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    Also known as: 138890-62-7, Azopt, Al-4862, Al 4862, (4r)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide, (4r)-4-(ethylamino)-2-(3-methoxypropyl)-3,4-dihydro-2h-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide
    Molecular Formula
    C12H21N3O5S3
    Molecular Weight
    383.5  g/mol
    InChI Key
    HCRKCZRJWPKOAR-JTQLQIEISA-N
    FDA UNII
    9451Z89515
    Brinzolamide
    Brinzolamide is a sulfonamide and carbonic anhydrase inhibitor with specific affinity for carbonic anhydrase II. Following topical ocular administration, brinzolamide inhibits carbonic anhydrase II, an enzyme that is responsible for the movement of sodium and fluid transport in the eye. This inhibition leads to a decrease in aqueous humor secretion, probably by slowing the formation of bicarbonate ions, and results in a reduction in intraocular pressure. Brinzolamide is used to treat increased pressure in the eye caused by open-angle glaucoma.
    Brinzolamide is a Carbonic Anhydrase Inhibitor. The mechanism of action of brinzolamide is as a Carbonic Anhydrase Inhibitor.
    1 2D Structure

    Brinzolamide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide
    2.1.2 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
    2.1.3 InChI Key
    HCRKCZRJWPKOAR-JTQLQIEISA-N
    2.1.4 Canonical SMILES
    CCNC1CN(S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)CCCOC
    2.1.5 Isomeric SMILES
    CCN[C@H]1CN(S(=O)(=O)C2=C1C=C(S2)S(=O)(=O)N)CCCOC
    2.2 Other Identifiers
    2.2.1 UNII
    9451Z89515
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (r)-4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2h-thieno(3,2-e)-1,2-thiazine-6-sulfonamide 1,1-dioxide

    2. Azopt

    2.3.2 Depositor-Supplied Synonyms

    1. 138890-62-7

    2. Azopt

    3. Al-4862

    4. Al 4862

    5. (4r)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide

    6. (4r)-4-(ethylamino)-2-(3-methoxypropyl)-3,4-dihydro-2h-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide

    7. 138890-50-3

    8. Chebi:3176

    9. (r)-4-(ethylamino)-2-(3-methoxypropyl)-3,4-dihydro-2h-thieno[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide

    10. Nsc-760050

    11. (+)-4-ethylamino-3,4-dihydro-2-(methoxy)propyl-2h-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide

    12. (r)-4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2h-thieno(3,2-e)-1,2-thiazine-6-sulfonamide 1,1-dioxide

    13. (r)-4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2h-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide

    14. 2h-thieno(3,2-e)-1,2-thiazine-6-sulfonamide, 4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide, (r)-

    15. Brinzolamide [usan]

    16. Mfcd08067749

    17. Dsstox_cid_25531

    18. Dsstox_rid_80934

    19. Dsstox_gsid_45531

    20. 2h-thieno[3,2-e]-1,2-thiazine-6-sulfonamide, 4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide, (4r)-

    21. Bz1

    22. 9451z89515

    23. (4r)-4-(ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2h-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide

    24. Brinzolamide (brz)

    25. Azopt (tn)

    26. Brinzolamide (jan/usp/inn)

    27. 3znc

    28. Ncgc00016979-01

    29. Brinzolamide [usan:usp:inn:ban]

    30. Unii-9451z89515

    31. Brinzolamide- Bio-x

    32. Cas-138890-62-7

    33. Prestwick0_000365

    34. Prestwick1_000365

    35. Prestwick2_000365

    36. Prestwick3_000365

    37. Brinzolamide [mi]

    38. Brinzolamide [inn]

    39. Brinzolamide [jan]

    40. Brinzolamide [vandf]

    41. Schembl24636

    42. Brinzolamide [mart.]

    43. Bspbio_000489

    44. Mls002153787

    45. Bidd:gt0039

    46. Brinzolamide [usp-rs]

    47. Brinzolamide [who-dd]

    48. Spbio_002410

    49. Amy372

    50. Bpbio1_000539

    51. Chembl220491

    52. Gtpl6797

    53. Brinzolamide [ema Epar]

    54. Dtxsid6045531

    55. Bdbm10885

    56. Brinzolamide, >=98% (hplc)

    57. Brinzolamide [orange Book]

    58. Hms1569i11

    59. Hms2096i11

    60. Hms2234k06

    61. Hms3713i11

    62. Hms3885i11

    63. Brinzolamide [usp Impurity]

    64. Azarga Component Brinzolamide

    65. Bcp22330

    66. Hy-b0588

    67. Zinc3953037

    68. Brinzolamide [usp Monograph]

    69. Tox21_110722

    70. S3178

    71. Akos005145708

    72. Simbrinza Component Brinzolamide

    73. Tox21_110722_1

    74. Ac-5277

    75. Brinzolamide Component Of Azarga

    76. Ccg-220365

    77. Ccg-222516

    78. Db01194

    79. Nsc 760050

    80. Ncgc00179542-03

    81. Ncgc00179542-09

    82. Ncgc00179542-10

    83. As-35084

    84. Bb164262

    85. Brinzolamide Component Of Simbrinza

    86. Smr001233169

    87. Ab00513824

    88. B4258

    89. Sw197152-3

    90. Al4862;al 4862;al-4862

    91. C07760

    92. D00652

    93. Ab00513824_06

    94. Q411517

    95. Sr-01000838832

    96. Q-200751

    97. Sr-01000838832-2

    98. Brd-k74913225-001-03-3

    99. Brinzolamide, United States Pharmacopeia (usp) Reference Standard

    100. (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

    101. (4r)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-2h,3h,4h-1$l^{6},7,2-thieno[3,2-e][1,2]thiazine-6-sulfonamide

    102. (4r)-4-(ethylamino)-2-(3-methoxypropyl)-3,4-dihydro-2h-thieno[3,2-e][1,2]thiazine-6-sulfonamide-1,1-dioxide

    103. (4r)-4-ethylamino-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[4,5-e]thiazine-6-sulfonamide

    104. (5r)-5-ethylamino-3-(3-methoxypropyl)-2,2-dioxo-2,9-dithia-3-azabicyclo[4.3.0]nona-1(6)7-diene-8-sulfonamide

    105. (r)-3,4-dihydro-4-ethylamino-2-(3-methoxypropyl)-2h-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 383.5 g/mol
    Molecular Formula C12H21N3O5S3
    XLogP3-0.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count7
    Exact Mass383.06433430 g/mol
    Monoisotopic Mass383.06433430 g/mol
    Topological Polar Surface Area164 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity598
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameAzopt
    PubMed HealthBrinzolamide (Into the eye)
    Drug ClassesAntiglaucoma
    Drug LabelAZOPT (brinzolamide ophthalmic suspension) 1% contains a carbonic anhydrase inhibitor formulated for multidose topical ophthalmic use. Brinzolamide is described chemically as: (R)-(+)-4-Ethylamino-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno [3,2-e]-1...
    Active IngredientBrinzolamide
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength1%
    Market StatusPrescription
    CompanyAlcon Pharms

    2 of 2  
    Drug NameAzopt
    PubMed HealthBrinzolamide (Into the eye)
    Drug ClassesAntiglaucoma
    Drug LabelAZOPT (brinzolamide ophthalmic suspension) 1% contains a carbonic anhydrase inhibitor formulated for multidose topical ophthalmic use. Brinzolamide is described chemically as: (R)-(+)-4-Ethylamino-2-(3-methoxypropyl)-3,4-dihydro-2H-thieno [3,2-e]-1...
    Active IngredientBrinzolamide
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength1%
    Market StatusPrescription
    CompanyAlcon Pharms

    4.2 Drug Indication

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

    FDA Label

    Azopt is indicated to decrease elevated intraocular pressure in:

    - ocular hypertension;

    - open-angle glaucomaas monotherapy in adult patients unresponsive to beta-blockers or in adult patients in whom beta-blockers are contraindicated, or as adjunctive therapy to beta-blockers or prostaglandin analogues.

    5 Pharmacology and Biochemistry
    5.1 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.

    5.2 MeSH Pharmacological Classification

    Carbonic Anhydrase Inhibitors

    A class of compounds that reduces the secretion of H+ ions by the proximal kidney tubule through inhibition of CARBONIC ANHYDRASES. (See all compounds classified as Carbonic Anhydrase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    BRINZOLAMIDE
    5.3.2 FDA UNII
    9451Z89515
    5.3.3 Pharmacological Classes
    Carbonic Anhydrase Inhibitors [MoA]; Carbonic Anhydrase Inhibitor [EPC]
    5.4 ATC Code

    S01EC04

    S01EC04

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    S - Sensory organs

    S01 - Ophthalmologicals

    S01E - Antiglaucoma preparations and miotics

    S01EC - Carbonic anhydrase inhibitors

    S01EC04 - Brinzolamide

    5.5 Absorption, Distribution and Excretion

    Absorption

    Absorbed into systemic circulation following topical ocular application

    5.6 Metabolism/Metabolites

    Ophthalmic

    5.7 Biological Half-Life

    111 days

    5.8 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).

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    02-Jan-2021
    29-Oct-2024
    KGS
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