You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameDicyclomine
Accession NumberDB00804  (APRD00113)
TypeSmall Molecule
GroupsApproved
Description

A muscarinic antagonist used as an antispasmodic and in urinary incontinence. It has little effect on glandular secretion or the cardiovascular system. It does have some local anesthetic properties and is used in gastrointestinal, biliary, and urinary tract spasms. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(Diethylamino)ethyl 1-cyclohexylcyclohexanecarboxylateNot AvailableNot Available
Bicyclohexyl-1-carboxylic acid 2-diethylamino-ethyl esterNot AvailableNot Available
DicicloverinaSpanishINN
DICYCLOMINENot AvailableNot Available
DicycloverinNot AvailableNot Available
DicycloverineNot AvailableINN
DicycloverinumLatinINN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bentylcapsule10 mgoralAptalis Pharma US, Inc.1950-05-11Not AvailableUs
Bentyltablet20.6 mgoralAptalis Pharma US, Inc.1950-05-11Not AvailableUs
Bentylinjection, solution20 mg/2mLintramuscularAptalis Pharma US, Inc.1952-08-13Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dicyclominetablet20 mgoralWest ward Pharmaceutical Corp1996-10-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralWest ward Pharmaceutical Corp1997-02-28Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralMylan Pharmaceuticals Inc.2013-03-27Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralMylan Pharmaceuticals Inc.2013-03-27Not AvailableUs
Dicyclominetablet20 mgoralLiberty Pharmaceuticals, Inc.1996-10-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralLiberty Pharmaceuticals, Inc.1974-09-30Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralLannett Company, Inc.1974-09-30Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralLannett Company, Inc.1999-02-26Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralActavis Pharma, Inc.1986-06-19Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralActavis Pharma, Inc.1986-07-30Not AvailableUs
Dicyclomine Hydrochloridesolution10 mg/5mLoralQualitest Pharmaceuticals2005-06-23Not AvailableUs
Dicyclominecapsule10 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1997-02-28Not AvailableUs
Dicyclominetablet20 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1996-10-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1986-06-19Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs1986-07-30Not AvailableUs
Dicyclominetablet20 mgoralMajor Pharmaceuticals1996-10-01Not AvailableUs
Dicyclominetablet20 mgoralBlenheim Pharmacal, Inc.2011-04-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralStat Rx USA1997-02-28Not AvailableUs
Dicyclominetablet20 mgoralSTAT Rx USA LLC1996-10-01Not AvailableUs
Dicyclomine Hydrochloridesolution10 mg/5mLoralAtlantic Biologicals Corps2005-06-23Not AvailableUs
Dicyclominecapsule10 mgoralRebel Distributors Corp.1997-02-28Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralRebel Distributors Corp1999-02-26Not AvailableUs
Dicyclominetablet20 mgoralREMEDYREPACK INC.2013-03-15Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralREMEDYREPACK INC.2013-02-13Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralAidarex Pharmaceuticals LLC1999-02-26Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralAidarex Pharmaceuticals LLC1974-09-30Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralRebel Distributors Corp1986-06-19Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralPd Rx Pharmaceuticals, Inc.1986-07-30Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralPd Rx Pharmaceuticals, Inc.1986-06-19Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralREMEDYREPACK INC.2010-07-23Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralREMEDYREPACK INC.2010-11-20Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralLake Erie Medical DBA Quality Care Products LLC2011-11-18Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralLake Erie Medical DBA Quality Care Products LLC1974-09-30Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralA S Medication Solutions Llc1974-09-30Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralA S Medication Solutions Llc1974-09-30Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralA S Medication Solutions Llc1986-06-19Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralA S Medication Solutions Llc1986-06-19Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralA S Medication Solutions Llc1986-07-30Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralA S Medication Solutions Llc1999-02-26Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralUnit Dose Services1974-09-30Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralMylan Institutional Inc.1999-12-01Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralMylan Institutional Inc.1998-03-06Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralREMEDYREPACK INC.2013-05-29Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralREMEDYREPACK INC.2014-08-27Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralREMEDYREPACK INC.2013-03-09Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralREMEDYREPACK INC.2013-05-14Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralREMEDYREPACK INC.2013-06-24Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralREMEDYREPACK INC.2014-02-06Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralREMEDYREPACK INC.2013-07-01Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralREMEDYREPACK INC.2013-07-09Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralREMEDYREPACK INC.2013-07-16Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralREMEDYREPACK INC.2013-10-15Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralREMEDYREPACK INC.2014-02-20Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralREMEDYREPACK INC.2015-01-02Not AvailableUs
Dicyclominetablet20 mgoralH.J. Harkins Company, Inc.1996-10-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Dicyclominecapsule10 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Dicyclomine Hydrochloridetablet10 mgoralState of Florida DOH Central Pharmacy2009-07-01Not AvailableUs
