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Identification
Name Dicyclomine
Accession Number DB00804 (APRD00113)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Atumin
  • Bentomine
  • Bentyl
  • Bentyl Hydrochloride
  • Bentylol
  • Bentylol Hydrochloride
  • Di-Syntramine
  • Dicicloverina [INN-Spanish]
  • Dicyclomine Hcl
  • Dicyclomine Hydrochloride
  • Dicycloverin
  • Dicycloverin Hydrochloride
  • Dicycloverine
  • Dicycloverine Hydrochloride
  • Dicycloverinum [INN-Latin]
  • Diethylaminocarbethoxybicyclohexyl Hydrochloride
  • Diocyl
  • Diocyl Hydrochloride
  • Dyspas
  • Formulex
  • Kolantyl Hydrochloride
  • Mamiesan
  • Merbentyl
  • Oxityl-P
  • Procyclomin
  • Sawamin
  • Spasmoban
  • Wyovin
  • Wyovin Hydrochloride
Brand name mixtures Not Available
Categories
  • Muscarinic Antagonists
  • Antispasmodics
  • Antimuscarinics
  • Anticholinergic Agents
  • Parasympatholytics
CAS number 77-19-0
Weight Average: 309.4867
Monoisotopic: 309.266779369
Chemical Formula C19H35NO2
InChI Key InChIKey=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
Plain Text
IUPAC Name
2-(diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate
SMILES
CCN(CC)CCOC(=O)C1(CCCCC1)C1CCCCC1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Bicyclohexanes
Substructures
  • Carbonyl Compounds
  • Carboxylic Acids and Derivatives
  • Acetates
  • Ethers
  • Bicyclohexanes
  • Aliphatic and Aryl Amines
Pharmacology
Indication For the treatment of functional bowel/irritable bowel syndrome including Colicky abdominal pain; diverticulitis
Pharmacodynamics Dicyclomine 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 action Action 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).
Absorption Not Available
Volume of distribution
  • 3.65 L/kg [20 mg oral dose]
Protein binding >99%
Metabolism
Route of elimination The 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 life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Form Route Strength
Capsule Oral
Solution Intramuscular
Syrup Oral
Tablet Oral
Prices
Unit description Cost Unit
Bentyl 10 mg/ml ampul 12.28 USD ml
Dicyclomine 10 mg/ml vial 8.58 USD ml
Dicyclomine Hydrochloride 10 mg/ml 3.41 USD ml
Dicyclomine hcl powder 1.0 USD g
Bentyl 10 mg capsule 0.79 USD capsule
Bentyl 20 mg tablet 0.75 USD tablet
Dicyclomine HCl 10 mg capsule 0.47 USD capsule
Dicyclomine HCl 20 mg tablet 0.4 USD tablet
Dicyclomine 20 mg tablet 0.31 USD tablet
Bentylol 20 mg Tablet 0.23 USD tablet
Bentyl 10 mg/5ml Syrup 0.15 USD ml
Bentylol 10 mg Tablet 0.12 USD tablet
Dicyclomine HCl 10 mg/5ml Solution 0.1 USD ml
Bentylol 2 mg/ml Syrup 0.06 USD ml
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 5.5 PhysProp
Predicted Properties
Property Value Source
water solubility 3.27e-03 g/l ALOGPS
logP 5.82 ALOGPS
logP 4.93 ChemAxon Molconvert
logS -4.98 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 29.54 ChemAxon Molconvert
rotatable bond count 8 ChemAxon Molconvert
refractivity 91.78 ChemAxon Molconvert
polarizability 37.39 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C06951 Link_out
PubChem Compound 3042 Link_out
PubChem Substance 46505371 Link_out
ChemSpider 2934 Link_out
BindingDB 50010101 Link_out
ChEBI 4514 Link_out
ChEMBL 4514 Link_out
Therapeutic Targets Database DAP001118 Link_out
PharmGKB PA449299 Link_out
Drug Product Database 392820 Link_out
RxList http://www.rxlist.com/cgi/generic/dicyc.htm Link_out
Drugs.com http://www.drugs.com/cdi/dicyclomine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Dicyclomine Link_out
ATC Codes
  • A03AA07
AHFS Codes
  • 12:08.08
PDB Entries Not Available
FDA label show (229.5 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Take this medication 30 minutes before meals.
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 April 19, 2011 15:06

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.