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 8297	49.5 µM [IC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB00966	Partial Agonist 290	12.2 µM [IC50]
Type-1 angiotensin II receptor 40 Target ID: CHEMBL227 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf	Antagonist 2778	3.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf	Primary		Approved 8429	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 1998
Cardiovascular diseases 71 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf	Preventing		Approved 8429	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 1998

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
[Angiotensin receptor blockers--significance for the therapy of hypertension].	2001	11450162
The comparative pharmacology of angiotensin II receptor antagonists.	2001	11333013
Angiotensin II receptor antagonists: new paradigms in the treatment of hypertension. Introduction.	2001	11333012
Ambulatory blood pressure monitoring to assess the comparative efficacy and duration of action of a novel new angiotensin II receptor blocker--telmisartan.	2001	11333011
Expanded role for ARBs in cardiovascular and renal disease? Recent observations have far-reaching implications.	2001 Apr	11317462
Mild-to-moderate uncomplicated hypertension: further analysis of a cost-effectiveness study of five drugs.	2001 Jul	11481819
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
Effects of telmisartan, hydrochlorothiazide and their combination on blood pressure and renal excretory parameters in spontaneously hypertensive rats.	2001 Jun	11881111
Telmisartan plus hydrochlorothiazide versus telmisartan or hydrochlorothiazide monotherapy in patients with mild to moderate hypertension: a multicenter, randomized, double-blind, placebo-controlled, parallel-group trial.	2001 Jun	11440284
Comparative antihypertensive and renoprotective effects of telmisartan and lisinopril after long-term treatment in hypertensive diabetic rats.	2001 Mar	11881063
Effects of telmisartan on renal excretory function in conscious dogs.	2001 Mar-Apr	11393346
Efficacy and tolerability of a fixed-dose combination of telmisartan plus hydrochlorothiazide in patients uncontrolled with telmisartan monotherapy.	2001 Nov	11687919
pK(a) determination of angiotensin II receptor antagonists (ARA II) by spectrofluorimetry.	2001 Oct	11489393
[Angiotensin II receptor blocker telmisartan: effect on 24-hour blood pressure profile and left ventricular hypertrophy in patients with hypertension].	2002	12494207
[Hypotensive effects of telmisartan on blood pressure during rest and exercise in patients with mild and moderate arterial hypertension].	2002	12474774
Long-term efficacy and tolerability of telmisartan as monotherapy and in combination with other antihypertensive medications.	2002	12458653
Telmisartan. BIBR 277, Micardis, Pritor.	2002	12455201
Long-term exposure to telmisartan as monotherapy or combination therapy: efficacy and safety.	2002	12126264
Can angiotensin receptor antagonists be used safely in patients with previous ACE inhibitor-induced angioedema?	2002	11888349
Gateways to clinical trials.	2002 Dec	12616965
Optimization and validation of a capillary zone electrophoretic method for the analysis of several angiotensin-II-receptor antagonists.	2002 Dec 6	12498264
Application of capillary zone electrophoresis to the screening of some angiotensin II receptor antagonists.	2002 Jan	11840527
[Coronary heart disease patient with hypertension. Dangerously increased blood pressure despite gigantic therapy arsenal].	2002 Jan 24	11862803
The 24-hour blood pressure pattern: does it have implications for morbidity and mortality?	2002 Jan 24	11835909
A new fixed-dose combination for added blood pressure control: telmisartan plus hydrochlorothiazide.	2002 Jul-Aug	12235918
Comparison of telmisartan vs. valsartan in the treatment of mild to moderate hypertension using ambulatory blood pressure monitoring.	2002 Jul-Aug	12147926
Angiotensin II receptor antagonists role in arterial hypertension.	2002 Mar	11986904
Comparison of a fixed-dose combination of 40 mg telmisartan plus 12.5 mg hydrochlorothiazide with 40 mg telmisartan in the control of mild to moderate hypertension.	2002 Mar-Apr	11897925
Gateways to clinical trials.	2002 May	12092009
[Irbesartan: a new possibility in the treatment of hypertension].	2002 May 26	12073539
Rationale and design of diabetics exposed to telmisartan and enalapril (DETAIL) study.	2002 May-Jun	12015188
Angiotensin blockade prevents type 2 diabetes by formation of fat cells.	2002 Nov	12411451
Amlodipine versus Angiotensin-receptor blockers for nonhypertension indications.	2002 Nov	12398574
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	12462282
[Tendency and prospect of the development of new ARBs].	2002 Oct	12397678
The efficacy and tolerability of an angiotensin II receptor blocker, telmisartan, in Thai patients with mild to moderate essential hypertension.	2002 Sep	12450074
Sympatholytic properties of several AT1-receptor antagonists in the isolated rabbit thoracic aorta.	2002 Sep	12195125
In vitro and in vivo characterization of the activity of telmisartan: an insurmountable angiotensin II receptor antagonist.	2002 Sep	12183667
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
Angiotensin-converting enzyme inhibitors for stroke prevention: is there HOPE for PROGRESS After LIFE?	2003 Feb	12574534
Simultaneous determination of hydrochlorothiazide and several angiotensin-II-receptor antagonists by capillary electrophoresis.	2003 Feb 26	12609672
Optimization and validation of a micellar electrokinetic chromatographic method for the analysis of several angiotensin-II-receptor antagonists.	2003 Jan 10	12564683
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	12817175
Different effect of antihypertensive drugs on conduit artery endothelial function.	2003 Jun	12719441
[Improved protection of heart and kidneys in the hypertensive patient. ACE inhibitor and AT1 blocker combined?].	2003 Jun 5	12854231
Angioedema induced by angiotensin II blocker telmisartan.	2003 May	12752339
How cost-effective are new preventive strategies for cardiovascular disease?	2003 May 22	12781905
[Effects of angiotensin receptor inhibitors on cardiovascular endpoints--current and future evidence].	2003 May 4	12785235
[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 15 15:33:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:33:44 GMT 2023`
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