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Chemistry

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Also known as: 443-48-1, Flagyl, Metronidazol, 2-methyl-5-nitroimidazole-1-ethanol, Anagiardil, Gineflavir
Molecular Formula
C6H9N3O3
Molecular Weight
171.15  g/mol
InChI Key
VAOCPAMSLUNLGC-UHFFFAOYSA-N
FDA UNII
140QMO216E

Metronidazole
A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS.
Metronidazole is a Nitroimidazole Antimicrobial.
1 2D Structure

Metronidazole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-methyl-5-nitroimidazol-1-yl)ethanol
2.1.2 InChI
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
2.1.3 InChI Key
VAOCPAMSLUNLGC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=NC=C(N1CCO)[N+](=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
140QMO216E
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Methyl 5 Nitroimidazole 1 Ethanol

2. 2-methyl-5-nitroimidazole-1-ethanol

3. Bayer 5360

4. Clont

5. Danizol

6. Flagyl

7. Gineflavir

8. Metric

9. Metrodzhil

10. Metrogel

11. Metrogyl

12. Metronidazole Hydrochloride

13. Metronidazole Monohydrochloride

14. Metronidazole Phosphate

15. Metronidazole Phosphoester

16. Satric

17. Trichazol

18. Trichopol

19. Trivazol

20. Vagilen

2.3.2 Depositor-Supplied Synonyms

1. 443-48-1

2. Flagyl

3. Metronidazol

4. 2-methyl-5-nitroimidazole-1-ethanol

5. Anagiardil

6. Gineflavir

7. Metrogel

8. Deflamon

9. Orvagil

10. Trichazol

11. Bayer 5360

12. Meronidal

13. Metronidaz

14. Novonidazol

15. Trichopol

16. Trivazol

17. Danizol

18. Mexibol

19. Vagilen

20. Clont

21. Flagemona

22. Giatricol

23. Metronidazolo

24. Protostat

25. Sanatrichom

26. Takimetol

27. Trichocide

28. Trichomol

29. Trikacide

30. Acromona

31. Atrivyl

32. Efloran

33. Entizol

34. Flagesol

35. Monagyl

36. Monasin

37. Trichex

38. Tricocet

39. Trikamon

40. Trikojol

41. Trikozol

42. Trimeks

43. Vagimid

44. Vertisal

45. Wagitran

46. Arilin

47. Bexon

48. Elyzol

49. Eumin

50. Flagil

51. Klion

52. Klont

53. Metrocream

54. Metrolotion

55. Nalox

56. Satric

57. Tricom

58. 2-(2-methyl-5-nitro-1h-imidazol-1-yl)ethanol

59. Neo-tric

60. Tricowas B

61. Metrogel-vaginal

62. Deflamon-wirkstoff

63. Metromidol

64. Cont

65. Nida

66. Methronidazole

67. Noritate

68. Trichopal

69. Flegyl

70. Fossyol

71. Flagyl Er

72. Metro I.v.

73. Metronidazolum

74. 1h-imidazole-1-ethanol, 2-methyl-5-nitro-

75. Metrolyl

76. Vandazole

77. Zadstat

78. Metric 21

79. Rp 8823

80. Trichomonacid 'pharmachim'

81. 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole

82. Nsc-50364

83. 2-(2-methyl-5-nitroimidazol-1-yl)ethanol

84. Metronidazole In Plastic Container

85. 2-methyl-1-(2-hydroxyethyl)-5-nitroimidazole

86. 2-methyl-3-(2-hydroxyethyl)-4-nitroimidazole

87. Sc 10295

88. 1-(beta-ethylol)-2-methyl-5-nitro-3-azapyrrole

89. 1-(2-hydroxy-1-ethyl)-2-methyl-5-nitroimidazole

90. 2-(2-methyl-5-nitro-1h-imidazol-1-yl)ethan-1-ol

91. 2-(2-methyl-5-nitro-1-imidazolyl)ethanol

92. Mfcd00009750

93. 1-(beta-hydroxyethyl)-2-methyl-5-nitroimidazole

94. 1-hydroxyethyl-2-methyl-5-nitroimidazole

95. Flagyl I.v. Rtu In Plastic Container

96. 1-(beta-oxyethyl)-2-methyl-5-nitroimidazole

97. Nsc 50364

98. Imidazole-1-ethanol, 2-methyl-5-nitro-

99. 2-(2-methyl-5-nitro-imidazol-1-yl)ethanol

100. Bay-5360

101. Nsc69587

102. Nsc-69587

103. Rp-8823

104. Mls000028590

105. Bayer-5360

106. Chebi:6909

107. 140qmo216e

108. Metro Gel

109. Nsc50364

110. Ncgc00016446-06

111. Cas-443-48-1

112. Metrolag

113. Metrotop

114. Rathimed

115. Smr000058175

116. Tricho Cordes

117. Dsstox_cid_892

118. Metronidazolo [dcit]

119. Tricho-gynaedron

120. Dsstox_rid_75848

121. Dsstox_gsid_20892

122. Mexibol 'silanes'

123. Metro I.v. In Plastic Container

124. 1-(.beta.-ethylol)-2-methyl-5-nitro-3-azapyrrole

125. 1-(.beta.-hydroxyethyl)-2-methyl-5-nitroimidazole

126. Metronidazol [inn-spanish]

127. Metronidazolum [inn-latin]

128. Flagyl I.v. Rtu

129. Flagyl 375

130. Trichobrol

131. Florazole

132. Mepagyl

133. Nidagyl

134. Rosased

135. Zidoval

136. Caswell No. 579aa

137. Wln: T5n Cnj A2q B1 Enw

138. Noritate (tn)

139. Ccris 410

140. Metro Cream & Gel

141. Flagyl (tn)

142. Hsdb 3129

143. Wln: T6ntj Dq Anu1- Et5n Cnj A1 Bnw

144. Sr-01000000244

145. Einecs 207-136-1

146. Nsc 69587

147. Epa Pesticide Chemical Code 120401

148. Brn 0611683

149. Polibiotic

150. Trikhopol

151. Donnan

152. Flazol

153. Unii-140qmo216e

154. Cb-01-14 Mmx

155. Metro Iv

156. Vandazole (tn)

157. Metronidazole,(s)

158. Prestwick_334

159. Nuvessa (tn)

160. Idr-90105

161. Cimetrol 500lpci

162. Metronidazole Solution

163. Metronidazole, Bioxtra

164. Metronidazole (flagyl)

165. Spectrum_001035

166. Metronidazole [usan:usp:inn:ban:jan]

167. Helidac (salt/mix)

168. 2-(2-methyl-5-nitroimidazolyl)ethan-1-ol

169. Maybridge1_001999

170. Opera_id_1585

171. Prestwick0_000081

172. Prestwick1_000081

173. Prestwick2_000081

174. Prestwick3_000081

175. Spectrum2_000883

176. Spectrum3_000506

177. Spectrum4_000060

178. Spectrum5_001289

179. M0924

180. Metronidazole [mi]

181. Chembl137

182. Metronidazole [inn]

183. Metronidazole [jan]

184. Metronidazole [hsdb]

185. Metronidazole [iarc]

186. Metronidazole [usan]

187. Nciopen2_000337

188. Schembl23042

189. Bspbio_000002

190. Bspbio_002031

191. Kbiogr_000559

192. Kbioss_001515

193. Metronidazole [vandf]

194. 5-23-05-00063 (beilstein Handbook Reference)

