U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C33H30N4O2
Molecular Weight 514.6181
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TELMISARTAN

SMILES

CCCc1nc2c(C)cc(cc2n1Cc3ccc(cc3)-c4ccccc4C(=O)O)-c5nc6ccccc6n5C

InChI

InChIKey=RMMXLENWKUUMAY-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C33H30N4O2
Molecular Weight 514.6181
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf

Telmisartan is an orally active nonpeptide angiotensin II antagonist that acts on the AT1 receptor subtype. It was discovered by Boehringer Ingelheim and launched in 1999 as Micardis. 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. 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. Used alone or in combination with other classes of antihypertensives for the treatment of hypertension. Telmisartan is 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).

Originator

Curator's Comment:: # Boehringer Ingelheim Pharma KG

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MICARDIS

Approved Use

MICARDIS is an angiotensin II receptor blocker (ARB) indicated for: • Treatment of hypertension • Cardiovascular (CV) risk reduction in patients unable to take ACE inhibitors

Launch Date

9.1056957E11
Preventing
MICARDIS

Approved Use

MICARDIS is an angiotensin II receptor blocker (ARB) indicated for: • Treatment of hypertension • Cardiovascular (CV) risk reduction in patients unable to take ACE inhibitors

Launch Date

9.1056957E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3200 ng/mL
160 mg single, intravenous
dose: 160 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TELMISARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3320 ng × h/mL
160 mg single, intravenous
dose: 160 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TELMISARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
17.7 h
160 mg single, intravenous
dose: 160 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
TELMISARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
160 mg single, intravenous
Highest studied dose
Dose: 160 mg
Route: intravenous
Route: single
Dose: 160 mg
Sources: Page: p.159
healthy, 18 – 50
n = 12
Health Status: healthy
Age Group: 18 – 50
Sex: M
Population Size: 12
Sources: Page: p.159
320 mg 1 times / day multiple, oral
Highest studied dose
Dose: 320 mg, 1 times / day
Route: oral
Route: multiple
Dose: 320 mg, 1 times / day
Sources: Page: p.161
healthy, 18 – 50
n = 10
Health Status: healthy
Age Group: 18 – 50
Sex: M
Population Size: 10
Sources: Page: p.161
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension|Cardiovascular Risk Reduction
Sources: Page: p.1
Disc. AE: Disorder fetal, Hypotension...
AEs leading to
discontinuation/dose reduction:
Disorder fetal
Hypotension
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
Disorder fetal Disc. AE
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension|Cardiovascular Risk Reduction
Sources: Page: p.1
Hypotension Disc. AE
80 mg 1 times / day multiple, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Hypertension|Cardiovascular Risk Reduction
Sources: Page: p.1
PubMed

