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Chemistry

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Also known as: 59-66-5, Diamox, Acetamox, N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide, Glaupax, Acetazolamid
Molecular Formula
C4H6N4O3S2
Molecular Weight
222.3  g/mol
InChI Key
BZKPWHYZMXOIDC-UHFFFAOYSA-N
FDA UNII
O3FX965V0I

Acetazolamide
One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)
Acetazolamide is a Carbonic Anhydrase Inhibitor. The mechanism of action of acetazolamide is as a Carbonic Anhydrase Inhibitor.
1 2D Structure

Acetazolamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide
2.1.2 InChI
InChI=1S/C4H6N4O3S2/c1-2(9)6-3-7-8-4(12-3)13(5,10)11/h1H3,(H2,5,10,11)(H,6,7,9)
2.1.3 InChI Key
BZKPWHYZMXOIDC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)NC1=NN=C(S1)S(=O)(=O)N
2.2 Other Identifiers
2.2.1 UNII
O3FX965V0I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acetadiazol

2. Acetazolam

3. Acetazolamide Sodium, (sterile)

4. Acetazolamide, Monosodium Salt

5. Ak Zol

6. Ak-zol

7. Akzol

8. Apo Acetazolamide

9. Apo-acetazolamide

10. Apoacetazolamide

11. Dfiltran

12. Diacarb

13. Diamox

14. Diuramide

15. Edemox

16. Glauconox

17. Glaupax

18. Huma Zolamide

19. Huma-zolamide

20. Humazolamide

2.3.2 Depositor-Supplied Synonyms

1. 59-66-5

2. Diamox

3. Acetamox

4. N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide

5. Glaupax

6. Acetazolamid

7. Defiltran

8. Nephramide

9. Edemox

10. Phonurit

11. Diacarb

12. Donmox

13. Didoc

14. Cidamex

15. Diluran

16. Diuriwas

17. Dehydratin

18. Diuramid

19. Diutazol

20. Duiramid

21. Eumicton

22. Natrionex

23. Nephramid

24. Diakarb

25. Fonurit

26. Glupax

27. Vetamox

28. Sk-acetazolamide

29. 5-acetamido-1,3,4-thiadiazole-2-sulfonamide

30. Acetazolamidum

31. Acetazoleamide

32. Acetozalamide

33. Diureticum-holzinger

34. Acetamidothiadiazolesulfonamide

35. Acetazolamida

36. 4-diamox

37. Acetamide, N-[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]-

38. Carbonic Anhydrase Inhibitor No. 6063

39. 2-acetylamino-1,3,4-thiadiazole-5-sulfonamide

40. N-[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]acetamide

41. Atenezo

42. 2-acetamido-5-sulfonamido-1,3,4-thiadiazole

43. Carbonic Anhydrase Inhibitor 6063

44. Nsc 145177

45. 1,3,4-thiadiazole-2-sulfonamide, 5-acetamido-

46. N-(5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl)acetamide

47. 5-acetamide-1,3,4-thiadiazole-2-sulfonamide

48. Chembl20

49. Diamox (tn)

50. Nsc-145177

51. Mls000028435

52. O3fx965v0i

53. Acetamide, N-(5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl)-

54. Chebi:27690

55. Acetamide, N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-

56. Cas-59-66-5

57. Ncgc00015074-10

58. Acetazolamine

59. Atenezol

60. Glaumox

61. Smr000058394

62. Diamox Sequels

63. Dsstox_cid_2544

64. 5-acetylamino-1,3,4-thiadiazole-2-sulfonamide

65. Dsstox_rid_76621

66. Dsstox_gsid_22544

67. L 579486

68. Acetazolamidum [inn-latin]

69. Acetazolamida [inn-spanish]

70. N-[5-(aminosulfonyl)-1,3,5-thiadiazol-2-yl]acetamide

71. Ccris 5811

72. Acetazolamide (aaz)

73. Hsdb 3002

74. Sr-01000000065

75. Einecs 200-440-5

76. Mfcd00003105

77. Unii-o3fx965v0i

78. Ai3-52458

79. Prestwick_4

80. 1azm

81. 1yda

82. 1ydb

83. 1ydd

84. 1zsb

85. 2xtk

86. 3czv

87. 3ucj

88. Acetazolamide, 5

89. Acetazolamide [usp:inn:ban:jan]

90. Acerazolamide, Aaz

91. Acetazolamide, Aaz

92. Acetazolamide, Aza

93. Acetazolamide, Azm

94. Spectrum_000018

95. 1jd0

96. 2h4n

97. 2uy4

98. 3dc3

99. 3hs4

100. 3ml5

101. 4g0c

102. Opera_id_288

103. Aza2

104. Prestwick0_000003

105. Prestwick1_000003

106. Prestwick2_000003

107. Prestwick3_000003

108. Spectrum2_000082

109. Spectrum3_000284

110. Spectrum4_000139

111. Spectrum5_000738

112. Lopac-a-6011

113. Acetazolamide [mi]

114. A 6011

115. Acetazolamide [inn]

116. Acetazolamide [jan]

117. Acetazolamide [hsdb]

118. Lopac0_000039

119. Schembl23219

120. Acetazolamide [vandf]

121. Bspbio_000005

122. Bspbio_001788

123. Kbiogr_000558

124. Kbioss_000358

125. Mls001148438

126. Acetazolamide [mart.]

127. Bidd:gt0643

128. Divk1c_000017

129. Spectrum1500102

130. N-(5-sulfamoyl-[1,3,4]thiadiazol-2-yl)-acetamide

131. Spbio_000004

132. Spbio_001926

133. Acetazolamide [usp-rs]

134. Acetazolamide [who-dd]

135. Acetazolamide [who-ip]

136. Bpbio1_000007

137. Gtpl6792

138. (non-d)acetazolamide-13c2-d3

139. Acetazolamide, >=99%, Powder

140. Dtxsid7022544

141. Schembl11049053

142. Bdbm10880

143. Bzkpwhyzmxoidc-uhfffaoysa-

144. Hms500a19

145. Kbio1_000017

146. Kbio2_000358

147. Kbio2_002926

148. Kbio2_005494

149. Kbio3_001288

150. Acetazolamide (jp17/usp/inn)

151. Amy3289

152. N-[5-(aminosulfonyl)-1,3,4-thiadiozol-2-yl]-acetamide

153. Acetazolamide, Analytical Standard

154. Ninds_000017

155. Hms1568a07

156. Hms1920a05

157. Hms2091g05

158. Hms2095a07

159. Hms2232g23

160. Hms3259i13

161. Hms3260g19

162. Hms3370p01

163. Hms3712a07

164. Hms3744a21

165. Pharmakon1600-01500102

166. Wln: T5nn Dsj Cszw Emv1

167. Acetazolamide [ep Impurity]

168. Acetazolamide [orange Book]

169. Albb-023617

170. Bcp29616

171. Hy-b0782

172. Zinc3813042

173. Acetazolamide [ep Monograph]

174. Tox21_110078

175. Tox21_201559

176. Tox21_302773

177. Tox21_500039

178. Acetazolamide [usp Monograph]

179. Ccg-38900

180. Nsc145177

181. Nsc755854

182. S4506

183. Acetazolamidum [who-ip Latin]

184. Akos000715163

185. Tox21_110078_1

186. Cs-3568

187. Db00819

188. Lp00039

189. Nc00491

190. Nsc-755854

191. Sdccgsbi-0050028.p005

192. Idi1_000017

193. Ncgc00015074-01

194. Ncgc00015074-02

195. Ncgc00015074-03

196. Ncgc00015074-04

197. Ncgc00015074-05

198. Ncgc00015074-06

199. Ncgc00015074-07

200. Ncgc00015074-08

201. Ncgc00015074-09

202. Ncgc00015074-11

203. Ncgc00015074-12

204. Ncgc00015074-14

205. Ncgc00015074-15

206. Ncgc00015074-17

207. Ncgc00015074-22

208. Ncgc00023455-03

209. Ncgc00023455-04

210. Ncgc00023455-05

211. Ncgc00023455-06

212. Ncgc00023455-07

213. Ncgc00256374-01

214. Ncgc00259108-01

215. Ncgc00260724-01

216. Ac-12779

217. As-13169

218. Sbi-0050028.p004

219. 2-acetamido-5-sulfonamido-1,4-thiadiazole

220. 5-acetamide-1,4-thiadiazole-2-sulfonamide

221. Db-053437

222. 5-acetamido-1,3,4-thiadiazol-2-sulfonamide

223. Ab00051906

224. Eu-0100039

225. 1,4-thiadiazole-2-sulfonamide, 5-acetamido-

226. C06805

227. D00218

228. D88526

229. Ab00051906_15

230. 003a105

231. A832415

232. N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)ethanamide

233. Q413690

234. Q-200579

235. Q-200580

236. Sr-01000000065-2

237. Sr-01000000065-4

238. Sr-01000000065-6

239. Brd-k43457670-001-22-9

240. Brd-k43457670-001-26-0

241. Z277559108

242. (1z)-n-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)ethanimidic Acid

243. Acetazolamide, European Pharmacopoeia (ep) Reference Standard

244. Acetazolamide, United States Pharmacopeia (usp) Reference Standard

245. N - (5 - Sulfamoyl - 1,3, 4 - Thiadiazol - 2 - Yl) Acetamide

246. Acetazolamide For System Suitability, European Pharmacopoeia (ep) Reference Standard

247. Acetazolamide, Pharmaceutical Secondary Standard; Certified Reference Material

248. 124442-28-0

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 222.3 g/mol
Molecular Formula C4H6N4O3S2
XLogP3-0.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass221.98813241 g/mol
Monoisotopic Mass221.98813241 g/mol
Topological Polar Surface Area152 Ų
Heavy Atom Count13
Formal Charge0
Complexity297
Isotope Atom Count0
Defined Atom Stereocenter Count0
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 4  
Drug NameAcetazolamide
PubMed HealthAcetazolamide
Drug ClassesAnticonvulsant, Antiglaucoma, Cardiovascular Agent, Musculoskeletal Agent, Renal-Urologic Agent, Urinary Stone Agent
Drug LabelAcetazolamide, an inhibitor of the enzyme carbonic anhydrase is a white to faintly yellowish white crystalline, odorless powder, weakly acidic, very slightly soluble in water and slightly soluble in alcohol. The chemical name for acetazolamide is N-(...
Active IngredientAcetazolamide
Dosage FormTablet; Capsule, extended release
RouteOral
Strength250mg; 125mg; 500mg
Market StatusPrescription
CompanyMutual Pharm; Lannett; Taro; Zydus Pharms Usa; Heritage Pharms

2 of 4  
Drug NameDiamox
PubMed HealthAcetazolamide (By mouth)
Drug ClassesAnticonvulsant, Antiglaucoma, Cardiovascular Agent, Musculoskeletal Agent, Renal-Urologic Agent, Urinary Stone Agent
Drug LabelDIAMOX SEQUELS (Acetazolamide Extended-Release Capsules) are an inhibitor of the enzyme carbonic anhydrase.DIAMOX is a white to faintly yellowish white crystalline, odorless powder, weakly acidic, very slightly soluble in water, and slightly soluble...
Active IngredientAcetazolamide
Dosage FormCapsule, extended release
RouteOral
Strength500mg
Market StatusPrescription
CompanyDuramed Pharms Barr