195. Mls000758286

196. Mls001424018

197. Bidd:gt0107

198. Divk1c_000007

199. Metronidazole [mart.]

200. Spectrum1500412

201. Spbio_000666

202. Spbio_001941

203. Metronidazole [usp-rs]

204. Metronidazole [who-dd]

205. Metronidazole [who-ip]

206. Bpbio1_000004

207. Dtxsid2020892

208. Flagyl I.v. Rtu (salt/mix)

209. Bcbcmap01_000184

210. Gtpl10914

211. Hms500a09

212. Hms547c19

213. Kbio1_000007

214. Kbio2_001515

215. Kbio2_004083

216. Kbio2_006651

217. Kbio3_001531

218. Metronidazole (jp17/usp/inn)

219. Metronidazole, Analytical Standard

220. Ninds_000007

221. Hms1568a04

222. Hms1920n19

223. Hms2051g07

224. Hms2090b19

225. Hms2091f14

226. Hms2095a04

227. Hms2231e11

228. Hms3373o05

229. Hms3393g07

230. Hms3655e22

231. Hms3712a04

232. Pharmakon1600-01500412

233. Zinc113442

234. Metronidazole [ep Impurity]

235. Metronidazole [orange Book]

236. Bcp13757

237. Hy-b0318

238. Metronidazole [ep Monograph]

239. Metronidazole [usp Impurity]

240. Tox21_110441

241. Tox21_202413

242. Tox21_302794

243. Bbl005452

244. Bdbm50375309

245. Ccg-40016

246. Fp-250

247. Metronidazole [usp Monograph]

248. Nsc757118

249. Pylera Component Metronidazole

250. S1907

251. Stk177359

252. Helidac Component Metronidazole

253. Metronidazole 2.0 Mg/ml In Methanol

254. Akos000269646

255. Akos005169650

256. Tox21_110441_1

257. Db00916

258. Ks-5140

259. Nc00020

260. Nsc-757118

261. Idi1_000007

262. Metronidazole Component Of Pylera

263. Smp1_000189

264. Metronidazole Component Of Helidac

265. Ncgc00016446-01

266. Ncgc00016446-02

267. Ncgc00016446-03

268. Ncgc00016446-04

269. Ncgc00016446-05

270. Ncgc00016446-07

271. Ncgc00016446-08

272. Ncgc00016446-09

273. Ncgc00016446-11

274. Ncgc00016446-12

275. Ncgc00016446-17

276. Ncgc00022059-03

277. Ncgc00022059-04

278. Ncgc00022059-05

279. Ncgc00256513-01

280. Ncgc00259962-01

281. Ac-23968

282. Sy002821

283. Metronidazole 1000 Microg/ml In Methanol

284. Sbi-0051447.p003

285. Db-051212

286. Metronidazole, Saj First Grade, >=99.0%

287. Ab00052046

288. Bb 0218386

289. Ft-0603394

290. Metronidazole 100 Microg/ml In Acetonitrile

291. Sw196613-4

292. C07203

293. D00409

294. Ab00052046-17

295. Ab00052046_18

296. Ab00052046_19

297. A826552

298. Metronidazole, Vetranal(tm), Analytical Standard

299. Q169569

300. 2-(2-methyl-5-nitro-1h-imidazol-1-yl)-1-ethanol

301. 2-(2-methyl-5-nitro-1h-imidazol-1-yl)ethanol #

302. Metronidazole, Antibiotic For Culture Media Use Only

303. Q-201403

304. Sr-01000000244-4

305. Sr-01000000244-5

306. Brd-k52020312-001-05-2

307. Brd-k52020312-001-15-1

308. Metronidazole Benzoate Impurity A [ep Impurity]

309. Z87001124

310. F1773-0073

311. Metronidazole, Certified Reference Material, Tracecert(r)

312. Metronidazole, British Pharmacopoeia (bp) Reference Standard

313. Metronidazole, European Pharmacopoeia (ep) Reference Standard

314. Metronidazole, United States Pharmacopeia (usp) Reference Standard

315. Metronidazole Solution, 2.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

316. Metronidazole, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 171.15 g/mol
Molecular Formula C6H9N3O3
XLogP30
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass171.06439116 g/mol
Monoisotopic Mass171.06439116 g/mol
Topological Polar Surface Area83.9 Ų
Heavy Atom Count12
