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Chemistry

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Also known as: 1197-18-8, Trans-4-(aminomethyl)cyclohexanecarboxylic acid, Cyklokapron, 4-(aminomethyl)cyclohexanecarboxylic acid, Trans amcha, Tranexamsaeure
Molecular Formula
C8H15NO2
Molecular Weight
157.21  g/mol
InChI Key
GYDJEQRTZSCIOI-UHFFFAOYSA-N
FDA UNII
37YD696II6

Tranexamic Acid
Antifibrinolytic hemostatic used in severe hemorrhage.
Tranexamic acid is an Antifibrinolytic Agent. The physiologic effect of tranexamic acid is by means of Decreased Fibrinolysis.
1 2D Structure

Tranexamic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-(aminomethyl)cyclohexane-1-carboxylic acid
2.1.2 InChI
InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)
2.1.3 InChI Key
GYDJEQRTZSCIOI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CC(CCC1CN)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
37YD696II6
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Amca

2. Amcha

3. Amchafibrin

4. Anvitoff

5. Cyklokapron

6. Exacyl

7. Kabi 2161

8. Spotof

9. T-amcha

10. Trans-4-(aminomethyl)cyclohexanecarboxylic Acid

11. Transamin

12. Ugurol

2.3.2 Depositor-Supplied Synonyms

1. 1197-18-8

2. Trans-4-(aminomethyl)cyclohexanecarboxylic Acid

3. Cyklokapron

4. 4-(aminomethyl)cyclohexanecarboxylic Acid

5. Trans Amcha

6. Tranexamsaeure

7. Transamin

8. 701-54-2

9. Tranhexamic Acid

10. Cyclocapron

11. Amstat

12. Trans-amcha

13. 1197-17-7

14. Rikavarin

15. Tamcha

16. Amikapron

17. Anvitoff

18. Ugurol

19. Amcha

20. Frenolyse

21. Trasamlon

22. Carxamin

23. Emorhalt

24. Tranexan

25. Mastop

26. Rikavarin-s

27. Amca

28. Cis-4-(aminomethyl)cyclohexanecarboxylic Acid

29. Exacyl

30. Tranexmic Acid

31. Hexapromin

32. Transamlon

33. Hexatron

34. Spiramin

35. Tranex

36. Cis-amcha

37. Cis-tranexamic Acid

38. Trans-4-aminomethylcyclohexane-1-carboxylic Acid

39. 4-(aminomethyl)cyclohexane-1-carboxylic Acid

40. Trans-tranexamic Acid

41. Acidum Tranexamicum

42. Cyclohexanecarboxylic Acid, 4-(aminomethyl)-, Trans-

43. Lysteda

44. Acido Tranexamico

45. Cl 65336

46. Acide Tranexamique

47. Femstrual

48. Bay 3517

49. Cyclo-f

50. Rp 18,429

51. Cyclohexanecarboxylic Acid, 4-(aminomethyl)-

52. 4-(aminomethyl)-cyclohexanecarboxylic Acid

53. Cyclohexanecarboxylic Acid, 4-(aminomethyl)-, Cis-

54. Cyclokapron

55. Espercil

56. Haematrix

57. (1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic Acid

58. Cis-4-aminomethylcyclohexane-1-carboxylic Acid

59. Trans-p-(aminomethyl)cyclohexanecarboxylic Acid

60. Cl-65336

61. Dv 79

62. Dv79

63. Trans-4-(aminomethyl)-1-cyclohexanecarboxylic Acid

64. Lb1148

65. Mfcd00001466

66. Cis-4-(aminomethyl)cyclohexane-1-carboxylic Acid

67. Nsc-291305

68. Trans-1-(aminomethyl)cyclohexane-4-carboxylic Acid

69. Trans-4-(aminomethyl)cyclohexane-1-carboxylic Acid

70. Tranexamic Acid (transamin)

71. Retavase

72. Chebi:48669

73. 37yd696ii6

74. 6t84r30kc1

75. Nsc291305

76. Trans-4-(aminomethyl)cyclohexanecarboxylic Acid Ester

77. 4-aminomethylcyclohexanecarboxylic Acid

78. Ncgc00016569-01

79. Rp-18429

80. Cas-1197-18-8

81. 4-(aminomethyl)cyclohexanecarboxylic Acid (trans-)

