(4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1$l^{6},7,2-thieno[3,2-e][1$l^{6},2]thiazine-6-sulfonamide

• ChemBase ID: 1064
• Molecular Formular: C12H21N3O5S3
• Molecular Mass: 383.50724
• Monoisotopic Mass: 383.06433379
• SMILES: S1(=O)(=O)N(C[C@H](NCC)c2c1sc(S(=O)(=O)N)c2)CCCOC
• Canonical SMILES: COCCCN1C[C@H](NCC)c2c(S1(=O)=O)sc(c2)S(=O)(=O)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
• InChIKey: HCRKCZRJWPKOAR-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1$l^{6},7,2-thieno[3,2-e][1$l^{6},2]thiazine-6-sulfonamide
• IUPAC Traditional name: brinzolamide
• Brand Name: Azopt
• Synonyms: Brinzolamide

Database IDs

• CAS Number: 138890-62-7
• PubChem SID: 160964527; 46507071
• PubChem CID: 68844

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.194564
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.7519147
• LogD (pH = 7.4): -0.5946276
• Log P: -0.67452025
• Molar Refractivity: 87.1995 cm^3
• Polarizability: 36.01203 Å^3
• Polar Surface Area: 118.8 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.65
• LOG S: -2.73
• Solubility (Water): 7.13e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -1.8

DETAILS

DrugBank - DB01194

• Drug Groups: approved
• 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.
• Indication: For the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Ophthalmic
• Absorption: Absorbed into systemic circulation following topical ocular application
• Half Life: 111 days
• Protein Binding: Approximately 60%.
• References: Ermis SS, Ozturk F, Inan UU: Comparing the effects of travoprost and brinzolamide on intraocular pressure after phacoemulsification. Eye. 2005 Mar;19(3):303-7. [Pubmed] ; 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] ; 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] ; 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] ; DeSantis L: Preclinical overview of brinzolamide. Surv Ophthalmol. 2000 Jan;44 Suppl 2:S119-29. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• DeSantis L: Preclinical overview of brinzolamide. Surv Ophthalmol. 2000 Jan;44 Suppl 2:S119-29. Pubmed
• Ermis SS, Ozturk F, Inan UU: Comparing the effects of travoprost and brinzolamide on intraocular pressure after phacoemulsification. Eye. 2005 Mar;19(3):303-7. Pubmed
• 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
• 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
• 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