Identification

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Name
Dicyclomine
Accession Number
DB00804  (APRD00113)
Type
Small Molecule
Groups
Approved
Description

Dicyclomine is a muscarinic M1 and M2 receptor antagonist as well as a non-competitive inhibitor of histamine and bradykinin used to treat spasms of the intestines seen in functional bowel disorder and irritable bowel syndrome.3,4,5 Though it is commonly prescribed, its recommendation may have been based on a small amount of evidence and so its prescription is becoming less favourable.6

Dicyclomine was granted FDA approval on 11 May 1950.5

Structure
Thumb
Synonyms
  • 2-(diethylamino)ethyl 1-cyclohexylcyclohexanecarboxylate
  • Bicyclohexyl-1-carboxylic acid 2-diethylamino-ethyl ester
  • Dicicloverina
  • Dicyclomine
  • Dicycloverin
  • Dicycloverine
  • Dicycloverinum
Product Ingredients
IngredientUNIICASInChI Key
Dicyclomine hydrochlorideCQ903KQA3167-92-5GUBNMFJOJGDCEL-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BentylCapsule10 mg/1OralAllergan, Inc.1950-05-112018-08-31Us
BentylSyrup10 mg/5mLOralAxcan Scandipharm Inc.2006-10-232006-10-23Us
BentylInjection, solution20 mg/2mLIntramuscularA-S Medication Solutions1952-08-13Not applicableUs
BentylTablet20.6 mg/1OralPhysicians Total Care, Inc.1950-05-112011-06-30Us
BentylInjection, solution20 mg/2mLIntramuscularAllergan, Inc.1952-08-13Not applicableUs
BentylTablet20.6 mg/1OralAllergan, Inc.1950-05-11Not applicableUs
BentylolSyrupOralAptalis Pharma Canada Ulc1993-12-312018-11-19Canada
Bentylol Dospan 30mgTablet, extended releaseOralMerrell Pharms Inc., Division Of Merrell Dow (Can)1988-03-231996-09-09Canada
Bentylol Inj 10mg/mlLiquidIntramuscularMerrell Pharms Inc., Division Of Merrell Dow (Can)1965-12-311996-09-09Canada
Bentylol Tablet 10mgTabletOralAptalis Pharma Canada Ulc1995-12-312018-11-19Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DicyclomineTablet20 mg/1OralRemedy Repack2013-03-152013-08-23Us
DicyclomineTablet20 mg/1Oralbryant ranch prepack1996-10-012018-04-30Us63629 129920180907 15195 11uymea
DicyclomineCapsule10 mg/1OralGolden State Medical Supply1996-10-012018-09-10Us00143 3126 01 nlmimage10 af34d7f6
DicyclomineInjection20 mg/2mLIntramuscularAkorn2018-05-04Not applicableUs
DicyclomineCapsule10 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs1997-02-28Not applicableUs
DicyclomineTablet20 mg/1OralPd Rx Pharmaceuticals, Inc.1996-10-012018-07-31Us
DicyclomineTablet20 mg/1OralBlenheim Pharmacal, Inc.2011-04-01Not applicableUs
DicyclomineTablet20 mg/1OralStat Rx USA1996-10-01Not applicableUs
DicyclomineTablet20 mg/1OralMajor1996-10-012014-04-30Us
DicyclomineTablet20 mg/1OralPreferreed Pharmaceuticals Inc.1996-10-01Not applicableUs68788 993420180913 8702 v0x2an
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DiclophenDicyclomine hydrochloride (10 mg) + Phenobarbital (15 mg)CapsuleOralPro Doc Limitee1970-12-312009-07-23Canada
Spasmo Nil TabDicyclomine hydrochloride (2.5 mg) + Aluminum hydroxide (75 mg) + Dimethicone (7.5 mg) + Magnesium trisilicate (75 mg)TabletOralDuchesnay Inc.1978-12-312003-07-18Canada
International/Other Brands
Byclomine / Di-Spaz / Dibent / Dilomine / Dyspas (Savage) / Merbentyl (Sanofi)
Categories
UNII
4KV4X8IF6V
CAS number
77-19-0
Weight
Average: 309.4867
Monoisotopic: 309.266779369
Chemical Formula
C19H35NO2
InChI Key
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

Pharmacology

Indication

Dicyclomine is indicated for the treatment of functional bowel disorder and irritable bowel syndrome.5

Associated Conditions
Pharmacodynamics

Dicyclomine is an anticholinergic drug used to relax the smooth muscles of the intestines.5 It's duration of action is not especially long as it is usually taken 4 times daily with individual doses of 20-40mg orally or 10-20mg by intramuscular injection.5 Dicyclomine should not be administered intravenously.5

Mechanism of action

Dicyclomine achieves its action partially through direct antimuscarinic activity of the M1 and M2 receptors, and partially through antagonism of bradykinin and histamine.3,4,5 Dicyclomine non-competitively inhibits the action of bradykinin and histamine, resulting in direct action on the smooth muscle, and decreased strength of contractions seen in spasms of the ileum.4

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
UMuscarinic acetylcholine receptor M2
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

The bioavailability of dicyclomine has not been determined,2 though it is likely well absorbed as the primary route of elimination is in the urine.1,5 Dicyclomine has a Tmax of 1-1.5h.5

