BZ1

(+)-4-ETHYLAMINO-3,4-DIHYDRO-2-(METHOXY)PROPYL-2H-THIENO[3,2-E]-1,2-THIAZINE-6-SULFONAMIDE-1,1-DIOXIDE


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Chemical Component Summary

Name(+)-4-ETHYLAMINO-3,4-DIHYDRO-2-(METHOXY)PROPYL-2H-THIENO[3,2-E]-1,2-THIAZINE-6-SULFONAMIDE-1,1-DIOXIDE
SynonymsBrinzolamide
Identifiers(4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-bis(oxidanylidene)-3,4-dihydrothieno[3,2-e][1,2]thiazine-6-sulfonamide
FormulaC12 H21 N3 O5 S3
Molecular Weight383.507
TypeNON-POLYMER
Isomeric SMILESCCN[C@H]1CN(S(=O)(=O)c2c1cc(s2)S(=O)(=O)N)CCCOC
InChIInChI=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
InChIKeyHCRKCZRJWPKOAR-JTQLQIEISA-N

Chemical Details

Formal Charge0
Atom Count44
Chiral Atom Count1
Bond Count45
Aromatic Bond Count5

Drug Info: DrugBank

DrugBank IDDB01194 
NameBrinzolamide
Groups approved
DescriptionBrinzolamide is a highly specific, non-competitive, reversible carbonic anhydrase II (CA-II) inhibitor indicated to reduce ocular pressure in patients with ocular hypertension or open-angle glaucoma.[L35310] Although the exact pathophysiology of glaucoma is still unknown, one of the main hallmarks of this disease is vascular dysregulation and abnormalities.[A2049,A2051] The resulting vascular resistance increases intraocular pressure, thus impairing ocular perfusion.[A2049,A2051] Although systemic anti-carbonic anhydrase (CA) therapy has been used for almost 50 years with varying degrees of success, systemic administration results in an increase in incidences of adverse effects.[A2049,A2051] Brinzolamide was developed as a topical solution to the systemic side effects and [dorzolamide], the first-ever approved topical CA inhibitor with contrasting results and evidence.[A2051] Unlike [dorzolamide], brinzolamide has a higher lipophilicity to facilitate diffusion across the blood-retinal barrier.[A2051] Brinzolamide was approved by the FDA in 1998 as a standalone product and in 2013 as a combination product with brimonidine tartrate.[L35310,L35315] In Europe, it was also approved as a combination product with timolol in 2008.[L35320]
Synonyms
  • Brinzolamida
  • Brinzolamide
Brand Names
  • Azopt
  • Brinzolamide
  • Sandoz Brinzolamide
  • Azarga
  • Simbrinza
IndicationBrinzolamide, either as a standalone agent or in combination with brimonidine, is approved by the FDA for the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.[L46377,L35310] Brinzolamide is also approved in Europe to be used in combination with timolol to treat the same conditions.[L35320]
Categories
  • Amides
  • Antiglaucoma Preparations and Miotics
  • Carbonic Anhydrase Inhibitors
  • Cytochrome P-450 CYP2A6 Substrates
  • Cytochrome P-450 CYP2B6 Substrates
ATC-Code
  • S01EC54
  • S01EC04
  • G01AE10
CAS number138890-62-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Carbonic anhydrase 2MSHHWGYGKHNGPEHWHKDFPIAKGERQSPVDIDTHTAKYDPSLKPLSVS...unknowninhibitor
Carbonic anhydrase 1MASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISV...unknowninhibitor
Carbonic anhydrase 4MRMLLALLALSAARPSASAESHWCYEVQAESSNYPCLVPVKWGGNCQKDR...unknowninhibitor
Carbonic anhydrase 5A, mitochondrialMLGRNTWKTSAFSFLVEQMWAPLWSRSMRPGRWCSQRSCAWQTSNNTLHP...unknowninhibitor
Carbonic anhydrase 3MAKEWGYASHNGPDHWHELFPNAKGENQSPVELHTKDIRHDPSLQPWSVS...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL220491
PubChem 68844
ChEMBL CHEMBL220491
ChEBI CHEBI:3176
CCDC/CSD AKOFUD
COD 2241650