BRINZOLAMIDE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H21N3O5S3.ClH
Molecular Weight	419.968
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=UGAMYTZPFRXCOG-PPHPATTJSA-N

InChI=1S/C12H21N3O5S3.ClH/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);1H/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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 1998
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 1998

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
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
[Clinical investigation: the intraocular pressure-lowering efficacy and safety of brinzolamide combined with betaxolol].	2005 Dec	17162869
Intraocular pressure-lowering effects of all commonly used glaucoma drugs: a meta-analysis of randomized clinical trials.	2005 Jul	15921747
Corneal edema in glaucoma patients after the addition of brinzolamide 1% ophthalmic suspension.	2005 Jul-Aug	16075340
Water-drinking test in patients with primary open-angle glaucoma while treated with different topical medications.	2005 Jun	15969643
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
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
A comparative study on the cost of new antibiotics and drugs of other therapeutic categories.	2006 Dec 20	17183637
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
Screening for drug-induced spoliation of the hydrogel optic of the AlphaCor artificial cornea.	2006 May	16581286
The in vitro effects of some pesticides on carbonic anhydrase activity of Oncorhynchus mykiss and Cyprinus carpio carpio fish.	2006 May 20	16298474
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
[Blurred vision after instillation of topical carbonic anhydrase inhibitor].	2006 Sep	17025224
Ocular hypotensive efficacy and safety of brinzolamide ophthalmic suspension 1% added to travoprost ophthalmic solution 0.004% therapy in patients with open-angle glaucoma or ocular hypertension.	2006 Sep	16968567
Brinzolamide 1% versus apraclonidine 0.5% to prevent intraocular pressure elevation after neodymium:YAG laser posterior capsulotomy.	2006 Sep	16931262
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
Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors.	2007 Jan 25	17228881
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
Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells.	2007 Mar	17389174
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
Cost analysis of glaucoma medications.	2008 Jan	18154755
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
Good functional recovery following intervention for delayed suprachoroidal haemorrhage post bleb needling: a case report.	2008 Mar 13	18339199
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 `Sat Dec 16 08:58:12 GMT 2023` Edited by `admin` on `Sat Dec 16 08:58:12 GMT 2023`
Record UNII	N36YTS80H4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BRINZOLAMIDE HYDROCHLORIDE

Common Name

English

BRINZOLAMIDE HYDROCHLORIDE [MI]

Common Name

English

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

Systematic Name

English

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

Systematic Name

English

Code System Code Type Description

FDA UNII

N36YTS80H4