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{{Short description|Antispasmodic agent}} |
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{{Drugbox |
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{{Use dmy dates|date=August 2021}} |
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| verifiedrevid = 443636791 |
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{{Infobox drug |
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| IUPAC_name = 2-(diethylamino)ethyl bi(cyclohexane)-1-carboxylate |
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| Watchedfields = changed |
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| image = Dicyclomine-trans.png |
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| class = ] |
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| verifiedrevid = 460784129 |
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<!--Clinical data--> |
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| image = Dicyclomine.svg |
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| tradename = Byclomine, Bentyl, Dibent, Di-Spaz, Dilomine |
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| alt = <!--Clinical data--> |
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| Drugs.com = {{drugs.com|international|dicycloverine}} |
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| tradename = Byclomine, Bentyl, Dibent, others |
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| Drugs.com = {{drugs.com|monograph|dicyclomine-hydrochloride}} |
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| MedlinePlus = a684007 |
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| MedlinePlus = a684007 |
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| DailyMedID = Dicyclomine |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = B1 |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| ATC_prefix = A03 |
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| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
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| ATC_suffix = AA07 |
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| legal_UK = <!-- GSL / P / POM / CD --> |
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| legal_AU = S4 |
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| legal_US = <!-- OTC / Rx-only --> |
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| legal_CA = Rx-only |
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| legal_UK = POM |
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| legal_US = Rx-only |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data-->| routes_of_administration = ], ] |
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| protein_bound = >99% |
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| protein_bound = >99% |
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| elimination_half-life = 5 h |
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| elimination_half-life = 5 hours |
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<!--Identifiers--> |
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<!--Identifiers-->| CAS_number_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 77-19-0 |
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| CAS_number = 77-19-0 |
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| ATC_prefix = A03 |
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| ATC_suffix = AA07 |
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| PubChem = 3042 |
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| PubChem = 3042 |
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| IUPHAR_ligand = 355 |
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| IUPHAR_ligand = 355 |
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| ChEMBL = 1123 |
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| ChEMBL = 1123 |
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<!--Chemical data--> |
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<!--Chemical data-->| IUPAC_name = 2-(Diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate |
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| C=19 | H=35 | N=1 | O=2 |
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| C = 19 |
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| H = 35 |
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| molecular_weight = 309.487 g/mol |
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| N = 1 |
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| O = 2 |
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| smiles = O=C(OCCN(CC)CC)C1(CCCCC1)C2CCCCC2 |
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| smiles = O=C(OCCN(CC)CC)C1(CCCCC1)C2CCCCC2 |
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| InChI = 1/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 |
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| InChIKey = CURUTKGFNZGFSE-UHFFFAOYAD |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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}} |
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<!-- Definition and medical uses --> |
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'''Dicyclomine''', also known as '''dicycloverine''', is an ] that blocks ]. Dicycloverine was first synthesized in the United States circa 1947. |
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'''Dicycloverine''', also known as '''dicyclomine''', sold under the brand name '''Bentyl''' among others, is a ] that is used to treat ]s of the ] such as those that occur in ] (IBS).<ref name="BNF76">{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=759|edition=76}}</ref><ref name="AHFS2019" /> It is taken ] or by ].<ref name=AHFS2019/> While it has been used in ] and ], evidence does not support these uses.<ref name=AHFS2019/> |
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<!-- Side effects and mechanisms --> |
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== Clinical uses == |
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Common side effects include ], ], ], ], and ].<ref name=AHFS2019/> Serious side effects may include ] and breathing problems in babies.<ref name=AHFS2019/> Use in ] appears to be safe while use during ] is not recommended.<ref name=Preg2019>{{cite web |title=Dicyclomine Pregnancy and Breastfeeding Warnings|url=https://www.drugs.com/pregnancy/dicyclomine.html |website=Drugs.com |access-date=3 March 2019 |language=en}}</ref> How it works is not entirely clear.<ref name=AHFS2019>{{cite web |title=Dicyclomine Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/dicyclomine-hydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=3 March 2019 }}</ref> |