82. Amh

83. Tranexamic Acid Cis-form

84. Acide Tranexamique [inn-french]

85. Acido Tranexamico [inn-spanish]

86. Acidum Tranexamicum [inn-latin]

87. Dv-79

88. Cyklokapron (tn)

89. Rikavarin (tn)

90. Transamin (tn)

91. Haku

92. Sr-05000001794

93. Einecs 214-818-2

94. Trans-1-aminomethylcyclohexane-4-carboxylic Acid

95. Nsc 291305

96. Brn 2207452

97. Tranexamate

98. Tranexamic-acid

99. Unii-37yd696ii6

100. Unii-6t84r30kc1

101. 1ceb

102. Prestwick_476

103. Albb-006013

104. Tranexamic Acid,(s)

105. Spectrum_001391

106. Tranexamic Acid [usan:usp:inn:ban:jan]

107. Prestwick0_000171

108. Prestwick1_000171

109. Prestwick2_000171

110. Prestwick3_000171

111. Spectrum2_000655

112. Spectrum3_001189

113. Spectrum4_000046

114. Spectrum5_001258

115. Chembl877

116. Trans-4-(aminomethyl)cyclohexane-carboxylic Acid

117. Dsstox_cid_25350

118. Dsstox_rid_80817

119. Dsstox_gsid_45350

120. Oprea1_786414

121. Schembl16974

122. Bspbio_000061

123. Bspbio_002837

124. Kbiogr_000511

125. Kbioss_001871

126. Tranexamic Acid [mi]

127. 3-14-00-00868 (beilstein Handbook Reference)