Formal Charge0
Complexity170
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 24  
Drug NameFlagyl
PubMed HealthMetronidazole
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antiacne Antibacterial, Antibacterial, Antibiotic, Antiprotozoal, Antiulcer, Helicobacter Pylori
Drug LabelFLAGYL (metronidazole) tablets, 250 mg or 500 mg is an oral formulation of the synthetic nitroimidazole antimicrobial, 2-methyl-5-nitro-1H-imidazole-1-ethanol, which has the following structural formula:FLAGYL (metronidazole) tablets contain 250 mg o...
Active IngredientMetronidazole
Dosage FormTablet; Capsule
RouteOral
Strength250mg; 375mg; 500mg
Market StatusPrescription
CompanyGd Searle

2 of 24  
Drug NameFlagyl er
PubMed HealthMetronidazole (On the skin)
Drug ClassesAntiacne Antibacterial
Drug LabelFLAGYL metronidazole extended release tablets is an oral formulation of the synthetic nitroimidazole antimicrobial agent, 2-methyl-5-nitro-1H-imidazole-1-ethanol, which has the following structural formula:FLAGYL (metronidazole) extended release tabl...
Active IngredientMetronidazole
Dosage FormTablet, extended release
RouteOral
Strength750mg
Market StatusPrescription
CompanyGd Searle

3 of 24  
Drug NameFlagyl i.v. rtu in plastic container
PubMed HealthMetronidazole
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antiacne Antibacterial, Antibacterial, Antibiotic, Antiprotozoal, Antiulcer, Helicobacter Pylori
Drug LabelMETROCREAM Topical Cream contains metronidazole, USP, at a concentration of 7.5 mg per gram (0.75%) in an emollient cream consisting of benzyl alcohol, emulsifying wax, glycerin, isopropyl palmitate, purified water, sorbitol solution, lactic acid a...
Active IngredientMetronidazole
Dosage FormInjectable
RouteInjection
Strength500mg/100ml
Market StatusPrescription
CompanyBaxter Hlthcare; Pfizer

4 of 24  
Drug NameMetro i.v. in plastic container
PubMed HealthMetronidazole (On the skin)
Drug ClassesAntiacne Antibacterial
Drug LabelMETROGEL-VAGINAL is the intravaginal dosage form of the synthetic antibacterial agent, metronidazole, USP at a concentration of 0.75%. Metronidazole is a member of the imidazole class of antibacterial agents and is classified therapeutically as an an...
Active IngredientMetronidazole
Dosage FormInjectable
RouteInjection
Strength500mg/100ml
Market StatusPrescription
CompanyB Braun

5 of 24  
Drug NameMetrocream
PubMed HealthMetronidazole
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antiacne Antibacterial, Antibacterial, Antibiotic, Antiprotozoal, Antiulcer, Helicobacter Pylori
Drug LabelMETROGEL-VAGINAL is the intravaginal dosage form of the synthetic antibacterial agent, metronidazole, USP at a concentration of 0.75%. Metronidazole is a member of the imidazole class of antibacterial agents and is classified therapeutically as an an...
Active IngredientMetronidazole
Dosage FormCream
RouteTopical
Strength0.75%
Market StatusPrescription
CompanyGalderma Labs

6 of 24  
Drug NameMetrogel
Drug LabelMetroLotion (metronidazole lotion) Topical Lotion contains metronidazole, USP, at a concentration of 7.5 mg per gram (0.75% w/w) in a lotion consisting of benzyl alcohol, carbomer 941, cyclomethicone, glycerin, glyceryl stearate, light mineral oil,...
Active IngredientMetronidazole
Dosage FormGel
RouteTopical
Strength1%; 0.75%
Market StatusPrescription
CompanyGalderma Labs

