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

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 8297		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 8429	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 8429	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
Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters.	1992 Dec 15	1460006
Antiglaucomatous drugs effects on optic nerve head flow: design, baseline and preliminary report.	2001	11944863
Carbonic anhydrase inhibitors: topically acting antiglaucoma sulfonamides incorporating phthaloyl and phthalimido moieties.	2001	11765137
Comparison of topical brinzolamide 1% and dorzolamide 2% eye drops given twice daily in addition to timolol 0.5% in patients with primary open-angle glaucoma or ocular hypertension.	2001 Aug	11476685
Brinzolamide.	2001 Nov 15	11760914
[Innovative glaucoma therapy. Glaucoma therapy with topical carbonic anhydrase inhibitors].	2001 Oct	11699313
[The role of Brinzolamide 1% ophtalmic suspension in corneal edema].	2002	12723185
Advances in topical glaucoma therapy.	2002 Mar	11940242
New topical drugs for open-angle glaucoma.	2003 Feb	12630335
Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides.	2003 Mar 24	12643899
[A differentiated approach to the treatment of normal-pressure glaucoma].	2003 Sep-Oct	14598486
Effect of topical brinzolamide 1% and brimonidine 0.2% on intraocular pressure after phacoemulsification.	2004 Aug	15313300
Ocular hypotensive effect and safety of brinzolamide ophthalmic solution in open angle glaucoma patients.	2004 May	15216404
Intraocular pressure lowering effect of brinzolamide 1.0% as adjunctive therapy to latanoprost 0.005% in patients with open angle glaucoma or ocular hypertension: an uncontrolled, open-label study.	2005 Apr	15899098
The efficacy and safety of topical brinzolamide and dorzolamide when added to the combination therapy of latanoprost and a beta-blocker in patients with glaucoma.	2005 Apr	15857284
[Clinical investigation: the intraocular pressure-lowering efficacy and safety of brinzolamide combined with betaxolol].	2005 Dec	17162869
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
Medical control of intraocular pressure after phacoemulsification.	2005 Mar	15811735
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
[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
Effects of antiglaucoma drugs on calcium mobility in cultured corneal endothelial cells.	2006 Feb	16568722
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
Screening for drug-induced spoliation of the hydrogel optic of the AlphaCor artificial cornea.	2006 May	16581286
The efficacy and safety of timolol maleate versus brinzolamide each given twice daily added to travoprost in patients with ocular hypertension or primary open-angle glaucoma.	2006 Nov-Dec	17191187
The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents.	2007	17504129
Influence of ocular hypotensive eyedrops on intraocular pressure fluctuation with postural change in eyes with normal-tension glaucoma.	2007 Apr	17386282
[In vitro microstructural analysis of commercial ophthalmic suspensions by HRT II Rostock Cornea Module].	2007 Aug	17593371
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
Effect of concomitant use of latanoprost and brinzolamide on 24-hour variation of IOP in normal-tension glaucoma.	2007 Jun-Jul	17570997
Effect of antiglaucoma agents on postoperative intraocular pressure after cataract surgery with Viscoat.	2007 Nov	17964402
Daily cost of glaucoma medications in China.	2007 Oct-Nov	18091176
[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
Efficacy of brinzolamide and levobetaxolol in pediatric glaucomas: a randomized clinical trial.	2008 Jun	18289898
Brinzolamide.	2008 Mar	18312166
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.

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