128. Cis-4-(aminomethyl)cyclohexanecarboxylicacid

129. Divk1c_000655

130. Schembl186034

131. Schembl349408

132. Spectrum1502026

133. Tranexamic Acid [inn]

134. Tranexamic Acid [jan]

135. Tranexamic Acid, Cis-

136. Spbio_000689

137. Spbio_001982

138. Tranexamic Acid [inci]

139. Tranexamic Acid [usan]

140. Bpbio1_000069

141. Chembl292500

142. Gtpl6573

143. Schembl6885575

144. Schembl9885628

145. Tranexamic Acid [vandf]

146. Dtxsid3045350

147. Tranexamic Acid [mart.]

148. Chebi:94518

149. Hms502a17

150. Kbio1_000655

151. Kbio2_001871

152. Kbio2_004439

153. Kbio2_007007

154. Kbio3_002337

155. Dtxsid50904827

156. Tranexamic Acid [usp-rs]

157. Tranexamic Acid [who-dd]

158. Wln: L6tj Avq D1z -t

159. Ninds_000655

160. Hms1568d03

161. Hms1921f08

162. Hms2092p03

163. Hms2095d03

164. Hms3712d03

165. Hms3744g07

166. Pharmakon1600-01502026

167. Bcp13133

168. Bcp18146

169. Hy-b0149

170. Tranexamic Acid (jp17/usp/inn)

171. Zinc1542907

172. Tox21_110500

173. Bbl004469

174. Bdbm50428067

175. Ccg-39692

176. Mfcd00064951

177. Mfcd19706018

178. Nsc758176

179. S1875

180. Stk503668

181. Tranexamic Acid [orange Book]

182. Tranexamic Acid(random Configuration)

183. Akos005171632

184. Akos015854573

185. Akos024257901

186. Tranexamic Acid [ep Monograph]

187. Tranexamic Acid [usp Impurity]

188. Tranexamic Acid Cis-form [mi]

189. Zinc100007011

190. Zinc100071256

191. Ab86495

192. Ac-4687

193. Am84352

194. Bs-3867

195. Cs-1965

196. Db00302

197. Nsc-758176

198. Tranexamic Acid [usp Monograph]

199. 4-(aminomethyl)cyclohexanecarboxylicacid

200. 4-aminomethyl-cyclohexanecarboxylic Acid

201. Idi1_000655

202. Ncgc00016569-02

203. Ncgc00016569-03

204. Ncgc00016569-04

205. Ncgc00016569-05

206. Ncgc00016569-06

207. Ncgc00016569-08

208. Ncgc00016569-09

209. Ncgc00094944-01

210. Ncgc00094944-02

211. P-(aminomethyl)cyclohexanecarboxylic Acid

212. As-80121

213. Bp-12345

214. Sy011438

215. Tranexamic Acid Related Compound B

216. Ts-02090

217. Sbi-0051705.p002

218. Trans 4aminomethylcyclohexanecarboxylic Acid

219. Db-074265

220. Tranexamic Acid 100 Microg/ml In Methanol

221. Trans-4-aminomethylcyclohexylcarboxylic Acid

222. Trans-p-aminomethylcyclohexanecarboxylic Acid

223. A0236

224. Ab00052260

225. Bb 0260034

226. Cs-0013687

227. Cs-0055045

228. Ft-0654339

229. Ft-0675360

230. Ft-0700806

231. Trans 4-aminomethylcyclohexanecarboxylic Acid

232. Trans-4-aminomethylcyclohexanecarboxylic Acid

233. En300-91506

234. Trans-4(aminomethyl)cyclohexanecarboxylic Acid

235. Trans-4-(aminomethyl)cyclohexylcarboxylic Acid

236. Trans-4-aminomethyl Cyclohexanecarboxylic Acid

237. Trans-4-aminomethyl-cyclohexanecarboxylic Acid

238. Trans-4-aminomethylcyclohexane Carboxylic Acid

239. D01136

240. P15619

241. P20836

242. T71247

243. Trans-4-aminomethyl Cyclohexane Carboxylic Acid

244. Trans4-aminomethylcyclohexane-1-carboxylic Acid

245. Ab00052260-04

246. Ab00052260_05

247. Ab00052260_06

248. Tranexamic Acid Impurity B [ep Impurity]

249. Trans-4 -(aminomethyl)cyclohexanecarboxylic Acid

250. Trans-4-(aminomethyl)-cyclohexanecarboxylic Acid

251. Trans-4-(aminomethyl)cyclohexane Carboxylic Acid

252. Trans-4-aminomethyl-1-cyclohexanecarboxylic Acid

253. (1r,4r)-4-(aminomethyl)cyclohexanecarboxylic Acid

254. (trans)-4-(aminomethyl)cyclohexanecarboxylic Acid

255. 197t188

256. 4-trans-(aminomethyl)cyclohexanecarboxylic Acid #

257. Q418666

258. Trans-?4-?(aminomethyl)?cyclohexanecarboxylic Acid

259. Trans-4- (aminomethyl) Cyclohexanecarboxylic Acid

260. Trans-4-(aminomethyl)- Cyclohexane Carboxylic Acid

261. Trans-4-(aminomethyl)-cyclohexane Carboxylic Acid

262. Trans-4-aminomethyl-1-cyclohexane Carboxylic Acid

263. 4alpha-aminomethyl-1alpha-cyclohexanecarboxylic Acid

264. Q-201848

265. Sr-05000001794-1

266. Sr-05000001794-2

267. Sr-05000001794-3

268. Tranexamic Acid 100 Microg/ml In Acetonitrile:water

269. Brd-k15014948-001-01-2

270. Q27256710

271. Trans-4-(aminomethyl)cyclohexanecarboxylic Acid, 97%

272. 4-(aminomethyl)cyclohexanecarboxylic Acid;tranexamic Acid

273. F8886-7867

274. Tranexamic Acid Related Compound B [usp Impurity]

275. Z1741970429

276. Rel-(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic Acid

277. Tranexamic Acid, European Pharmacopoeia (ep) Reference Standard

278. 4-(aminomethyl)cyclohexanecarboxylic Acid (cis- And Trans- Mixture)

