BRINZOLAMIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H21N3O5S3
Molecular Weight	383.507
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

InChI

InChIKey=HCRKCZRJWPKOAR-JTQLQIEISA-N

InChI=1S/C12H21N3O5S3/c1-3-14-10-8-15(5-4-6-20-2)23(18,19)12-9(10)7-11(21-12)22(13,16)17/h7,10,14H,3-6,8H2,1-2H3,(H2,13,16,17)/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C12H21N3O5S3
Molecular Weight	383.507
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/20816lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/brinzolamide-ophthalmic.html http://www.rxlist.com/azopt-drug.htm http://www.wikidoc.org/index.php/Brinzolamide

Brinzolamide reduces the amount of fluid in the eye, which decreases pressure inside the eye. Brinzolamide is a carbonic anhydrase inhibitor that is FDA approved for the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Common adverse reactions include abnormal taste in mouth and blurred vision. The concomitant administration of brinzolamide and oral carbonic anhydrase inhibitors is not recommended. Plus, in patients treated with oral carbonic anhydrase inhibitors, rare instances of acid-base alterations have occurred with high-dose salicylate therapy.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Carbonic anhydrase II 88 Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10665514 \| http://www.drugbank.ca/drugs/DB01194	Inhibitor 8228		3.19 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Open-angle glaucoma 51 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/20816lbl.pdf	Primary		Approved 8360	AZOPT Approved Use INDICATIONS & USAGE SECTION SIMBRINZA† (brinzolamide/brimonidine tartrate ophthalmic suspension) 1%/0.2% is a fixed combination of a carbonic anhydrase inhibitor and an alpha 2 adrenergic receptor agonist indicated for the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension. SIMBRINZA is a fixed combination of a carbonic anhydrase inhibitor and an alpha 2 adrenergic receptor agonist indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. (1) Launch Date 8.9138882E11
Ocular hypertension 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1998/20816lbl.pdf	Primary		Approved 8360	AZOPT Approved Use INDICATIONS & USAGE SECTION SIMBRINZA† (brinzolamide/brimonidine tartrate ophthalmic suspension) 1%/0.2% is a fixed combination of a carbonic anhydrase inhibitor and an alpha 2 adrenergic receptor agonist indicated for the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension. SIMBRINZA is a fixed combination of a carbonic anhydrase inhibitor and an alpha 2 adrenergic receptor agonist indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. (1) Launch Date 8.9138882E11

C_max

Value	Dose	Co-administered	Analyte	Population
2.17 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/10665514	3 % 3 times / day multiple, ocular dose: 3 % route of administration: Ocular experiment type: MULTIPLE co-administered:		BRINZOLAMIDE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
111 day REVIEW https://pubmed.ncbi.nlm.nih.gov/10665514	3 % 3 times / day multiple, ocular dose: 3 % route of administration: Ocular experiment type: MULTIPLE co-administered:		BRINZOLAMIDE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
40% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020816s019lbl.pdf	unknown, unknown		BRINZOLAMIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3176	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3176
ChemicalBook	CB3458912	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3458912
MolPort	MolPort-005-940-291	https://www.molport.com/shop/molecule-link/MolPort-005-940-291
Selleck Chemicals	brinzolamide	http://www.selleckchem.com/products/brinzolamide.html
ZINC	ZINC000003953037	http://zinc15.docking.org/substances/ZINC000003953037
eMolecules	36553023	https://www.emolecules.com/cgi-bin/more?vid=36553023

