Identification

Name
Telmisartan
Accession Number
DB00966  (APRD01247)
Type
Small Molecule
Groups
Approved, Investigational
Description

Telmisartan is an angiotensin II receptor antagonist (ARB) used in the management of hypertension. Generally, angiotensin II receptor blockers (ARBs) such as telmisartan bind to the angiotensin II type 1 (AT1) receptors with high affinity, causing inhibition of the action of angiotensin II on vascular smooth muscle, ultimately leading to a reduction in arterial blood pressure. Recent studies suggest that telmisartan may also have PPAR-gamma agonistic properties that could potentially confer beneficial metabolic effects.

Structure
Thumb
Synonyms
  • 4'-((1,4'-Dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl)methyl)-(1,1'-biphenyl)-2-carboxylic acid
  • 4'-((4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylic acid
  • 4'-[(1,4'-Dimethyl-2'propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic acid
  • 4'-[(1,7'-Dimethyl-2'-propyl-1H,3'h-2,5'-bibenzimidazol-3'-yl)methyl]biphenyl-2-carboxylic acid
  • BIBR 277
  • Telmisartan
External IDs
BIBR 277 / BIBR 277 SE / BIBR 277SE / BIBR-277 / C09CA07
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act TelmisartanTablet40 mgOralActavis Pharma Company2012-10-19Not applicableCanada
Act TelmisartanTablet80 mgOralActavis Pharma Company2012-10-19Not applicableCanada
KinzalmonoTablet40 mgOralBayer Ag1998-12-16Not applicableEu
KinzalmonoTablet80 mgOralBayer Ag1998-12-16Not applicableEu
KinzalmonoTablet20 mgOralBayer Ag1998-12-16Not applicableEu
KinzalmonoTablet20 mgOralBayer Ag1998-12-16Not applicableEu
KinzalmonoTablet80 mgOralBayer Ag1998-12-16Not applicableEu
KinzalmonoTablet40 mgOralBayer Ag1998-12-16Not applicableEu
KinzalmonoTablet40 mgOralBayer Ag1998-12-16Not applicableEu
KinzalmonoTablet80 mgOralBayer Ag1998-12-16Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-telmisartanTablet80 mgOralApotex Corporation2014-07-18Not applicableCanada
Apo-telmisartanTablet40 mgOralApotex Corporation2014-07-18Not applicableCanada
Auro-telmisartanTablet80 mgOralAuro Pharma Inc2016-04-08Not applicableCanada
Auro-telmisartanTablet40 mgOralAuro Pharma Inc2016-04-08Not applicableCanada
Mar-telmisartanTablet80 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Mar-telmisartanTablet40 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Mylan-telmisartanTablet80 mgOralMylan Pharmaceuticals2012-01-10Not applicableCanada
Mylan-telmisartanTablet40 mgOralMylan Pharmaceuticals2012-01-10Not applicableCanada
Ntp-telmisartanTablet40 mgOralTevaNot applicableNot applicableCanada
Ntp-telmisartanTablet80 mgOralTevaNot applicableNot applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ach-telmisartan HctzTelmisartan (80 mg) + Hydrochlorothiazide (25 mg)TabletOralAccord Healthcare Limited2014-05-27Not applicableCanada
Ach-telmisartan HctzTelmisartan (80 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAccord Healthcare Limited2014-05-27Not applicableCanada
Act Telmisartan/hctTelmisartan (80 mg) + Hydrochlorothiazide (12.5 mg)TabletOralActavis Pharma Company2012-10-02Not applicableCanada
Act Telmisartan/hctTelmisartan (80 mg) + Hydrochlorothiazide (25 mg)TabletOralActavis Pharma Company2012-10-02Not applicableCanada
Actelsar HCTTelmisartan (80 mg) + Hydrochlorothiazide (25 mg)TabletOralActavis Group Hf2013-03-13Not applicableEu
Actelsar HCTTelmisartan (80 mg) + Hydrochlorothiazide (12.5 mg)TabletOralActavis Group Hf2013-03-13Not applicableEu
Actelsar HCTTelmisartan (80 mg) + Hydrochlorothiazide (12.5 mg)TabletOralActavis Group Hf2013-03-13Not applicableEu
Actelsar HCTTelmisartan (40 mg) + Hydrochlorothiazide (12.5 mg)TabletOralActavis Group Hf2013-03-13Not applicableEu
Actelsar HCTTelmisartan (80 mg) + Hydrochlorothiazide (12.5 mg)TabletOralActavis Group Hf2013-03-13Not applicableEu
Actelsar HCTTelmisartan (80 mg) + Hydrochlorothiazide (25 mg)TabletOralActavis Group Hf2013-03-13Not applicableEu
International/Other Brands
Micardis / Pritor
Categories
UNII
U5SYW473RQ
CAS number
144701-48-4
Weight
Average: 514.6169
Monoisotopic: 514.236876224
Chemical Formula
C33H30N4O2
InChI Key
RMMXLENWKUUMAY-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-(4-{[4-methyl-6-(1-methyl-1H-1,3-benzodiazol-2-yl)-2-propyl-1H-1,3-benzodiazol-1-yl]methyl}phenyl)benzoic acid
SMILES
CCCC1=NC2=C(C=C(C=C2C)C2=NC3=CC=CC=C3N2C)N1CC1=CC=C(C=C1)C1=CC=CC=C1C(O)=O

