Brinzolamide

Title: Brinzolamide
CAS Registry Number: 138890-62-7
CAS Name: (4R)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide
Manufacturers' Codes: AL-4682
Trademarks: Azopt (Alcon)
Molecular Formula: C12H21N3O5S3
Molecular Weight: 383.51
Percent Composition: C 37.58%, H 5.52%, N 10.96%, O 20.86%, S 25.08%
Literature References: Carbonic anhydrase inhibitor. Prepn: T. R. Dean et al., WO 9115486; eidem, US 5378703 (1991, 1995 both to Alcon). Clinical trial: L. H. Silver, Am. J. Ophthalmol. 126, 400 (1998).
Properties: Sol in ethanol.
Derivative Type: Hydrochloride
CAS Registry Number: 150937-43-2
Molecular Formula: C12H21N3O5S3.HCl
Molecular Weight: 419.97
Percent Composition: C 34.32%, H 5.28%, N 10.01%, O 19.05%, S 22.91%, Cl 8.44%
Properties: Crystals from methanol + methylene chloride, mp 175-177°. [a]D +10.35° (c = 1 in water).
Melting point: mp 175-177°
Optical Rotation: [a]D +10.35° (c = 1 in water)
Therap-Cat: Antiglaucoma agent.
Keywords: Antiglaucoma; Carbonic Anhydrase Inhibitor.
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Brinzolamide
Brinzolamide.svg
Systematic (IUPAC) name
(5R)-5-ethylamino-3-(3-methoxypropyl)-
2,2-dioxo-2λ6,9-dithia-
3-azabicyclo[4.3.0]nona-7,10-diene-
8-sulfonamide
Clinical data
Trade names Azopt
AHFS/Drugs.com monograph
MedlinePlus a601233
Licence data EMA:Link, US FDA:link
Pregnancy cat. C (US)
Legal status -only (US)
Routes Ophthalmic
Pharmacokinetic data
Bioavailability Absorbed systemically, but below detectable levels (less than 10 ng/mL)
Protein binding ~60%
Half-life 111 days
Excretion Renal (60%)
Identifiers
CAS number 138890-62-7
ATC code S01EC04
PubChem CID 68844
DrugBank DB01194
ChemSpider 62077 YesY
UNII 9451Z89515 YesY
KEGG D00652 YesY
ChEBI CHEBI:3176 YesY
ChEMBL CHEMBL220491 YesY
Chemical data
Formula C12H21N3O5S3 
Mol. mass 383.51 g/mol
 YesY (what is this?)  (verify)

Brinzolamide (trade name Azopt, Alcon Laboratories, Inc.) is a carbonic anhydrase inhibitor used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension.