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Ethoxzolamide

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Chemistry

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Also known as: 452-35-7, 6-ethoxy-2-benzothiazolesulfonamide, Ethoxyzolamide, Ethoxazolamide, Ethamide, Cardrase

Molecular Formula

C₉H₁₀N₂O₃S₂

Molecular Weight

258.3 g/mol

InChI Key

OUZWUKMCLIBBOG-UHFFFAOYSA-N

FDA UNII

Z52H4811WX

A carbonic anhydrase inhibitor used as diuretic and in glaucoma. It may cause hypokalemia.

1 2D Structure

Ethoxzolamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-ethoxy-1,3-benzothiazole-2-sulfonamide

2.1.2 InChI

InChI=1S/C9H10N2O3S2/c1-2-14-6-3-4-7-8(5-6)15-9(11-7)16(10,12)13/h3-5H,2H2,1H3,(H2,10,12,13)

2.1.3 InChI Key

OUZWUKMCLIBBOG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCOC1=CC2=C(C=C1)N=C(S2)S(=O)(=O)N

2.2 Other Identifiers

2.2.1 UNII

Z52H4811WX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ethamide

2. Ethoxazolamide

3. Ethoxyzolamide

2.3.2 Depositor-Supplied Synonyms

1. 452-35-7

2. 6-ethoxy-2-benzothiazolesulfonamide

3. Ethoxyzolamide

4. Ethoxazolamide

5. Ethamide

6. Cardrase

7. Etoxzolamide

8. Glaucotensil

9. 6-ethoxy-1,3-benzothiazole-2-sulfonamide

10. Diuretic C

11. Redupresin

12. 2-benzothiazolesulfonamide, 6-ethoxy-

13. 6-ethoxybenzo[d]thiazole-2-sulfonamide

14. 6-ethoxyzolamide

15. 6-ethoxybenzothiazole-2-sulfonamide

16. U-4191

17. Nsc 10679

18. Chembl18

19. Nsc-10679

20. Redupresin;l-643786;pnu-4191

21. Mls000028637

22. 6-ethoxy-benzothiazole-2-sulfonic Acid Amide

23. Mingoral

24. Chebi:101096

25. Z52h4811wx

26. 6-ethoxy-2-benzothiazole8ulfonamide

27. Ncgc00018249-04

28. Smr000059148

29. Dsstox_cid_3021

30. 6-ethoxybenzothiazole-2-sulphonamide

31. Dsstox_rid_76834

32. Dsstox_gsid_23021

33. Cardrase (tn)

34. Cas-452-35-7

35. Ezl

36. Ethoxzolamide [usp]

37. Hsdb 3268

38. Einecs 207-199-5

39. Brn 0212240

40. Athamid

41. Unii-z52h4811wx

42. Ai3-50805

43. 3caj

44. 3dcw

45. 3mdz

46. Ethoxzolamide, Ezm

47. Mfcd00057089

48. 3dd0

49. Opera_id_1207

50. Ethoxzolamide [mi]

51. 6-(ethyloxy)-1,3-benzothiazole-2-sulfonamide

52. Ethoxzolamide [hsdb]

53. Schembl63941

54. 4-27-00-04404 (beilstein Handbook Reference)

55. Mls001077357

56. Ethoxzolamide [who-dd]

57. Gtpl6814

58. Dtxsid1023021

59. Bdbm10882

60. Zinc56721

61. Hms2093j03

62. Hms2094m03

63. Hms2233n09

64. Hms3373k15

65. Hms3715f20

66. Hms3746m15

67. Pharmakon1600-01505426

68. Ethoxzolamide [orange Book]

69. Bcp24088

70. Hy-b1480

71. Nsc10679

72. Pnu-4191

73. Tox21_110848

74. 6-ethoxy-2-benzothiazole Sulfonamide

75. Nsc759129

76. Wln: T56 Bn Dsj Cszw Go2

77. Akos015915628

78. Tox21_110848_1

79. Ccg-213432

80. Cs-7836

81. Db00311

82. Nsc-759129

83. Vs-0126

84. Benzothiazole, 6-ethoxy-2-sulfonamide-

85. Ncgc00018249-01

86. Ncgc00018249-02

87. Ncgc00018249-03

88. Ncgc00018249-05

89. Ncgc00022533-04

90. Ncgc00186657-01

91. 6-ethoxy-2-benzothiazolesulfonamide, 97%

92. Sbi-0206851.p001

93. 6-ethoxy-1,3-benzothiazole-2-sulfonamide #

94. Ft-0707866

95. Sw220095-1

96. D02441

97. Ab00383049_12

98. Ab00383049_13

99. Q265352

100. Sr-01000000236

101. L-643786

102. Sr-01000000236-2

103. Brd-k18131774-001-10-1

104. Ethoxzolamide, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₀N₂O₃S₂
Molecular Weight	258.3 g/mol
XLogP3	2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	258.01328453 g/mol
Monoisotopic Mass	258.01328453 g/mol
Topological Polar Surface Area	119 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	341
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 Therapeutic Uses