Dicyclominetablet20 mgoralState of Florida DOH Central Pharmacy2014-01-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralA S Medication Solutions Llc1986-06-19Not AvailableUs
Dicyclominetablet20 mgoralA S Medication Solutions Llc1996-10-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralPhysicians Total Care, Inc.1995-10-26Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralPhysicians Total Care, Inc.1995-01-23Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralCardinal Health2011-08-16Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralCardinal Health2011-08-16Not AvailableUs
Dicyclominetablet20 mgoralPd Rx Pharmaceuticals, Inc.1996-10-01Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralClinical Solutions Wholesale1986-07-30Not AvailableUs
Dicyclominecapsule10 mgoralGolden State Medical Supply, Inc.1996-10-01Not AvailableUs
Dicyclominetablet20 mgoralGolden State Medical Supply, Inc.1996-10-01Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralSt. Mary's Medical Park Pharmacy1986-07-30Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralREMEDYREPACK INC.2015-01-24Not AvailableUs
Dicyclominetablet20 mgoralbryant ranch prepack1996-10-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralbryant ranch prepack1997-02-28Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralTYA Pharmaceuticals1974-09-30Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralDispensing Solutions, Inc.1986-06-19Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralPreferred Pharmaceuticals, Inc.2014-02-21Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralPreferred Pharmaceuticals, Inc.2013-02-18Not AvailableUs
Dicyclominetablet20 mgoralPreferred Pharmaceuticals, Inc1996-10-01Not AvailableUs
Dicyclomine Hydrochloridecapsule10 mgoralPreferred Pharmaceuticals, Inc2012-01-17Not AvailableUs
Dicyclomine Hydrochloridetablet20 mgoralLife Line Home Care Services, Inc.2012-02-07Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
BentylolAxcan
ByclomineNot Available
Di-SpazNot Available
DibentNot Available
DilomineNot Available
DyspasSavage
MerbentylSanofi
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Dicyclomine Hydrochloride
Thumb
  • InChI Key: GUBNMFJOJGDCEL-UHFFFAOYSA-N
  • Monoisotopic Mass: 345.243457108
  • Average Mass: 345.948
DBSALT000698
Categories
CAS number77-19-0
WeightAverage: 309.4867
Monoisotopic: 309.266779369
Chemical FormulaC19H35NO2
InChI KeyCURUTKGFNZGFSE-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-(diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate
SMILES
CCN(CC)CCOC(=O)C1(CCCCC1)C1CCCCC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbo atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of functional bowel/irritable bowel syndrome including Colicky abdominal pain; diverticulitis
PharmacodynamicsDicyclomine is an anticholinergic drug, a medication that reduces the effect of acetylcholine, a chemical released from nerves that stimulates muscles, by blocking the receptors for acetylcholine on smooth muscle (a type of muscle). It also has a direct relaxing effect on smooth muscle. Dicyclomine is used to treat or prevent spasm in the muscles of the gastrointestinal tract in the irritable bowel syndrome. In addition, Dicyclomine inhibits gastrointestinal propulsive motility and decreases gastric acid secretion and controls excessive pharyngeal, tracheal and bronchial secretions.
Mechanism of actionAction is achieved via a dual mechanism: (1) a specific anticholinergic effect (antimuscarinic) at the acetylcholine-receptor sites and (2) a direct effect upon smooth muscle (musculotropic).
AbsorptionNot Available
Volume of distribution
  • 3.65 L/kg [20 mg oral dose]
Protein binding>99%
Metabolism
Route of eliminationThe principal route of elimination is via the urine (79.5% of the dose). Excretion also occurs in the feces, but to a lesser extent (8.4%).
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.9769
Caco-2 permeable+0.6616
P-glycoprotein substrateSubstrate0.6141
P-glycoprotein inhibitor INon-inhibitor0.6115
P-glycoprotein inhibitor IINon-inhibitor0.5806
Renal organic cation transporterInhibitor0.5184
CYP450 2C9 substrateNon-substrate0.8373
CYP450 2D6 substrateNon-substrate0.8226
CYP450 3A4 substrateSubstrate0.5092
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6193
Ames testNon AMES toxic0.8524
CarcinogenicityNon-carcinogens0.52
BiodegradationNot ready biodegradable0.9876
Rat acute toxicity3.1919 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.873
hERG inhibition (predictor II)Inhibitor0.6714
Pharmacoeconomics
Manufacturers
  • Axcan pharma us inc
  • Lannett co inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Pioneer pharmaceuticals inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Bedford laboratories div ben venue laboratories inc
  • Alpharma us pharmaceuticals division
  • Mikart inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral10 mg
Injection, solutionintramuscular20 mg/2mL
Solutionoral10 mg/5mL
Tabletoral10 mg
Tabletoral20 mg
Tabletoral20.6 mg
Prices
Unit descriptionCostUnit
Bentyl 10 mg/ml ampul12.28USD ml
Dicyclomine 10 mg/ml vial8.58USD ml
Dicyclomine Hydrochloride 10 mg/ml3.41USD ml
Dicyclomine hcl powder1.0USD g
Bentyl 10 mg capsule0.79USD capsule
Bentyl 20 mg tablet0.75USD tablet
Dicyclomine HCl 10 mg capsule0.47USD capsule
Dicyclomine HCl 20 mg tablet0.4USD tablet
Dicyclomine 20 mg tablet0.31USD tablet
Bentylol 20 mg Tablet0.23USD tablet
Bentyl 10 mg/5ml Syrup0.15USD ml
Bentylol 10 mg Tablet0.12USD tablet
Dicyclomine HCl 10 mg/5ml Solution0.1USD ml
Bentylol 2 mg/ml Syrup0.06USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point165-166Van Campen, M.G. Jr. and Tilford, C.H.; US.Patent 2,474,796; June 28, 1949; assigned to The Wm. S. Merrell Company.
logP5.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00327 mg/mLALOGPS
logP5.82ALOGPS
logP4.93ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity91.78 m3·mol-1ChemAxon
Polarizability37.39 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Van Campen, M.G. Jr. and Tilford, C.H.; US.Patent 2,474,796; June 28, 1949; assigned to
The Wm. S. Merrell Company.