PubMed

TitleDatePubMed
Use of ambulatory blood pressure monitoring to evaluate the selective angiotensin II receptor antagonist, telmisartan, and other antihypertensive drugs.
2000
Telmisartan: a review of its use in hypertension.
2001
The comparative pharmacology of angiotensin II receptor antagonists.
2001
Angiotensin II receptor antagonists: new paradigms in the treatment of hypertension. Introduction.
2001
Ambulatory blood pressure monitoring to assess the comparative efficacy and duration of action of a novel new angiotensin II receptor blocker--telmisartan.
2001
The role of angiotensin II receptor antagonists in the management of diabetes.
2001
Effects of the replacement of the angiotensin converting enzyme inhibitor enalapril by the angiotensin II receptor blocker telmisartan in patients with congestive heart failure. The replacement of angiotensin converting enzyme inhibition (REPLACE) investigators.
2001 Feb
[Angiotensin II antagonism. Critical morning hours are covered].
2001 Feb 22
Comparison of 26-week efficacy and tolerability of telmisartan and atenolol, in combination with hydrochlorothiazide as required, in the treatment of mild to moderate hypertension: a randomized, multicenter study.
2001 Jan
Combination treatment with telmisartan and hydrochlorothiazide in black patients with mild to moderate hypertension.
2001 Jan
Effects of telmisartan, hydrochlorothiazide and their combination on blood pressure and renal excretory parameters in spontaneously hypertensive rats.
2001 Jun
Angiotensin II-induced stimulation of collagen secretion and production in cardiac fibroblasts is mediated via angiotensin II subtype 1 receptors.
2001 Jun
Comparative antihypertensive and renoprotective effects of telmisartan and lisinopril after long-term treatment in hypertensive diabetic rats.
2001 Mar
Effects of telmisartan on renal excretory function in conscious dogs.
2001 Mar-Apr
Effect of telmisartan on arterial distensibility and central blood pressure in patients with mild to moderate hypertension and Type 2 diabetes mellitus.
2001 Sep
Long-term efficacy and tolerability of telmisartan as monotherapy and in combination with other antihypertensive medications.
2002
Telmisartan. BIBR 277, Micardis, Pritor.
2002
Gateways to clinical trials.
2002 Dec
Comparison of trough effect of telmisartan vs perindopril using self blood pressure measurement: EVERESTE study.
2002 Dec
Application of capillary zone electrophoresis to the screening of some angiotensin II receptor antagonists.
2002 Jan
[Coronary heart disease patient with hypertension. Dangerously increased blood pressure despite gigantic therapy arsenal].
2002 Jan 24
Angiotensin II receptor antagonists role in arterial hypertension.
2002 Mar
Gateways to clinical trials.
2002 May
Angiotensin blockade prevents type 2 diabetes by formation of fat cells.
2002 Nov
Amlodipine versus Angiotensin-receptor blockers for nonhypertension indications.
2002 Nov
[These hypertensive patients are especially at risk for myocardial infarct in the morning. Screen for non-dippers].
2002 Nov 14
[Lowering blood pressure with sartans. Are there differences?].
2002 Nov 21
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
ABPM comparison of the anti-hypertensive profiles of telmisartan and enalapril in patients with mild-to-moderate essential hypertension.
2002 Nov-Dec
A multicenter, open-label study of the efficacy and safety of telmisartan in mild to moderate hypertensive patients.
2002 Oct
The efficacy and tolerability of an angiotensin II receptor blocker, telmisartan, in Thai patients with mild to moderate essential hypertension.
2002 Sep
Simultaneous determination of hydrochlorothiazide and several angiotensin-II-receptor antagonists by capillary electrophoresis.
2003 Feb 26
[Despite therapy morning dangerous RR spikes. Headache and vertigo are alarm signals].
2003 Jan 23
Evaluation of angiotensin II receptor blockers for 24-hour blood pressure control: meta-analysis of a clinical database.
2003 Jan-Feb
Patents

