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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:56 UTC
HMDB IDHMDB0015325
Secondary Accession Numbers
  • HMDB15325
Metabolite Identification
Common NameBrinzolamide
DescriptionBrinzolamide, also known as azopt, 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. Brinzolamide is a drug which is used for the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Brinzolamide is a very strong basic compound (based on its pKa). Due to the abundance of readily-bound erythrocytes and minimal known metabolism, Brinzolamide's whole blood half-life is very long (111 days). Following ocular instillation, the suspension is systemically absorbed to some degree; however the plasma concentrations are low and generally below the limits of detection (less than 10 ng/mL) due to extensive binding by tissues and erythrocytes. Inhibition of carbonic anhydrase in the ciliary processes of the eye decreases aqueous humor secretion and thus lowers the intraocular pressure in the anterior chamber, presumably by reducing the rate of formation of bicarbonate ions with subsequent reduction in sodium and fluid transport; this may alleviate the effects of open-angle glaucoma.The recommended frequency for topical application is two times per day. Brinzolamide is a carbonic anhydrase inhibitor (specifically, carbonic anhydrase II). This combination may be more effective than either medication alone. Use for the treatment of open-angle glaucoma and raised intraocular pressure due to either excess aqueous humor production or inadequate drainage of the humor via the trabecular meshwork. While definitive sites of metabolism have not been firmly established, there are several metabolites worthy of note. Brinzolamide is excreted primarily unchanged (60%) in the urine, although the renal clearance rate has not been definitively determined. N-Desethylbrinzolamide is also found in the urine along with lower concentrations of the inactive metabolites, N-Desmethoxypropylbrinzolamide and O-Desmethylbrinzolamide; exact levels have not been definitively determined. Oral administration is less-favored due to variable absorption from the stomach mucosa and an increased side-effect profile versus ophthalmic administration. N-Desethylbrinzolamide is an active metabolite of the parent compound, and thus exhibits carbonic anhydrase inhibitory activity (largely carbonic anhydrase-I, when in the presence of Brinzolamide) and also accumulates in the erythrocytes. Brinzolamide (trade names Azopt, Alcon Laboratories, Befardin, Fardi Medicals, ) is a carbonic anhydrase inhibitor used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension.
Structure
Data?1582753284
Synonyms
ValueSource
AzoptChEBI
Alcon brand OF brinzolamideHMDB
Allphar brand OF brinzolamideHMDB
(R)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno(3,2-e)-1,2-thiazine-6-sulfonamide 1,1-dioxideHMDB
Chemical FormulaC12H21N3O5S3
Average Molecular Weight383.507
Monoisotopic Molecular Weight383.064332867
IUPAC Name(4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[3,2-e][1,2]thiazine-6-sulfonamide
Traditional Namebrinzolamide
CAS Registry Number138890-62-7
SMILES
CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O
InChI Identifier
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
InChI KeyHCRKCZRJWPKOAR-JTQLQIEISA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThienothiazines
Sub ClassNot Available
Direct ParentThienothiazines
Alternative Parents
Substituents
  • Thienothiazine
  • 2,3,5-trisubstituted thiophene
  • Aralkylamine
  • Ortho-thiazine
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Thiophene
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Azacycle
  • Organic nitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point131 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.71 g/LNot Available
LogP-1.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.71 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.2 m³·mol⁻¹ChemAxon
Polarizability37.93 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.55631661259
DarkChem[M-H]-178.79831661259
DeepCCS[M+H]+183.67630932474
DeepCCS[M-H]-181.31830932474
DeepCCS[M-2H]-214.95530932474
DeepCCS[M+Na]+190.96230932474
AllCCS[M+H]+181.332859911
AllCCS[M+H-H2O]+178.832859911
AllCCS[M+NH4]+183.632859911
AllCCS[M+Na]+184.332859911
AllCCS[M-H]-177.332859911
AllCCS[M+Na-2H]-177.832859911
AllCCS[M+HCOO]-178.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BrinzolamideCCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O4748.9Standard polar33892256
BrinzolamideCCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O3523.1Standard non polar33892256
BrinzolamideCCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O3261.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Brinzolamide,1TMS,isomer #1CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S23144.8Semi standard non polar33892256
Brinzolamide,1TMS,isomer #1CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S23109.4Standard non polar33892256
Brinzolamide,1TMS,isomer #1CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S24625.0Standard polar33892256
Brinzolamide,1TMS,isomer #2CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C3055.4Semi standard non polar33892256
Brinzolamide,1TMS,isomer #2CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C3201.6Standard non polar33892256
Brinzolamide,1TMS,isomer #2CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C5402.1Standard polar33892256
Brinzolamide,2TMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C3095.4Semi standard non polar33892256
Brinzolamide,2TMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C3349.8Standard non polar33892256
Brinzolamide,2TMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C4330.9Standard polar33892256
