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Revision as of 10:34, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 452937715 of page Dorzolamide for the Chem/Drugbox validation project (updated: 'DrugBank', 'KEGG', 'CAS_number').		Latest revision as of 03:00, 6 January 2025 edit ThoughtWarden (talk | contribs)Extended confirmed users1,110 edits Open access status updates in citations with OAbot #oabotTag: OAbot [2.1]
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			{{Short description|Chemical compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
			{{Use dmy dates|date=February 2024}}
	{{Drugbox		{{Drugbox
			| Verifiedfields = changed
⚫	| verifiedrevid = 443711657
			| Watchedfields = changed
⚫	| IUPAC_name = (4''S'',6''S'')-2-ethylamino-4-methyl-5,5-dioxo-<br/>5λ<sup>6</sup>,7-dithiabicyclonona-8,10-diene-8-sulfonamide
		⚫	| verifiedrevid = 461091269
	| image = Dorzolamide Structural Formulae.png		| image = Dorzolamide.svg
	| width = 200		| width = 200
			| alt =
	| image2 = Dorzolamide-3D-balls.png		| image2 = Dorzolamide-3D-balls.png
			| alt2 =
	<!--Clinical data-->		<!-- Clinical data -->
	| tradename = Trusopt		| tradename = Trusopt, others
	| Drugs.com = {{drugs.com|monograph|dorzolamide-hydrochloride}}		| Drugs.com = {{drugs.com|monograph|dorzolamide-hydrochloride}}
	| MedlinePlus = a602022		| MedlinePlus = a602022
	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->		| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
			| routes_of_administration = ]s
	| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	| ATC_prefix = S01
	| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
		⚫	| ATC_suffix = EC03
			| ATC_supplemental = {{ATC|S01|EE52}}
			| legal_AU = S4
			| legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}}</ref>
			| legal_CA = Rx-only
			| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=Health Canada | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}}</ref>
	| legal_UK = <!-- GSL / P / POM / CD -->		| legal_UK = <!-- GSL / P / POM / CD -->
	| legal_US = <!-- OTC / Rx-only -->		| legal_US = Rx-only
	<!--Pharmacokinetic data-->		<!-- Pharmacokinetic data -->
	| protein_bound = ~33%		| protein_bound = ~33%
	| elimination_half-life = 4 months		| elimination_half-life = 4 months
	<!--Identifiers-->		<!-- Identifiers -->
			| IUPHAR_ligand = 6810
	| CAS_number = <!-- blanked - oldvalue: 130693-82-2 -->
	| CAS_supplemental = {{CAS|120279-96-1}}		| CAS_number_Ref = {{cascite|changed|??}}
			| CAS_number = 120279-96-1
⚫	| ATC_prefix = S01
			| CAS_supplemental =
⚫	| ATC_suffix = EC03
	| PubChem = 5284549		| PubChem = 5284549
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 9JDX055TW1		| UNII = 9JDX055TW1
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|changed|kegg}}
	| KEGG = D00653		| KEGG = D07871
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 4702		| ChEBI = 4702
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	| ChEMBL = 218490		| ChEMBL = 218490
			| index2_label = HCl
⚫	<!--Chemical data-->
			| CAS_number2_Ref = {{cascite|correct|CAS}}
			| CAS_number2 = 130693-82-2
			| UNII2_Ref = {{fdacite|correct|FDA}}
			| UNII2 = QZO5366EW7
		⚫	<!-- Chemical data -->
		⚫	| IUPAC_name = (4''S'',6''S'')-4-(ethylamino)-6-methyl-7,7-dioxo-5,6-dihydro-4''H''-thienothiopyran-2-sulfonamide
	| C=10 | H=16 | N=2 | O=4 | S=3		| C=10 | H=16 | N=2 | O=4 | S=3
	| molecular_weight = 324.443 g/mol
	| smiles = CCNC1CC(C)S(=O)(=O)c2sc(cc12)S(=O)(=O)N		| smiles = CCNC1CC(C)S(=O)(=O)c2sc(cc12)S(=O)(=O)N
	| InChI = 1/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1
	| InChIKey = IAVUPMFITXYVAF-XPUUQOCRBK
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1		| StdInChI = 1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1
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	| StdInChIKey = IAVUPMFITXYVAF-XPUUQOCRSA-N		| StdInChIKey = IAVUPMFITXYVAF-XPUUQOCRSA-N
	}}		}}
			<!-- Definition and medical uses -->
			'''Dorzolamide''', sold under the brand name '''Trusopt''' among others, is a medication used to treat ], including in cases of ].<ref name=AHFS2019/> It is used as an eye drop.<ref name=AHFS2019/> Effects begin within three hours and last for at least eight hours.<ref name=AHFS2019/> It is also available as the combination ].<ref name=AHFS2019/><ref>{{Cite web |title=Dorzolamide (Ophthalmic Route) Description and Brand Names |url=https://www.mayoclinic.org/drugs-supplements/dorzolamide-ophthalmic-route/description/drg-20063524 |access-date=3 November 2023 |website=Mayo Clinic }}</ref>