Pharmacology

Indication

Used alone or in combination with other classes of antihypertensives for the treatment of hypertension. Also 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).

Associated Conditions
Pharmacodynamics

Telmisartan is an orally active nonpeptide angiotensin II antagonist that acts on the AT1 receptor subtype. 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.

Mechanism of action

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.

TargetActionsOrganism
AType-1 angiotensin II receptor
antagonist
Human
APeroxisome proliferator-activated receptor gamma
partial agonist
Human
Absorption

Absolute bioavailability depends on dosage. Food slightly decreases the bioavailability (a decrease of about 6% is seen when the 40-mg dose is administered with food).

Volume of distribution
  • 500 L
Protein binding

Highly bound to plasma proteins (>99.5%), mainly albumin and a1-acid glycoprotein. Binding is not dose-dependent.

Metabolism

Minimally metabolized by conjugation to form a pharmacologically inactive acylglucuronide; the glucuronide of the parent compound is the only metabolite that has been identified in human plasma and urine. The cytochrome P450 isoenzymes are not involved in the metabolism of telmisartan.

Route of elimination

Following either intravenous or oral administration of 14C-labeled telmisartan, most of the administered dose (>97%) was eliminated unchanged in feces via biliary excretion; only minute amounts were found in the urine (0.91% and 0.49% of total radioactivity, respectively).

Half life

Bi-exponential decay kinetics with a terminal elimination half-life of approximately 24 hours.

Clearance
  • >800 mL/min
Toxicity

Intravenous LD50 in rats is 150-200 mg/kg in males and 200 to 250 mg/kg in females. Acute oral toxicity is low: no deaths and no changes occurred in rats or dogs at 2000 mg/kg, the highest dose tested. Limited data are available with regard to overdosage in humans. The most likely manifestations of overdosage with telmisartan would be hypotension, dizziness and tachycardia; bradycardia could occur from parasympathetic (vagal) stimulation.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Telmisartan Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Telmisartan.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Telmisartan.
AbemaciclibTelmisartan may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Telmisartan.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Telmisartan is combined with Aceclofenac.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Telmisartan is combined with Acemetacin.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Telmisartan.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Telmisartan.
AcetyldigoxinThe serum concentration of Acetyldigoxin can be increased when it is combined with Telmisartan.
Acetylsalicylic acidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Telmisartan is combined with Acetylsalicylic acid.
Food Interactions
Not Available

References

Synthesis Reference

Kumar AS, Ghosh S, Mehta GN: Efficient and improved synthesis of Telmisartan. Beilstein J Org Chem. 2010 Mar 11;6:25. Pubmed.