Brinzolamide,2TMS,isomer #2CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S23082.3Semi standard non polar33892256
Brinzolamide,2TMS,isomer #2CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S23296.2Standard non polar33892256
Brinzolamide,2TMS,isomer #2CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S24428.2Standard polar33892256
Brinzolamide,3TMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C3134.4Semi standard non polar33892256
Brinzolamide,3TMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C3547.2Standard non polar33892256
Brinzolamide,3TMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C4160.3Standard polar33892256
Brinzolamide,1TBDMS,isomer #1CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S23361.8Semi standard non polar33892256
Brinzolamide,1TBDMS,isomer #1CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S23378.0Standard non polar33892256
Brinzolamide,1TBDMS,isomer #1CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S24622.3Standard polar33892256
Brinzolamide,1TBDMS,isomer #2CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C3282.7Semi standard non polar33892256
Brinzolamide,1TBDMS,isomer #2CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C3432.5Standard non polar33892256
Brinzolamide,1TBDMS,isomer #2CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C5398.1Standard polar33892256
Brinzolamide,2TBDMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C3518.9Semi standard non polar33892256
Brinzolamide,2TBDMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C3859.0Standard non polar33892256
Brinzolamide,2TBDMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C4329.9Standard polar33892256
Brinzolamide,2TBDMS,isomer #2CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S23575.5Semi standard non polar33892256
Brinzolamide,2TBDMS,isomer #2CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S23795.1Standard non polar33892256
Brinzolamide,2TBDMS,isomer #2CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S24408.5Standard polar33892256
Brinzolamide,3TBDMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C3794.5Semi standard non polar33892256
Brinzolamide,3TBDMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C4287.5Standard non polar33892256
Brinzolamide,3TBDMS,isomer #1CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C4200.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Brinzolamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-9363000000-c2ce0727d8312538cab42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Brinzolamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Brinzolamide LC-ESI-qTof , Positive-QTOFsplash10-000i-3940000000-29878662225bb11586ed2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Brinzolamide , positive-QTOFsplash10-000i-3940000000-29878662225bb11586ed2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 10V, Positive-QTOFsplash10-00sr-2019000000-988ac9cefa8fb23facba2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 20V, Positive-QTOFsplash10-0fk9-3690000000-c40760f0b6f44cc24c8e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 40V, Positive-QTOFsplash10-00dl-9100000000-f485ec4bc8d717b8b51b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 10V, Negative-QTOFsplash10-017i-6893000000-c3e14fd7fd97db2351702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 20V, Negative-QTOFsplash10-0fb9-7189000000-719789413373ebe829042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 40V, Negative-QTOFsplash10-004i-9010000000-929e6fe33dd2964ee5582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 10V, Positive-QTOFsplash10-001i-0009000000-3c94e44f36675ba706e32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 20V, Positive-QTOFsplash10-001i-0009000000-986efaaf32a24d0fac0f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 40V, Positive-QTOFsplash10-00lr-0091000000-e7907c2f053f25cc99212021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 10V, Negative-QTOFsplash10-001i-0009000000-de46e421dd0efb4be9dd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 20V, Negative-QTOFsplash10-003r-3119000000-aafd05e736363b690ad12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brinzolamide 40V, Negative-QTOFsplash10-06vi-9378000000-faad917334f371082bf72021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01194 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01194 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01194
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID62077
KEGG Compound IDC07760
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBrinzolamide
METLIN IDNot Available
PubChem Compound68844
PDB IDBZ1
ChEBI ID3176
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. DeSantis L: Preclinical overview of brinzolamide. Surv Ophthalmol. 2000 Jan;44 Suppl 2:S119-29. [PubMed:10665514 ]
  2. 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 ]
  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. 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 ]
  5. 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 ]

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular weight:
28870.0
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 ]
General function:
Involved in carbonate dehydratase activity
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 into the anterior chamber of the eye.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular weight:
29245.895
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 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Low activity.
Gene Name:
CA5A
Uniprot ID:
P35218
Molecular weight:
34750.21
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 ]
General function:
Involved in carbonate dehydratase activity
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 and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular weight:
35032.075
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 ]