Volume of distribution

The volume of distribution for a 20mg oral dose is 3.65L/kg.5

Protein binding

Data regarding plasma protein binding of dicyclomine is not readily available.5

Metabolism

The metabolism of dicyclomine has not been well researched.1

Route of elimination

Dicyclomine is 79.5% eliminated in the urine and 8.4% in the feces.1,5

Half life

The mean plasma elimination half life is approximately 1.8 hours.1,5

Clearance

Data regarding the clearance of dicyclomine is not readily available.5

Toxicity

Patients experiencing an overdose may present with headache, nausea, vomiting, blurred vision, dilated pupils, dizziness, dry mouth, difficulty swallowing, CNS stimulation, as well as hot, dry skin.5 Treat patients with gastric lavage, emetics, activated charcoal, sedatives for excitement, and a cholinergic agent if indicated.5

The oral LD50 in mice is 625mg/kg.5

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of Tachycardia can be increased when Dicyclomine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may increase the central nervous system depressant (CNS depressant) activities of Dicyclomine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Dicyclomine.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the central nervous system depressant (CNS depressant) activities of Dicyclomine.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may increase the central nervous system depressant (CNS depressant) activities of Dicyclomine.
7-Nitroindazole7-Nitroindazole may increase the central nervous system depressant (CNS depressant) activities of Dicyclomine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the central nervous system depressant (CNS depressant) activities of Dicyclomine.
AbacavirDicyclomine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbediterolThe risk or severity of Tachycardia can be increased when Dicyclomine is combined with Abediterol.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
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Food Interactions
  • Avoid alcohol.
  • Take this medication 30 minutes before meals.

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 References
  1. Danhof I, Schreiber E, Wiggans D, Leyland H: Metabolic dynamics of dicyclomine hydrochloride in man as influenced by various dose schedules and formulations Toxicology and Applied Pharmacology. 1967 Dec 18;13(1):16-23.
  2. Walker BJ, Lang JF, Okerholm RA: Quantitative analysis of dicyclomine in human plasma by capillary gas chromatography and nitrogen-selective detection. J Chromatogr. 1987 Apr 24;416(1):150-3. doi: 10.1016/0378-4347(87)80496-6. [PubMed:3597632]
  3. 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:9059856]
  4. MCGRATH WR, LEWIS RE, KUHN WL: THE DUAL MODE OF THE ANTISPASMODIC EFFECT OF DICYCLOMINE HYDROCHLORIDE. J Pharmacol Exp Ther. 1964 Dec;146:354-8. [PubMed:14254329]
  5. FDA Approved Drug Products: Dicyclomine Oral Capsules, Oral Tablets, and Intramuscular Injections [Link]
  6. Canadian Agency for Drugs and Technologies in Health: Dicyclomine for Gastrointestinal Conditions: A Review of the Clinical Effectiveness, Safety, and Guidelines [Link]
External Links
Human Metabolome Database
HMDB0014942
KEGG Compound
C06951
PubChem Compound
3042
PubChem Substance
46505371
ChemSpider
2934
BindingDB
50010101
ChEBI
4514
ChEMBL
CHEMBL1123
Therapeutic Targets Database
DAP001118
PharmGKB
PA164744928
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dicyclomine
ATC Codes
A03AA07 — Dicycloverine
AHFS Codes
  • 12:08.00 — Anticholinergic Agents
  • 12:08.08 — Antimuscarinics Antispasmodics
FDA label
Download (230 KB)

Clinical Trials

Clinical Trials
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
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Axcan Pharma Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Endo Pharmaceuticals Inc.
  • Gallipot
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Huffman Laboratories
  • International Ethical Labs Inc.
  • Lannett Co. Inc.
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Merrell Pharmaceuticals Inc.
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Patheon Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharma Pac LLC
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Santec Chemicals Corp.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Taylor Pharmaceuticals
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Veratex Corp.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
SyrupOral10 mg/5mL
TabletOral20.6 mg/1
SyrupOral
Tablet, extended releaseOral
LiquidIntramuscular
TabletOral
CapsuleOral
InjectionIntramuscular20 mg/2mL
TabletOral20 mg/1
CapsuleOral10 mg/1
InjectionIntramuscular10 mg/1mL
Injection, solutionIntramuscular10 mg/1mL
Injection, solutionIntramuscular20 mg/2mL
SolutionOral10 mg/5mL
SyrupOral10 mg/1mL
TabletOral10 mg/1
SolutionIntramuscular
CapsuleOral
TabletOral
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)165-166Van Campen, M.G. Jr. and Tilford, C.H.; US.Patent 2,474,796; June 28, 1949; assigned to The Wm. S. Merrell Company.
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 RuleNoChemAxon
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 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.796
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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0109000000-67a7b4058325a5b3b7b5

Taxonomy

Description
This compound belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Carboxylic acid derivatives
Direct Parent
Carboxylic acid esters
Alternative Parents
Trialkylamines / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Tertiary aliphatic amine / Tertiary amine / Carboxylic acid ester / Amino acid or derivatives / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
tertiary amine, carboxylic ester (CHEBI:4514)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
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:17139284]
  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:17016423]
  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. doi: 10.1002/jnr.22159. [PubMed:19533734]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
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:9059856]

Drug created on June 13, 2005 07:24 / Updated on November 11, 2019 06:36