Dorzolamide

Dorzolamide
Clinical data
Trade names	Trusopt, others
AHFS/Drugs.com	Monograph
MedlinePlus	a602022
Routes of; administration	eye drops
ATC code	S01EC03 (WHO) S01EE52 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only;
Pharmacokinetic data
Protein binding	~33%
Elimination half-life	4 months
Identifiers
	IUPAC name (4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide;
CAS Number	120279-96-1 ; HCl: 130693-82-2 ;
PubChem CID	5284549;
IUPHAR/BPS	6810;
DrugBank	DB00869 ;
ChemSpider	4447604 ;
UNII	9JDX055TW1; HCl: QZO5366EW7 ;
KEGG	D07871 ;
ChEBI	CHEBI:4702 ;
ChEMBL	ChEMBL218490 ;
CompTox Dashboard (EPA)	DTXSID7022960 ;
ECHA InfoCard	100.229.271
Chemical and physical data
Formula	C10H16N2O4S3
Molar mass	324.43 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCNC1CC(C)S(=O)(=O)c2sc(cc12)S(=O)(=O)N;
	InChI InChI=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 ; Key:IAVUPMFITXYVAF-XPUUQOCRSA-N ;
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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.^[3] It is used as an eye drop.^[3] Effects begin within three hours and last for at least eight hours.^[3] It is also available as the combination dorzolamide/timolol.^[3]^[4]

Common side effects include eye discomfort, eye redness, taste changes, and blurry vision.^[3] Serious side effects include Steven Johnson syndrome.^[3] Those allergic to sulfonamides may be allergic to dorzolamide.^[3]^[5] Use is not recommended in pregnancy or breastfeeding.^[5] It is a carbonic anhydrase inhibitor and works by decreasing the production of aqueous humor.^[3]

Dorzolamide was approved for medical use in the United States in 1994.^[3] It is available as a generic medication.^[5] In 2022, it was the 201st most commonly prescribed medication in the United States, with more than 2 million prescriptions.^[6]^[7]

Medical uses

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.^[8] 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

Dorzolamide lowers intraocular pressure by about 20%.^[8] Normally, carbonic anhydrase converts carbonic acid (H₂CO₃) into bicarbonate (HCO₃), releasing a proton (H⁺) into solution. The H⁺ is then exchanged for sodium (Na⁺) ions, which facilitates the production of aqueous humor ^{[citation needed]}. 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]}.

History

Dorzolamide, developed by 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.^[8]

References