7 of 24  
Drug NameMetrogel-vaginal
Drug LabelMetronidazole is an oral synthetic antiprotozoal and antibacterial agent, 1-(which has the following structural formula:Metronidazole 250 mg and 500 mg tablets, for oral administration, contain the inactive ingredients: colloidal silicon dioxide, hyd...
Active IngredientMetronidazole
Dosage FormGel
RouteVaginal
Strength0.75%
Market StatusPrescription
CompanyMedicis

8 of 24  
Drug NameMetrolotion
Drug LabelNORITATE (metronidazole cream) Cream, 1%, contains metronidazole, USP. Chemically, metronidazole is 2-methyl-5-nitro-1H-imidazole-1-ethanol. The molecular formula for metronidazole is C6H9N3O3. It has the following structural formula:Metronidazole ha...
Active IngredientMetronidazole
Dosage FormLotion
RouteTopical
Strength0.75%
Market StatusPrescription
CompanyGalderma Labs

9 of 24  
Drug NameMetronidazole
Drug LabelVANDAZOLE (metronidazole vaginal gel, 0.75%) is the vaginal dosage form of the nitroimidazole antimicrobial metronidazole at a concentration of 0.75%. Chemically, metronidazole is a 2-methyl-5-nitroimidazole-1-ethanol. C6H9N3O3 M.W. 171.16VANDAZOLE...
Active IngredientMetronidazole
Dosage FormTablet, extended release; Tablet; Cream; Capsule; Lotion; Gel
RouteOral; Topical; Vaginal
Strength250mg; 1%; 375mg; 500mg; 0.75%; 750mg; 1.3%
Market StatusPrescription
CompanyAlembic; Alembic Pharms; Teva Pharms Usa; Taro; Par Pharm; Watson Labs; Fougera Pharms; Mutual Pharm; Tolmar; Pliva; G And W Labs; Unichem Labs

10 of 24  
Drug NameMetronidazole in plastic container
Active IngredientMetronidazole
Dosage FormInjectable
RouteInjection
Strength500mg/100ml
Market StatusPrescription
CompanyHospira; Claris Lifesciences

11 of 24  
Drug NameNoritate
Active IngredientMetronidazole
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyValeant Bermuda

12 of 24  
Drug NameVandazole
Active IngredientMetronidazole
Dosage FormGel
RouteVaginal
Strength0.75%
Market StatusPrescription
CompanyTeva Pharms

13 of 24  
Drug NameFlagyl
PubMed HealthMetronidazole
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antiacne Antibacterial, Antibacterial, Antibiotic, Antiprotozoal, Antiulcer, Helicobacter Pylori
Drug LabelFLAGYL (metronidazole) tablets, 250 mg or 500 mg is an oral formulation of the synthetic nitroimidazole antimicrobial, 2-methyl-5-nitro-1H-imidazole-1-ethanol, which has the following structural formula:FLAGYL (metronidazole) tablets contain 250 mg o...
Active IngredientMetronidazole
Dosage FormTablet; Capsule
RouteOral
Strength250mg; 375mg; 500mg
Market StatusPrescription
CompanyGd Searle

14 of 24  
Drug NameFlagyl er
PubMed HealthMetronidazole (On the skin)
Drug ClassesAntiacne Antibacterial
Drug LabelFLAGYL metronidazole extended release tablets is an oral formulation of the synthetic nitroimidazole antimicrobial agent, 2-methyl-5-nitro-1H-imidazole-1-ethanol, which has the following structural formula:FLAGYL (metronidazole) extended release tabl...
Active IngredientMetronidazole
Dosage FormTablet, extended release
RouteOral
Strength750mg
Market StatusPrescription
CompanyGd Searle

15 of 24  
Drug NameFlagyl i.v. rtu in plastic container
PubMed HealthMetronidazole
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antiacne Antibacterial, Antibacterial, Antibiotic, Antiprotozoal, Antiulcer, Helicobacter Pylori
Drug LabelMETROCREAM Topical Cream contains metronidazole, USP, at a concentration of 7.5 mg per gram (0.75%) in an emollient cream consisting of benzyl alcohol, emulsifying wax, glycerin, isopropyl palmitate, purified water, sorbitol solution, lactic acid a...
Active IngredientMetronidazole
Dosage FormInjectable
RouteInjection
Strength500mg/100ml
Market StatusPrescription
CompanyBaxter Hlthcare; Pfizer

16 of 24  
Drug NameMetro i.v. in plastic container
PubMed HealthMetronidazole (On the skin)
Drug ClassesAntiacne Antibacterial
Drug LabelMETROGEL-VAGINAL is the intravaginal dosage form of the synthetic antibacterial agent, metronidazole, USP at a concentration of 0.75%. Metronidazole is a member of the imidazole class of antibacterial agents and is classified therapeutically as an an...
Active IngredientMetronidazole
Dosage FormInjectable
RouteInjection
Strength500mg/100ml
Market StatusPrescription
CompanyB Braun

17 of 24  
Drug NameMetrocream
PubMed HealthMetronidazole
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antiacne Antibacterial, Antibacterial, Antibiotic, Antiprotozoal, Antiulcer, Helicobacter Pylori
Drug LabelMETROGEL-VAGINAL is the intravaginal dosage form of the synthetic antibacterial agent, metronidazole, USP at a concentration of 0.75%. Metronidazole is a member of the imidazole class of antibacterial agents and is classified therapeutically as an an...
Active IngredientMetronidazole
Dosage FormCream
RouteTopical
Strength0.75%
Market StatusPrescription
CompanyGalderma Labs

