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Synopsis

Synopsis

Chemistry

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Also known as: 144701-48-4, Micardis, Pritor, Kinzalmono, Bibr 277, Semintra
Molecular Formula
C33H30N4O2
Molecular Weight
514.6  g/mol
InChI Key
RMMXLENWKUUMAY-UHFFFAOYSA-N
FDA UNII
U5SYW473RQ

Telmisartan
A biphenyl compound and benzimidazole derivative that acts as an angiotensin II type 1 receptor antagonist. It is used in the management of HYPERTENSION.
Telmisartan is an Angiotensin 2 Receptor Blocker. The mechanism of action of telmisartan is as an Angiotensin 2 Receptor Antagonist.
1 2D Structure

Telmisartan

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]methyl]phenyl]benzoic acid
2.1.2 InChI
InChI=1S/C33H30N4O2/c1-4-9-30-35-31-21(2)18-24(32-34-27-12-7-8-13-28(27)36(32)3)19-29(31)37(30)20-22-14-16-23(17-15-22)25-10-5-6-11-26(25)33(38)39/h5-8,10-19H,4,9,20H2,1-3H3,(H,38,39)
2.1.3 InChI Key
RMMXLENWKUUMAY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCC1=NC2=C(N1CC3=CC=C(C=C3)C4=CC=CC=C4C(=O)O)C=C(C=C2C)C5=NC6=CC=CC=C6N5C
2.2 Other Identifiers
2.2.1 UNII
U5SYW473RQ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1h-benzimidazol)-1'-yl)methyl)-(1,1'-biphenyl)-2-carboxylic Acid

2. Bibr 277

3. Bibr-277

4. Micardis

5. Pritor

2.3.2 Depositor-Supplied Synonyms

1. 144701-48-4

2. Micardis

3. Pritor

4. Kinzalmono

5. Bibr 277

6. Semintra

7. 4'-((1,7'-dimethyl-2'-propyl-1h,3'h-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-carboxylic Acid

8. Bibr-277

9. Tolura

10. Bibr 277se

11. Telmisartan [inn]

12. Telmisattan

13. Telmisartan Teva

14. Telmisartan Actavis

15. Bibr-277-se

16. 4'-[(1,7'-dimethyl-2'-propyl-1h,3'h-2,5'-bibenzimidazol-3'-yl)methyl]biphenyl-2-carboxylic Acid

17. Bibr-277se

18. Bibr 277 Se

19. C09ca07

20. 2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]methyl]phenyl]benzoic Acid

21. Mfcd00918125

22. 4'-((4-methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylic Acid

23. Chembl1017

24. U5syw473rq

25. Bibr-277 Se

26. Chebi:9434

27. 4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1h-benzimidazol)-1'-yl)methyl)-(1,1'-biphenyl)-2-carboxylic Acid

28. (1,1'-biphenyl)-2-carboxylic Acid, 4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1h-benzimidazol)-1'-yl)methyl)-

29. [1,1'-biphenyl]-2-carboxylic Acid, 4'-[(1,4'-dimethyl-2'-propyl[2,6'-bi-1h-benzimidazol]-1'-yl)methyl]-

30. Ncgc00095150-01

31. Targit

32. Dsstox_cid_3636

33. Dsstox_rid_77121

34. Dsstox_gsid_23636

35. 2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propyl-benzimidazol-1-yl]methyl]phenyl]benzoic Acid

36. 4'-[(1,4'-dimethyl-2'propyl[2,6'-bi-1h-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic Acid

37. 4'[(1,4'-dimethyl-2'-propyl[2,6'-bi-1h-benzimidazol]-1'-yl)methyl][1,1'-biphenyl]-2-carboxylic Acid

38. Kinzal

39. Tazlok

40. Kinzal/pritor

41. Micardis (tn)

42. 4'-((1,7'-dimethyl-2'-propyl-1h,3'h-2,5'-bibenzo[d]imidazol-3'-yl)methyl)biphenyl-2-carboxylic Acid

43. Smr000466326

44. Cas-144701-48-4

45. Bay 68-9291

46. Sr-01000759355

47. Unii-u5syw473rq

48. Telmisartana

49. Telmisartar

50. Telsite

51. Telday

52. Hsdb 7590

53. 4'-[(1,4'-dimethyl-2'-propyl[2,6'-bi-1h-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic Acid

54. 4'-[[4-methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]-2-biphenylcarboxylic Acid

