Identification

Name
Brinzolamide
Accession Number
DB01194
Description

Brinzolamide is a highly specific, non-competitive, reversible carbonic anhydrase inhibitor. Carbonic anhydrase (CA) is an enzyme found in many tissues of the body including the eye. It catalyzes the reversible reaction involving the hydration of carbon dioxide and the dehydration of carbonic acid. In humans, carbonic anhydrase exists as a number of isoenzymes, the most active being carbonic anhydrase II (CA-II). Inhibition of carbonic anhydrase in the ciliary processes of the eye decreases aqueous humor secretion, presumably by slowing the formation of bicarbonate ions with subsequent reduction in sodium and fluid transport. The result is a reduction in intraocular pressure. Brinzolamide is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 383.507
Monoisotopic: 383.064332867
Chemical Formula
C12H21N3O5S3
Synonyms
  • Brinzolamida
  • Brinzolamide
External IDs
  • AL-4862

Pharmacology

Indication

For the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Used in the treatment of glaucoma, brinzolamide inhibits aqueous humor formation and reduces elevated intraocular pressure. Elevated intraocular pressure is a major risk factor in the pathogenesis of optic nerve damage and glaucomatous visual field loss. Brinzolamide can decrease intraocular pressure by approximately 16-19% in patients with elevated intraocular pressure.

Mechanism of action

Brinzolamide is a highly specific inhibitor of CA-II, which is the main CA isoenzyme involved in the secretion of aqueous humor. Inhibition of CA in the ciliary process of the eye slows the formation of bicarbonate, and reduces sodium and fluid transport. This results in a reduction in the rate of aqueous humor secretion and the intraocular pressure. Brinzolamide is absorbed systemically following topical ocular administration. Since it has a high affinity for CA-II, brinzolamide binds extensively to red blood cells, where CA-II is primarily found. As sufficient CA-II activity remains, adverse effects resulting from the systemic inhibition of CA by brinzolamide are not observed. The metabolite N-desethyl brinzolamide is also formed. This metabolite binds to CA and accumulates in red blood cells as well. In the presence of brinzolamide, the metabolite binds mainly to carbonic anhydrase I (CA-I).

TargetActionsOrganism
ACarbonic anhydrase 2
inhibitor
Humans
UCarbonic anhydrase 1
inhibitor
Humans
UCarbonic anhydrase 4
inhibitor
Humans
UCarbonic anhydrase 5A, mitochondrial
inhibitor
Humans
UCarbonic anhydrase 3
inhibitor
Humans
Absorption

Absorbed into systemic circulation following topical ocular application

Volume of distribution
Not Available
Protein binding

Approximately 60%.

Metabolism

Ophthalmic

Route of elimination
Not Available
Half-life

111 days

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Brinzolamide can be increased when it is combined with Abametapir.
BenzylpenicillinBrinzolamide may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level.
CenobamateThe serum concentration of Brinzolamide can be decreased when it is combined with Cenobamate.
EmpagliflozinEmpagliflozin may increase the diuretic activities of Brinzolamide.
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Brinzolamide.
MagnesiumThe serum concentration of Magnesium can be decreased when it is combined with Brinzolamide.
MeloxicamThe therapeutic efficacy of Brinzolamide can be decreased when used in combination with Meloxicam.
OliceridineThe therapeutic efficacy of Brinzolamide can be decreased when used in combination with Oliceridine.
RitonavirThe serum concentration of Brinzolamide can be increased when it is combined with Ritonavir.
SatralizumabThe serum concentration of Brinzolamide can be decreased when it is combined with Satralizumab.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AzargaSuspension / dropsOphthalmicNovartis Europharm Limited2008-11-25Not applicableEU flag
AzargaSuspension / dropsOphthalmicNovartis Europharm Limited2008-11-25Not applicableEU flag
AzoptSuspension / drops10 mg/1mLOphthalmicALCON LABORATORIES, INC.1998-04-30Not applicableUS flag
AzoptSuspension1 %OphthalmicNovartis1998-11-11Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Sandoz BrinzolamideSuspensionOphthalmicSandoz Canada IncorporatedNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AzargaBrinzolamide (1 %) + Timolol (0.5 %)SuspensionOphthalmicNovartis2009-08-25Not applicableCanada flag
SimbrinzaBrinzolamide (10 mg/ml) + Brimonidine tartrate (2 mg/ml)Suspension / dropsOphthalmicNovartis Europharm Limited2014-07-18Not applicableEU flag
SimbrinzaBrinzolamide (1 %) + Brimonidine tartrate (0.2 %)SuspensionOphthalmicNovartis2015-02-17Not applicableCanada flag
SimbrinzaBrinzolamide (10 mg/1mL) + Brimonidine tartrate (2 mg/1mL)Suspension / dropsOphthalmicALCON LABORATORIES, INC.2013-05-01Not applicableUS flag
SimbrinzaBrinzolamide (10 mg/ml) + Brimonidine tartrate (2 mg/ml)Suspension / dropsOphthalmicNovartis Europharm Limited2014-07-18Not applicableEU flag
SimbrinzaBrinzolamide (10 mg/1mL) + Brimonidine tartrate (2 mg/1mL)Suspension / dropsOphthalmicNovartis Pharmaceuticals Corporation2013-05-01Not applicableUS flag

Categories

ATC Codes
S01EC54 — Brinzolamide, combinationsS01EC04 — BrinzolamideG01AE10 — Combinations of sulfonamides
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as thienothiazines. These are heterocyclic compounds containing a thiophene ring fused to a thiazine. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Thiazine is a 6-membered ring consisting of four carbon, one nitrogen and one sulfur atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thienothiazines
Sub Class
Not Available
Direct Parent
Thienothiazines
Alternative Parents
2,3,5-trisubstituted thiophenes / Aralkylamines / Organosulfonamides / 1,2-thiazines / Heteroaromatic compounds / Aminosulfonyl compounds / Dialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
2,3,5-trisubstituted thiophene / Amine / Aminosulfonyl compound / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Dialkyl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfonamide, thienothiazine (CHEBI:41212)

Chemical Identifiers

UNII
9451Z89515
CAS number
138890-62-7
InChI Key
HCRKCZRJWPKOAR-JTQLQIEISA-N
InChI
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
IUPAC Name
(4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[3,2-e][1,2]thiazine-6-sulfonamide
SMILES
CCN[[email protected]]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

References

Synthesis Reference

Alessandro Falchi, Ottorino De Lucchi, Andrea Castellin, "PROCESS FOR THE PREPARATION OF BRINZOLAMIDE." U.S. Patent US20110118461, issued May 19, 2011.

US20110118461
General References
  1. Ermis SS, Ozturk F, Inan UU: Comparing the effects of travoprost and brinzolamide on intraocular pressure after phacoemulsification. Eye (Lond). 2005 Mar;19(3):303-7. [PubMed:15258611]
  2. Iester M, Altieri M, Michelson G, Vittone P, Traverso CE, Calabria G: Retinal peripapillary blood flow before and after topical brinzolamide. Ophthalmologica. 2004 Nov-Dec;218(6):390-6. [PubMed:15564757]
  3. Kaup M, Plange N, Niegel M, Remky A, Arend O: Effects of brinzolamide on ocular haemodynamics in healthy volunteers. Br J Ophthalmol. 2004 Feb;88(2):257-62. [PubMed:14736787]
  4. Iester M: Brinzolamide ophthalmic suspension: a review of its pharmacology and use in the treatment of open angle glaucoma and ocular hypertension. Clin Ophthalmol. 2008 Sep;2(3):517-23. [PubMed:19668749]
  5. DeSantis L: Preclinical overview of brinzolamide. Surv Ophthalmol. 2000 Jan;44 Suppl 2:S119-29. [PubMed:10665514]
Human Metabolome Database
HMDB0015325
KEGG Drug
D00652
KEGG Compound
C07760
PubChem Compound
68844
PubChem Substance
46507071
ChemSpider
62077
BindingDB
10885
RxNav
194881
ChEBI
3176
ChEMBL
CHEMBL220491
ZINC
ZINC000003953037
Therapeutic Targets Database
DAP000602
PharmGKB
PA164744929
PDBe Ligand
BZ1
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Brinzolamide
AHFS Codes
  • 52:40.12 — Carbonic Anhydrase Inhibitors
PDB Entries
3znc / 4m2r / 4m2v / 6bbs
FDA label
Download (580 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableOcular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedPreventionOcular Hypertension / Posterior Capsule Opacification1
4CompletedTreatmentGlaucoma11
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension2
4CompletedTreatmentGlaucoma, Primary Open Angle (POAG) / Ocular Hypertension / Pigment Dispersion Glaucoma1
4CompletedTreatmentGlaucoma / Ocular Hypertension6
4CompletedTreatmentGlaucoma / Ocular Hypertension / Open-angle Glaucoma (OAG)1
4CompletedTreatmentInfantile Nystagmus Syndrome1
4CompletedTreatmentOcular Hypertension / Open Angle Glaucoma (OAG) / Open-angle Glaucoma (OAG)2
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Alcon Laboratories
Dosage Forms
FormRouteStrength
Suspension / dropsOphthalmic
SuspensionOphthalmic5 mg/ml
SuspensionOphthalmic1 %
Suspension / dropsOphthalmic10 mg/1mL
Solution / drops; suspension / dropsOphthalmic10 MG/ML
Suspension
Solution / dropsOphthalmic10 MG/ML
Solution / dropsOphthalmic1 %
Suspension / dropsOphthalmic10 mg/ml
SuspensionOphthalmic
SuspensionOphthalmic
Suspension / dropsOphthalmic
SuspensionOphthalmic2 mg
Prices
Unit descriptionCostUnit
Azopt 1% Suspension 15ml Bottle163.11USD bottle
Azopt 1% Suspension 10ml Bottle108.83USD bottle
Azopt 1% eye drops8.05USD ml
Azopt 1 % Suspension3.63USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5461081No1995-10-242013-04-24US flag
US5240923No1993-08-312010-08-31US flag
CA2080223No2000-11-072011-04-03Canada flag
US6316441No2001-11-132019-12-07US flag
US9044484No2015-06-022030-10-30US flag
US9421265No2016-08-232030-06-17US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)131 °CNot Available
logP-1.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.713 mg/mLALOGPS
logP-0.65ALOGPS
logP-0.67ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8.19ChemAxon
pKa (Strongest Basic)6.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area118.8 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.2 m3·mol-1ChemAxon
Polarizability37.93 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9765
Blood Brain Barrier+0.8754
Caco-2 permeable-0.7123
P-glycoprotein substrateSubstrate0.8185
P-glycoprotein inhibitor INon-inhibitor0.6795
P-glycoprotein inhibitor IINon-inhibitor0.9245
Renal organic cation transporterNon-inhibitor0.8276
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6431
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8588
Ames testNon AMES toxic0.5982
CarcinogenicityNon-carcinogens0.7712
BiodegradationNot ready biodegradable0.9834
Rat acute toxicity2.4930 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7097
hERG inhibition (predictor II)Non-inhibitor0.5167
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-3940000000-29878662225bb11586ed

Targets

Details
1. Carbonic anhydrase 2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 Da
References
  1. Stams T, Chen Y, Boriack-Sjodin PA, Hurt JD, Liao J, May JA, Dean T, Laipis P, Silverman DN, Christianson DW: Structures of murine carbonic anhydrase IV and human carbonic anhydrase II complexed with brinzolamide: molecular basis of isozyme-drug discrimination. Protein Sci. 1998 Mar;7(3):556-63. [PubMed:9541386]
  2. DeSantis L: Preclinical overview of brinzolamide. Surv Ophthalmol. 2000 Jan;44 Suppl 2:S119-29. [PubMed:10665514]
  3. Winum JY, Casini A, Mincione F, Starnotti M, Montero JL, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg Med Chem Lett. 2004 Jan 5;14(1):225-9. [PubMed:14684332]
  4. Boriack-Sjodin PA, Zeitlin S, Chen HH, Crenshaw L, Gross S, Dantanarayana A, Delgado P, May JA, Dean T, Christianson DW: Structural analysis of inhibitor binding to human carbonic anhydrase II. Protein Sci. 1998 Dec;7(12):2483-9. [PubMed:9865942]
  5. Ilies M, Supuran CT, Scozzafava A, Casini A, Mincione F, Menabuoni L, Caproiu MT, Maganu M, Banciu MD: Carbonic anhydrase inhibitors: sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions. Bioorg Med Chem. 2000 Aug;8(8):2145-55. [PubMed:11003159]
  6. Iester M: Brinzolamide ophthalmic suspension: a review of its pharmacology and use in the treatment of open angle glaucoma and ocular hypertension. Clin Ophthalmol. 2008 Sep;2(3):517-23. [PubMed:19668749]
  7. Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem. 2004 Feb 26;47(5):1272-9. [PubMed:14971907]
Details
2. Carbonic anhydrase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name
CA1
Uniprot ID
P00915
Uniprot Name
Carbonic anhydrase 1
Molecular Weight
28870.0 Da
References
  1. Winum JY, Casini A, Mincione F, Starnotti M, Montero JL, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg Med Chem Lett. 2004 Jan 5;14(1):225-9. [PubMed:14684332]
  2. Herkel U, Pfeiffer N: Update on topical carbonic anhydrase inhibitors. Curr Opin Ophthalmol. 2001 Apr;12(2):88-93. [PubMed:11224713]
Details
3. Carbonic anhydrase 4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina an...
Gene Name
CA4
Uniprot ID
P22748
Uniprot Name
Carbonic anhydrase 4
Molecular Weight
35032.075 Da
References
  1. Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem. 2004 Feb 26;47(5):1272-9. [PubMed:14971907]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Low activity.
Gene Name
CA5A
Uniprot ID
P35218
Uniprot Name
Carbonic anhydrase 5A, mitochondrial
Molecular Weight
34750.21 Da
References
  1. Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem. 2004 Feb 26;47(5):1272-9. [PubMed:14971907]
Details
5. Carbonic anhydrase 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide.
Gene Name
CA3
Uniprot ID
P07451
Uniprot Name
Carbonic anhydrase 3
Molecular Weight
29557.215 Da
References
  1. Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [PubMed:17826101]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
  2. Australian Government: Public Assessment Report for Brinzolamide/ Timolol Maleate [Link]

Drug created on June 13, 2005 07:24 / Updated on September 22, 2020 02:11

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