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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
DicicloverinaSpanishINN
DicycloverinNot AvailableNot Available
DicycloverineNot AvailableINN
DicycloverinumLatinINN
Salts
Name/CAS Structure Properties
Dicyclomine Hydrochloride
Thumb
  • InChI Key: GUBNMFJOJGDCEL-UHFFFAOYSA-N
  • Monoisotopic Mass: 345.243457108
  • Average Mass: 345.948
DBSALT000698
Brand names
NameCompany
BentylNot Available
BentylolNot Available
ByclomineNot Available
Di-SpazNot Available
DibentNot Available
DilomineNot Available
DyspasNot Available
MerbentylNot Available
Brand mixturesNot Available
Categories
CAS number77-19-0
WeightAverage: 309.4867
Monoisotopic: 309.266779369
Chemical FormulaC19H35NO2
InChI KeyInChIKey=CURUTKGFNZGFSE-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassCarboxylic Acid Derivatives
Direct parentCarboxylic Acid Esters
Alternative parentsTertiary Amines; Polyamines; Ethers; Enolates
Substituentsether; enolate; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the carboxylic acid esters. These are carboxylic acid derivatives in which the carbo atom from the carbonyl group is atached to an alkyl or oaryl moiety through an oxygen atom (forming an ester group).
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
Property Value Probability
Human Intestinal Absorption + 0.995
Blood Brain Barrier + 0.9769
Caco-2 permeable + 0.6616
P-glycoprotein substrate Substrate 0.6141
P-glycoprotein inhibitor I Non-inhibitor 0.6115
P-glycoprotein inhibitor II Non-inhibitor 0.5806
Renal organic cation transporter Inhibitor 0.5184
CYP450 2C9 substrate Non-substrate 0.8373
CYP450 2D6 substrate Non-substrate 0.8226
CYP450 3A4 substrate Substrate 0.5092
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Inhibitor 0.796
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6193
Ames test Non AMES toxic 0.8524
Carcinogenicity Non-carcinogens 0.52
Biodegradation Not ready biodegradable 0.9876
Rat acute toxicity 3.1919 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.873
hERG inhibition (predictor II) Inhibitor 0.6714
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
CapsuleOral
SolutionIntramuscular
SyrupOral
TabletOral
Prices
Unit descriptionCostUnit
Bentyl 10 mg/ml ampul12.28USDml
Dicyclomine 10 mg/ml vial8.58USDml
Dicyclomine Hydrochloride 10 mg/ml3.41USDml
Dicyclomine hcl powder1.0USDg
Bentyl 10 mg capsule0.79USDcapsule
Bentyl 20 mg tablet0.75USDtablet
Dicyclomine HCl 10 mg capsule0.47USDcapsule
Dicyclomine HCl 20 mg tablet0.4USDtablet
Dicyclomine 20 mg tablet0.31USDtablet
Bentylol 20 mg Tablet0.23USDtablet
Bentyl 10 mg/5ml Syrup0.15USDml
Bentylol 10 mg Tablet0.12USDtablet
Dicyclomine HCl 10 mg/5ml Solution0.1USDml
Bentylol 2 mg/ml Syrup0.06USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP5.5Not Available
Predicted Properties
PropertyValueSource
water solubility3.27e-03 g/lALOGPS
logP5.82ALOGPS
logP4.93ChemAxon
logS-5ALOGPS
pKa (strongest basic)8.96ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area29.54ChemAxon
rotatable bond count8ChemAxon
refractivity91.78ChemAxon
polarizability37.39ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC06951
PubChem Compound3042
PubChem Substance46505371
ChemSpider2934
BindingDB50010101
ChEBI4514
ChEMBLCHEMBL1123
Therapeutic Targets DatabaseDAP001118
PharmGKBPA164744928
IUPHAR355
Guide to Pharmacology355
Drug Product Database392820
RxListhttp://www.rxlist.com/cgi/generic/dicyc.htm
Drugs.comhttp://www.drugs.com/cdi/dicyclomine.html
WikipediaDicyclomine
ATC CodesA03AA07
AHFS Codes
  • 12:08.08
PDB EntriesNot Available
FDA labelshow(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.

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

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
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12