55. Telmisartan [usan:usp:inn:ban]

56. Telmisartan- Bio-x

57. Ym-086

58. Bay68-9291

59. Telmisartan (micardis)

60. Cpd000466326

61. Telmisartan [mi]

62. Spectrum2_001976

63. Spectrum3_001089

64. Spectrum4_001261

65. Spectrum5_001053

66. Telmisartan [jan]

67. Telmisartan [hsdb]

68. Telmisartan [usan]

69. Telmisartan [vandf]

70. Schembl4464

71. Telmisartan [mart.]

72. Bspbio_002738

73. Gtpl592

74. Kbiogr_001842

75. Telmisartan [usp-rs]

76. Telmisartan [who-dd]

77. Mls000759432

78. Mls001076687

79. Mls001424174

80. Mls006011851

81. Bidd:gt0365

82. Spectrum1505261

83. Telmisartan Teva Pharma

84. Spbio_002131

85. Telmisartan [ema Epar]

86. Telmisartan (jp17/usp/inn)

87. Dtxsid8023636

88. Telmisartan [green Book]

89. Kbio3_001958

90. Telmisartan [ep Impurity]

91. Telmisartan [orange Book]

92. Telmisartan For System Suitability

93. Hms1922p07

94. Hms2051p16

95. Hms2090p17

96. Hms2093m22

97. Hms2231p07

98. Hms3393p16

99. Hms3655c08

100. Hms3715l17

101. Hms3750e19

102. Pharmakon1600-01505261

103. Telmisartan [ep Monograph]

104. Telmisartan For Peak Identification

105. Telmisartan [usp Monograph]

106. Albb-028954

107. Bcp04513

108. Onduarp Component Telmisartan

109. Twynsta Component Telmisartan

110. Zinc1530886

111. Tox21_111452

112. Bbl029085

113. Bdbm50043280

114. Ccg-39514

115. Dl-511

116. Nsc759811

117. S1738

118. Stk624049

119. Tolucombi Component Telmisartan

120. Akos005557501

121. Kinzalkomb Component Telmisartan

122. Pritorplus Component Telmisartan

123. Telmisartan, >=98% (hplc), Solid

124. Tox21_111452_1

125. Ab07687

126. Ac-2013

127. Am90292

128. Cs-1699

129. Db00966

130. Ks-1215

131. Nc00296

132. Nsc 759811

133. Nsc-759811

134. Telmisartan Component Of Onduarp

135. Telmisartan Component Of Twynsta

136. Bay-68-9291

137. Micardis Hct Component Telmisartan

138. Micardisplus Component Telmisartan

139. Ncgc00095150-02

140. Ncgc00095150-03

141. Ncgc00095150-04

142. Ncgc00095150-06

143. Ncgc00095150-07

144. Ncgc00095150-08

145. Telmisartan [ema Epar Veterinary]

146. Telmisartan Component Of Tolucombi

147. 2-(4-{[4-methyl-6-(1-methyl-1h-1,3-benzodiazol-2-yl)-2-propyl-1h-1,3-benzodiazol-1-yl]methyl}phenyl)benzoic Acid

148. 4'-[(1,7'-dimethyl-2'-propyl-1h,3'h-2,5'-bibenzimidazol-3'-yl)methyl][1,1'-biphenyl]-2-carboxylic Acid

149. Bt164444

150. Hy-13955

151. Sy052776

152. Telmisartan Component Of Kinzalkomb

153. Telmisartan Component Of Pritorplus

154. Bcp0726000055

155. Sbi-0206733.p001

156. Telmisartan Component Of Micardiplus

157. Telmisartan Component Of Micardisplus

158. Ft-0631170

159. Ft-0674836

160. Sw197676-3

161. T-170

162. T2861

163. C07710

164. D00627

165. Ab00639941-06

166. Ab00639941-07

167. Ab00639941_08

168. Ab00639941_09

169. 701t484

170. A808270

171. L001035

172. Q733186

173. Q-101933

174. Sr-01000759355-4

175. Sr-01000759355-5

176. Brd-k73999723-001-02-2

177. Z2210710360

178. Telmisartan, European Pharmacopoeia (ep) Reference Standard

179. Telmisartan, United States Pharmacopeia (usp) Reference Standard

180. Telmisartan, Pharmaceutical Secondary Standard; Certified Reference Material

181. 4-(1,4-dimethyl-2-propyl-2,6-bi-1h-benzimidazol-1-yl)methyl-1,1-biphenyl-2-carboxylicacid

182. Telmisartan For Peak Identification, European Pharmacopoeia (ep) Reference Standard

183. Telmisartan For System Suitability, European Pharmacopoeia (ep) Reference Standard

184. 2-[4-[[4-methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]phenyl]benzoic Acid

185. 2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]methyl]phenyl]benzoic Acid.

