DICYCLOMINE

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007409s040,007961s026,008370s031lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/24396252

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 Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2432979	Antagonist 2778
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3612532	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Irritable bowel syndrome 60 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007409s040,007961s026,008370s031lbl.pdf	Palliative		Approved 8429	BENTYL Approved Use Dicyclomine hydrochloride oral solution is indicated for the treatment of functional bowel/irritable bowel syndrome. Launch Date 1984

C_max

Value	Dose	Co-administered	Analyte	Population
50.47 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/40230_Dicyclomine%20Hydrochloride_Bioeqr.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/40230_Dicyclomine%20Hydrochloride_Bioeqr.pdf	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

Value	Dose	Co-administered	Analyte	Population
202.67 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/40230_Dicyclomine%20Hydrochloride_Bioeqr.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/40230_Dicyclomine%20Hydrochloride_Bioeqr.pdf	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

T_1/2

Value	Dose	Analyte	Population
6.66 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/40230_Dicyclomine%20Hydrochloride_Bioeqr.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/40230_Dicyclomine%20Hydrochloride_Bioeqr.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	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

Dose	Population	Adverse events
600 mg single, oral Highest recorded dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007409s040,007961s026,008370s031lbl.pdf	unhealthy, 10 months n = 1 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: 10 months Sex: unknown Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007409s040,007961s026,008370s031lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007409s040,007961s026,008370s031lbl.pdf
1500 mg single, oral Highest recorded dose Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007409s040,007961s026,008370s031lbl.pdf	unhealthy, adult n = 1 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007409s040,007961s026,008370s031lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/007409s040,007961s026,008370s031lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	Other AEs: Dry mouth, Dizziness... Other AEs: Dry mouth (33%) Dizziness (40%) Vision blurred (27%) Nausea (14%) Somnolence (9%) Asthenia (7%) Nervousness (6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf	unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/007409s041lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1A1 108

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A1 218	inducer 1573 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000077190	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4515	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4515
ChemicalBook	CB2285591	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2285591
MolPort	MolPort-003-666-161	https://www.molport.com/shop/molecule-link/MolPort-003-666-161
eMolecules	537444	https://www.emolecules.com/cgi-bin/more?vid=537444