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<!-- Society and culture --> |
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Dicyclomine is used to treat ], the symptoms of ] (IBS) (also known as spastic colon). It relieves muscle spasms and cramping in the gastrointestinal tract by blocking the activity of ] on ] (or ]) receptors on the surface of muscle cells. It is a ] relaxant. |
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Dicycloverine was approved for medical use in the United States in 1950.<ref name=AHFS2019/> It is available as a ].<ref name=BNF76/> In 2022, it was the 176th most commonly prescribed medication in the United States, with more than 2{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Dicyclomine Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Dicyclomine | access-date = 30 August 2024 }}</ref> |
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==Medical uses== |
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In America, it is sold under the trade names: Byclomine, Bentyl, Dibent, Di-Spaz, Dilomine. |
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===Irritable bowel syndrome=== |
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Dicycloverine is used to treat the symptoms of ], specifically ], in adults.<ref name="CADTH2015">{{cite journal | author = Canadian Agency for Drugs and Technologies in Health | title = Dicyclomine for Gastrointestinal Conditions: A Review of the Clinical Effectiveness, Safety, and Guidelines | journal = CADTH Rapid Response Reports. | date = 3 December 2015 | pmid = 26985553 }}</ref><ref name="mono">{{cite book |author=AHFS Staff |date=2006 |title=AHFS DI Essentials |chapter=Dicyclomine hydrochloride |location=Bethesda, MD |publisher=American Society of Health-System Pharmacists / drugs.com |chapter-url=https://www.drugs.com/monograph/dicyclomine-hydrochloride.html |access-date=25 November 2018}}</ref> As of 2016, clinical guidelines recommended dicycloverine and other ]s for IBS with diarrhea as a first line treatment.<ref name="CADTH2015" /> |
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It is present in antibacterial burn cream (trade name Ambix) in combination with phenol. |
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===Anxiety=== |
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Another clinical use for dicycloverine has been as an ] in some studies involving various aspects of the use of opioids such as ], ], ], ] &c. |
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Dicycloverine can also be helpful for the treatment of ], but this is an ] use.<ref>{{cite web |url=https://cabinethealth.com/blogs/journal/dicyclomine-a-potential-treatment-for-anxiety |title=Dicyclomine: A Potential Treatment for Anxiety |date=12 March 2023 }}</ref> |
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In the UK it is sold under the trade names: Merbentyl (containing 10 mg dicycloverine) and Merbentyl 20 (containing 20 mg dicycloverine). |
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==Contraindications== |
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It is also sold in the UK as part of a multi-ingredient preparation under the trade name ] (Peckforton Pharmaceuticals), which in addition to dicycloverine, contains an ] (]) and two ] (] and ]). |
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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.<ref name="mono" /> |
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It should not be given to children or infants with colic due to the risks of convulsions, difficult breathing, irritability, and restlessness,<ref name="WHO" /> and there is little evidence to support the efficacy in such use in any case.<ref>{{cite journal | vauthors = Biagioli E, Tarasco V, Lingua C, Moja L, Savino F | title = Pain-relieving agents for infantile colic | journal = The Cochrane Database of Systematic Reviews | volume = 2016 | pages = CD009999 | date = September 2016 | issue = 9 | pmid = 27631535 | pmc = 6457752 | doi = 10.1002/14651858.CD009999.pub2 | hdl = 2434/444531 }} {{open access}}</ref> |
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It is sold under the trade names Bentylol (Hoechst Marion Roussel), Formulex (ICN), and Lomine (Riva) in Canada. |
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it is sold under the trade names spasmo proxyvon and spasmo plus in India |
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Dicycloverine is known to impair thinking and coordination.<ref name="mono" /> |
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== Side effects == |
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The effect on the baby during pregnancy or breastfeeding is not well understood.<ref name="mono" /> |
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Dicyclomine can cause a range of anticholinergic side effects such as ], ] and at higher doses, ] effects. Brief euphoria and an aphrodisiac effect are also known to occur in some cases. Recreational use of this drug has been reported in Brazil,<ref name=Carlini1993/> as well as in Egypt, Iran, Russia, Ukraine and India.{{Citation needed|date=February 2011}} |
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==Adverse effects== |
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Breastfeeding is not recommended while using this drug. Consult a doctor or pharmacist for clarification. Dicyclomine's effects may be intensified with alcohol. Users should use care when operating vehicles and/or dangerous machines. |
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Dicycloverine can cause a range of ] side effects such as dry mouth, nausea, blurred vision, dizziness, confusion, severe constipation, stomach pain, heart palpitations, difficulty urinating, and seizures.<ref name="CADTH2015" /> |
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==References== |
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==Pharmacology== |
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===Pharmacodynamics=== |
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{{Reflist|refs= |
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Dicycloverine is a ] ] ] ].<ref name="GiachettiGIraldoLadinsky1986">{{cite journal | vauthors = Giachetti A, Giraldo E, Ladinsky H, Montagna E | title = Binding and functional profiles of the selective M1 muscarinic receptor antagonists trihexyphenidyl and dicyclomine | journal = Br J Pharmacol | volume = 89 | issue = 1 | pages = 83–90 | date = September 1986 | pmid = 2432979 | pmc = 1917044 | doi = 10.1111/j.1476-5381.1986.tb11123.x | url = }}</ref> It blocks the action of ] on muscarinic receptors on ]s in the ], relaxing the smooth muscle.<ref name="CADTH2015" /> |
