World Library  
Flag as Inappropriate
Email this Article

Brinzolamide

Article Id: WHEBN0006131224
Reproduction Date:

Title: Brinzolamide  
Author: World Heritage Encyclopedia
Language: English
Subject: Carbonic anhydrase inhibitors, Glaucoma medication, Dorzolamide, Glaucoma, Atropine
Collection:
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Brinzolamide

Brinzolamide
Systematic (IUPAC) name
(5R)-5-ethylamino-3-(3-methoxypropyl)-
2,2-dioxo-2λ6,9-dithia-
3-azabicyclo[4.3.0]nona-7,10-diene-
8-sulfonamide
Clinical data
Trade names Azopt, Befardin
AHFS/Drugs.com
MedlinePlus
Licence data EMA:, US FDA:
Pregnancy
category
  • US: C (Risk not ruled out)
Legal status
Routes of
administration
Ophthalmic
Pharmacokinetic data
Bioavailability Absorbed systemically, but below detectable levels (less than 10 ng/mL)
Protein binding ~60%
Biological half-life 111 days
Excretion Renal (60%)
Identifiers
CAS Registry Number
ATC code S01
PubChem CID:
IUPHAR/BPS
DrugBank  YesY
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
Chemical data
Formula C12H21N3O5S3
Molecular mass 383.51 g/mol
 YesY   

Brinzolamide (trade names Azopt, Alcon Laboratories, Befardin,[1] Fardi Medicals,[2] ) is a carbonic anhydrase inhibitor used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

Chemistry

Brinzolamide is a carbonic anhydrase inhibitor (specifically, carbonic anhydrase II). Carbonic anhydrase is found primarily in erythrocytes (but also in other tissues including the eye). It exists as a number of isoenzymes, the most active of which is carbonic anhydrase II (CA-II).

Indications

Use for the treatment of open-angle glaucoma and raised intraocular pressure due to excess aqueous humor production.

Pharmacodynamics

Inhibition of carbonic anhydrase in the ciliary processes of the eye decreases aqueous humor secretion and thus lowers the intraocular pressure in the anterior chamber, presumably by reducing the rate of formation of bicarbonate ions with subsequent reduction in sodium and fluid transport; this alleviates the effects of open-angle glaucoma.

Pharmacokinetics

Absorption

The recommended frequency for topical application is two times per day. Following ocular instillation, the suspension is systemically absorbed to some degree; however the plasma concentrations are low and generally below the limits of detection (less than 10 ng/mL) due to extensive binding by tissues and erythrocytes. Oral administration is less-favored due to variable absorption from the stomach mucosa and an increased side-effect profile versus ophthalmic administration.

Distribution

The compound is fairly well protein-bound (60%), but adheres extensively to the carbonic anhydrase-containing erythrocytes. Due to the abundance of readily-bound erythrocytes and minimal known metabolism, Brinzolamide's whole blood half-life is very long (111 days).

Metabolism

While definitive sites of metabolism have not been firmly established, there are several metabolites worthy of note. N-Desethylbrinzolamide is an active metabolite of the parent compound, and thus exhibits carbonic anhydrase inhibitory activity (largely carbonic anhydrase-I, when in the presence of Brinzolamide) and also accumulates in the erythrocytes. However, Brinzolamide's other known metabolites (N-Desmethoxypropylbrinzolamide and O-Desmethylbrinzolamide) either have no activity or their activity is currently unknown.

Excretion

Brinzolamide is excreted primarily unchanged (60%) in the urine, although the renal clearance rate has not been definitively determined. N-Desethylbrinzolamide is also found in the urine along with lower concentrations of the inactive metabolites, N-Desmethoxypropylbrinzolamide and O-Desmethylbrinzolamide; exact levels have not been definitively determined.

Cautions

Side effects

  • Common, but mild: Blurred vision; bitter, sour, or unusual taste; itching, pain, watering, or dryness of the eyes; feeling that something is in the eye; headache; runny nose
  • Rare, but serious: Fast or irregular heartbeat; fainting; skin rash, hives, or itching; severe eye irritation, redness, or swelling; swelling in the face, lips, or throat; wheezing or trouble breathing

Precautions

  • Hypersensitivity to other sulfonamides
  • Acute angle-closure glaucoma
  • Concomitant administration of oral carbonic anhydrase inhibitors
  • Moderate-to-severe renal or hepatic insufficiency

Combination with timolol

The combination of brinzolamide with timolol is marketed under the trade name Azarga. Clinical studies have shown this combination to be more effective than either of the medications taken as monotherapy.[3]

References

  1. ^ http://www.vidal.ge/drugs/3650
  2. ^ http://92.51.96.98/files/Administraciuli_Aqtebi/01_REGISTRACIA/2014/12/30-12-2014/02-1873.pdf
  3. ^ Croxtall JD, Scott, LJ.[1].Drugs&Aging 2009;26(5):437-446. doi:10.2165/00002512-200926050-00007.
  • Product Information: Azopt(R), brinzolamide. Alcon Laboratories, Inc, Fort Worth, TX, 1998b.
  • Sall KN, Greff LJ, Johnson-Pratt LR, et al.: Dorzolamide/timolol combination versus concomitant administration of brimonidine and timolol: six-month comparison of efficacy and tolerability. Ophthalmology 2003; 110:615-624.
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.