Dorzolamide

Last updated
Dorzolamide
Dorzolamide.svg
Dorzolamide-3D-balls.png
Clinical data
Trade names Trusopt, others
AHFS/Drugs.com Monograph
MedlinePlus a602022
Routes of
administration
Topical (eye drops)
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding ~33%
Elimination half-life 4 months
Identifiers
  • (4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.229.271 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H16N2O4S3
Molar mass 324.43 g·mol−1
3D model (JSmol)
  • CCNC1CC(C)S(=O)(=O)c2sc(cc12)S(=O)(=O)N
  • 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 Yes check.svgY
  • Key:IAVUPMFITXYVAF-XPUUQOCRSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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. [1] It is used as an eye drop. [1] Effects begin within three hours and last for at least eight hours. [1] It is also available as the combination dorzolamide/timolol. [1] [2]

Contents

Common side effects include eye discomfort, eye redness, taste changes, and blurry vision. [1] Serious side effects include Steven Johnson syndrome. [1] Those allergic to sulfonamides may be allergic to dorzolamide. [1] [3] Use is not recommended in pregnancy or breastfeeding. [3] It is a carbonic anhydrase inhibitor and works by decreasing the production of aqueous humour. [1]

Dorzolamide was approved for medical use in the United States in 1994. [1] It is available as a generic medication. [3] In 2020, it was the 216th most commonly prescribed medication in the United States, with more than 2 million prescriptions. [4] [5] It is a second-generation carbonic anhydrase inhibitor.

Medical uses

Dorzolamide hydrochloride 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. [6] 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%. [6] 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

This drug, developed by Merck, was the first drug 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. [6]

Related Research Articles

<span class="mw-page-title-main">Glaucoma</span> Group of eye diseases

Glaucoma is a group of eye diseases that lead to damage of the optic nerve, which transmits visual information from the eye to the brain. Glaucoma may cause vision loss if left untreated. It has been called the "silent thief of sight" because the loss of vision usually occurs slowly over a long period of time. A major risk factor for glaucoma is increased pressure within the eye, known as intraocular pressure (IOP). It is associated with old age, a family history of glaucoma, and certain medical conditions or medications. The word glaucoma comes from the Ancient Greek word γλαυκóς, meaning 'gleaming, blue-green, gray'.

<span class="mw-page-title-main">Acetazolamide</span> Chemical compound

Acetazolamide, sold under the trade name Diamox among others, is a medication used to treat glaucoma, epilepsy, acute mountain sickness, periodic paralysis, idiopathic intracranial hypertension, heart failure and to alkalinize urine. It may be used long term for the treatment of open angle glaucoma and short term for acute angle closure glaucoma until surgery can be carried out. It is taken by mouth or injection into a vein. Acetazolamide is a first generation carbonic anhydrase inhibitor and it decreases the ocular fluid and osmolality in the eye to decrease intraocular pressure.

<span class="mw-page-title-main">Pilocarpine</span> Medication used to treat glaucoma and dry mouth

Pilocarpine is a medication used to reduce pressure inside the eye and treat dry mouth. As an eye drop it is used to manage angle closure glaucoma until surgery can be performed, ocular hypertension, primary open angle glaucoma, and to constrict the pupil after dilation. However, due to its side effects it is no longer typically used for long-term management. Onset of effects with the drops is typically within an hour and lasts for up to a day. By mouth it is used for dry mouth as a result of Sjögren syndrome or radiation therapy.

<span class="mw-page-title-main">Ciliary body</span> Part of the eye

The ciliary body is a part of the eye that includes the ciliary muscle, which controls the shape of the lens, and the ciliary epithelium, which produces the aqueous humor. The aqueous humor is produced in the non-pigmented portion of the ciliary body. The ciliary body is part of the uvea, the layer of tissue that delivers oxygen and nutrients to the eye tissues. The ciliary body joins the ora serrata of the choroid to the root of the iris.

<span class="mw-page-title-main">Betaxolol</span> Chemical compound

Betaxolol is a selective beta1 receptor blocker used in the treatment of hypertension and angina. It is also a adrenergic blocker with no partial agonist action and minimal membrane stabilizing activity. Being selective for beta1 receptors, it typically has fewer systemic side effects than non-selective beta-blockers, for example, not causing bronchospasm as timolol may. Betaxolol also shows greater affinity for beta1 receptors than metoprolol. In addition to its effect on the heart, betaxolol reduces the pressure within the eye. This effect is thought to be caused by reducing the production of the liquid within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the optic nerve and loss of vision in patients with elevated intraocular pressure due to glaucoma.

