Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Dorzolamide: Difference between pages

{{Short description|Chemical compound}}

{{Use dmy dates|date=February 2024}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 461091269

| image = Dorzolamide.svg

| alt =

| alt2 =

<!-- Clinical data -->

| tradename = Trusopt, others

| routes_of_administration = [[Ophthalmic drug administration|eye drop]]s

| ATC_prefix = S01

| ATC_suffix = EC03

| 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_US = Rx-only

<!-- Pharmacokinetic data -->

<!-- Identifiers -->

| IUPHAR_ligand = 6810

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 120279-96-1

| CAS_supplemental =

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D07871

| index2_label = HCl

| 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''-thieno[2,3-b]thiopyran-2-sulfonamide

<!-- Definition and medical uses -->

'''Dorzolamide''', sold under the brand name '''Trusopt''' among others, is a medication used to treat [[high pressure inside the eye]], including in cases of [[glaucoma]].<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 [[dorzolamide/timolol]].<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 [[Steven Johnson syndrome]].<ref name=AHFS2019/> Those allergic to [[sulfonamides]] 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 [[pregnancy]] or [[breastfeeding]].<ref name=BNF76/> It is a [[carbonic anhydrase inhibitor]] and works by decreasing the production of [[aqueous humor]].<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 |language=en}}</ref> It is available as a [[generic medication]].<ref name=BNF76/> In 2021, it was the 202nd most commonly prescribed medication in the United States, with more than 2{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Dorzolamide - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Dorzolamide | access-date = 14 January 2024}}</ref>

==Medical uses==

{{unreferenced section|date=February 2024}}

Dorzolamide is used to lower excessive [[intraocular pressure]] in open-angle [[glaucoma]] and [[ocular hypertension]]. 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 [[myopia]]. 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 [[intraocular pressure]] by about 20%.<ref name=dor/> Normally, [[carbonic anhydrase]] converts [[carbonic acid]] ({{chem2|H2CO3}}) into [[bicarbonate]] ({{chem2|HCO3}}), releasing a proton (H⁺) into solution. The H⁺ is then exchanged for [[Sodium | sodium (Na⁺) ions]], which facilitates the production of aqueous humor {{Citation needed|date=June 2022}}. By blocking the function of carbonic anhydrase, the Na⁺/H⁺ exchange is unable to occur, which leads to a decrease in Na⁺ in the cell and prevents aqueous humor production {{Citation needed|date=June 2022}}.

==History==

Dorzolamide, developed by [[Merck & Co.|Merck]], was the first medication in human therapy (market introduction 1995) that resulted from structure-based [[drug design]]. It was developed to circumvent the systemic side effects of [[acetazolamide]] 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 = [[J Recept Signal Transduct Res]] | 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 }}

{{Antiglaucoma preparations and miotics}}

[[Category:Wikipedia medicine articles ready to translate]]

[[Category:Carbonic anhydrase inhibitors]]

[[Category:Sulfones]]

[[Category:Sulfonamides]]

[[Category:Drugs developed by Merck & Co.]]

[[Category:Amines]]

[[Category:Ophthalmology drugs]]