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Brinzolamide

Synopsis

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Chemistry

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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 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 Formula	C₁₂H₂₁N₃O₅S₃
Molecular Weight	383.5 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	383.06433430 g/mol
Monoisotopic Mass	383.06433430 g/mol
Topological Polar Surface Area	164 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	598
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Azopt
PubMed Health	Brinzolamide (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	AZOPT (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 Ingredient	Brinzolamide
Dosage Form	Suspension/drops
Route	Ophthalmic
Strength	1%
Market Status	Prescription
Company	Alcon Pharms

2 of 2
Drug Name	Azopt
PubMed Health	Brinzolamide (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	AZOPT (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 Ingredient	Brinzolamide
Dosage Form	Suspension/drops
Route	Ophthalmic
Strength	1%
Market Status	Prescription
Company	Alcon 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

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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API Reference Price

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