18 of 24  
Drug NameMetrogel
Drug LabelMetroLotion (metronidazole lotion) Topical Lotion contains metronidazole, USP, at a concentration of 7.5 mg per gram (0.75% w/w) in a lotion consisting of benzyl alcohol, carbomer 941, cyclomethicone, glycerin, glyceryl stearate, light mineral oil,...
Active IngredientMetronidazole
Dosage FormGel
RouteTopical
Strength1%; 0.75%
Market StatusPrescription
CompanyGalderma Labs

19 of 24  
Drug NameMetrogel-vaginal
Drug LabelMetronidazole is an oral synthetic antiprotozoal and antibacterial agent, 1-(which has the following structural formula:Metronidazole 250 mg and 500 mg tablets, for oral administration, contain the inactive ingredients: colloidal silicon dioxide, hyd...
Active IngredientMetronidazole
Dosage FormGel
RouteVaginal
Strength0.75%
Market StatusPrescription
CompanyMedicis

20 of 24  
Drug NameMetrolotion
Drug LabelNORITATE (metronidazole cream) Cream, 1%, contains metronidazole, USP. Chemically, metronidazole is 2-methyl-5-nitro-1H-imidazole-1-ethanol. The molecular formula for metronidazole is C6H9N3O3. It has the following structural formula:Metronidazole ha...
Active IngredientMetronidazole
Dosage FormLotion
RouteTopical
Strength0.75%
Market StatusPrescription
CompanyGalderma Labs

21 of 24  
Drug NameMetronidazole
Drug LabelVANDAZOLE (metronidazole vaginal gel, 0.75%) is the vaginal dosage form of the nitroimidazole antimicrobial metronidazole at a concentration of 0.75%. Chemically, metronidazole is a 2-methyl-5-nitroimidazole-1-ethanol. C6H9N3O3 M.W. 171.16VANDAZOLE...
Active IngredientMetronidazole
Dosage FormTablet, extended release; Tablet; Cream; Capsule; Lotion; Gel
RouteOral; Topical; Vaginal
Strength250mg; 1%; 375mg; 500mg; 0.75%; 750mg; 1.3%
Market StatusPrescription
CompanyAlembic; Alembic Pharms; Teva Pharms Usa; Taro; Par Pharm; Watson Labs; Fougera Pharms; Mutual Pharm; Tolmar; Pliva; G And W Labs; Unichem Labs

22 of 24  
Drug NameMetronidazole in plastic container
Active IngredientMetronidazole
Dosage FormInjectable
RouteInjection
Strength500mg/100ml
Market StatusPrescription
CompanyHospira; Claris Lifesciences

23 of 24  
Drug NameNoritate
Active IngredientMetronidazole
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyValeant Bermuda

24 of 24  
Drug NameVandazole
Active IngredientMetronidazole
Dosage FormGel
RouteVaginal
Strength0.75%
Market StatusPrescription
CompanyTeva Pharms

4.2 Therapeutic Uses

Mesh Heading: Anti-infective agents, antiprotozoal agents, radiation-sensitizing agents

National Library of Medicine, SIS; ChemIDplus Record for <> <<(CAS#) i.e.(7440-04-2).>> Available from the search page at https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp as of <>.


MEDICATION (VET): Antiprotozoal (Trichomonas); antiamebic; antibacterial

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1097


MEDICATION (VET): The success of metronidazole in treating human infections of giardiasis, vaginal and oral trichomoniasis, and hepatic and intestinal amoebiasis has lead to investigation of its potential use against certain protozoan diseases of domestic animals. These are principally bovine urogenital trichomoniasis and canine, feline, or primate intestinal giardiasis, trichomoniasis, amoebiasis, or Balantidium infection. ...

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 885


Oral metronidazole (extended release formulation) is used in the treatment of bacterial vaginosis caused by Gardnerella vaginalis, Mobiluncus spp, mycoplasma hominis and anaerobes (peptostreptococcus spp and Bacteroides spp). /Included in US or Canadian product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2069


For more Therapeutic Uses (Complete) data for METRONIDAZOLE (25 total), please visit the HSDB record page.


4.3 Drug Warning

Metronidazole crosses the placenta and enters the fetal circulation rapidly. Adequate and well-controlled studies in humans have not been done. ... However, the use of metronidazole in the treatment of trichomoniasis is not recommended during the first trimester. If metronidazole is used during the second and the third trimesters for trichomoniasis it is recommended that its use be limited to those patients whose symptoms are not controlled by local palliative treatment. Also, the 1 day course of therapy should not be used since this results in higher maternal and fetal serum concentrations.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2070


No information is available on the relationship of age to the effects of metronidazole in geriatric patients. However, elderly patients are more likely to have an age-related decrease in hepatic function, which may require an adjustment in dosage in patients receiving metronidazole.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2070


