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Chemistry

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Also known as: 19387-91-8, Tindamax, Trimonase, Fasigyn, Tricolam, Fasigin
Molecular Formula
C8H13N3O4S
Molecular Weight
247.27  g/mol
InChI Key
HJLSLZFTEKNLFI-UHFFFAOYSA-N
FDA UNII
033KF7V46H

Tinidazole
A nitroimidazole alkylating agent that is used as an antitrichomonal agent against TRICHOMONAS VAGINALIS; ENTAMOEBA HISTOLYTICA; and GIARDIA LAMBLIA infections. It also acts as an antibacterial agent for the treatment of BACTERIAL VAGINOSIS and anaerobic bacterial infections.
Tinidazole is a Nitroimidazole Antimicrobial.
1 2D Structure

Tinidazole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(2-ethylsulfonylethyl)-2-methyl-5-nitroimidazole
2.1.2 InChI
InChI=1S/C8H13N3O4S/c1-3-16(14,15)5-4-10-7(2)9-6-8(10)11(12)13/h6H,3-5H2,1-2H3
2.1.3 InChI Key
HJLSLZFTEKNLFI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCS(=O)(=O)CCN1C(=NC=C1[N+](=O)[O-])C
2.2 Other Identifiers
2.2.1 UNII
033KF7V46H
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bioshik

2. Cp 12,574

3. Cp 12574

4. Cp-12,574

5. Cp-12574

6. Cp12,574

7. Cp12574

8. Fasigin

9. Fasigyn

10. Fasigyne

11. Fasygin

12. Simplotan

13. Tricolam

2.3.2 Depositor-Supplied Synonyms

1. 19387-91-8

2. Tindamax

3. Trimonase

4. Fasigyn

5. Tricolam

6. Fasigin

7. 1-(2-(ethylsulfonyl)ethyl)-2-methyl-5-nitro-1h-imidazole

8. Simplotan

9. 1-(2-ethylsulfonylethyl)-2-methyl-5-nitroimidazole

10. 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitro-1h-imidazole

11. Timidazole

12. Haisigyn

13. Cp-12574

14. 1h-imidazole, 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitro-

15. Cp-12,574

16. 1-(2-(ethylsulfonyl)ethyl)-2-methyl-5-nitroimidazole

17. 1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1h-imidazole

18. Tinidazol

19. Chebi:63627

20. 1h-imidazole, 1-(2-(ethylsulfonyl)ethyl)-2-methyl-5-nitro-

21. Nsc-758189

22. Mls000069717

23. 148159-84-6

24. Bioshik

25. 033kf7v46h

26. 1-(2-ethylsulfonylethyl)-2-methyl-5-nitro-imidazole

27. Ncgc00016741-01

28. Tinidazolum

29. Smr000058194

30. Sorquetan

31. Pletil

32. Tinidazole 100 Microg/ml In Acetonitrile

33. Cas-19387-91-8

34. Dsstox_cid_3676

35. Dsstox_rid_77141

36. Dsstox_gsid_23676

37. 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole

38. Glongyn

39. Amtiba

40. Cp 12574

41. Tinidazol [inn-spanish]

42. Tinidazolum [inn-latin]

43. 1h-imidazole, 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitro-, Radical Ion(1-)

