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Details

Stereochemistry ACHIRAL
Molecular Formula C33H30N4O2
Molecular Weight 514.6169
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TELMISARTAN

SMILES

CCCC1=NC2=C(C=C(C=C2C)C3=NC4=C(C=CC=C4)N3C)N1CC5=CC=C(C=C5)C6=CC=CC=C6C(O)=O

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 514.6169
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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).

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
[Angiotensin II receptor blocker telmisartan: effect on 24-hour blood pressure profile and left ventricular hypertrophy in patients with hypertension].
2002
[Hypotensive effects of telmisartan on blood pressure during rest and exercise in patients with mild and moderate arterial hypertension].
2002
Long-term efficacy and tolerability of telmisartan as monotherapy and in combination with other antihypertensive medications.
2002
Telmisartan. BIBR 277, Micardis, Pritor.
2002
Efficacy of eplerenone added to renin-angiotensin blockade in hypertensive patients.
2002 Aug
Gateways to clinical trials.
2002 Dec
Comparison of trough effect of telmisartan vs perindopril using self blood pressure measurement: EVERESTE study.
2002 Dec
Optimization and validation of a capillary zone electrophoretic method for the analysis of several angiotensin-II-receptor antagonists.
2002 Dec 6
[Evaluation of blood pressure self-monitoring of the residual efficacy of telmisartan compared to perindopril. The EVERESTE study].
2002 Jul-Aug
A new fixed-dose combination for added blood pressure control: telmisartan plus hydrochlorothiazide.
2002 Jul-Aug
Sympatho-inhibitory properties of various AT1 receptor antagonists.
2002 Jun
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
Treatment of hypertension with an angiotensin II-receptor antagonist compared with an angiotensin-converting enzyme inhibitor: a review of clinical studies of telmisartan and enalapril.
2002 Oct
A multicenter, open-label study of the efficacy and safety of telmisartan in mild to moderate hypertensive patients.
2002 Oct
[Tendency and prospect of the development of new ARBs].
2002 Oct
Effects of telmisartan on arterial stiffness in Type 2 diabetes patients with essential hypertension.
2002 Sep
Stimulation of collagen gel contraction by angiotensin II and III in cardiac fibroblasts.
2002 Sep
The efficacy and tolerability of an angiotensin II receptor blocker, telmisartan, in Thai patients with mild to moderate essential hypertension.
2002 Sep
Sympatholytic properties of several AT1-receptor antagonists in the isolated rabbit thoracic aorta.
2002 Sep
In vitro and in vivo characterization of the activity of telmisartan: an insurmountable angiotensin II receptor antagonist.
2002 Sep
Drug interactions with angiotensin receptor blockers: a comparison with other antihypertensives.
2003
Effects of telmisartan and losartan on left ventricular mass in mild-to-moderate hypertension. A randomized, double-blind trial.
2003
Neonatal acute renal failure secondary to maternal exposure to telmisartan, angiotensin II receptor antagonist.
2003 Apr-May
Telmisartan vs losartan plus hydrochlorothiazide in the treatment of mild-to-moderate essential hypertension--a randomised ABPM study.
2003 Aug
Experimental design approach for the optimisation of a HPLC-fluorimetric method for the quantitation of the angiotensin II receptor antagonist telmisartan in urine.
2003 Aug 8
Angiotensin-converting enzyme inhibitors for stroke prevention: is there HOPE for PROGRESS After LIFE?
2003 Feb
Simultaneous determination of hydrochlorothiazide and several angiotensin-II-receptor antagonists by capillary electrophoresis.
2003 Feb 26
Angiotensin II receptor blockade: is there truly a benefit of adding an ACE inhibitor?
2003 Jan
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of several angiotensin-II-receptor antagonists.
2003 Jan 10
[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
Prospective, randomized, open-label, blinded-endpoint (PROBE) designed trials yield the same results as double-blind, placebo-controlled trials with respect to ABPM measurements.
2003 Jul
Comparison of telmisartan versus losartan: meta-analysis of titration-to-response studies.
2003 Jun
Defining the antihypertensive properties of the angiotensin receptor blocker telmisartan by a practice-based clinical trial.
2003 Jun
Different effect of antihypertensive drugs on conduit artery endothelial function.
2003 Jun
Cardiology patient page. Angiotensin receptor blockers.
2003 Jun 24
[Improved protection of heart and kidneys in the hypertensive patient. ACE inhibitor and AT1 blocker combined?].
2003 Jun 5
Efficacy and tolerability of fixed-dose combinations of telmisartan plus HCTZ compared with losartan plus HCTZ in patients with essential hypertension.
2003 May
Angioedema induced by angiotensin II blocker telmisartan.
2003 May
[Morning or evening, in the physicians office or at home. Measured blood pressure values have their peculiarities].
2003 May 15
The ongoing telmisartan alone and in combination with ramipril global endpoint trial program.
2003 May 22
How cost-effective are new preventive strategies for cardiovascular disease?
2003 May 22
[Effects of angiotensin receptor inhibitors on cardiovascular endpoints--current and future evidence].
2003 May 4
[Diurnal blood pressure control in the optimal treatment of hypertension].
2003 May 4
Effect of telmisartan on the proteinuria and circadian blood pressure profile in chronic renal patients.
2003 May-Jun
Patents

Sample Use Guides

In Vivo Use Guide
Hypertension - 40 to 80 mg once daily Cardiovascular Risk Reduction - 80 mg once daily
Route of Administration: Oral
In Vitro Use Guide
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 Mon Oct 21 19:52:14 UTC 2019
Edited
by admin
on Mon Oct 21 19:52:14 UTC 2019
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 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
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 [USP]
Common 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 Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS TELMISARTAN ACTAVIS (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
WHO-VATC QC09DA07
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS KINZALKOMB (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
NCI_THESAURUS C66930
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS TOLURA (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
WHO-ATC C09DB04
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
WHO-VATC QC09DB04
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA VETERINARY ASSESSMENT REPORTS SEMINTRA [AUTHORIZED]
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS TOLUCOMBI (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
WHO-VATC QC09CA07
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS ONDUARP (WITHDRAWN: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
WHO-ATC C09CA07
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
WHO-ATC C09DA07
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS PRITOR (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS KINZALMONO (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS TELMISARTAN TEVA PHARMA (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
NDF-RT N0000175561
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS TELMISARTAN TEVA (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS TWYNSTA (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS MICARDISPLUS (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
NDF-RT N0000000070
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS MICARDIS (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
EMA ASSESSMENT REPORTS PRITORPLUS (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
Code System Code Type Description
MESH
C084178
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
WIKIPEDIA
TELMISARTAN
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
IUPHAR
592
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
MERCK INDEX
M10541
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL1017
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
PUBCHEM
65999
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
DRUG BANK
DB00966
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
CAS
144701-48-4
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
RXCUI
73494
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY RxNorm
EVMPD
SUB10874MIG
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
EPA CompTox
144701-48-4
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
NCI_THESAURUS
C47746
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
HSDB
144701-48-4
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
INN
7144
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
LactMed
144701-48-4
Created by admin on Mon Oct 21 19:52:14 UTC 2019 , Edited by admin on Mon Oct 21 19:52:14 UTC 2019
PRIMARY
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