U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of BRINZOLAMIDE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.19 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.17 μg/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
111 day
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
unknown, unknown
BRINZOLAMIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides.
2004 Oct 15
Concomitant administration of travoprost and brinzolamide versus fixed latanoprost/timolol combined therapy: three-month comparison of efficacy and safety.
2004 Sep
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
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
Effects of glaucoma drugs on ocular hemodynamics in normal tension glaucoma: a randomized trial comparing bimatoprost and latanoprost with dorzolamide [ISRCTN18873428].
2005 Apr 5
[Clinical investigation: the intraocular pressure-lowering efficacy and safety of brinzolamide combined with betaxolol].
2005 Dec
Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides.
2005 Feb 15
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
Corneal edema in glaucoma patients after the addition of brinzolamide 1% ophthalmic suspension.
2005 Jul-Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Medical control of intraocular pressure after phacoemulsification.
2005 Mar
Brinzolamide induced reversible corneal decompensation.
2005 Mar
[Therapeutic difficulties in neovascular glaucoma].
2006
[Combined therapy in glaucoma treatment: travoprost 0.004% and brinzolamid].
2006
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
Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori.
2006 Apr 15
A comparative study on the cost of new antibiotics and drugs of other therapeutic categories.
2006 Dec 20
Effects of antiglaucoma drugs on calcium mobility in cultured corneal endothelial cells.
2006 Feb
Topical brinzolamide and metabolic acidosis.
2006 Feb
Switching from dorzolamide to brinzolamide: effect on intraocular pressure and patient comfort.
2006 Jan-Feb
The management of glaucoma and intraocular hypertension: current approaches and recent advances.
2006 Jun
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
Screening for drug-induced spoliation of the hydrogel optic of the AlphaCor artificial cornea.
2006 May
The in vitro effects of some pesticides on carbonic anhydrase activity of Oncorhynchus mykiss and Cyprinus carpio carpio fish.
2006 May 20
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
[Blurred vision after instillation of topical carbonic anhydrase inhibitor].
2006 Sep
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
Brinzolamide 1% versus apraclonidine 0.5% to prevent intraocular pressure elevation after neodymium:YAG laser posterior capsulotomy.
2006 Sep
The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents.
2007
Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides.
2007 Dec 1
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
Effect of concomitant use of latanoprost and brinzolamide on 24-hour variation of IOP in normal-tension glaucoma.
2007 Jun-Jul
Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells.
2007 Mar
Effect of antiglaucoma agents on postoperative intraocular pressure after cataract surgery with Viscoat.
2007 Nov
Daily cost of glaucoma medications in China.
2007 Oct-Nov
[Additive therapy with carboanhydrase inhibitors for open angle glaucoma previously treated with timolol 0.5% drops].
2007 Sep
The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents.
2008
Bestrophin-2 is involved in the generation of intraocular pressure.
2008 Apr
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
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
Comparison of ocular hypotensive effect and safety of brinzolamide and timolol added to latanoprost.
2008 Apr-May
Cost analysis of glaucoma medications.
2008 Jan
Tear film and ocular surface alterations in chronic users of antiglaucoma medications.
2008 Jan-Feb
Intraocular pressure reduction with travoprost/timolol fixed combination, with and without adjunctive brinzolamide, in glaucoma.
2008 Jun
Efficacy of brinzolamide and levobetaxolol in pediatric glaucomas: a randomized clinical trial.
2008 Jun
Brinzolamide.
2008 Mar
Advanced juvenile open-angle glaucoma in an 8-year-old Haitian girl.
2008 Mar
Good functional recovery following intervention for delayed suprachoroidal haemorrhage post bleb needling: a case report.
2008 Mar 13
Brimonidine purite 0.1% versus brinzolamide 1% as adjunctive therapy to latanoprost in patients with glaucoma or ocular hypertension.
2008 May
Short-term effect of topical brinzolamide on human central corneal thickness.
2008 May-Jun
Patents

Sample Use Guides

One drop of 1% brinzolamide ophthalmic suspension in the affected eye(s) three times daily.
Route of Administration: Topical
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 17:12:39 GMT 2023
Edited
by admin
on Sat Dec 16 17:12:39 GMT 2023
Record UNII
9451Z89515
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BRINZOLAMIDE
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
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
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
NDF-RT N0000175517
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
NCI_THESAURUS C29577
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
EMA ASSESSMENT REPORTS SIMBRINZA (AUTHORIZED: GLAUCOMA, OPEN-ANGLE
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
EMA ASSESSMENT REPORTS AZARGA (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
NDF-RT N0000000235
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
EMA ASSESSMENT REPORTS AZOPT (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
EMA ASSESSMENT REPORTS SIMBRINZA (AUTHORIZED: OCULAR HYPERTENSION)
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
WHO-VATC QS01EC04
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
WHO-ATC S01EC04
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
EMA ASSESSMENT REPORTS AZARGA (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
NCI_THESAURUS C29705
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
EMA ASSESSMENT REPORTS AZOPT (AUTHORIZED: GLAUCOMA, OPEN-ANGLE)
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C47420
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
MERCK INDEX
m2652
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1076363
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
MESH
C111827
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
USAN
II-13
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL220491
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
INN
7532
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID6045531
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
PUBCHEM
68844
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
CAS
138890-62-7
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
IUPHAR
6797
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
RXCUI
194881
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY RxNorm
CHEBI
3176
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
SMS_ID
100000085244
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
NSC
760050
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
DAILYMED
9451Z89515
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
EVMPD
SUB05892MIG
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
DRUG CENTRAL
396
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
LACTMED
Brinzolamide
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
WIKIPEDIA
BRINZOLAMIDE
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
DRUG BANK
DB01194
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
FDA UNII
9451Z89515
Created by admin on Sat Dec 16 17:12:41 GMT 2023 , Edited by admin on Sat Dec 16 17:12:41 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
ENANTIOMER -> ENANTIOMER
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
URINE
METABOLITE ACTIVE -> PARENT
IC50 (CAII): 1.28 nM; IC50 (CAIV): 128 nM
BINDING
IC50
METABOLITE -> PARENT
URINE
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
International patent application: WO2013168186
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC