Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C33H29N4O2.Na |
| Molecular Weight | 536.5987 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].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=RSGAIWOEJXRYRV-UHFFFAOYSA-M
InChI=1S/C33H30N4O2.Na/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);/q;+1/p-1
DescriptionSources: http://www.drugbank.ca/drugs/DB00966Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020850s032lbl.pdf
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).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map00590 |
49.5 µM [IC50] | ||
Target ID: CHEMBL235 Sources: http://www.drugbank.ca/drugs/DB00966 |
12.2 µM [IC50] | ||
Target ID: CHEMBL227 |
3.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | MICARDIS Approved UseMICARDIS is an angiotensin II receptor blocker (ARB) indicated for:
• Treatment of hypertension
• Cardiovascular (CV) risk reduction in patients unable to take ACE inhibitors Launch Date1998 |
|||
| Preventing | MICARDIS Approved UseMICARDIS is an angiotensin II receptor blocker (ARB) indicated for:
• Treatment of hypertension
• Cardiovascular (CV) risk reduction in patients unable to take ACE inhibitors Launch Date1998 |
Cmax
| 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 |
T1/2
| 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: 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 Sources: Page: p.1Hypotension |
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: 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
| Title | Date | PubMed |
|---|---|---|
| [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 |
|
| 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 |
|
| [Therapy of hypertension. Pulse pressure must also be reduced]. | 2003 May 1 |
|
| [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 |
Sample Use Guides
Hypertension - 40 to 80 mg once daily
Cardiovascular Risk Reduction - 80 mg once daily
Route of Administration:
Oral
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DTXSID50199539
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K15TQY55Q7
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23677803
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515815-47-1
Created by
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SUBSTANCE RECORD