Peripheral neuropathy, characterized by numbness, tingling, or paresthesia of an extremity, and convulsive seizures have been reported rarely with oral or IV metronidazole. Peripheral neuropathy is usually reversible if metronidazole is discontinued but may persist in patients who receive prolonged therapy or higher than recommended dosage of the drug. Dizziness, vertigo, incoordination, ataxia, confusion, irritability, depression, weakness, insomnia, headache, syncope, tinnitus, and hearing loss have also occurred with metronidazole. Headache occurred in 18% of nonpregnant women receiving oral metronidazole (administered as extended-release tablets) for bacterial vaginosis, and among those reporting headache, 10% described it as severe.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 889


Urethral burning or discomfort, dysuria, cystitis, polyuria, incontinence, a sense of pelvic pressure, dryness of the vagina or vulva, dyspareunia, and decreased libido have been reported with oral metronidazole. Urine may be dark or reddish-brown in color following oral or IV administration of metronidazole due to the presence of water-soluble pigments which result from metabolism of the drug. Vulvovaginal candidiasis (or yeast vaginitis) was reported in 15% of nonpregnant women receiving oral metronidazole (administered as extended-release tablets) and in 12% of those receiving clindamycin phosphate (2% clindamycin) vaginal cream in a comparative study for the treatment of bacterial vaginosis. Although a definite causal relationship to the drug has not been established, genital pruritus, dysmenorrhea, and urinary tract infection have been reported in 5, 3, and 2%, respectively, of nonpregnant women receiving oral metronidazole (administered as extended-release tablets) for the treatment of bacterial vaginosis.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 890


For more Drug Warnings (Complete) data for METRONIDAZOLE (18 total), please visit the HSDB record page.


4.4 Drug Indication

Metronidazole is indicated for the treatment of confirmed trichomoniasis caused by Trichomonas vaginalis (except for in the first trimester of pregnancy) and the patient's sexual partners, bacterial vaginosis, certain types of amebiasis, and various anaerobic infections. The above anaerobic infections may occur on the skin and skin structures, the abdomen, the heart, reproductive organs, central nervous system, and the respiratory system. Some may also be present in the bloodstream in cases of septicemia. Common infections treated by metronidazole are Bacteroides species infections, Clostridium infections, and Fusobacterium infections, as well as Peptococcus and Peptostreptococcus infections. It is also used off-label in the treatment of Crohn's disease and rosacea, as a prophylactic agent after surgery, and in the treatment of Helicobacter pylori infection. It has also been studied in the prevention of preterm births and to treat periodontal disease.


Treatment of Helicobacter spp. infections


5 Pharmacology and Biochemistry
5.1 Pharmacology

Metronidazole treats amebiasis, trichomoniasis, and giardiasis, exerting both antibacterial and antiprotozoal activities. Metronidazole is an effective treatment for some anaerobic bacterial infections. Metronidazole has shown antibacterial activity against the majority of obligate anaerobes, however, during in vitro studies, it does not demonstrate significant action against facultative anaerobes or obligate aerobes. The nitro group reduction of metronidazole by anaerobic organisms is likely responsible for the drug's antimicrobial cytotoxic effects, causing DNA strand damage to microbes. A note on convulsions and neuropathy and carcinogenesis It is important to be aware of the risk of peripheral neuropathy and convulsions associated with metronidazole, especially at higher doses. If convulsions or numbness of an extremity occur, discontinue the drug immediately. Metronidazole has been found to be carcinogenic in mice and rats. The relevance to this effect in humans is unknown. It is advisable to only administer metronidazole when clinically necessary and only for its approved indications.


5.2 MeSH Pharmacological Classification

Antiprotozoal Agents

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)


Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
METRONIDAZOLE
5.3.2 FDA UNII
140QMO216E
5.3.3 Pharmacological Classes
Nitroimidazoles [CS]; Nitroimidazole Antimicrobial [EPC]
5.4 ATC Code

J01XD01

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


A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB17 - Metronidazole


D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06B - Chemotherapeutics for topical use

D06BX - Other chemotherapeutics

D06BX01 - Metronidazole


G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AF - Imidazole derivatives

G01AF01 - Metronidazole


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01X - Other antibacterials

J01XD - Imidazole derivatives

J01XD01 - Metronidazole


P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01A - Agents against amoebiasis and other protozoal diseases

P01AB - Nitroimidazole derivatives

P01AB01 - Metronidazole


5.5 Absorption, Distribution and Excretion

Absorption

After the intravenous infusion of a 1.5g dose, peak concentration was reached within 1 hour and was peak level of 30-40 mg/L. When a multiple-dose regimen of 500mg three times a day administered intravenously, steady-state concentrations were achieved within about 3 days and peak concentration was measured at 26 mg/L. When administered orally in the tablet form, metronidazole is absorbed entirely absorbed, showing a bioavailability of greater than 90%. One resource indicates that Cmax after a single oral dose of 500mg metronidazole ranges from 8 to 13 mg/L, with a Tmax of 25 minutes to 4 hours. The AUC following a single 500mg oral dose of metronidazole was 122 10.3 mg/L h. A note on the absorption of topical preparations Insignificant percutaneous absorption of metronidazole occurs after the application of 1% metronidazole cream topically. Healthy volunteers applied one 100 mg dose of 14C-labelled metronidazole 2% cream to unbroken skin. After 12 hours, metronidazole was not detected in the plasma. Approximately 0.1% to 1% of the administered metronidazole was measured in the urine and feces.