			<!-- Side effects and mechanism -->
			Common side effects include eye discomfort, eye redness, taste changes, and blurry vision.<ref name=AHFS2019/> Serious side effects include ].<ref name=AHFS2019/> Those allergic to ] may be allergic to dorzolamide.<ref name=AHFS2019/><ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=1148|edition=76}}</ref> Use is not recommended in ] or ].<ref name=BNF76/> It is a ] and works by decreasing the production of ].<ref name=AHFS2019/>
			<!-- History and culture -->
			Dorzolamide was approved for medical use in the United States in 1994.<ref name=AHFS2019>{{cite web |title=Dorzolamide Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/dorzolamide-hydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=26 March 2019 }}</ref> It is available as a ].<ref name=BNF76/> In 2022, it was the 201st most commonly prescribed medication in the United States, with more than 2{{nbsp}}million prescriptions.<ref name="Top 300 of 2022">{{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 = Dorzolamide Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Dorzolamide | access-date = 30 August 2024 }}</ref>
			==Medical uses==
			{{unreferenced section|date=February 2024}}
			Dorzolamide is used to lower excessive ] in open-angle ] and ]. This drug is able to cross the cornea, reach the ciliary body of the eye, and produce systemic effects on the carbonic anhydrase enzyme within the eye.
			==Side effects==
			Ocular stinging, burning, itching and bitter taste.<ref name=dor/> It causes shallowing of the anterior chamber and leads to transient ]. As a second generation carbonic anhydrase inhibitor, dorzolamide avoids systemic effects associated with first generation carbonic anhydrase inhibitors such as acetazolamide, methazolamide, and dichlorphenamide.
			==Pharmacodynamics==
			{{Expand section|date=January 2019}}
			Dorzolamide lowers ] by about 20%.<ref name=dor/> Normally, ] converts ] ({{chem2|H2CO3}}) into ] ({{chem2|HCO3}}), releasing a proton (H<sup>+</sup>) into solution. The H<sup>+</sup> is then exchanged for ], which facilitates the production of aqueous humor {{Citation needed|date=June 2022}}. By blocking the function of carbonic anhydrase, the Na<sup>+</sup>/H<sup>+</sup> exchange is unable to occur, which leads to a decrease in Na<sup>+</sup> in the cell and prevents aqueous humor production {{Citation needed|date=June 2022}}.
			==History==
			Dorzolamide, developed by ], was the first medication in human therapy (market introduction 1995) that resulted from structure-based ]. It was developed to circumvent the systemic side effects of ] which has to be taken orally.<ref name=dor>{{cite book|title=Essentials of Medical Pharmacology|publisher=Jaypee Brothers Medical Publishers(P) Ltd.|isbn=81-8061-187-6|page=88|author=KD Tripari MD|year=2004|edition=5th}}</ref>
			== References ==
			{{reflist}}
			==Further reading==
			* {{cite journal | author = Kubinyi H | year = 1999 | title = Chance favors the prepared mind--from serendipity to rational drug design | journal = ] | volume = 19 | issue = 1–4 | pages = 15–39 | pmid = 10071748 | doi = 10.3109/10799899909036635}}
			* {{cite journal | vauthors = Plummer C, MacKay E, Gelatt K | title = Comparison of the effects of topical administration of a fixed combination of dorzolamide-timolol to monotherapy with timolol or dorzolamide on IOP, pupil size, and heart rate in glaucomatous dogs | journal = Veterinary Ophthalmology | volume = 9 | issue = 4 | pages = 245–9 | year = 2006| pmid = 16771760 | doi = 10.1111/j.1463-5224.2006.00469.x}}
			* {{cite journal | vauthors = Grover S, Apushkin M, Fishman G | title = Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa | journal = Am J Ophthalmol | volume = 141 | issue = 5 | pages = 850–8 | year = 2006 | pmid = 16546110 | doi = 10.1016/j.ajo.2005.12.030}}
			* {{cite journal | vauthors = Almeida G, Faria e Souza S | title = Effect of topical dorzolamide on rabbit central corneal thickness | journal = Braz J Med Biol Res | volume = 39 | issue = 2 | pages = 277–81 | year = 2006 | pmid = 16470316 | doi = 10.1590/S0100-879X2006000200015| doi-access = free | s2cid = 31212591 | url = http://pdfs.semanticscholar.org/111f/36dde2d5aa1031b325293347d41279f155f1.pdf }}
			{{Antiglaucoma preparations and miotics}}
			]
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