44. Ccris 7621

45. Hsdb 7362

46. Sr-01000000210

47. Einecs 243-014-4

48. Brn 0618182

49. Symplotan

50. Ethyl (2-(2-methyl-5-nitro-1-imidazolyl)ethyl)sulfone

51. Unii-033kf7v46h

52. Fasigyntrade Mark

53. Tindamaxtrade Mark

54. Tinidazole,(s)

55. Simplotantrade Mark

56. Haisigyn (tn)

57. Tindamax (tn)

58. Prestwick_136

59. Cp12574

60. Tinidazole [usan:usp:inn:ban:jan]

61. Spectrum_001266

62. Opera_id_779

63. Specplus_000708

64. Tinidazole [mi]

65. Tinidazole [inn]

66. Tinidazole [jan]

67. Prestwick0_000766

68. Prestwick1_000766

69. Prestwick2_000766

70. Prestwick3_000766

71. Spectrum2_000648

72. Spectrum3_001512

73. Spectrum4_000230

74. Spectrum5_001715

75. Tinidazole [hsdb]

76. Tinidazole [usan]

77. Tinidazole [vandf]

78. Tinidazole [mart.]

79. Chembl1220

80. Tinidazole [usp-rs]

81. Tinidazole [who-dd]

82. Oprea1_342844

83. Schembl21141

84. Bspbio_000812

85. Bspbio_003183

86. Kbiogr_000899

87. Kbioss_001746

88. Methyl-5-nitro-1h-imidazole

89. 5-23-05-00067 (beilstein Handbook Reference)

90. Mls001146883

91. Mls001424192

92. Divk1c_006804

93. Spectrum1502127

94. Spbio_000655

95. Spbio_002751

96. Bpbio1_000894

97. Tinidazole (jp17/usp/inn)

98. 1-(ethylsulfonyl)-2-(2-methyl-5-nitroimidazolyl)ethane

99. Dtxsid4023676

100. Tinidazole [orange Book]

101. Kbio1_001748

102. Kbio2_001746

103. Kbio2_004314

104. Kbio2_006882

105. Kbio3_002683

106. Imidazole, 1-(2-(ethylsulfonyl)ethyl)-2-methyl-5-nitro-

107. Tinidazole [ep Monograph]

108. 1-(2-(ethylsulfonyl)ethyl)-2-

109. Hms1570i14

110. Hms1921l06

111. Hms2052c09

112. Hms2090b14

113. Hms2092d14

114. Hms2097i14

115. Hms2231e23

116. Hms3374p07

117. Hms3394c09

118. Hms3652a08

119. Hms3714i14

120. Pharmakon1600-01502127

121. Tinidazole [usp Monograph]

122. Zinc113446

123. Bcp20694

124. Hy-b0177

125. Tox21 110586

126. Tox21_110586

127. Bbl010767

128. Bdbm50248360

129. Ccg-39907

130. Mfcd00057217

131. Nsc758189

132. S4068

133. Stk801761

134. Akos000747070

135. Tinidazole 100 Microg/ml In Methanol

136. Tox21_110586_1

137. Ac-1618

138. Cs-2055

139. Db00911

140. Ks-5180

141. Mcule 2580495783

142. Nc00346

143. Nsc 758189

144. Ncgc00016741-02

145. Ncgc00016741-03

146. Ncgc00016741-04

147. Ncgc00016741-05

148. Ncgc00016741-06

149. Ncgc00016741-07

150. Ncgc00016741-09

151. Ncgc00022212-03

152. Ncgc00022212-04

153. Ncgc00022212-05

154. Sbi-0052674.p002

155. Ab00053176

156. Ft-0675241

157. Sw196447-4

158. T3058

159. Vu0239922-6

160. D01426

161. Tinidazole, Vetranal(tm), Analytical Standard

162. Ab00053176-16

163. Ab00053176_17

164. Ab00053176_18

165. A813669

166. Q1321320

167. Sr-01000000210-3

168. Sr-01000000210-5

169. Sr-01000000210-6

170. 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazol

171. Brd-k89125793-001-05-4

172. Z56763819

173. 1-(2'-(ethylsulfonyl)-ethyl]-2-methyl-5-nitroimidazole

174. Tinidazole, European Pharmacopoeia (ep) Reference Standard

175. Tinidazole, United States Pharmacopeia (usp) Reference Standard

176. Imidazole, 1-(2-(ethylsulfonyl)ethyl)-2-methyl-4-nitro-

177. Timtec-bb Sbb006917 Tinidazole 1-(2-(ethylsulfonyl)ethyl)-2-methyl-5-nitro-1h-imidazol

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 247.27 g/mol
Molecular Formula C8H13N3O4S
XLogP3-0.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass247.06267708 g/mol
Monoisotopic Mass247.06267708 g/mol
Topological Polar Surface Area106 Ų
Heavy Atom Count16
Formal Charge0
Complexity345
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 NameTindamax
PubMed HealthTinidazole (By mouth)
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antibiotic, Antiprotozoal
Drug LabelTinidazole is a synthetic antiprotozoal and antibacterial agent. It is 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole, a second-generation 2-methyl-5-nitroimidazole, which has the following chemical structure:Tindamax pink oral tablets contain...
Active IngredientTinidazole
Dosage FormTablet
Routeoral; Oral
Strength250mg; 500mg
Market StatusPrescription
CompanyMission Pharma