General References
  1. Sharpe M, Jarvis B, Goa KL: Telmisartan: a review of its use in hypertension. Drugs. 2001;61(10):1501-29. [PubMed:11558835]
  2. Smith DH: 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. Clin Ther. 2002 Oct;24(10):1484-501. [PubMed:12462282]
  3. Kumar AS, Ghosh S, Mehta GN: Efficient and improved synthesis of Telmisartan. Beilstein J Org Chem. 2010 Mar 11;6:25. doi: 10.3762/bjoc.6.25. [PubMed:20502601]
  4. Galzerano D, Capogrosso C, Di Michele S, Galzerano A, Paparello P, Lama D, Gaudio C: New standards in hypertension and cardiovascular risk management: focus on telmisartan. Vasc Health Risk Manag. 2010 Mar 24;6:113-33. [PubMed:20448797]
External Links
Human Metabolome Database
HMDB0015101
KEGG Drug
D00627
KEGG Compound
C07710
PubChem Compound
65999
PubChem Substance
46505370
ChemSpider
59391
BindingDB
50043280
ChEBI
9434
ChEMBL
CHEMBL1017
Therapeutic Targets Database
DAP000766
PharmGKB
PA451605
IUPHAR
592
Guide to Pharmacology
GtP Drug Page
HET
TLS
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Telmisartan
ATC Codes
C09DB04 — Telmisartan and amlodipineC09DA07 — Telmisartan and diureticsC09CA07 — Telmisartan
AHFS Codes
  • 24:32.08 — Angiotensin Ii Receptor Antagonists
PDB Entries
3vn2
FDA label
Download (47.4 KB)
MSDS
Download (101 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedNot AvailableHigh Blood Pressure (Hypertension)1
1CompletedBasic ScienceHealthy Volunteers4
1CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
1CompletedSupportive CareHealthy Male Volunteers1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentDiseases of the Circulatory System / Hypertension,Essential1
1CompletedTreatmentHealthy Male Volunteers2
1CompletedTreatmentHealthy Volunteers32
1CompletedTreatmentHigh Blood Pressure (Hypertension)3
1CompletedTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias3
1CompletedTreatmentHyperlipidemias / Hypertension,Essential1
1CompletedTreatmentHypertension With Hyperlipidemia / Hypertention With Hyperlipidemia1
1CompletedTreatmentHypertension and Dyslipidemia1
1RecruitingNot AvailableAcute HIV Infection / Human Immunodeficiency Virus (HIV) Infections1
1RecruitingOtherHyperlipidemia, Hypertriglyceridemia1
1RecruitingPreventionAlzheimer's Disease (AD)1
1TerminatedTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias1
2Active Not RecruitingTreatmentAcute HIV Infection / HIV CNS Involvement1
2CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
2CompletedTreatmentBMI >30 kg/m2 / Insulin Resistance1
2CompletedTreatmentEndothelial Dysfunction1
2CompletedTreatmentHigh Blood Pressure (Hypertension)4
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I1
2CompletedTreatmentTransplant, Kidney1
2RecruitingTreatmentAlzheimer's Disease (AD) / High Blood Pressure (Hypertension)1
2, 3CompletedPreventionCoronary Artery Disease / Diabetes Mellitus (DM) / Heart Failure, Unspecified1
3CompletedBasic ScienceHigh Blood Pressure (Hypertension) / Hypertriglyceridemias / Metabolic Syndromes1
3CompletedDiagnosticMetabolic Syndromes1
3CompletedPreventionCardiac Diseases1
3CompletedPreventionHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
3CompletedTreatmentAcquired Kidney Disease / Children / Chronic Renal Failure (CRF) / Congenital Kidney Disease / High Blood Pressure (Hypertension)1
3CompletedTreatmentDiabetic Nephropathies1
3CompletedTreatmentDyslipidemia With Hypertension1
3CompletedTreatmentDyslipidemias / High Blood Pressure (Hypertension)2
3CompletedTreatmentHigh Blood Pressure (Hypertension)25
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias1
3CompletedTreatmentHypertension With Hyperlipidemia1
3CompletedTreatmentHypertension,Essential1
