TELMISARTAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C33H30N4O2
Molecular Weight	514.6169
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC1=NC2=C(C)C=C(C=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C(O)=O)C5=NC6=C(C=CC=C6)N5C

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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00966
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).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Arachidonic acid metabolism 5 Target ID: map00590 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26632190	Inhibitor 8146	49.5 µM [IC50]
Peroxisome proliferator-activated receptor gamma 106 Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB00966	Partial Agonist 283	12.2 µM [IC50]
Type-1 angiotensin II receptor 39 Target ID: CHEMBL227 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf	Antagonist 2737	3.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 546 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf	Primary		Approved 8307	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
Cardiovascular diseases 71 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf	Preventing		Approved 8307	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

C_max

Value	Dose	Co-administered	Analyte	Population
3200 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11014323	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

Value	Dose	Co-administered	Analyte	Population
3320 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11014323	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
17.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/11014323	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

Dose	Population	Adverse events
160 mg single, intravenous Highest studied dose Dose: 160 mg Route: intravenous Route: single Dose: 160 mg Sources: https://pubmed.ncbi.nlm.nih.gov/11014323 Page: p.159	healthy, 18 – 50 n = 12 Health Status: healthy Age Group: 18 – 50 Sex: M Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/11014323 Page: p.159	Sources: https://pubmed.ncbi.nlm.nih.gov/11014323 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: https://pubmed.ncbi.nlm.nih.gov/11014323 Page: p.161	healthy, 18 – 50 n = 10 Health Status: healthy Age Group: 18 – 50 Sex: M Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/11014323 Page: p.161	Sources: https://pubmed.ncbi.nlm.nih.gov/11014323 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Hypertension\|Cardiovascular Risk Reduction Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf Page: p.1	Disc. AE: Disorder fetal, Hypotension... AEs leading to discontinuation/dose reduction: Disorder fetal Hypotension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Hypertension\|Cardiovascular Risk Reduction Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Hypertension\|Cardiovascular Risk Reduction Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf Page: p.1

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9434	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9434
ChemicalBook	CB4266172	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4266172
MolPort	MolPort-003-666-621	https://www.molport.com/shop/molecule-link/MolPort-003-666-621
Selleck Chemicals	Telmisartan(Micardis)	http://www.selleckchem.com/products/Telmisartan(Micardis).html
ZINC	ZINC000001530886	http://zinc15.docking.org/substances/ZINC000001530886
eMolecules	2725948	https://www.emolecules.com/cgi-bin/more?vid=2725948

PubMed

Title	Date	PubMed
Use of ambulatory blood pressure monitoring to evaluate the selective angiotensin II receptor antagonist, telmisartan, and other antihypertensive drugs.	2000	10904241
[Angiotensin receptor blockers--significance for the therapy of hypertension].	2001	11450162
Ambulatory blood pressure monitoring to assess the comparative efficacy and duration of action of a novel new angiotensin II receptor blocker--telmisartan.	2001	11333011
The role of angiotensin II receptor antagonists in the management of diabetes.	2001	11333010
Renal effects of angiotensin II receptor antagonists.	2001	11333009
Study at up to 700 sites will build on landmark HOPE trial.	2001 Apr-May	11474703
Combination treatment with telmisartan and hydrochlorothiazide in black patients with mild to moderate hypertension.	2001 Jan	11195609
Effect of telmisartan on angiotensin II-mediated collagen gel contraction by adult rat cardiac fibroblasts.	2001 Jul	11444501
AT1 receptor antagonist telmisartan administered peripherally inhibits central responses to angiotensin II in conscious rats.	2001 Jul	11408526
Comparative antihypertensive and renoprotective effects of telmisartan and lisinopril after long-term treatment in hypertensive diabetic rats.	2001 Mar	11881063
[Hypotensive effects of telmisartan on blood pressure during rest and exercise in patients with mild and moderate arterial hypertension].	2002	12474774
Telmisartan. BIBR 277, Micardis, Pritor.	2002	12455201
Can angiotensin receptor antagonists be used safely in patients with previous ACE inhibitor-induced angioedema?	2002	11888349
Gateways to clinical trials.	2002 Dec	12616965
The 24-hour blood pressure pattern: does it have implications for morbidity and mortality?	2002 Jan 24	11835909
From the HOPE to the ONTARGET and the TRANSCEND studies: challenges in improving prognosis.	2002 Jan 24	11835907
Angiotensin II and trials of cardiovascular outcomes.	2002 Jan 24	11835905
Comparative effects of telmisartan in the treatment of hypertension.	2002 Jul-Aug	12147925
Search of antimicrobial activity of selected non-antibiotic drugs.	2002 Nov-Dec	12669766
A multicenter, open-label study of the efficacy and safety of telmisartan in mild to moderate hypertensive patients.	2002 Oct	12426643
The efficacy and tolerability of an angiotensin II receptor blocker, telmisartan, in Thai patients with mild to moderate essential hypertension.	2002 Sep	12450074
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	12899971
Simultaneous determination of hydrochlorothiazide and several angiotensin-II-receptor antagonists by capillary electrophoresis.	2003 Feb 26	12609672
Angiotensin II receptor blockade: is there truly a benefit of adding an ACE inhibitor?	2003 Jan	12511526
Comparison of telmisartan versus losartan: meta-analysis of titration-to-response studies.	2003 Jun	12900588
Angioedema induced by angiotensin II blocker telmisartan.	2003 May	12752339
How cost-effective are new preventive strategies for cardiovascular disease?	2003 May 22	12781905
[Diurnal blood pressure control in the optimal treatment of hypertension].	2003 May 4	12785233

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 `Fri Dec 16 17:27:16 UTC 2022` Edited by `admin` on `Fri Dec 16 17:27:16 UTC 2022`
Record UNII	U5SYW473RQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TELMISARTAN

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

TELMISARTAN [EP IMPURITY]

Common Name

English

BIBR-277

Code

English

TELMISARTAN [GREEN BOOK]

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

NBK548042