Carbonic Anhydrase Inhibitors; Diuretics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

.../USED FOR/ ADJUNCTIVE TREATMENT OF CHRONIC SIMPLE (OPEN-ANGLE) GLAUCOMA, SECONDARY GLAUCOMA, & PREOPERATIVELY IN ACUTE ANGLE-CLOSURE GLAUCOMA TO LOWER INTRAOCULAR PRESSURE PRIOR TO SURGERY.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 867

EFFECTIVE DOSE APPEARS TO VARY FROM 125 TO 1000 MG/DAY, GIVEN ORALLY IN DIVIDED DOSES.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 828

MEDICATION (VET): AS DIURETIC IN MILD CONGESTIVE CARDIAC EDEMAS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 207

For more Therapeutic Uses (Complete) data for ETHOXZOLAMIDE (6 total), please visit the HSDB record page.

4.2 Drug Warning

... CARBONIC ANHYDRASE INHIBITORS SHOULD BE USED CAUTIOUSLY IN PATIENTS WITH OBSTRUCTIVE PULMONARY DISEASE BECAUSE THEY MAY PRECIPITATE ACUTE RESP FAILURE. /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2117

SINCE CARBONIC ANHYDRASE INHIBITORS MAY HAVE TERATOGENIC EFFECTS, THESE DRUGS SHOULD BE AVOIDED DURING EARLY PREGNANCY. /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2117

CARBONIC ANHYDRASE INHIBITORS ALSO ARE ADMINISTERED FOR PREOPERATIVE TREATMENT OF ACUTE ANGLE-CLOSURE AND CONGENITAL GLAUCOMAS. ... mORE THAN 50% OF PATIENTS ... MUST DISCONTINUE THERAPY BECAUSE OF ADVERSE REACTIONS. ... OSMOTIC AGENTS ARE USED TO REDUCE INTRAOCULAR PRESSURE AND VITREOUS VOLUME RAPIDLY PRIOR TO IRIDECTOMY AND OTHER OCULAR SURGICAL PROCEDURES. /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 808

RENAL COLIC, HEMATURIA & OLIGURIA OR ANURIA MAY OCCUR DURING PROLONGED THERAPY... CARBONIC ANHYDRASE INHIBITORS REDUCE URIC ACID EXCRETION & INCR BLOOD URIC ACID LEVEL. ... HYPERURICEMIA IS USUALLY ASYMPTOMATIC BUT RARELY HAS LED TO AN EXACERBATION OF GOUT. /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2116

For more Drug Warnings (Complete) data for ETHOXZOLAMIDE (7 total), please visit the HSDB record page.

4.3 Drug Indication

For use in the treatment of duodenal ulcers, as a diuretic, and in the treatment of glaucoma, and may also be useful in the treatment of seizures associated with epilepsy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ethoxzolamide is an inhibitor of the carbonic anhydrase enzyme in proximal renal tubules that works by decreasing the reabsorption of water, sodium, potassium, bicarbonate. It also decreases the activity of carbonic anhydrase expressed in the CNS, which leads to increased seizure threshold. Inhibition of carbonic anhydrase in the eye contributes to its effect of reducing intraocular pressure and decreasing aqueous humor.

5.2 MeSH Pharmacological Classification

Diuretics

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

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 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed with 65% bioavailability

ABSORBED FROM GI TRACT...DISTRIBUTED IN PLASMA, MUSCLES, BRAIN, KIDNEYS, LIVER, LUNGS, ERYTHROCYTES, AQUEOUS HUMOR, & CSF. APPROX 40%...EXCRETED UNCHANGED BY KIDNEYS /HUMAN, ORAL/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976

5.4 Biological Half-Life

2.5-5.5 hours

5.5 Mechanism of Action

Ethoxzolamide binds to and inhibits carbonic anhydrase I, which plays an essential role in facilitating the transport of CO2 and H+ in the intracellular space, across biological membranes, and in the layers of the extracellular space. Through inhibition of the enzyme, the balance of applicable membrane equilibrium systems are affected.

MAJOR PHARMACOLOGICAL ACTION...IS INHIBITION OF...CARBONIC ANHYDRASE. STUDIES WITH PURIFIED ENZYME HAVE SHOWN THAT INHIBITION IS NONCOMPETITIVE. NONCATALYZED HYDRATION OR DEHYDRATION REACTION CAN TAKE PLACE, OF COURSE, IN ABSENCE OF ENZYME.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 826

CARBONIC ANHYDRASE INHIBITORS...DECR CONCN OF HYDROGEN IONS AVAIL FOR EXCHANGE WITH SODIUM & POTASSIUM & TO COMBINE WITH BICARBONATE TO FORM CARBONIC ACID. /CARBONIC ANHYDRASE INHIBITORS/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 862

...EFFECT /OF CARBONIC ANHYDRASE INHIBITORS/ ON INTRAOCULAR PRESSURE DOES NOT DEPEND UPON DIURESIS. THEY REDUCE AQUEOUS PRODN ... & THUS LOWER PRESSURE. /CARBONIC ANHYDRASE INHIBITORS/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2116

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