Route of Elimination

Metronidazole and metabolites are 60 to 80% eliminated in the urine, and 6-15% excreted in the feces.


Volume of Distribution

Metronidazole is widely distributed throughout the body and various body fluids. They include the bile, saliva, breastmilk, cerebrospinal fluid, and the placenta. Steady-state volume distribution of metronidazole in adults ranges from 0.51 to 1.1 L/kg. It attains 60 to 100% of plasma concentrations in various tissues, such as the central nervous system, however, is not measured in high concentrations in the placental tissue.


Clearance

Dose adjustments may be required in patients with hepatic impairment, as clearance is impaired in these patients. The clearance of metronidazole in the kidneys is estimated at 10 mL/min/1.73 m2. The total clearance from serum is about 2.1 to 6.4 L/h/kg.


Well absorbed orally; bioavailability at least 80%.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2069


Distributed to saliva, bile, seminal fluid, breast milk, bone, liver and liver abscesses, lungs, and vaginal secretions; crosses the placenta and blood-brain barrier, also.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2069


At least 80% of an oral dose of metronidazole is absorbed from the GI tract. Following oral administration of a single 250-mg, 500-mg, or 2-g dose of metronidazole as immediate-release (conventional) preparations in healthy, fasting adults, peak plasma concentrations of unchanged drug and active metabolites are attained within 1-3 hours and average 4.6-6.5 ug/mL, 11.5-13 ug/mL, and 30-45 ug/mL, respectively. When a single 750-mg dose of metronidazole is administered as two 375-mg capsules or three 250-mg conventional tablets in healthy, fasting adult women, average peak plasma concentrations of unchanged drug and active metabolites of 20.4-21.4 ug/mL are attained in an average of 1.4-1.6 hours; metronidazole capsules and conventional tablets are bioequivalent at a single dose of 750 mg. The rate of absorption and peak plasma concentrations of metronidazole are decreased when conventional tablets or capsules of the drug are administered with food; however, the total amount of drug absorbed is not affected.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 892


Following oral administration of metronidazole 750 mg once daily as the extended-release tablet for 7 consecutive days in healthy, adult women, steady-state peak plasma concentrations average 12.5 mcg/mL and are attained an average of 6.8 hours after the dose when the drug is given under fasting conditions; when the drug is given at the same dosage under nonfasting conditions, steady-state peak plasma concentrations average 19.4 mcg/mL and are attained an average of 4.6 hours after the dose. Administration of metronidazole extended-release tablets with food increases the rate of absorption and peak plasma concentrations of the drug. According to the manufacturer, metronidazole extended-release and conventional tablets are bioequivalent at a dose of 750 mg given under fasting conditions.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 892


For more Absorption, Distribution and Excretion (Complete) data for METRONIDAZOLE (12 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Metronidazole undergoes hepatic metabolism via hydroxylation, oxidation, and glucuronidation. The metabolism of metronidazole yields 5 metabolites. The hydroxy metabolite, 1-(2-hydroxy-ethyl)-2-hydroxy methyl-5-nitroimidazole, is considered the major active metabolite. Unchanged metronidazole is found in the plasma along with small amounts of its 2- hydroxymethyl metabolite. Several metabolites of metronidazole are found in the urine. They are primarily a product of side-chain oxidation in addition to glucuronide conjugation. Only 20% of the dose found in the urine is accounted for by unchanged metronidazole. The two main oxidative metabolites of metronidazole are hydroxy and acetic acid metabolites.


Approximately 30-60% of an oral or IV dose of metronidazole is metabolized in the liver by hydroxylation, side-chain oxidation, and glucuronide conjugation. The major metabolite, 2-hydroxy metronidazole, has some antibacterial and antiprotozoal activity.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 892


... Four other nitro-group-containing metabolites have been identified, each derived from side-chain oxidation of ethyl and/or methyl group. They include 1-acetic acid-2-methyl-5-nitroimidazole and 1-(2-hydroxyethyl)-2-carboxylic acid-5-nitroimidazole salt.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 118 (1977)


The liver is the main site of metabolism, and this accounts for over 50% of the systemic clearance of metronidazole. The 2 principal metabolites result from oxidation of side chains, a hydroxy derivative and an acid. The hydroxy metabolite has a longer half-life (about 12 hr) and nearly 50% of the antitrichomonal activity of metronidazole. Formation of glucuronides also is observed. Small quantities of reduced metabolites, including ring-cleavage products, are formed by the gut flora. The urine of some patients may be reddish-brown owing to the presence of unidentified pigments derived from the drug.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1106


5.7 Biological Half-Life

The elimination half-life of metronidazole is 7.3 1.0 after a single 500mg IV dose in healthy subjects. Another resource indicates that the elimination half-life for metronidazole ranges from 6 to 10 hours.


The plasma half-life of metronidazole is reported to be 6-8 hours in adults with normal renal and hepatic function. In one study using radiolabeled metronidazole hydrochloride, the half-life of unchanged metronidazole averaged 7.7 hours and the half-life of total radioactivity averaged 11.9 hours. The plasma half-life of metronidazole is not affected by changes in renal function; however, the half-life may be prolonged in patients with impaired hepatic function. In one study in adults with alcoholic liver disease and impaired hepatic function, half-life of metronidazole averaged 18.3 hours (range: 10.3-29.5 hours).