PubMed

Title	Date	PubMed
[Efficacy of ophthalmic suspension of Brinzolamide (Azopt) in the primary or combined therapy for patients with hypertensive glaucomas].	2001	12035596
Antiglaucomatous drugs effects on optic nerve head flow: design, baseline and preliminary report.	2001	11944863
Acetazolamide: future perspective in topical glaucoma therapeutics.	2002 Nov 6	12429455
Brinzolamide : a review of its use in the management of primary open-angle glaucoma and ocular hypertension.	2003	14565787
Medical therapy cost considerations for glaucoma.	2003 Jul	12834665
[Therapy of normal tension glaucoma: effect of brinzolamide on ocular haemodynamics].	2003 May	12766822
Effect of topical brinzolamide 1% and brimonidine 0.2% on intraocular pressure after phacoemulsification.	2004 Aug	15313300
[Cost-effectivity analysis of the most used antiglaucoma drugs].	2004 Aug	15306964
Effects of brinzolamide on ocular haemodynamics in healthy volunteers.	2004 Feb	14736787
Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits.	2004 Jan 5	14684332
Inhibition of endothelin-1 and KCL-induced increase of [CA2+]i by antiglaucoma drugs in cultured A7r5 vascular smooth-muscle cells.	2004 Jun	15279725
Carbonic anhydrase inhibitors: the first QSAR study on inhibition of tumor-associated isoenzyme IX with aromatic and heterocyclic sulfonamides.	2004 Jun 21	15149691
Ocular hypotensive effect and safety of brinzolamide ophthalmic solution in open angle glaucoma patients.	2004 May	15216404
Retinal peripapillary blood flow before and after topical brinzolamide.	2004 Nov-Dec	15564757
Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides.	2004 Oct 15	15388166
Concomitant administration of travoprost and brinzolamide versus fixed latanoprost/timolol combined therapy: three-month comparison of efficacy and safety.	2004 Sep	15383180
Short-term ocular tolerability of dorzolamide 2% and brinzolamide 1% vs placebo in primary open-angle glaucoma and ocular hypertension subjects.	2004 Sep	15002017
Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides.	2005 Feb 15	15686895
Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs?	2005 Feb 15	15686894
Corneal edema in glaucoma patients after the addition of brinzolamide 1% ophthalmic suspension.	2005 Jul-Aug	16075340
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Brinzolamide induced reversible corneal decompensation.	2005 Mar	15722328
Comparing the effects of travoprost and brinzolamide on intraocular pressure after phacoemulsification.	2005 Mar	15258611
The efficacy and ocular discomfort of substituting brinzolamide for dorzolamide in combination therapy with latanoprost, timolol, and dorzolamide.	2005 Oct	16245966
Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides.	2005 Sep 1	16039848
[Therapeutic difficulties in neovascular glaucoma].	2006	16927763
[Combined therapy in glaucoma treatment: travoprost 0.004% and brinzolamid].	2006	16848197
A randomized, investigator-masked, 4-week study comparing timolol maleate 0.5%, brinzolamide 1%, and brimonidine tartrate 0.2% as adjunctive therapies to travoprost 0.004% in adults with primary open-angle glaucoma or ocular hypertension.	2006 Apr	16750466
Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori.	2006 Apr 15	16459077
Effects of antiglaucoma drugs on calcium mobility in cultured corneal endothelial cells.	2006 Feb	16568722
Topical brinzolamide and metabolic acidosis.	2006 Feb	16424547
Switching from dorzolamide to brinzolamide: effect on intraocular pressure and patient comfort.	2006 Jan-Feb	16453193
The management of glaucoma and intraocular hypertension: current approaches and recent advances.	2006 Jun	18360593
Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs.	2006 Mar 23	16539401
The in vitro effects of some pesticides on carbonic anhydrase activity of Oncorhynchus mykiss and Cyprinus carpio carpio fish.	2006 May 20	16298474
Influence of ocular hypotensive eyedrops on intraocular pressure fluctuation with postural change in eyes with normal-tension glaucoma.	2007 Apr	17386282
Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.	2007 Dec 1	17826101
Comparison of the ocular hypotensive efficacy of adjunctive brimonidine 0.15% or brinzolamide 1% in combination with travoprost 0.004%.	2007 Jul	17509688
Changes in medical and surgical treatments of glaucoma between 1997 and 2003 in France.	2007 Jul-Aug	17671925
[Additive therapy with carboanhydrase inhibitors for open angle glaucoma previously treated with timolol 0.5% drops].	2007 Sep	18044479
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents.	2008	18336310
Bestrophin-2 is involved in the generation of intraocular pressure.	2008 Apr	18385076
A comparative study of the effects of brinzolamide and dorzolamide on retinal oxygen saturation and ocular microcirculation in patients with primary open-angle glaucoma.	2008 Apr	18369067
Carbonic anhydrase inhibitors: the X-ray crystal structure of ethoxzolamide complexed to human isoform II reveals the importance of thr200 and gln92 for obtaining tight-binding inhibitors.	2008 Apr 15	18359629
Comparison of ocular hypotensive effect and safety of brinzolamide and timolol added to latanoprost.	2008 Apr-May	18414111
Tear film and ocular surface alterations in chronic users of antiglaucoma medications.	2008 Jan-Feb	18408831
Intraocular pressure reduction with travoprost/timolol fixed combination, with and without adjunctive brinzolamide, in glaucoma.	2008 Jun	18479590
Advanced juvenile open-angle glaucoma in an 8-year-old Haitian girl.	2008 Mar	18302954
Brimonidine purite 0.1% versus brinzolamide 1% as adjunctive therapy to latanoprost in patients with glaucoma or ocular hypertension.	2008 May	18402717
Short-term effect of topical brinzolamide on human central corneal thickness.	2008 May-Jun	18465712

Patents

Sample Use Guides

In Vivo Use Guide

One drop of 1% brinzolamide ophthalmic suspension in the affected eye(s) three times daily.

Route of Administration: Topical

In Vitro Use Guide

Protein-binding study in human plasma showed binding in the range of 58.5% to 62.7%,which was independent of brinzolamide concentration over the range of 0.01 to 10 mg/g.

Substance Class	Chemical Created by `admin` on `Thu Jul 06 22:37:00 UTC 2023` Edited by `admin` on `Thu Jul 06 22:37:00 UTC 2023`
Record UNII	9451Z89515
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BRINZOLAMIDE

Official Name

English

SIMBRINZA COMPONENT BRINZOLAMIDE

Brand Name

English

BRINZOLAMIDE [ORANGE BOOK]

Common Name

English

BRINZOLAMIDE [MI]

Common Name

English

BRINZOLAMIDE [MART.]

Common Name

English

BRINZOLAMIDE COMPONENT OF AZARGA

Brand Name

English

BRINZOLAMIDE [USP MONOGRAPH]

Common Name

English

BRINZOLAMIDE [USAN]

Common Name

English

BRINZOLAMIDE [USP-RS]

Common Name

English

2H-THIENO(3,2-E)-1,2-THIAZINE-6-SULFONAMIDE, 4-(ETHYLAMINO)-3,4-DIHYDRO-2-(3-METHOXYPROPYL)-, 1,1-DIOXIDE, (R)-

Systematic Name

English

brinzolamide [INN]

Common Name

English

BRINZOLAMIDE [JAN]

Common Name

English

BRINZOLAMIDE [VANDF]

Common Name

English

Brinzolamide [WHO-DD]

Common Name

English

BRINZOLAMIDE [EMA EPAR]

Common Name

English

AZARGA COMPONENT BRINZOLAMIDE

Brand Name

English

AZOPT

Brand Name

English

BRINZOLAMIDE COMPONENT OF SIMBRINZA

Brand Name

English

AL-4862

Code

English

BRINZOLAMIDE [USP IMPURITY]

Common Name

English

NSC-760050

Code

English

Classification Tree Code System Code

WHO-ATC

S01EC54