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T8949

Telmisartan

≥98% (HPLC), AT1 angiotensin receptor antagonist, solid

Synonym(s):

4′[(1,4′-Dimethyl-2′-propyl[2,6′-bi-1H-benzimidazol]-1′-yl)methyl][1,1′-biphenyl]-2-carboxylic acid, BIBR 277

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About This Item

Empirical Formula (Hill Notation):
C33H30N4O2
CAS Number:
144701-48-4
Molecular Weight:
514.62
UNSPSC Code:
12352200
PubChem Substance ID:
329826889
NACRES:
NA.77
MDL number:
MFCD00918125
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
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Product Name

Telmisartan, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >5 mg/mL at 60 °C, H2O: insoluble

originator

Boehringer Ingelheim

SMILES string

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

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)

InChI key

RMMXLENWKUUMAY-UHFFFAOYSA-N

Gene Information

human ... AGTR1(185)

Application

Telmisartan has been used as an AT1 receptor antagonist to study its effects on mouse models of myocardial infarction. This study reported that telmisartan inhibited the CCN1 upregulation and reduced CCN2 levels atrial cardiomyocytes. Telmisartan has also been used to evaluate its effect on the expression of CCN1 in kidney cortex of mice subjected to myocardial infarction. Furthermore, telmisartan has been used to test its efficacy against tumor growth in mouse models of colorectal cancer.

Biochem/physiol Actions

Telmisartan is a non-peptide AT1 angiotensin receptor antagonist.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Angiotensin Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Boehringer Ingelheim. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Telmisartan is soluble in DMSO at a concentration that is greater than 5 mg/ml. It is insoluble in water.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000524766
0000524766
0000450906
0000450906
0000405737

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Marc P Maillard et al.
The Journal of pharmacology and experimental therapeutics, 302(3), 1089-1095 (2002-08-17)
In vitro studies have shown that telmisartan is an insurmountable angiotensin II subtype-1 (AT1) receptor antagonist. Herein, the molecular basis of this insurmountable antagonism has been investigated in vitro, and the effect of telmisartan has been compared in vivo with
Maurizio Cortada et al.
Audiology & neuro-otology, 25(6), 297-308 (2020-05-06)
Telmisartan is an angiotensin II receptor blocker that has pleiotropic effects and protective properties in different cell types. Moreover, telmisartan has also shown partial agonism on the peroxisome proliferator-activated receptor γ (PPAR-γ). Auditory hair cells (HCs) express PPAR-γ, and the
M Sharpe et al.
Drugs, 61(10), 1501-1529 (2001-09-18)
Telmisartan is an angiotensin II receptor antagonist that is highly selective for type 1 angiotensin II receptors. It was significantly more effective than placebo in large (n >100), double-blind, randomised, multicentre clinical trials in patients with mild to moderate hypertension.
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