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 892


Half-life: Neonates 25-75 hours; Others: 6-8 hours, increases with hepatic impairment.

Lelkin, J.B., Paloucek, F.P., Poisoning & Toxicology Compendium. LEXI-COMP Inc. & American Pharmaceutical Association, Hudson, OH 1998., p. 390


The elimination half-life in dogs is 4.5hr, and in horses 1.5-3.3hr

Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2098


5.8 Mechanism of Action

The exact mechanism of action of metronidazole has not been fully established, however, it is possible that an intermediate in the reduction of metronidazole which is only made by anaerobic bacteria and protozoa, binds deoxyribonucleic acid and electron-transport proteins of organisms, blocking nucleic acid synthesis. After administration, metronidazole enters cells by passive diffusion. Following this, ferredoxin or flavodoxin reduce its nitro group to nitro radicals. The redox potential of the electron transport portions of anaerobic or microaerophilic microorganisms renders metronidazole selective to these organisms, which cause nitro group reduction, leading to the production of toxic metabolites. These include N-(2-hydroxyethyl) oxamic acid and acetamide, which may damage DNA of replicating organisms.


Microbicidal; active against most obligate anaerobic bacteria and protozoa by undergoing intracellular chemical reduction via mechanisms unique to anaerobic metabolism. Reduced metronidazole, which is cytotoxic but short-lived, interacts with DNA to cause loss of helical structure, strand breakage, and resultant inhibition of nucleic acid synthesis and cell death.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2069


Metronidazole is bactericidal, amebicidal, and trichomonacidal in action. The exact mechanism of action of the drug has not been fully elucidated. Metronidazole is un-ionized at physiologic pH and is readily taken up by anaerobic organisms or cells. In susceptible organisms or cells, metronidazole is reduced by low-redox-potential electron transport proteins (e.g., nitroreductases such as ferredoxin) to unidentified polar product(s) which lack the nitro group. The reduction product(s) appears to be responsible for the cytotoxic and antimicrobial effects of the drug which include disruption of DNA and inhibition of nucleic acid synthesis. Metronidazole is equally effective against dividing and nondividing cells.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 891


In in vivo studies in rats given metronidazole in dosages of 2-4 mg/100 g of body weight, the drug reportedly inhibited the development of formalin-induced edema in the rat paw. In vitro in neutrophils, metronidazole has a dose-dependent inhibitory effect on generation of hydrogen peroxide and hydroxyl radicals, oxidants that may cause tissue injury at the site of inflammation. This antioxidant effect appears to be caused by a direct effect on neutrophil function and may contribute to the drug's anti-inflammatory effect in vivo.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 891


Results of in vitro studies using leukocytes obtained from patients with Crohn's disease indicate that exposing the cells to metronidazole concentrations of 10 or 50 mcg/mL improved both spontaneous and induced leukocyte migration in cells that previously exhibited reduced migration; the drug had no effect on leukocytes obtained from healthy adults or patients with Crohn's disease when the cells exhibited normal migration prior to exposure to the drug. This effect on leukocyte migration also was observed in vivo in adults with Crohn's disease who received a single 400-mg dose of metronidazole. It has been suggested that metronidazole may increase leukocyte migration by a direct effect on the leukocytes, possibly by causing the release of surface-bound immune complexes from the cell surface.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 891


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05-Jan-2021
29-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 250MG

USFDA APPLICATION NUMBER - 12623

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DOSAGE - TABLET;ORAL - 500MG

USFDA APPLICATION NUMBER - 12623

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DOSAGE - INJECTABLE;INJECTION - 500MG/100ML

USFDA APPLICATION NUMBER - 18890

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DOSAGE - INJECTABLE;INJECTION - 500MG/100ML

USFDA APPLICATION NUMBER - 18900

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DOSAGE - GEL;TOPICAL - 0.75%

USFDA APPLICATION NUMBER - 19737

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DOSAGE - GEL;VAGINAL - 0.75%

USFDA APPLICATION NUMBER - 20208

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DOSAGE - GEL;VAGINAL - 1.3%

USFDA APPLICATION NUMBER - 205223

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DOSAGE - CREAM;TOPICAL - 0.75%

USFDA APPLICATION NUMBER - 20531

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DOSAGE - SUSPENSION;ORAL - 500MG/5ML

USFDA APPLICATION NUMBER - 216755

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DOSAGE - GEL;TOPICAL - 1%

USFDA APPLICATION NUMBER - 21789

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Controlled & Modified Release

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Disintegrants & Superdisintegrants

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Topical

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Granulation

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Parenteral

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Film Formers & Plasticizers

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Lubricants & Glidants

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Co-Processed Excipients

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Taste Masking

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Chewable & Orodispersible Aids

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Empty Capsules

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Emulsifying Agents

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API Stability Enhancers

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Coloring Agents

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Rheology Modifiers

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Vegetarian Capsules

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Surfactant & Foaming Agents

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Soft Gelatin

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NEWS #PharmaBuzz

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