibitory avoidance task.
2005 Nov 30
[Drug treatment of irritable bowel syndrome: an unmet need].
2007 Mar
Improving the detection limits of antispasmodic drugs electrodes by using modified membrane sensors with inner solid contact.
2007 May 9
Blockade of M1 muscarinic acetylcholine receptors modulates the methamphetamine-induced psychomotor stimulant effect.
2008 Jun 2
Dicyclomine, an M1 muscarinic antagonist, reduces biomarker levels, but not neuronal degeneration, in fluid percussion brain injury.
2008 Nov
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.
2008 Nov 13
Development of functional gastrointestinal disorders after Giardia lamblia infection.
2009 Apr 21
Antispasmodic and bronchodilator activities of Artemisia vulgaris are mediated through dual blockade of muscarinic receptors and calcium influx.
2009 Dec 10
Self-medication for infants with colic in Lagos, Nigeria.
2009 Feb 4
[Characterization of muscarinic receptors in undifferentiated thyroid cells in Fisher rats].
2009 Mar
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
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. 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
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 HYDROCHLORIDE
JAN   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
DICYCLOVERINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
2-(Diethylamino)ethyl [bicyclohexyl]-1-carboxylate hydrochloride
Systematic Name English
DICYCLOMINE HYDROCHLORIDE [USP-RS]
Common Name English
BENTYL
Brand Name English
DIETHYLAMINOCARBETHOXY-BICYCLOHEXYL HYDROCHLORIDE
Systematic Name English
DICYCLOMINE HYDROCHLORIDE [MI]
Common Name English
DICYCLOMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
DICYCLOMINE HYDROCHLORIDE [JAN]
Common Name English
NSC-404381
Code English
WYOVIN
Brand Name English
DICYCLOVERINE HYDROCHLORIDE
EP   MART.   WHO-DD  
Common Name English
DICYCLOMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
KOLANTYL HYDROCHLORIDE
Brand Name English
MERBENTYL
Brand Name English
BENTYLOL
Brand Name English
DICYCLOVERINE HYDROCHLORIDE [MART.]
Common Name English
(BICYCLOHEXYL)-1-CARBOXYLIC ACID, 2-(DIETHYLAMINO)ETHYL ESTER, HYDROCHLORIDE
Common Name English
DICYCLOMINE HYDROCHLORIDE [VANDF]
Common Name English
Dicycloverine hydrochloride [WHO-DD]
Common Name English
1-CYCLOHEXYLHEXAHYDROBENZOIC ACID(BETA)-DIETHYLAMINOETHYL ESTER HYDROCHLORIDE
Systematic Name English
DICYCLOMINE HCL
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.201
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C28987
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
PUBCHEM
441344
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
SMS_ID
100000090526
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
DAILYMED
CQ903KQA31
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
EVMPD
SUB01676MIG
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
CAS
67-92-5
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
RS_ITEM_NUM
1191000
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
RXCUI
152021
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID0058778
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
MERCK INDEX
m4378
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1123
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-671-1
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
DRUG BANK
DBSALT000698
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
CHEBI
4515
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
NSC
404381
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY
FDA UNII
CQ903KQA31
Created by admin on Fri Dec 15 15:09:46 UTC 2023 , Edited by admin on Fri Dec 15 15:09:46 UTC 2023
PRIMARY