186. 4''-((1,4''-dimethyl-2''-propyl(2,6''-bi-1h-benzimidazol)-1''-yl)methyl)-(1,1''-biphenyl)-2-carboxylic Acid

187. 4''-((4-methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylic Acid

188. 4''-[(1,4''-dimethyl-2''propyl[2,6''-bi-1h-benzimidazol]-1''-yl)methyl]-[1,1''-biphenyl]-2-carboxylic Acid

189. 4''-[(1,7''-dimethyl-2''-propyl-1h,3''h-2,5''-bibenzimidazol-3''-yl)methyl][1,1''-biphenyl]-2-carboxylic Acid

190. 4''-[(1,7''-dimethyl-2''-propyl-1h,3''h-2,5''-bibenzimidazol-3''-yl)methyl]biphenyl-2-carboxylic Acid

191. 4'-((1,7'-dimethyl-2'-propyl-1h,3'h-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-carboxylicacid

192. 4'-(1,7'-dimethyl-2'-propyl-1h-[2,5']bibenzoimidazolyl-3'-ylmethyl)-biphenyl-2-carboxylic Acid

193. 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylic Acid

194. 4'-[[4-methyl-6-(1-methyl-1h-benzimidazol-2-yl)-2-propyl-1h-benzimidazol-1-yl]methyl]biphenyl-2-carboxylic Acid

195. 4'-[2-n-propyl-4-methyl-6-(1-methyl Benzimidazol-2-yl)benzimidazol-1-yl Methyl]biphenyl-2-carboxylic Acid

196. 4'-{[4-methyl-6-(1-methyl-1h-1,3-benzodiazol-2-yl)-2-propyl-1h-1,3-benzodiazol-1-yl]methyl}-[1,1'-biphenyl]-2-carboxylic Acid

197. Tls

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 514.6 g/mol
Molecular Formula C33H30N4O2
XLogP36.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass514.23687621 g/mol
Monoisotopic Mass514.23687621 g/mol
Topological Polar Surface Area72.9 Ų
Heavy Atom Count39
Formal Charge0
Complexity831
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 NameMicardis
PubMed HealthTelmisartan (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelMICARDIS is a non-peptide angiotensin II receptor (type AT1) antagonist.Telmisartan is chemically described as 4'-[(1,4'-dimethyl-2'-propyl [2,6'-bi-1H-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic acid. Its empiri
Active IngredientTelmisartan
Dosage FormTablet
RouteOral
Strength80mg; 40mg; 20mg
Market StatusPrescription
CompanyBoehringer Ingelheim

2 of 4  
Drug NameTelmisartan
PubMed HealthTelmisartan (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelTelmisartanis a non-peptide angiotensin II receptor (type AT1) antagonist. Telmisartan is chemically described as 4-[(1,4-dimethyl-2-propyl [2,6-bi-1H-benzimidazol]-1-yl)methyl]-[1,1-biphenyl]-2-carboxylic acid. Its empirical formul...
Active IngredientTelmisartan
Dosage FormTablet
RouteOral
Strength80mg; 40mg; 20mg
Market StatusPrescription
CompanyMylan Pharms; Alembic Pharms; Torrent Pharms; Watson Labs; Glenmark Generics; Zydus Pharms Usa

3 of 4  
Drug NameMicardis
PubMed HealthTelmisartan (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelMICARDIS is a non-peptide angiotensin II receptor (type AT1) antagonist.Telmisartan is chemically described as 4'-[(1,4'-dimethyl-2'-propyl [2,6'-bi-1H-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic acid. Its empiri
Active IngredientTelmisartan
Dosage FormTablet
RouteOral
Strength80mg; 40mg; 20mg
Market StatusPrescription
CompanyBoehringer Ingelheim

4 of 4  
Drug NameTelmisartan
PubMed HealthTelmisartan (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelTelmisartanis a non-peptide angiotensin II receptor (type AT1) antagonist. Telmisartan is chemically described as 4-[(1,4-dimethyl-2-propyl [2,6-bi-1H-benzimidazol]-1-yl)methyl]-[1,1-biphenyl]-2-carboxylic acid. Its empirical formul...
Active IngredientTelmisartan
Dosage FormTablet
RouteOral
Strength80mg; 40mg; 20mg
Market StatusPrescription
CompanyMylan Pharms; Alembic Pharms; Torrent Pharms; Watson Labs; Glenmark Generics; Zydus Pharms Usa