General ReferenceNot Available
External Links
ATC CodesA03AA07
AHFS Codes
  • 12:08.08
PDB EntriesNot Available
FDA labelDownload (230 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
HaloperidolThe anticholinergic increases the risk of psychosis and tardive dyskinesia
RivastigminePossible antagonism of action
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Dicyclomine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TrimethobenzamideTrimethobenzamide and Dicyclomine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Dicyclomine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrospiumTrospium and Dicyclomine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Avoid alcohol.
  • Take this medication 30 minutes before meals.

Targets

1. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Jin CH, Shin EJ, Park JB, Jang CG, Li Z, Kim MS, Koo KH, Yoon HJ, Park SJ, Choi WC, Yamada K, Nabeshima T, Kim HC: Fustin flavonoid attenuates beta-amyloid (1-42)-induced learning impairment. J Neurosci Res. 2009 Dec;87(16):3658-70. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

References:

  1. Pavia J, Munoz M, Jimenez E, Martos F, Gonzalez-Correa JA, De la Cruz JP, Garcia V, Sanchez de la Cuesta F: Pharmacological characterization and distribution of muscarinic receptors in human placental syncytiotrophoblast brush-border and basal plasma membranes. Eur J Pharmacol. 1997 Feb 12;320(2-3):209-14. Pubmed

Enzymes

1. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on April 11, 2014 15:09