Basic information
- CAS
67-92-5- Standard SMILES
CCN(CC)CCOC(=O)C1(C2CCCCC2)CCCCC1- InChIKey
CURUTKGFNZGFSE-UHFFFAOYSA-N- Molecular formula
- C19H35NO2
- Average molar mass
- 309.5 g/mol
- Monoisotopic mass
- 309.26677936
Overview
Dicyclomine is the ester resulting from the formal condensation of 1-cyclohexylcyclohexanecarboxylic acid with 2-(diethylamino)ethanol. An anticholinergic, it is used as the hydrochloride to treat or prevent spasm in the muscles of the gastrointestinal tract, particularly that associated with irritable bowel syndrome. It has a role as a muscarinic antagonist, a parasympatholytic and an antispasmodic drug. It is a tertiary amine and a carboxylic ester. It is functionally related to a 2-diethylaminoethanol and a 1,1'-bi(cyclohexyl)-1-carboxylic acid.
Names & identifiers
- Preferred name
- Dicyclomine
- IUPAC
- 2-(diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate
- English name
- dicycloverine
- Molecular formula
- C19H35NO2
- Molecular weight
- 309.49
Names & synonyms
dicyclomineDicycloverineDicycloverin77-19-0DiocylDicicloverinaDicycloverinumDicymine2-(diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylateDTXSID10229264KV4X8IF6V(Bicyclohexyl)-1-carboxylic acid, 2-(diethylamino)ethyl ester
Show more names
C06951WyovinicyclomineDicycloverine-D3,D4Dicycloverine (Dicyclomine)1,1'-Bicyclohexane-1-carboxylic acid 2-(diethylamino)ethyl
[1,1'-Bicyclohexyl]-1-carboxylic acid, 2-(diethylamino)ethyl ester2-(diethylamino)ethyl 1-cyclohexylcyclohexanecarboxylate(1,1'-Bicyclohexyl)-1-carboxylic acid, 2-(diethylamino)ethyl ester2-diethylaminoethyl 1-cyclohexylcyclohexane-1-carboxylateBicyclohexyl-1-carboxylic acid 2-diethylamino-ethyl esterCHEBI:4514DTXCID002926[Bicyclohexyl]-1-carboxylic acid, 2-(diethylamino)ethyl ester
Database identifiers
- CAS
67-92-5、77-19-0- PubChem CID
- 3042
- DTXSID
DTXSID1022926- ChEMBL
CHEMBL1123- ChEBI
CHEBI:4514- UNII
- 4KV4X8IF6V
- EC Number
- 201-009-4
- Nikkaji
- J4.195E
Properties
Computed structural properties
- XLogP
- 5.5
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 8
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 326
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP5.5
Solubility
SOL IN WATER ABOUT 25% /HYDROCHLORIDE/
1 G IN 13 ML WATER, 5 ML ALC, 2.5 ML CHLOROFORM, 770 ML ETHER; INSOL IN ALKALINE AQ MEDIUM /HCL/
3.27e-03 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Muscarinic Antagonists; Parasympatholytics
Melting Point165-166
Physical DescriptionSolid
Stability/Shelf LifeSTABLE IN AIR & TO MODERATE HEAT /HYDROCHLORIDE/
Collision Cross Section179.29 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental Properties
MP 164-166 °C /HYDROCHLORIDE/
PRACTICALLY ODORLESS & HAS VERY BITTER TASTE /HYDROCHLORIDE/
CRYSTALS FROM BUTANONE /HYDROCHLORIDE/
FINE, WHITE, CRYSTALLINE POWDER /HYDROCHLORIDE/
Physicochemical properties
- Boiling point
- 142 · 142-143 °C(Press: 0.5 Torr)
- Density
- 0.99 · 0.990±0.06 g/cm3(Predicted)
- pka
- 9.24 · 9.24±0.25(Predicted)
- FDA UNII
- 4 KV4X8IF6V · 4KV4X8IF6V
- ATC code
- 3 AA07 · A03AA07
- EPA Substance Registry System
- 1 · [1,1'-Bicyclohexyl]-1-carboxylic acid, 2-(diethylamino)ethyl ester (77-19-0)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
- TSCA
- TSCA listed
- Hazardous Substances Data
- 77 · 77-19-0(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory InformationREACH registered substance: Dicycloverine (EC: 201-009-4)
Other Safety InformationIMAP assessments - [1,1'-Bicyclohexyl]-1-carboxylic acid, 2-(diethylamino)ethyl ester: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Interactions...ANTICHOLINERGIC AGENTS, SUCH AS...DICYCLOMINE...WOULD BE EXPECTED TO INTERACT WITH DIGOXIN...
HepatotoxicityLike other anticholinergic agents, dicyclomine has not been linked to episodes of liver enzyme elevations or clinically apparent liver injury. The metabolism of dicyclomine is not well defined but it is likely metabolized by the liver.
