Dicycloverine

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Dicycloverine
Clinical data
Trade namesByclomine, Bentyl, Dibent, others
AHFS/Drugs.comMonograph
MedlinePlusa684007
License data
Pregnancy
category
  • AU: B1
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding>99%
Elimination half-life5 h
Identifiers
  • 2-(Diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate
JSmol)
  • O=C(OCCN(CC)CC)C1(CCCCC1)C2CCCCC2
  • 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 checkY
  • Key:CURUTKGFNZGFSE-UHFFFAOYSA-N checkY
  (verify)

Dicycloverine, also known as dicyclomine, sold under the brand name Bentyl among others, is a

injection into a muscle.[2] While it has been used in baby colic and enterocolitis, evidence does not support these uses.[2]

Common side effects include dry mouth, blurry vision, weakness, sleepiness, and lightheadedness.[2] Serious side effects may include psychosis and breathing problems in babies.[2] Use in pregnancy appears to be safe while use during breastfeeding is not recommended.[3] How it works is not entirely clear.[2]

Dicycloverine was approved for medical use in the United States in 1950.

generic medication.[1] In 2021, it was the 148th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[4][5]

Medical uses

Dicycloverine is used to treat the symptoms of irritable bowel syndrome, specifically hypermotility, in adults.[6][7] As of 2016, clinical guidelines recommended dicycloverine and other antispasmodics for IBS with diarrhea as a first line treatment.[6]

Contraindications

This medicine should not be used for people who have an obstructive GI or urinary condition, severe ulcerative colitis, reflux, any unstable cardiac condition, glaucoma, myasthenia gravis, and anyone who is acutely bleeding.[7]

It should not be given to children or infants with colic due to the risks of convulsions, difficult breathing, irritability, and restlessness,[8] and there is little evidence to support the efficacy in such use in any case.[9]

Dicycloverine is known to impair thinking and coordination.[7]

The effect on the baby during pregnancy or breastfeeding is not well understood.[7]

Adverse effects

Dicycloverine can cause a range of anticholinergic side effects such as dry mouth, nausea, blurred vision, dizziness, confusion, severe constipation, stomach pain, heart palpitations, difficulty urinating, and seizures.[6]

Pharmacology

Dicycloverine blocks the action of

cholinergic receptors on smooth muscles in the GI tract, relaxing the smooth muscle.[6]

History

A 10-mg oral capsule of dicyclomine hydrochloride

Dicycloverine was first synthesized chemically in the United States circa 1945 by scientists at William S. Merrell Company.[10]

It was first marketed in 1952 for gastrointestinal disorders, including colic in infants.

Bendectin, along with doxylamine and vitamin B6 which was launched in the US in 1956; Dicycloverine was removed from the formulation in 1976 after Merrell determined that it added no value. Bendectin became the subject of many lawsuits due to allegations that it had caused birth defects similar to thalidomide, which Merrell had also marketed in the US and Canada.[12]

In the 1980s, several governments restricted its use in infants due to reports of convulsions, difficult breathing, irritability, and restlessness in infants given the drug.[8]

In 1994, the US

Endo Pharmaceuticals. By 2000 several other generic competitors had started selling the medication. The case was part of the reshaping of the US pharmaceutical market that occurred in the 1990s, to favor generic entry.[13]

Society and culture

Rarely, there have been reports of dicycloverine abuse. Dicycloverine is an antagonist at

5-HT2A[15] receptor sites, though its affinities for these targets are roughly one-fifth to one-tenth as strong as its affinities for CHRM1[16] and CHRM4[17] (its clinical targets). It is also a relatively non-polar tertiary amine, able to cross the blood-brain barrier, leading to delirium at high concentrations.[6][18]

References

  1. ^
    ISBN 9780857113382
    .
  2. ^ a b c d e f g "Dicyclomine Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  3. ^ "Dicyclomine Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  4. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  5. ^ "Dicyclomine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  6. ^
    PMID 26985553
    .
  7. ^ a b c d AHFS Staff (2006). "Dicyclomine hydrochloride". AHFS DI Essentials. Bethesda, MD: American Society of Health-System Pharmacists / drugs.com. Retrieved 25 November 2018.
  8. ^ a b c Consolidated List of Products Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments (PDF) (12 ed.). World Health Organization. 2005. p. 106. Archived from the original (PDF) on 7 April 2014. Retrieved 25 November 2018.
  9. PMID 27631535. Open access icon
  10. ^ "Dicyclomine". Pubchem. Retrieved 25 November 2018.
  11. ^ "International Nonproprietary Names for Pharmaceutical Preparations List #3" (PDF). WHO Chronicle. 13 (12): 463–474. December 1959. Retrieved 25 November 2018.
  12. ^ Sanders J (January 1992). "The Bendectin Litigation: A Case Study in the Life Cycle of Mass Torts" (PDF). Hastings Law Journal. 43 (2): 317. Retrieved 25 November 2018.
  13. JSTOR 24116860
    .
  14. ^ "Bioactivity for AID 625223 - SID 103318016".
  15. ^ "Bioactivity for AID 625192 - SID 103318016".
  16. ^ "AID 625151 - DRUGMATRIX: Muscarinic M1 radioligand binding (Ligand: [3H] N-Methylscopolamine) - PubChem".
  17. ^ "AID 625154 - DRUGMATRIX: Muscarinic M4 radioligand binding (Ligand: [3H] N-Methylscopolamine) - PubChem".
  18. PMID 24396252
    .

External links

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