Sample Use Guides

Hypertension - 40 to 80 mg once daily Cardiovascular Risk Reduction - 80 mg once daily
Route of Administration: Oral
Telmisartan (0.01-10 nmol/l) concentration dependently attenuated the angiotensin II-mediated (1 nmol/l) enhancement of EFS-evoked sympathetic outflow in the isolated rabbit thoracic aorta.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:03:21 UTC 2021
Edited
by admin
on Fri Jun 25 21:03:21 UTC 2021
Record UNII
U5SYW473RQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TELMISARTAN
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
TELMISARTAN COMPONENT OF MICARDISPLUS
Brand Name English
BIBR 277 SE
Code English
TELMISARTAN [EMA EPAR]
Common Name English
KINZALMONO
Brand Name English
BIBR-277
Code English
TELMISARTAN [GREEN BOOK]
Common Name English
TELMISARTAN [EP]
Common Name English
TELMISARTAN [USP MONOGRAPH]
Common Name English
TELMISARTAN COMPONENT OF ONDUARP
Brand Name English
TELMISARTAN [USP-RS]
Common Name English
TELMISARTAN [MART.]
Common Name English
TOLURA
Brand Name English
TELMISARTAN [JAN]
Common Name English
TELMISARTAN TEVA
Brand Name English
KINZALKOMB COMPONENT TELMISARTAN
Brand Name English
TELMISARTAN [EMA EPAR VETERINARY]
Common Name English
MICARDISPLUS COMPONENT TELMISARTAN
Brand Name English
BIBR-277 SE
Code English
TELMISARTAN COMPONENT OF KINZALKOMB
Brand Name English
PRITORPLUS COMPONENT TELMISARTAN
Brand Name English
(1,1'-BIPHENYL)-2-CARBOXYLIC ACID, 4'-((1,4'-DIMETHYL-2'-PROPYL(2,6'-BI-1H-BENZIMIDAZOL)-1'-YL)METHYL)-
Common Name English
TELMISARTAN COMPONENT OF TOLUCOMBI
Brand Name English
TELMISARTAN [USAN]
Common Name English
TWYNSTA COMPONENT TELMISARTAN
Common Name English
ONDUARP COMPONENT TELMISARTAN
Brand Name English
TELMISARTAN [INN]
Common Name English
MICARDIS HCT COMPONENT TELMISARTAN
Common Name English
TELMISARTAN COMPONENT OF MICARDIPLUS
Brand Name English
C09CA07
Code English
TELMISARTAN [EP MONOGRAPH]
Common Name English
PRITOR
Brand Name English
TELMISARTAN [MI]
Common Name English
TELMISARTAN [WHO-DD]
Common Name English
MICARDIS
Brand Name English
TELMISARTAN [VANDF]
Common Name English
TELMISARTAN COMPONENT OF TWYNSTA
Common Name English
BIBR-277-SE
Code English
TELMISARTAN COMPONENT OF PRITORPLUS
Brand Name English
TELMISARTAN TEVA PHARMA
Brand Name English
SEMINTRA
Brand Name English
TELMISARTAN [ORANGE BOOK]
Common Name English
TELMISARTAN [HSDB]
Common Name English
TOLUCOMBI COMPONENT TELMISARTAN
Brand Name English
TELMISARTAN ACTAVIS
Brand Name English
4'-((4-METHYL-6-(1-METHYL-2-BENZIMIDAZOLYL)-2-PROPYL-1-BENZIMIDAZOLYL)METHYL)-2-BIPHENYLCARBOXYLIC ACID
Systematic Name English
Classification Tree Code System Code
LIVERTOX 930
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS TELMISARTAN ACTAVIS (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
WHO-VATC QC09DA07
Created by admin on Fri Jun 25 21:03:22 UTC 2021 , Edited by admin on Fri Jun 25 21:03:22 UTC 2021
EMA ASSESSMENT REPORTS KINZALKOMB (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
NCI_THESAURUS C66930
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS TOLURA (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
WHO-ATC C09DB04
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
WHO-VATC QC09DB04
Created by admin on Fri Jun 25 21:03:22 UTC 2021 , Edited by admin on Fri Jun 25 21:03:22 UTC 2021
EMA VETERINARY ASSESSMENT REPORTS SEMINTRA [AUTHORIZED]
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS TOLUCOMBI (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
WHO-VATC QC09CA07
Created by admin on Fri Jun 25 21:03:22 UTC 2021 , Edited by admin on Fri Jun 25 21:03:22 UTC 2021
EMA ASSESSMENT REPORTS ONDUARP (WITHDRAWN: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
WHO-ATC C09CA07
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
WHO-ATC C09DA07
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS PRITOR (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS KINZALMONO (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS TELMISARTAN TEVA PHARMA (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
NDF-RT N0000175561
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS TELMISARTAN TEVA (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS TWYNSTA (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS MICARDISPLUS (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
NDF-RT N0000000070
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS MICARDIS (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
EMA ASSESSMENT REPORTS PRITORPLUS (AUTHORIZED: HYPERTENSION)
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
Code System Code Type Description
MESH
C084178
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
WIKIPEDIA
TELMISARTAN
Created by admin on Fri Jun 25 21:03:22 UTC 2021 , Edited by admin on Fri Jun 25 21:03:22 UTC 2021
PRIMARY
LACTMED
Telmisartan
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
IUPHAR
592
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
MERCK INDEX
M10541
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1017
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
DRUG CENTRAL
2583
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
USP_CATALOG
1643419
Created by admin on Fri Jun 25 21:03:22 UTC 2021 , Edited by admin on Fri Jun 25 21:03:22 UTC 2021
PRIMARY USP-RS
PUBCHEM
65999
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
DRUG BANK
DB00966
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
CAS
144701-48-4
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
RXCUI
73494
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY RxNorm
FDA UNII
U5SYW473RQ
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
EVMPD
SUB10874MIG
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
EPA CompTox
144701-48-4
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
NCI_THESAURUS
C47746
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
HSDB
7590
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
INN
7144
Created by admin on Fri Jun 25 21:03:21 UTC 2021 , Edited by admin on Fri Jun 25 21:03:21 UTC 2021
PRIMARY
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