4.2 Therapeutic Uses

Angiotensin II Type 1 Receptor Blockers; Antihypertensive Agents

National Library of Medicine's Medical Subject Headings. Telmisartan. Online file (MeSH, 2014). Available from, as of September 2, 2014: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html


Micardis is indicated for the treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. These benefits have been seen in controlled trials of antihypertensive drugs from a wide variety of pharmacologic classes including the class to which this drug principally belongs. Control of high blood pressure should be part of comprehensive cardiovascular risk management, including, as appropriate, lipid control, diabetes management, antithrombotic therapy, smoking cessation, exercise, and limited sodium intake. Many patients will require more than one drug to achieve blood pressure goals. ... Numerous antihypertensive drugs, from a variety of pharmacologic classes and with different mechanisms of action, have been shown in randomized controlled trials to reduce cardiovascular morbidity and mortality, and it can be concluded that it is blood pressure reduction, and not some other pharmacologic property of the drugs, that is largely responsible for those benefits. The largest and most consistent cardiovascular outcome benefit has been a reduction in the risk of stroke, but reductions in myocardial infarction and cardiovascular mortality also have been seen regularly. Elevated systolic or diastolic pressure causes increased cardiovascular risk, and the absolute risk increase per mmHg is greater at higher blood pressures, so that even modest reductions of severe hypertension can provide substantial benefit. Relative risk reduction from blood pressure reduction is similar across populations with varying absolute risk, so the absolute benefit is greater in patients who are at higher risk independent of their hypertension (for example, patients with diabetes or hyperlipidemia), and such patients would be expected to benefit from more aggressive treatment to a lower blood pressure goal. Some antihypertensive drugs have smaller blood pressure effects (as monotherapy) in black patients, and many antihypertensive drugs have additional approved indications and effects (e.g., on angina, heart failure, or diabetic kidney disease). These considerations may guide selection of therapy. /Micardis/ may be used alone or in combination with other antihypertensive agents /Included in US product labeling/

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


Micardis is indicated for reduction of the risk of myocardial infarction, stroke, or death from cardiovascular causes in patients 55 years of age or older at high risk of developing major cardiovascular events who are unable to take ACE inhibitors. High risk for cardiovascular events can be evidenced by a history of coronary artery disease, peripheral arterial disease, stroke, transient ischemic attack, or high-risk diabetes (insulin-dependent or non-insulin dependent) with evidence of end-organ damage. Micardis can be used in addition to other needed treatment (such as antihypertensive, antiplatelet or lipid-lowering therapy). Studies of telmisartan in this setting do not exclude the possibility that telmisartan may not preserve a meaningful fraction of the effect of the ACE inhibitor to which it was compared. Consider using the ACE inhibitor first, and, if it is stopped for cough only, consider re-trying the ACE inhibitor after the cough resolves. /Included in US product label/

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


Both angiotensin II receptor antagonists /including telmisartan/ and ACE inhibitors have been shown to slow the rate of progression of renal disease in hypertensive patients with diabetes mellitus and microalbuminuria or overt nephropathy, and use of a drug from either class is recommended in such patients. /NOT included in US product label/

American Society of Health-System Pharmacists 2014; Drug Information 2014. Bethesda, MD. 2014, p. 2072


For more Therapeutic Uses (Complete) data for TELMISARTAN (8 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ WARNING: FETAL TOXICITY. When pregnancy is detected, discontinue Micardis as soon as possible. Drugs that act directly on the renin-angiotensin system can cause injury and death to the developing fetus.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


Use of drugs that act on the renin-angiotensin system during the second and third trimesters of pregnancy reduces fetal renal function and increases fetal and neonatal morbidity and death. Resulting oligohydramnios can be associated with fetal lung hypoplasia and skeletal deformations. Potential neonatal adverse effects include skull hypoplasia, anuria, hypotension, renal failure, and death. When pregnancy is detected, discontinue Micardis as soon as possible. These adverse outcomes are usually associated with use of these drugs in the second and third trimester of pregnancy. Most epidemiologic studies examining fetal abnormalities after exposure to antihypertensive use in the first trimester have not distinguished drugs affecting the renin-angiotensin system from other antihypertensive agents. Appropriate management of maternal hypertension during pregnancy is important to optimize outcomes for both mother and fetus. In the unusual case that there is no appropriate alternative to therapy with drugs affecting the reninangiotensin system for a particular patient, apprise the mother of the potential risk to the fetus. Perform serial ultrasound examinations to assess the intra-amniotic environment. If oligohydramnios is observed, discontinue Micardis, unless it is considered lifesaving for the mother. Fetal testing may be appropriate, based on the week of pregnancy. Patients and physicians should be aware, however, that oligohydramnios may not appear until after the fetus has sustained irreversible injury.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