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<ref name=Carlini1993>{{cite journal | author = Carlini E. A. | title = Preliminary note: dangerous use of anticholinergic drugs in Brazil | journal = ] | year = 1993 | volume = 32 | issue = 1 | pages = 1–7 | pmid = 8486081 | doi = 10.1016/0376-8716(93)90016-J }}</ref> |
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}} |
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==History== |
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] |
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Dicycloverine was first ] in the United States ''circa'' 1945 by scientists at ].<ref>{{cite web |title=Dicyclomine |url=https://pubchem.ncbi.nlm.nih.gov/compound/3042#section=Use-and-Manufacturing |publisher=Pubchem |access-date=25 November 2018}}</ref> |
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It was first marketed in 1952 for gastrointestinal disorders, including colic in infants.<ref name=WHO/> The INN name "dicycloverine" was recommended in 1959.<ref>{{cite journal |title=International Nonproprietary Names for Pharmaceutical Preparations List #3 |journal=WHO Chronicle |date=December 1959 |volume=13 |issue=12 |pages=463–474 |url=https://www.who.int/medicines/publications/druginformation/innlists/RL03.pdf?ua=1 |format=PDF |access-date=25 November 2018}}</ref> It was included in the ] for morning sickness called ], along with ] and ] 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 ], which Merrell had also marketed in the US and Canada.<ref>{{cite journal |last1=Sanders |first1=Joseph |name-list-style=vanc |title=The Bendectin Litigation: A Case Study in the Life Cycle of Mass Torts |journal=Hastings Law Journal |date=January 1992 |volume=43 |issue=2 |page=317 |url=https://repository.uchastings.edu/cgi/viewcontent.cgi?article=3055&context=hastings_law_journal |format=PDF |access-date=25 November 2018}}</ref> |
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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.<ref name="WHO">{{cite book |title=Consolidated List of Products Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or Not Approved by Governments |edition=12 |date=2005 |publisher=World Health Organization |page=106 |url=http://apps.who.int/medicinedocs/documents/s16780e/s16780e.pdf |archive-url=https://web.archive.org/web/20140407083428/http://apps.who.int/medicinedocs/documents/s16780e/s16780e.pdf |url-status=dead |archive-date=7 April 2014 |access-date=25 November 2018}}</ref> |
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In 1994, the US ] ordered ], which had acquired Rugby Darby—the only generic manufacturer of dicycloverine in the US—to promise to grant licenses to its intellectual property on the drug to any company that wanted it, based on ] concerns. The US market for the medication at that time was around $8 million; Dow had 60% of it and Rugby had 40%. The next year, ], which by that time had acquired the business, granted a license to ]. 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.<ref>{{cite journal |last1=Chien |first1=Colleen |name-list-style=vanc |title=Cheap Drugs at What Price to Innovation: Does the Compulsory Licensing of Pharmaceuticals Hurt Innovation? |journal=Berkeley Technology Law Journal |date=2003 |volume=18 |issue=3 |pages=853–907 |jstor=24116860}}</ref> |
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==Society and culture== |
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Rarely, there have been reports of dicycloverine abuse. Dicycloverine is an antagonist at ]<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/bioassay/625223#sid=103318016|title=Bioactivity for AID 625223 - SID 103318016}}</ref> and ]<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/bioassay/625192#sid=103318016§ion=Version|title=Bioactivity for AID 625192 - SID 103318016}}</ref> receptor sites, though its affinities for these targets are roughly one-fifth to one-tenth as strong as its affinities for ]<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/bioassay/625151|title=AID 625151 - DRUGMATRIX: Muscarinic M1 radioligand binding (Ligand: [3H] N-Methylscopolamine) - PubChem}}</ref> and ]<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/bioassay/625154|title=AID 625154 - DRUGMATRIX: Muscarinic M4 radioligand binding (Ligand: [3H] N-Methylscopolamine) - PubChem}}</ref> (its clinical targets). It is also a relatively non-polar tertiary amine, able to cross the ], leading to ] at high concentrations.<ref name="CADTH2015" /><ref>{{cite journal | vauthors = Das S, Mondal S, Datta A, Bandyopadhyay S | title = A rare case of dicyclomine abuse | journal = Journal of Young Pharmacists | volume = 5 | issue = 3 | pages = 106–7 | date = September 2013 | pmid = 24396252 | pmc = 3812884 | doi = 10.1016/j.jyp.2013.08.004 }}</ref> |
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== Notes == |
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== References == |
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{{Reflist}} |
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* Brenner, G. M. (2000). ''Pharmacology.'' Philadelphia, PA: W.B. Saunders Company. ISBN 0-7216-7757-6 |
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* Canadian Pharmacists Association (2000). ''Compendium of Pharmaceuticals and Specialties'' (25th ed.). Toronto, ON: Webcom. ISBN 0-919115-76-4 |
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== External links == |
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== External links == |
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{{Commons category}} |
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* on Medicine Net |
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* on Medline Plus |
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{{Drugs for functional gastrointestinal disorders }} |
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{{Drugs for functional gastrointestinal disorders}} |
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{{Hallucinogens}} |
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{{Hallucinogens}} |
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{{Muscarinic acetylcholine receptor modulators}} |
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{{Cholinergics}} |
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{{Portal bar | Medicine}} |
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