Dicycloverine

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Dicycloverine
Dicyclomine.svg
Systematic (IUPAC) name
2-(diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate
Clinical data
Trade names Byclomine, Bentyl, Dibent, Di-Spaz, Dilomine
AHFS/Drugs.com International Drug Names
MedlinePlus a684007
Pregnancy cat.
Legal status
Pharmacokinetic data
Protein binding >99%
Half-life 5 h
Identifiers
CAS number 77-19-0 YesY
ATC code A03AA07
PubChem CID 3042
IUPHAR ligand 355
DrugBank DB00804
ChemSpider 2934 YesY
UNII 4KV4X8IF6V YesY
KEGG D07820 YesY
ChEBI CHEBI:4514 YesY
ChEMBL CHEMBL1123 YesY
Chemical data
Formula C19H35NO2 
Mol. mass 309.487 g/mol
 YesY (what is this?)  (verify)

Dicycloverine, also known as dicyclomine, is an anticholinergic that blocks muscarinic receptors. Dicycloverine was first synthesized in the United States circa 1947.[1]

Medical uses[edit]

A 10-mg oral capsule of dicyclomine hydrochloride, manufactured by Mylan

Dicyclomine is used to treat intestinal hypermotility and the symptoms of irritable bowel syndrome (also known as spastic colon). It relieves muscle spasms and cramping in the gastrointestinal tract by blocking the activity of acetylcholine on cholinergic (or muscarinic) receptors on the surface of muscle cells. It is a smooth muscle relaxant.[2]

In the UK, it is an ingredient of a multiple-ingredient preparation, with an antiflatulent (simethicone) and two antacids, under the trade name Kolanticon. In France, it is an ingredient of a multiple-ingredient preparation, with colchicine, under the brand Colchimax. In India, it is of a compound with paracetamol under the trade name Cyclopam. It is also marketed as Meftal-SPAS containing mefenamic acid along with dicyclomine hydrochloride as an analgesic and antispasmodic.

Side effects[edit]

Dicyclomine can cause a range of anticholinergic side effects such as dry mouth, nausea, and, at higher doses, deliriant effects.[2] Recreational use of this drug for its anticholinergic effects (both low dose for euphoria and high dose for delirium) has been rarely reported; it is also reputed to cause a rapid increase in libido in the first 10-135 minutes after dosing.

Caution[edit]

Breastfeeding is not recommended while using this drug. Users should use care when operating vehicles and/or dangerous machines.[2]

Synthesis[edit]

Dicycloverine synthesis[1]
  1. Double alkylation of phenylacetonitrile with 1,5-dibromopentane leads to the corresponding cyclohexane.
  2. This intermediate is then saponified and the resulting acid esterified with 2-(diethylamino)ethanol.
  3. Catalytic reduction of the aromatic ring yields dicyclomine.

References[edit]

  1. ^ a b Tilford, C. H.; Campen, M. G. V.; Shelton, R. S. (1947). "Aminoesters of Substituted Alicylic Carboxylic Acids1". Journal of the American Chemical Society 69 (11): 2902. doi:10.1021/ja01203a077.  edit
  2. ^ a b c "Dicyclomine hydrochloride". Monograph. Drugs.com. 

Further reading[edit]

  • Brenner, G. M. (2000). Pharmacology. Philadelphia, PA: W.B. Saunders Company. ISBN 0-7216-7757-6
  • Canadian Pharmacists Association (2000). Compendium of Pharmaceuticals and Specialties (25th ed.). Toronto, ON: Webcom. ISBN 0-919115-76-4

See also[edit]

External links[edit]