Neonates with a history of in utero exposure to Micardis: If oliguria or hypotension occurs, direct attention toward support of blood pressure and renal perfusion. Exchange transfusions or dialysis may be required as a means of reversing hypotension and/or substituting for disordered renal function.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


FDA Pregnancy Risk Category: D /POSITIVE EVIDENCE OF RISK. Studies in humans, or investigational or post-marketing data, have demonstrated fetal risk. Nevertheless, potential benefits from the use of the drug may outweigh the potential risk. For example, the drug may be acceptable if needed in a life-threatening situation or serious disease for which safer drugs cannot be used or are ineffective./

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


For more Drug Warnings (Complete) data for TELMISARTAN (17 total), please visit the HSDB record page.


4.4 Drug Indication

Used alone or in combination with other classes of antihypertensives for the treatment of hypertension. Also used in the treatment of diabetic nephropathy in hypertensive patients with type 2 diabetes mellitus, as well as the treatment of congestive heart failure (only in patients who cannot tolerate ACE inhibitors).


FDA Label


Treatment of essential hypertension in adults.


Reduction of proteinuria associated with chronic kidney disease (CKD).


* Hypertension:

Treatment of essential hypertension in adults.

* Cardiovascular prevention:

Reduction of cardiovascular morbidity in patients with:

- manifest atherothrombotic cardiovascular disease (history of coronary heart disease or peripheral arterial disease) or;

- type 2 diabetes mellitus with documented target organ damage.


* Hypertension:

Treatment of essential hypertension in adults.

* Cardiovascular prevention:

Reduction of cardiovascular morbidity in patients with:

- manifest atherothrombotic cardiovascular disease (history of coronary heart disease, stroke, or peripheral arterial disease) or;

- type-2 diabetes mellitus with documented target-organ damage.


Treatment of essential hypertension in adults


* Hypertension:

Treatment of essential hypertension in adults.

* Cardiovascular prevention:

Reduction of cardiovascular morbidity in patients with:

- manifest atherothrombotic cardiovascular disease (history of coronary heart disease, stroke, or peripheral arterial disease) or;

- type 2 diabetes mellitus with documented target organ damage.


* Hypertension:

Treatment of essential hypertension in adults.

* Cardiovascular prevention:

Reduction of cardiovascular morbidity in patients with:

- manifest atherothrombotic cardiovascular disease (history of coronary heart disease, stroke, or peripheral arterial disease) or;

- type-2 diabetes mellitus with documented target-organ damage.


* Hypertension:

Treatment of essential hypertension in adults.

* Cardiovascular prevention:

Reduction of cardiovascular morbidity in patients with:

- manifest atherothrombotic cardiovascular disease (history of coronary heart disease, stroke, or peripheral arterial disease) or;

- type-2 diabetes mellitus with documented target-organ damage.


Treatment of essential hypertension in adults:

* Add on therapy:

Onduarp is indicated in adults whose blood pressure is not adequately controlled on amlodipine.

* Replacement therapy:

Adult patients receiving telmisartan and amlodipine from separate tablets can instead receive tablets of Onduarp containing the same component doses.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Telmisartan is an orally active nonpeptide angiotensin II antagonist that acts on the AT1 receptor subtype. It has the highest affinity for the AT1 receptor among commercially available ARBS and has minimal affinity for the AT2 receptor. New studies suggest that telmisartan may also have PPARγ agonistic properties that could potentially confer beneficial metabolic effects, as PPARγ is a nuclear receptor that regulates specific gene transcription, and whose target genes are involved in the regulation of glucose and lipid metabolism, as well as anti-inflammatory responses. This observation is currently being explored in clinical trials. Angiotensin II is formed from angiotensin I in a reaction catalyzed by angiotensin-converting enzyme (ACE, kininase II). Angiotensin II is the principal pressor agent of the renin-angiotensin system, with effects that include vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation, and renal reabsorption of sodium. Telmisartan works by blocking the vasoconstrictor and aldosterone secretory effects of angiotensin II.


5.2 MeSH Pharmacological Classification

Angiotensin II Type 1 Receptor Blockers

Agents that antagonize ANGIOTENSIN II TYPE 1 RECEPTOR. Included are ANGIOTENSIN II analogs such as SARALASIN and biphenylimidazoles such as LOSARTAN. Some are used as ANTIHYPERTENSIVE AGENTS. (See all compounds classified as Angiotensin II Type 1 Receptor Blockers.)


Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TELMISARTAN
5.3.2 FDA UNII
U5SYW473RQ
5.3.3 Pharmacological Classes
Angiotensin 2 Receptor Blocker [EPC]; Angiotensin 2 Receptor Antagonists [MoA]
5.4 ATC Code

C09CA07


QC09CA07


C09CA07


C09CA07


C09CA07


C09CA07


C09CA07


C09CA07


C09DB04


C09CA07

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


C - Cardiovascular system

C09 - Agents acting on the renin-angiotensin system

C09C - Angiotensin ii receptor blockers (arbs), plain

C09CA - Angiotensin ii receptor blockers (arbs), plain

C09CA07 - Telmisartan


5.5 Absorption, Distribution and Excretion

Absorption

Absolute bioavailability depends on dosage. Food slightly decreases the bioavailability (a decrease of about 6% is seen when the 40-mg dose is administered with food).


Route of Elimination

Following either intravenous or oral administration of 14C-labeled telmisartan, most of the administered dose (>97%) was eliminated unchanged in feces via biliary excretion; only minute amounts were found in the urine (0.91% and 0.49% of total radioactivity, respectively).


Volume of Distribution

500 L


Clearance

>800 mL/min


Following either intravenous or oral administration of (14)C-labeled telmisartan, most of the administered dose (>97%) was eliminated unchanged in feces via biliary excretion; only minute amounts were found in the urine (0.91% and 0.49% of total radioactivity, respectively).

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


Following oral administration, peak concentrations (Cmax) of telmisartan are reached in 0.5 to 1 hour after dosing. Food slightly reduces the bioavailability of telmisartan, with a reduction in the area under the plasma concentration-time curve (AUC) of about 6% with the 40 mg tablet and about 20% after a 160 mg dose. The absolute bioavailability of telmisartan is dose dependent. At 40 and 160 mg the bioavailability was 42% and 58%, respectively. The pharmacokinetics of orally administered telmisartan are nonlinear over the dose range 20 to 160 mg, with greater than proportional increases of plasma concentrations (Cmax and AUC) with increasing doses. Telmisartan shows bi-exponential decay kinetics with a terminal elimination half life of approximately 24 hours. Trough plasma concentrations of telmisartan with once daily dosing are about 10% to 25% of peak plasma concentrations. Telmisartan has an accumulation index in plasma of 1.5 to 2.0 upon repeated once daily dosing.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


Telmisartan is highly bound to plasma proteins (>99.5%), mainly albumin and a1 - acid glycoprotein. Plasma protein binding is constant over the concentration range achieved with recommended doses. The volume of distribution for telmisartan is approximately 500 liters indicating additional tissue binding.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


It is not known whether telmisartan is excreted in human milk, but telmisartan was shown to be present in the milk of lactating rats.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


To study the pharmacolkinetics of telmisartan in healthy Chinese male subjects after oral administration of two dosage levels, 36 healthy subjects were divided into two groups and given a single oral dose of 40 or 80 mg telmisartan (CAS 144701-48-4, MicardisPlus). A sensitive liquid chromatography-tandem mass spectrometry method (LC-MS-MS) was used for the determination of telmisartan in plasma. Both, a non-compartmental and compartmental method were used for analysis of parameters of kinetics. The main pharmacokinetic parameters of the 40 mg and 80 mg regimen group were as follows: t(max) (1.76 +/- 1.75) h, (1.56 +/- 1.09) h, C(max) (163.2 +/- 128.4) ng/mL, (905.7 +/- 583.4) ng/mL, t1/2 (23.6 +/- 10.8) h, (23.0 +/- 6.4) h, AUC(o-t) (1456 +/- 1072) ng x h/mL, (6759 +/- 3754) ng x h/mL, AUC(o-infinity (1611 +/- 1180) ng x h/mL, (7588 +/- 4661) ng x h/mL, respectively. After dose normalization, there was significant difference for main pharmacokinetic parameters C(max) AUC(o-t) and AUC(o-infinity) between two dosage level groups. The plasma concentration-time profile of telmisartan was characterized by a high degree of inter-individual variability and the disposition of telmisartan in healthy Chinese subjects was dose-dependent. The pharmacokinetic parameters C(max) and AUC(o-inifinity) of the 80 mg regimen group increased to about 5-fold compared to that of the 40 mg regimen group, but there was no significant difference for t(max) and t1/2 between the two dose groups.

PMID:17009837 Zhang P et al; Arzneimittelforschung 56 (8): 569-73 (2006)


5.6 Metabolism/Metabolites

Minimally metabolized by conjugation to form a pharmacologically inactive acylglucuronide; the glucuronide of the parent compound is the only metabolite that has been identified in human plasma and urine. The cytochrome P450 isoenzymes are not involved in the metabolism of telmisartan.