279. Tranexamic Acid, United States Pharmacopeia (usp) Reference Standard

280. 4-(aminomethyl)cyclohexanecarboxylic Acid (cis- And Trans- Mixture);

281. Tranexamic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 157.21 g/mol
Molecular Formula C8H15NO2
XLogP3-2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass157.110278721 g/mol
Monoisotopic Mass157.110278721 g/mol
Topological Polar Surface Area63.3 Ų
Heavy Atom Count11
Formal Charge0
Complexity139
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 6  
Drug NameCyklokapron
PubMed HealthTranexamic Acid
Drug ClassesHemostatic
Drug LabelEach mL of the sterile solution for intravenous injection contains 100 mg tranexamic acid and Water for Injection to 1 mL....
Active IngredientTranexamic acid
Dosage FormInjectable
RouteInjection
Strength100mg/ml
Market StatusPrescription
CompanyPharmacia And Upjohn

2 of 6  
Drug NameLysteda
PubMed HealthTranexamic Acid
Drug ClassesHemostatic
Drug LabelLYSTEDA is an antifibrinolytic drug. The chemical name is trans-4-aminomethyl-cyclohexanecarboxylic acid. The structural formula is:Tranexamic acid is a white crystalline...
Active IngredientTranexamic acid
Dosage FormTablet
RouteOral
Strength650mg
Market StatusPrescription
CompanyFerring Pharms As

3 of 6  
Drug NameTranexamic acid
PubMed HealthTranexamic Acid
Drug ClassesHemostatic
Drug LabelTranexamic Acid Tablets is an antifibrinolytic drug. The chemical name is trans-4-aminomethyl-cyclohexanecarboxylic acid. The structural formula is:Tranexamic acid is a white crystalline powder. It is freely soluble in water and in glacial acetic aci...
Active IngredientTranexamic acid
Dosage FormTablet; Injectable
RouteInjection; Oral
Strength650mg; 650 mg; 100mg/ml
Market StatusPrescription
CompanyActavis Labs Fl; Apotex; Acic Fine Chems; Emcure Pharms; Fresenius Kabi Usa; Versapharm; Mylan Institutional; X-gen Pharms; Luitpold

4 of 6  
Drug NameCyklokapron
PubMed HealthTranexamic Acid
Drug ClassesHemostatic
Drug LabelEach mL of the sterile solution for intravenous injection contains 100 mg tranexamic acid and Water for Injection to 1 mL....
Active IngredientTranexamic acid
Dosage FormInjectable
RouteInjection
Strength100mg/ml
Market StatusPrescription
CompanyPharmacia And Upjohn

5 of 6  
Drug NameLysteda
PubMed HealthTranexamic Acid
Drug ClassesHemostatic
Drug LabelLYSTEDA is an antifibrinolytic drug. The chemical name is trans-4-aminomethyl-cyclohexanecarboxylic acid. The structural formula is:Tranexamic acid is a white crystalline...
Active IngredientTranexamic acid
Dosage FormTablet
RouteOral
Strength650mg
Market StatusPrescription
CompanyFerring Pharms As

6 of 6  
Drug NameTranexamic acid
PubMed HealthTranexamic Acid
Drug ClassesHemostatic
Drug LabelTranexamic Acid Tablets is an antifibrinolytic drug. The chemical name is trans-4-aminomethyl-cyclohexanecarboxylic acid. The structural formula is:Tranexamic acid is a white crystalline powder. It is freely soluble in water and in glacial acetic aci...
Active IngredientTranexamic acid
Dosage FormTablet; Injectable
RouteInjection; Oral
Strength650mg; 650 mg; 100mg/ml
Market StatusPrescription
CompanyActavis Labs Fl; Apotex; Acic Fine Chems; Emcure Pharms; Fresenius Kabi Usa; Versapharm; Mylan Institutional; X-gen Pharms; Luitpold