2 of 4  
Drug NameTinidazole
PubMed HealthTinidazole (By mouth)
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antibiotic, Antiprotozoal
Drug LabelTinidazole is a synthetic antiprotozoal and antibacterial agent. It is 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole, a second-generation 2-methyl-5-nitroimidazole, which has the following chemical structure:Tinidazole tablets contain 250 mg o...
Active IngredientTinidazole
Dosage FormTablet
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyUnique Pharm Labs; Novel Labs; Roxane

3 of 4  
Drug NameTindamax
PubMed HealthTinidazole (By mouth)
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antibiotic, Antiprotozoal
Drug LabelTinidazole is a synthetic antiprotozoal and antibacterial agent. It is 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole, a second-generation 2-methyl-5-nitroimidazole, which has the following chemical structure:Tindamax pink oral tablets contain...
Active IngredientTinidazole
Dosage FormTablet
Routeoral; Oral
Strength250mg; 500mg
Market StatusPrescription
CompanyMission Pharma

4 of 4  
Drug NameTinidazole
PubMed HealthTinidazole (By mouth)
Drug ClassesAmebicide, Extraintestinal, Amebicide, Intestinal, Antibiotic, Antiprotozoal
Drug LabelTinidazole is a synthetic antiprotozoal and antibacterial agent. It is 1-[2-(ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole, a second-generation 2-methyl-5-nitroimidazole, which has the following chemical structure:Tinidazole tablets contain 250 mg o...
Active IngredientTinidazole
Dosage FormTablet
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyUnique Pharm Labs; Novel Labs; Roxane

4.2 Therapeutic Uses

Antitrichomonal Agents

National Library of Medicine, SIS; ChemIDplus Record for Tinidazole (19387-91-8), MESH heading. Available from, as of March 15, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp


MEDICATION: Antiprotozoal (Trichomonas, Giardia); 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. 1685


Oral tinidazole is indicated in the treatment of amebic liver abscess caused by Entamoeba histolytica in both adults and pediatric patients older than three years of age. /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2831


Oral tinidazole is indicated in the treatment of intestinal amebiasis caused by Entamoeba histolytica in both adults and pediatric patients older than three years of age. /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2831


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


4.3 Drug Warning

Tinidazole is distributed into breast milk at concentrations similar to those in serum. Because tinidazole can be detected in breast milk for up to 72 hours after administration, interruption of breast-feeding during tinidazole therapy and for three days following the last dose is recommended.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2832


FDA Pregnancy Risk Category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2832


Tinidazole crosses the placenta, and enters the fetal circulation. Therefore, it should not be administered to pregnant women during the first trimester.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2832


Adverse effects occurring in 1% or more of patients receiving tinidazole include GI effects (metallic/bitter taste, nausea, anorexia, dyspepsia/cramps/epigastric discomfort, vomiting, constipation) and nervous system effects (weakness/fatigue/malaise, dizziness, headache).

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 875


For more Drug Warnings (Complete) data for TINIDAZOLE (11 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of trichomoniasis caused by T. vaginalis in both female and male patients. Also for the treatment of giardiasis caused by G. duodenalis in both adults and pediatric patients older than three years of age and for the treatment of intestinal amebiasis and amebic liver abscess caused by E. histolytica in both adults and pediatric patients older than three years of age.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Tinidazole is a synthetic antiprotozoal agent. Tinidazole demonstrates activity both in vitro and in clinical infections against the following protozoa: Trichomonas vaginalis, Giardia duodenalis (also termed G. lamblia), and Entamoeba histolytica. Tinidazole does not appear to have activity against most strains of vaginal lactobacilli.


5.2 MeSH Pharmacological Classification

Antitrichomonal Agents

Agents used to treat trichomonas infections. (See all compounds classified as Antitrichomonal Agents.)