Telmisartan is metabolized by conjugation to form a pharmacologically inactive acyl glucuronide; the glucuronide of the parent compound is the only metabolite that has been identified in human plasma and urine. After a single dose, the glucuronide represents approximately 11% of the measured radioactivity in plasma. The cytochrome P450 isoenzymes are not involved in the metabolism of telmisartan.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


5.7 Biological Half-Life

Bi-exponential decay kinetics with a terminal elimination half-life of approximately 24 hours.


Telmisartan shows bi-exponential decay kinetics with a terminal elimination half life of approximately 24 hours.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


5.8 Mechanism of Action

Telmisartan interferes with the binding of angiotensin II to the angiotensin II AT1-receptor by binding reversibly and selectively to the receptors in vascular smooth muscle and the adrenal gland. As angiotensin II is a vasoconstrictor, which also stimulates the synthesis and release of aldosterone, blockage of its effects results in decreases in systemic vascular resistance. Telmisartan does not inhibit the angiotensin converting enzyme, other hormone receptors, or ion channels. Studies also suggest that telmisartan is a partial agonist of PPARγ, which is an established target for antidiabetic drugs. This suggests that telmisartan can improve carbohydrate and lipid metabolism, as well as control insulin resistance without causing the side effects that are associated with full PPARγ activators.


Migration of CD4-positive lymphocytes into the vessel wall represents an important step in early atherogenesis. Telmisartan is an angiotensin type 1 receptor (AT1R) blocker with peroxisome proliferator-activated receptor (PPAR)-gamma-activating properties. The present study examined the effect of telmisartan on CD4-positive cell migration and the role of PPARgamma in this context. CD4-positive lymphocytes express both the AT1R and PPARgamma. Stimulation of CD4-positive lymphocytes with stromal cell-derived factor (SDF)-1 leads to a 4.1+/-3.1-fold increase in cell migration. Pretreatment of cells with telmisartan reduces this effect in a concentration-dependent manner to a maximal 1.6+/-0.7-fold induction at 10 mumol/L of telmisartan (P<0.01 compared with SDF-1-treated cells; n=22). Three different PPARgamma activators, rosiglitazone, pioglitazone, and GW1929, had similar effects, whereas eprosartan, a non-PPARgamma-activating AT1R blocker, did not affect chemokine-induced lymphocyte migration. Telmisartan's effect on CD4-positive lymphocyte migration was mediated through an early inhibition of chemokine-induced phosphatidylinositol 3-kinase activity. Downstream, telmisartan inhibited F-actin formation, as well as intercellular adhesion molecule-3 translocation. Transfection of CD4-positive lymphocytes with PPARgamma small interfering RNA abolished telmisartan's effect on migration, whereas blockade of the AT1R had no such effect. Telmisartan inhibits chemokine-induced CD4-positive cell migration independent of the AT1R via PPARgamma. These data provide a novel mechanism to explain how telmisartan modulates lymphocyte activation by its PPARgamma-activating properties.

PMID:18158351 Walcher D et al; Hypertension 51 (2): 259-66 (2008)


Angiotensin II is formed from angiotensin I in a reaction catalyzed by angiotensin-converting enzyme (ACE, kininase II). Angiotensin II is the principal pressor agent of the renin-angiotensin system, with effects that include vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation, and renal reabsorption of sodium. Telmisartan blocks the vasoconstrictor and aldosterone-secreting effects of angiotensin II by selectively blocking the binding of angiotensin II to the AT1 receptor in many tissues, such as vascular smooth muscle and the adrenal gland. Its action is therefore independent of the pathways for angiotensin II synthesis. There is also an AT2 receptor found in many tissues, but AT2 is not known to be associated with cardiovascular homeostasis. Telmisartan has much greater affinity (>3,000 fold) for the AT1 receptor than for the AT2 receptor. Blockade of the renin-angiotensin system with ACE inhibitors, which inhibit the biosynthesis of angiotensin II from angiotensin I, is widely used in the treatment of hypertension. ACE inhibitors also inhibit the degradation of bradykinin, a reaction also catalyzed by ACE. Because telmisartan does not inhibit ACE (kininase II), it does not affect the response to bradykinin. Whether this difference has clinical relevance is not yet known. Telmisartan does not bind to or block other hormone receptors or ion channels known to be important in cardiovascular regulation. Blockade of the angiotensin II receptor inhibits the negative regulatory feedback of angiotensin II on renin secretion, but the resulting increased plasma renin activity and angiotensin II circulating levels do not overcome the effect of telmisartan on blood pressure.