4.2 Drug Indication

Taken orally, tranexamic acid is indicated for the treatment of hereditary angioedema, cyclic heavy menstrual bleeding in premenopausal females, and other instances of significant bleeding in the context of hyperfibrinolysis. Given intravenously, tranexamic acid is indicated for short-term use (2-8 days) in patients with hemophilia to prevent or reduce bleeding following tooth extraction.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Tranexamic acid is an antifibrinolytic that competitively inhibits the activation of plasminogen to plasmin. At much higher concentrations it behaves as a noncompetitive inhibitor of plasmin similar to [aminocaproic acid], a similar antifibrinolytic which is 10-fold less potent. Tranexamic acid binds more strongly than aminocaproic acid to both the strong and weak receptor sites of the plasminogen molecule in a ratio corresponding to the difference in potency between the compounds. In patients with hereditary angioedema, inhibition of the formation and activity of plasmin by tranexamic acid may prevent attacks of angioedema by decreasing plasmin-induced activation of the first complement protein (C1). Off-target antagonism of GABA(A) receptors may be associated with the development of convulsions and hyperexcitability following tranexamic acid administration - the risk appears higher with improper administration or administration during cardiovascular surgery. Consider EEG monitoring of patients with a history of seizure.


5.2 MeSH Pharmacological Classification

Antifibrinolytic Agents

Agents that prevent fibrinolysis or lysis of a blood clot or thrombus. Several endogenous antiplasmins are known. The drugs are used to control massive hemorrhage and in other coagulation disorders. (See all compounds classified as Antifibrinolytic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TRANEXAMIC ACID
5.3.2 FDA UNII
6T84R30KC1
5.3.3 Pharmacological Classes
Decreased Fibrinolysis [PE]; Antifibrinolytic Agent [EPC]
5.4 ATC Code

B02AA02

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


B - Blood and blood forming organs

B02 - Antihemorrhagics

B02A - Antifibrinolytics

B02AA - Amino acids

B02AA02 - Tranexamic acid


5.5 Absorption, Distribution and Excretion

Absorption

The bioavailability of tranexamic acid after oral administration in humans is approximately 30 to 50% of the ingested dose and is not affected by food intake. The Cmax and Tmax following multiple oral doses (1300 mg three times daily x 5 days) were 16.41 mcg/mL and 2.5 h, respectively.


Route of Elimination

Urinary excretion is the primary means of tranexamic acid elimination, with >95% of an administered dose excreted in the urine as unchanged parent drug. The rate of excretion is dependent on the route of administration - approximately 90% of an intravenously administered dose is excreted within 24 hours whereas only 39% of an orally administered dose is excreted within the same time frame.


Volume of Distribution

The initial volume of distribution of tranexamic acid is 0.18 L/kg and its steady-state volume of distribution is 0.39 L/kg. Tranexamic acid distributes into cerebrospinal fluid and the aqueous humor of the eye at concentrations approximately 1/10th of typical plasma concentrations. Tranexamic acid is also able to cross the placenta, found in cord blood at concentrations equivalent to maternal plasma concentrations.


Clearance

The plasma clearance of tranexamic acid is 110-116 mL/min.


5.6 Metabolism/Metabolites

Tranexamic acid metabolism is poorly characterized but does not appear to be a significant means of drug elimination. According to prescribing information, approximately 1% and 0.5% of an orally administered dose are excreted as a dicarboxylic acid and acetylated metabolite, respectively.


5.7 Biological Half-Life

Following intravenous administration, the apparent elimination half-life is approximately 2 hours and the mean terminal half-life is approximately 11 hours.


5.8 Mechanism of Action

Tranexamic acid competitively and reversibly inhibits the activation of plasminogen via binding at several distinct sites, including four or five low-affinity sites and one high-affinity site, the latter of which is involved in its binding to fibrin. The binding of plasminogen to fibrin induces fibrinolysis - by occupying the necessary binding sites tranexamic acid prevents this dissolution of fibrin, thereby stabilizing the clot and preventing hemorrhage.


API Reference Price

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01-Jan-2021
30-Aug-2024
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DOSAGE - INJECTABLE;INJECTION - 100MG/ML

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