Alkylating Agents

Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases. (See all compounds classified as Alkylating Agents.)


Anti-Bacterial Agents

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


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TINIDAZOLE
5.3.2 FDA UNII
033KF7V46H
5.3.3 Pharmacological Classes
Nitroimidazoles [CS]; Nitroimidazole Antimicrobial [EPC]
5.4 ATC Code

J01XD02

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


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01X - Other antibacterials

J01XD - Imidazole derivatives

J01XD02 - Tinidazole


P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01A - Agents against amoebiasis and other protozoal diseases

P01AB - Nitroimidazole derivatives

P01AB02 - Tinidazole


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and completely absorbed under fasting conditions. Administration with food results in a delay in Tmax of approximately 2 hours and a decline in Cmax of approximately 10% and an AUC of 901.6 ± 126.5 mcg hr/mL.


Route of Elimination

Tinidazole crosses the placental barrier and is secreted in breast milk. Tinidazole is excreted by the liver and the kidneys. Tinidazole is excreted in the urine mainly as unchanged drug (approximately 20-25% of the administered dose). Approximately 12% of the drug is excreted in the feces.


Volume of Distribution

50 L


Tinidazole is distributed into virtually all tissues and body fluids. Tinidazole also crosses the blood-brain barrier, placental barrier and is distributed into breast milk. Volume of distribution (VolD): about 50 L.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2831


Under fasted conditions tinidazole is rapidly and completely absorbed. Administration with food resulted in a delay in Tmax of approximately 2 hours and a decline in Cmax of approximately 10% and an AUC of 901.6 + or - 126.5 ug hr/mL.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2831


Time to peak concentration: 1.6 (+ or - 0.7 hours)

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2831


Elimination: Renal: 20 to 25% as unchanged drug. Fecal: 12%. In hemodialysis: 43% eliminated during 6 hour hemodialysis session.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2831


For more Absorption, Distribution and Excretion (Complete) data for TINIDAZOLE (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic, mainly via CYP3A4. Tinidazole, like metronidazole, is significantly metabolized in humans prior to excretion. Tinidazole is partly metabolized by oxidation, hydroxylation and conjugation. Tinidazole is the major drug-related constituent in plasma after human treatment, along with a small amount of the 2-hydroxymethyl metabolite.


Tinidazole, like metronidazole, is significantly metabolized in humans prior to excretion. Tinidazole is partly metabolized by oxidation, hydroxylation and conjugation. Tinidazole is the major drug-related constituent in plasma after human treatment, along with a small amount of the 2-hydroxymethyl metabolite. Tinidazole is biotransformed mainly by CYP3A4. In an in vitro metabolic drug interaction study, tinidazole concentrations of up to 75 ug/mL did not inhibit the enzyme activities of CYP1A2, CYP2B6, CYP2C9, CYP2D6, CYP2E1 and CYP3A4.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2670


5.7 Biological Half-Life

The elimination half-life is 13.21.4 hours and the plasma half-life is 12 to 14 hours.


Elimination: 13.2 (+ or - 1.4) hours. Plasma: approximately 12 to 14 hours.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2831


5.8 Mechanism of Action

Tinidazole is a prodrug and antiprotozoal agent. The nitro group of tinidazole is reduced in Trichomonas by a ferredoxin-mediated electron transport system. The free nitro radical generated as a result of this reduction is believed to be responsible for the antiprotozoal activity. It is suggested that the toxic free radicals covalently bind to DNA, causing DNA damage and leading to cell death. The mechanism by which tinidazole exhibits activity against Giardia and Entamoeba species is not known, though it is probably similar.


The nitro group of tinidazole is reduced by cell extracts of Trichomonas. As a result of this reduction a free nitro radical is generated which may be responsible for the antiprotozoal activity. The mechanism by which tinidazole exhibits activity against Giardia and Entamoeba species is not known.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 2831


API Reference Price

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14-Jan-2021
30-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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DOSAGE - TABLET;ORAL - 250MG

USFDA APPLICATION NUMBER - 21618

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DOSAGE - TABLET;ORAL - 500MG

USFDA APPLICATION NUMBER - 21618

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