3 of 4  
Drug NameAcetazolamide
PubMed HealthAcetazolamide
Drug ClassesAnticonvulsant, Antiglaucoma, Cardiovascular Agent, Musculoskeletal Agent, Renal-Urologic Agent, Urinary Stone Agent
Drug LabelAcetazolamide, an inhibitor of the enzyme carbonic anhydrase is a white to faintly yellowish white crystalline, odorless powder, weakly acidic, very slightly soluble in water and slightly soluble in alcohol. The chemical name for acetazolamide is N-(...
Active IngredientAcetazolamide
Dosage FormTablet; Capsule, extended release
RouteOral
Strength250mg; 125mg; 500mg
Market StatusPrescription
CompanyMutual Pharm; Lannett; Taro; Zydus Pharms Usa; Heritage Pharms

4 of 4  
Drug NameDiamox
PubMed HealthAcetazolamide (By mouth)
Drug ClassesAnticonvulsant, Antiglaucoma, Cardiovascular Agent, Musculoskeletal Agent, Renal-Urologic Agent, Urinary Stone Agent
Drug LabelDIAMOX SEQUELS (Acetazolamide Extended-Release Capsules) are an inhibitor of the enzyme carbonic anhydrase.DIAMOX is a white to faintly yellowish white crystalline, odorless powder, weakly acidic, very slightly soluble in water, and slightly soluble...
Active IngredientAcetazolamide
Dosage FormCapsule, extended release
RouteOral
Strength500mg
Market StatusPrescription
CompanyDuramed Pharms Barr

4.2 Therapeutic Uses

Anticonvulsants; Carbonic Anhydrase Inhibitors; Diuretics

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


MEDICATION (VET): IN LAMINITIS, UDDER EDEMA, ENTEROTOXEMIA, ASCITES, & GLAUCOMA IN VARIOUS SPECIES.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 2


Carbonic anhydrase inhibitors are indicated primarily as adjuncts to other agents in the treatment of open-angle (chronic simple) glaucoma and secondary glaucoma, and to lower intraocular pressure prior to surgery for some types of glaucoma. /Carbonic anhydrase inhibitors; Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 747


Acetazolamide is used to lower intraocular pressure in the treatment of malignant (ciliary block) glaucoma, which may occur after inflammation surgery, trauma, or use of miotics. /NOT included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 747


For more Therapeutic Uses (Complete) data for ACETAZOLAMIDE (13 total), please visit the HSDB record page.


4.3 Drug Warning

VET: CONTRAINDICATED IN ADRENAL FAILURE OR LOW POTASSIUM AND SODIUM SYNDROMES.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 2


SAFE USE OF THESE AGENTS DURING PREGNANCY HAS NOT BEEN ESTABLISHED. THESE AGENTS ARE CONTRAINDICATED IN PT WITH IDIOPATHIC RENAL HYPERCHLOREMIC ACIDOSIS, RENAL FAILURE, KNOWN DEPLETION OF SODIUM & OF POTASSIUM, ADDISON'S DISEASE, & PT KNOWN TO BE SENSITIVE TO THIS CLASS OF DRUGS. /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. 866


DIURETICS, SUCH AS ACETAZOLAMIDE & THIAZIDES, CAN ALKALINIZE URINE & THUS THEORETICALLY WOULD LIMIT USEFULNESS OF METHENAMINE AS WELL AS ITS MANDELATE & HIPPURATE SALTS AS URINARY TRACT ANTI-INFECTIVE AGENTS.

Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 391


Maternal Medication usually Compatible with Breast-Feeding: Acetazolamide: Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 140 (1994)


For more Drug Warnings (Complete) data for ACETAZOLAMIDE (13 total), please visit the HSDB record page.


4.4 Drug Indication

For adjunctive treatment of: edema due to congestive heart failure; drug-induced edema; centrencephalic epilepsies; chronic simple (open-angle) glaucoma


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Acetazolamide is a potent carbonic anhydrase inhibitor, effective in the control of fluid secretion, in the treatment of certain convulsive disorders and in the promotion of diuresis in instances of abnormal fluid retention. Acetazolamide is not a mercurial diuretic. Rather, it is a nonbacteriostatic sulfonamide possessing a chemical structure and pharmacological activity distinctly different from the bacteriostatic sulfonamides.


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.)


Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)


5.3 FDA Pharmacological Classification