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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...