Human Toxicity Excerpts
SIDE EFFECTS OF DICYCLOMINE INCL DIZZINESS, FEELING OF ABDOMINAL FULLNESS, & DRY MOUTH. CONSTIPATION, BLURRED VISION, FATIGUE, SEDATION, NAUSEA, VOMITING, HEADACHE, IMPOTENCE, URINARY RETENTION, & RASH OCCUR RARELY.
THERE IS ONE REPORT THAT WHEN PT UNDER TREATMENT FOR GLAUCOMA OF UNSPECIFIED TYPE WERE GIVEN 10 MG OF DICYCLOVERINE HYDROCHLORIDE ORALLY, THEY HAD RISE OF 3-10 MM HG FOR 2-3 HR. IN MOST CASES NO RISE OF OCULAR PRESSURE HAS BEEN FOUND, REGARDLESS OF TYPE OF GLAUCOMA. /HYDROCHLORIDE/
INCIDENCE OF BIRTH DEFECTS IN OFFSPRING OF WOMEN WHO TOOK BENDECTIN CONTAINING 10 MG DICYCLOMINE HCL DURING PREGNANCY WAS INVESTIGATED. BIRTHS WERE TRACED FOR 2,298 PT & INCIDENCE OF DEFECTS COMPARED WITH THOSE IN RELEVANT POPULATIONS. NO EVIDENCE OF TERATOGENICITY FOUND.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
dicyclomine
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Dicyclomine
1.9
7.9
The recommended initial dose is 20 mg four times a day. After one week treatment with the initial dose, the dose may be increased to 40 mg four times a day unless side effects limit dosage escalation.
Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 80 mg/day, Lowest Therapeutic Dose (LTD): 1.0 mg/kg-day, and Screening Dose: 0.0003 mg/kg-day.
31-May-18
Safety data
- tsca
- TSCA listed
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- REACH Registrations
- Active
- Precautionary statements
- P264-P270-P301+P312-P330-P501
- Hazardous Substances Data
- 77-19-0(Hazardous Substances Data)
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Protein BindingData regarding plasma protein binding of dicyclomine is not readily available.
Pharmacodynamics
Dicyclomine is an anticholinergic drug used to relax the smooth muscles of the intestines. 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. Dicyclomine should not be administered intravenously.
Mechanism of Action
Dicyclomine achieves its action partially through direct antimuscarinic activity of the M1, M3, and M2 receptors; and partially through antagonism of bradykinin and histamine. 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.
...MAJOR ACTION APPEARS TO BE NONSPECIFIC DIRECT RELAXANT ACTION ON SMOOTH MUSLCE RATHER THAN COMPETITIVE ANTAGONISM OF ACH.
Biological Half-LifeThe mean plasma elimination half life is approximately 1.8 hours.
Metabolism/MetabolitesThe metabolism of dicyclomine has not been well researched.
FDA Pharmacological Classification
4KV4X8IF6V
DICYCLOMINE
Established Pharmacologic Class [EPC] - Anticholinergic
Mechanisms of Action [MoA] - Cholinergic Antagonists
Dicyclomine is an Anticholinergic. The mechanism of action of dicyclomine is as a Cholinergic Antagonist.
MeSH Pharmacological Classification
Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.
Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.
Absorption, Distribution and Excretion
The bioavailability of dicyclomine has not been determined, though it is likely well absorbed as the primary route of elimination is in the urine. Dicyclomine has a Tmax of 1-1.5h.
Dicyclomine is 79.5% eliminated in the urine and 8.4% in the feces.
The volume of distribution for a 20mg oral dose is 3.65L/kg.
Data regarding the clearance of dicyclomine is not readily available.
Cellular LocationsMembrane
Uses & manufacturing
Uses
MEDICATION
Use (kg) in USA (2002): 2250
Methods of Manufacturing
US PATENT 2,474,796. /HYDROCHLORIDE/
PREPD FROM 1-CYCLOHEXYLCYCLOHEXYL CYANIDE BY ALCOHOLYSIS & ESTERIFICATION... /HYDROCHLORIDE/
Formulations/PreparationsDICYCLOMINE HYDROCHLORIDE, USP, BENTYL; CAPSULES: 10 MG; TABLETS: 20 MG; SYRUP: 2 MG/ML, 10 TO 20 MG. ALSO AVAILABLE IN SOLN OR AS POWDER FOR DISSOLUTION FOR INJECTION. /HYDROCHLORIDE/
General Manufacturing Information[1,1'-Bicyclohexyl]-1-carboxylic acid, 2-(diethylamino)ethyl ester: INACTIVE
Applications
UsesAnticholinergic.
Upstream & downstream products
Upstream raw materials
Suppliers9 total
北京华美互利生物化工010-56205725 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]
南京世洲生物科技有限公司17301488900 · [email protected]
Additional notes
DefinitionChEBI: The ester resulting from the formal condensation of 1-cyclohexylcyclohexanecarboxylic acid with 2-(diethylamino)ethanol. An anticholinergic, it is used as the hydrochloride to treat or prevent spasm in the muscles of the gastrointestinal tract, particularl that associated with irritable bowel syndrome.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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