<span class="mw-page-title-main">Latanoprost</span> Chemical compound

Latanoprost, sold under the brand name Xalatan among others, is a medication used to treat increased pressure inside the eye. This includes ocular hypertension and open-angle glaucoma. Latanaprost is applied as eye drops to the eyes. Onset of effects is usually within four hours, and they last for up to a day.

<span class="mw-page-title-main">Timolol</span> Chemical compound

Timolol is a beta blocker medication used either by mouth or as eye drops. As eye drops it is used to treat increased pressure inside the eye such as in ocular hypertension and glaucoma. By mouth it is used for high blood pressure, chest pain due to insufficient blood flow to the heart, to prevent further complications after a heart attack, and to prevent migraines.

Ocular hypertension is the presence of elevated fluid pressure inside the eye, usually with no optic nerve damage or visual field loss.

Dorzolamide/timolol, sold under the brand name Cosopt among others, is a medication used to treat high pressure inside the eye including glaucoma. It is a combination of dorzolamide hydrochloride and timolol maleate. It may be used when a beta blocker, like timolol, is not sufficient alone. It is used as an eye drop.

<span class="mw-page-title-main">Brimonidine</span> Chemical compound

Brimonidine is an α2 agonist medication used to treat open-angle glaucoma, ocular hypertension, and rosacea. In rosacea it improves the redness. It is used as eye drops or applied to the skin.

<span class="mw-page-title-main">Carbonic anhydrase inhibitor</span> Class of pharmaceuticals

Carbonic anhydrase inhibitors are a class of pharmaceuticals that suppress the activity of carbonic anhydrase. Their clinical use has been established as anti-glaucoma agents, diuretics, antiepileptics, in the management of mountain sickness, gastric and duodenal ulcers, idiopathic intracranial hypertension, neurological disorders, or osteoporosis.

<span class="mw-page-title-main">Brinzolamide</span> Chemical compound

Brinzolamide is a carbonic anhydrase inhibitor used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

<span class="mw-page-title-main">Levobunolol</span> Chemical compound

Levobunolol is a non-selective beta blocker. It is used topically in the form of eye drops to manage ocular hypertension and open-angle glaucoma.

<span class="mw-page-title-main">Bimatoprost</span> Chemical compound

Bimatoprost, sold under the brand name Lumigan among others, is a medication used to treat high pressure inside the eye including glaucoma. Specifically it is used for open angle glaucoma when other agents are not sufficient. It may also be used to increase the size of the eyelashes. It is used as an eye drop and effects generally occur within four hours.

Brimonidine/timolol, sold under the brand name Combigan among others, is a fixed-dose combination medication eye drop used for the treatment of glaucoma. It is a combination of brimonidine and timolol.

<span class="mw-page-title-main">Tafluprost</span> Chemical compound

Tafluprost is a prostaglandin analogue. It is used topically to control the progression of open-angle glaucoma and in the management of ocular hypertension, alone or in combination with other medication. It reduces intraocular pressure by increasing the outflow of aqueous fluid from the eyes.

<span class="mw-page-title-main">Glaucoma medication</span> Eye condition medication

Glaucoma medication is divided into groups based on chemical structure and pharmacologic action. The goal of currently available glaucoma therapy is to preserve visual function by lowering intraocular pressure (IOP), below a level that is likely to produce further damage to the nerve.

Ripasudil, a derivative of fasudil, is a rho kinase inhibitor drug used for the treatment of glaucoma and ocular hypertension.

Brinzolamide/brimonidine, sold under the brand name Simbrinza, is a fixed-dose combination medication used to reduce intra-ocular pressure in adults with ocular hypertension or in those with an eye condition known as open-angle glaucoma. It contains brinzolamide and brimonidine tartrate. It is used as an eye drop.

Posner–Schlossman syndrome (PSS) also known as glaucomatocyclitic crisis (GCC) is a rare acute ocular condition with unilateral attacks of mild granulomatous anterior uveitis and elevated intraocular pressure. It is sometimes considered as a secondary inflammatory glaucoma.

References

  1. 1 2 3 4 5 6 7 8 9 "Dorzolamide Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 26 March 2019.
  2. "Dorzolamide (Ophthalmic Route) Description and Brand Names - Mayo Clinic". www.mayoclinic.org. Retrieved 2023-11-03.
  3. 1 2 3 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1148. ISBN   9780857113382.
  4. "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  5. "Dorzolamide - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  6. 1 2 3 KD Tripari MD (2004). Essentials of Medical Pharmacology (5th ed.). Jaypee Brothers Medical Publishers(P) Ltd. p. 88. ISBN   81-8061-187-6.

Further reading