NIH; DailyMed. Current Medication Information for MIicardis (Telmisartan) Tablet (Revised: October 2012). Available from, as of October 9, 2014: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=cfb9309f-e0df-4a55-9542-0e869fce05fb


... The receptor-independent protective role of an angiotensin II receptor 1 blocker (ARB) /was investigated/ using primary-cultured mesangial cells from angiotensin II receptor 1 knockout or wild-type mice and a highly lipophilic ARB, telmisartan. Intracellular reactive oxygen species were estimated using a fluorogenic probe, CM-H2DCFDA. Non-angiotensin II-induced reactive oxygen species production was generated by exposing cells to hydrogen peroxide alone or after treatment with telmisartan. Flow cytometry analysis showed that angiotensin II induced an increase in oxidant production in a dose-dependent manner in wild-type cells, but not in knockout cells. In contrast, hydrogen peroxide induced oxidative stress in both wild-type and knockout cells. Interestingly, telmisartan attenuated the oxidative stress induced by hydrogen peroxide in both cells, suggesting that it acted via a receptor-independent antioxidant effect. Intracellular concentrations of telmisartan were confirmed by high-performance liquid chromatography analysis. Expression of plasminogen activator inhibitor 1, which is stimulated by oxidative stress, was also attenuated by telmisartan in a receptor-independent as well as receptor-dependent manner. Telmisartan did not change expression levels of antioxidative enzymes such as catalase or glutathione peroxidase. Furthermore, the amelioration of oxidative stress by telmisartan did not involve the peroxisome proliferator-activated receptor-gamma pathway. Telmisartan inhibits intracellular oxidative stress, at least in part, in a receptor-independent manner, possibly owing to its lipophilic and antioxidant structure.

PMID:17620961 Shao J et al; J Hypertens 25 (8): 1643-9 (2007)


Telmisartan, an angiotensin II type 1 receptor (AT1R) antagonist, was found to have a unique property: it is a partial agonist of peroxisome proliferator-activated receptor gamma (PPARgamma). ... /This study/ examined whether telmisartan affects AT1R expression in vascular smooth muscle cells ... derived from the thoracic aorta of Wistar-Kyoto rat. ... Telmisartan decreased the expression of AT1R at the mRNA and protein levels in a dose- and time-dependent manner. Decreased AT1R promoter activity with unchanged mRNA stability suggested that telmisartan suppressed AT1R gene expression at the transcriptional level. However, the expression of AT1R was not suppressed by other AT1R antagonists such as candesartan or olmesartan. Since the suppression of AT1R expression was prevented by pretreatment with GW9662, a PPARgamma antagonist, PPARgamma should have participated in the process. The deletion and mutation analysis of the AT1R gene promoter indicated that a GC box located in the proximal promoter region is responsible for the telmisartan-induced downregulation. Data provides a novel insight into an effect of telmisartan: telmisartan inhibits AT1R gene expression through PPARgamma activation. The dual inhibition of angiotensin II function by telmisartan - AT1R blockade and downregulation - would contribute to more complete inhibition of the renin-angiotensin system.

PMID:16938288 Imayama I et al; Cardiovasc Res 72 (1): 184-90 (2006)


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

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Total Quantity (KGS)

Total Value (USD)

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 - 20MG

USFDA APPLICATION NUMBER - 20850

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DOSAGE - TABLET;ORAL - 40MG

USFDA APPLICATION NUMBER - 20850

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DOSAGE - TABLET;ORAL - 80MG

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DOSAGE - TABLET;ORAL - 12.5MG;40MG

USFDA APPLICATION NUMBER - 21162

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DOSAGE - TABLET;ORAL - 12.5MG;80MG

USFDA APPLICATION NUMBER - 21162

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DOSAGE - TABLET;ORAL - 25MG;80MG

USFDA APPLICATION NUMBER - 21162

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DOSAGE - TABLET;ORAL - EQ 10MG BASE;40MG **Fe...DOSAGE - TABLET;ORAL - EQ 10MG BASE;40MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22401

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DOSAGE - TABLET;ORAL - EQ 10MG BASE;80MG **Fe...DOSAGE - TABLET;ORAL - EQ 10MG BASE;80MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22401

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DOSAGE - TABLET;ORAL - EQ 5MG BASE;40MG **Fed...DOSAGE - TABLET;ORAL - EQ 5MG BASE;40MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22401

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DOSAGE - TABLET;ORAL - EQ 5MG BASE;80MG **Fed...DOSAGE - TABLET;ORAL - EQ 5MG BASE;80MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 22401

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