PubMed

Title	Date	PubMed
Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells.	1989 Apr	2704370
The effect of M1 muscarinic blockade on behavior and physiological responses following traumatic brain injury in the rat.	1990 Mar 12	2331611
Antinociceptive and antiamnesic properties of the presynaptic cholinergic amplifier PG-9.	1998 Mar	9495837
Alternative therapies of morning sickness.	2001 Dec	11600848
The expert witness. Neither Frye nor Daubert solved the problem: what can be done?	2001 Jan-Mar	11215302
Evidence based management of nocturnal enuresis.	2001 Nov 17	11711411
Bendectin.	2001 Nov-Dec	11738529
Cimetropium bromide in the treatment of crisis in infantile colic.	2002 Apr	11930101
Prenatal prescription of macrolide antibiotics and infantile hypertrophic pyloric stenosis.	2003 Apr	12681897
Infantile colic.	2003 Dec	15555098
Bendectin and birth defects: hopefully, the final chapter.	2003 Feb	12769503
The effect of fennel (Foeniculum Vulgare) seed oil emulsion in infantile colic: a randomized, placebo-controlled study.	2003 Jul-Aug	12868253
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.	2003 Mar	12601066
Antibacterial potential of an antispasmodic drug dicyclomine hydrochloride.	2003 Nov	14723484
[Hyperemesis gravidarum--etiology and treatment].	2003 Sep-Oct	14994923
Dicycloverine for persistent crying in babies: beware recommending dicycloverine treatment in babies.	2004 Apr 17	15087360
Infantile colic.	2004 Jun	15652013
Trospium chloride: an update on a quaternary anticholinergic for treatment of urge urinary incontinence.	2005 Jun	18360555
Muscarinic M2 and M4 receptors in anterior cingulate cortex: relation to neuropsychiatric symptoms in dementia with Lewy bodies.	2005 Jun 20	15922057
Post-marketing surveillance using pharmacy-based cohorts: results of a pilot study.	2005 May	15372672
Treatment of overactive bladder in the aging population: focus on darifenacin.	2006	18046909
Current gut-directed therapies for irritable bowel syndrome.	2006 Jul	16836950
American Gastroenterological Association institute medical position statement on the use of gastrointestinal medication in pregnancy.	2007 Feb	17261292
[Drug treatment of irritable bowel syndrome: an unmet need].	2007 Mar	17374325
Gastrointestinal, selective airways and urinary bladder relaxant effects of Hyoscyamus niger are mediated through dual blockade of muscarinic receptors and Ca2+ channels.	2008 Feb	18251725
Anticholinergic activity of 107 medications commonly used by older adults.	2008 Jul	18510583
Antagonism of muscarinic M1 receptors by dicyclomine inhibits the consolidation of morphine-associated contextual memory.	2008 Jul 1	18502314
Blockade of M1 muscarinic acetylcholine receptors modulates the methamphetamine-induced psychomotor stimulant effect.	2008 Jun 2	18455881
Topiramate induced acute angle closure glaucoma.	2008 Mar 28	19478906
Mechanisms underlying the antispasmodic and bronchodilatory properties of Terminalia bellerica fruit.	2008 Mar 28	18289813
Dicyclomine, an M1 muscarinic antagonist, reduces biomarker levels, but not neuronal degeneration, in fluid percussion brain injury.	2008 Nov	19061379
Preserving cognitive function for patients with overactive bladder: evidence for a differential effect with darifenacin.	2008 Nov	18699842
Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis.	2008 Nov 13	19008265
Interaction between glutamatergic-NMDA and cholinergic-muscarinic systems in classical fear conditioning.	2008 Sep 30	18582541
Liver Injury with Features Mimicking Autoimmune Hepatitis following the Use of Black Cohosh.	2009	20130783
Antispasmodic and bronchodilator activities of Artemisia vulgaris are mediated through dual blockade of muscarinic receptors and calcium influx.	2009 Dec 10	19751814
Self-medication for infants with colic in Lagos, Nigeria.	2009 Feb 4	19193235
Rapid Hemodynamic Deterioration and Death due to Acute Severe Refractory Septic Shock.	2009 Jun	22505976
[Characterization of muscarinic receptors in undifferentiated thyroid cells in Fisher rats].	2009 Mar	19627722
Oxybutynin extended release for the management of overactive bladder: a clinical review.	2009 Sep 21	19920931
Use of potentially inappropriate medicines in elderly: A prospective study in medicine out-patient department of a tertiary care teaching hospital.	2010 Apr	20711374
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.	2010 Apr 7	20396637
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Survey on the use of psychotropic drugs by twelve military police units in the municipalities of Goiânia and Aparecida de Goiânia, state of Goiás, Brazil.	2010 Dec	21308260
Opioid substitution therapy in manipur and nagaland, north-east india: operational research in action.	2010 Dec 1	21122129
Chiropractic diagnosis and management of non-musculoskeletal conditions in children and adolescents.	2010 Jun 2	20525197
New approaches in the management of multiple sclerosis.	2010 Nov 24	21151622
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
A computer-automated touchscreen paired-associates learning (PAL) task for mice: impairments following administration of scopolamine or dicyclomine and improvements following donepezil.	2011 Mar	21086119
A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis.	2013 Feb	23243064

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.

Name

Type

Language

DICYCLOMINE

Common Name

English

Dicycloverine [WHO-DD]

Common Name

English

DICYCLOMINE [MI]

Common Name

English

DICYCLOMINE [HSDB]

Common Name

English

dicycloverine [INN]

Common Name

English

DICYCLOVERINE

Official Name

English

DICYCLOMINE [VANDF]

Common Name

English

DICYMINE

Brand 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