Dicyclomine
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Dicyclomine
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CAS No:
77-19-0
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Formula:
C19H35NO2
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Chemical Name:
Dicyclomine
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Synonyms:
[1,1′-Bicyclohexyl]-1-carboxylic acid,2-(diethylamino)ethyl ester;[Bicyclohexyl]-1-carboxylic acid,2-(diethylamino)ethyl ester;Bentyl;Bentylol;Dicyclomine;Dicycloverine;Diocyl;Wyovin;Dicycloverin;2-(Diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate;104959-55-9;856995-49-8
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CAS No:
Description
Solid
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, an antispasmodic drug and a parasympatholytic. It is a tertiary amine and a carboxylic ester. It derives from a 2-diethylaminoethanol and a 1,1'-bi(cyclohexyl)-1-carboxylic acid.|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. 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. Dicyclomine was granted FDA approval on 11 May 1950.|Dicyclomine is an Anticholinergic. The mechanism of action of dicyclomine is as a Cholinergic Antagonist.|Dicyclomine is an anticholinergic agent used to treat gastrointestinal conditions such as acid peptic disease and irritable bowel syndrome. Dicyclomine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.|Dicyclomine is a carboxylic acid derivative and a selective anticholinergic with antispasmodic activity. Dicyclomine blocks acetylcholine from binding to muscarinic receptors on smooth muscle. This agent has a direct relaxing effect on smooth muscle and therefore prevents spasms in the muscles of the gastrointestinal tract, inhibits gastrointestinal propulsive motility, decreases gastric acid secretion and controls excessive pharyngeal, tracheal and bronchial secretion.|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.
Dicyclomine Basic Attributes
309.5 g/mol
309.49
201-009-4
4KV4X8IF6V
404381
DTXSID1022926
C61720
A - Alimentary tract and metabolism
Characteristics
29.5 Ų
5.5
165-166
142-143 °C @ Press: 0.5 Torr
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
MP 164-166 °C /HYDROCHLORIDE/|PRACTICALLY ODORLESS & HAS VERY BITTER TASTE /HYDROCHLORIDE/|CRYSTALS FROM BUTANONE /HYDROCHLORIDE/|FINE, WHITE, CRYSTALLINE POWDER /HYDROCHLORIDE/
Safety Information
STABLE IN AIR & TO MODERATE HEAT /HYDROCHLORIDE/
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
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. Treat patients with gastric lavage, emetics, activated charcoal, sedatives for excitement, and a cholinergic agent if indicated. The oral LD50 in mice is 625mg/kg.
Like 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.
...ANTICHOLINERGIC AGENTS, SUCH AS...DICYCLOMINE...WOULD BE EXPECTED TO INTERACT WITH DIGOXIN...
Data regarding plasma protein binding of dicyclomine is not readily available.
Drug Information
Dicyclomine is indicated for the treatment of functional bowel disorder and irritable bowel syndrome.|FDA Label
Dicyclomine is an anticholinergic agent used to treat gastrointestinal conditions such as acid peptic disease and irritable bowel syndrome. Dicyclomine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.
Anticholinergic Agents
Muscarinic Antagonists; Parasympatholytics|...OFTEN CLASSIFIED WITH ANTIMUSCARINIC AGENTS AS "ANTISPASMODICS," DO NOT PROPERLY BELONG TO GROUP OF ANTIMUSCARINIC AGENTS. ...DICYCLOMINE HYDROCHLORIDE, VSP-DECR SPASM OF GI TRACT, BILIARY TRACT, URETER, & UTERUS WITHOUT PRODUCING CHARACTERISTIC ATROPINIC EFFECTS ON SALIVARY, SWEAT, OR GI GLANDS, EYE, CV SYSTEM... /HCL/|IT DECR MOTILITY BUT DOES NOT SUPPRESS GASTRIC SECRETION. IT IS USED IN TREATMENT OF IRRITABLE COLON, SPASTIC CONSTIPATION, MUCOUS COLITIS, SPASTIC COLITIS, PYLOROSPASM, & BILIARY DYSKINESIA. IN TREATMENT OF PEPTIC ULCER IT IS USED TO DELAY GASTRIC EMPTYING. /HYDROCHLORIDE/|ANTICHOLINERGIC /HYDROCHLORIDE/
DICYCLOMINE SHOULD BE USED CAUTIOUSLY IN PT WITH PROSTATIC HYPERTROPHY, BLADDER NECK OBSTRUCTION, PYLORIC OBSTRUCTION, & CARDIOSPASM. EVEN THOUGH IT DOES NOT APPEAR TO RAISE INTRAOCULAR PRESSURE IN NARROW-ANGLE GLAUCOMA, IT IS ADVISABLE TO MONITOR PRESSURE OF SUCH PT.|CLINICAL USE OF.../BENTYL/ HAS BEEN DISAPPOINTING.|A 3-YR-OLD MALE INGESTED APPROX 100 TABLETS OF BENDECTIN & DEVELOPED TONIC-CLONIC SEIZURES FOLLOWED BY CARDIAC ARREST. ANALYSIS YIELDED HIGH LEVELS OF DOXYLAMINE, DICYCLOMINE & PYRIDOXINE. DOXYLAMINE APPEARS TO BE TOXIC CONSTITUENT.
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.
Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)|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. (See all compounds classified as Muscarinic Antagonists.)
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.
The metabolism of dicyclomine has not been well researched.
The mean plasma elimination half life is approximately 1.8 hours.
Dicyclomine achieves its action partially through direct antimuscarinic activity of the M1 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.
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.
Bentyl
Dicyclomine Use and Manufacturing
US PATENT 2,474,796. /HYDROCHLORIDE/|PREPD FROM 1-CYCLOHEXYLCYCLOHEXYL CYANIDE BY ALCOHOLYSIS & ESTERIFICATION... /HYDROCHLORIDE/
DICYCLOMINE 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/
[1,1'-Bicyclohexyl]-1-carboxylic acid, 2-(diethylamino)ethyl ester: INACTIVE
GLC METHOD AFFORDED SATISFACTORY SENSITIVITY & REPRODUCIBILITY & ALLOWED DIRECT SIMULTANEOUS DETECTION OF SEVERAL CONSTITUENTS IN MULTICOMPONENT SYSTEM.|COMPUTERIZED GAS-LIQ CHROMATOGRAPHIC METHOD FOR CONTENT UNIFORMITY ANALYSIS OF DICYCLOMINE HYDROCHLORIDE CAPSULES & TABLETS. GLC RESULTS WERE COMPARABLE (WITHIN 1%) TO THOSE OBTAINED USING USP PROCEDURE.
GLC METHOD SUITABLE FOR DETERMINING BLOOD LEVELS FOLLOWING NORMAL THERAPEUTIC DOSES.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:309.5
XLogP3:5.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:8
Exact Mass:309.266779359
Monoisotopic Mass:309.266779359
Topological Polar Surface Area:29.5
Heavy Atom Count:22
Complexity:326
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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