3CompletedTreatmentKidney, Polycystic2
3CompletedTreatmentMetabolic Syndromes1
3Not Yet RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
3Unknown StatusTreatmentHigh Blood Pressure (Hypertension) / Hyperlipidemias1
4CompletedNot AvailableHigh Blood Pressure (Hypertension)1
4CompletedPreventionCardiovascular Disease (CVD)1
4CompletedPreventionHigh Blood Pressure (Hypertension)1
4CompletedPreventionNonvalvular Atrial Fibrillation2
4CompletedPreventionStrokes1
4CompletedTreatmentAbdominal Aortic Aneurysms (AAA)1
4CompletedTreatmentBMI >30 kg/m2 / High Blood Pressure (Hypertension)1
4CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Hypertension,Essential / Strokes1
4CompletedTreatmentChronic Kidney Disease (CKD) / Proteinuria1
4CompletedTreatmentCongestive Heart Failure (CHF)1
4CompletedTreatmentCoronary Arteriosclerosis / High Blood Pressure (Hypertension)1
4CompletedTreatmentCoronary Artery Disease / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension)1
4CompletedTreatmentDiabetic Nephropathies1
4CompletedTreatmentDiabetic Nephropathies / High Blood Pressure (Hypertension)2
4CompletedTreatmentEnd-Stage Renal Disease (ESRD) / Inflammatory Reaction1
4CompletedTreatmentEssential Hypertension Complicated by Type 2 Diabetes Mellitus1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHigh Blood Pressure (Hypertension)17
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Impaired Glucose Tolerance (IGT)1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Metabolic Syndromes1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Other and unspecified effects of high altitude1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedTreatmentMetabolic Syndromes1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
4Not Yet RecruitingTreatmentChronic Kidney Disease (CKD) / Proteinuria1
4Not Yet RecruitingTreatmentDyslipidemias / High Blood Pressure (Hypertension)1
4RecruitingPreventionBlood Pressures / High Blood Pressure (Hypertension) / Strokes1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)3
4RecruitingTreatmentHypertension,Essential1
4RecruitingTreatmentMetabolic Syndromes1
4RecruitingTreatmentNonalcoholic Fatty Liver Disease (NAFLD)1
4TerminatedTreatmentArterial Hypertension / Diabetes Mellitus Type 2 IRC or NIR1
4TerminatedTreatmentCoronary Arteriosclerosis / High Blood Pressure (Hypertension)1
4TerminatedTreatmentHigh Blood Pressure (Hypertension)1
4Unknown StatusTreatmentAcute Coronary Syndromes (ACS) / Coronary Heart Disease (CHD) / Myocardial Infarction1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension)2
4Unknown StatusTreatmentHypertension,Essential1
4WithdrawnTreatmentDiabetic Nephropathy Type 21
Not AvailableCompletedNot AvailableArterial Hypertension1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)34
Not AvailableCompletedNot AvailableHypertension,Essential1
Not AvailableCompletedNot AvailableNeoplasms1
Not AvailableCompletedDiagnosticArterial Hypertension1
Not AvailableCompletedTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableRecruitingTreatmentGraft Versus Host Disease (GVHD)1
Not AvailableRecruitingTreatmentPeripheral Artery Disease (PAD)1
Not AvailableTerminatedPreventionAcute Coronary Syndromes (ACS) / Acute Myocardial Infarction (AMI) / Angina Pectoris / High Blood Pressure (Hypertension) / Myocardial Ischemia1
Not AvailableUnknown StatusTreatmentDyslipidemias / High Blood Pressure (Hypertension) / Insulin Resistance1
Not AvailableUnknown StatusTreatmentHigh Blood Pressure (Hypertension)1

Pharmacoeconomics

Manufacturers
  • Boehringer ingelheim
Packagers
  • A-S Medication Solutions LLC
  • Boehringer Ingelheim Ltd.
  • Lake Erie Medical and Surgical Supply
  • Physicians Total Care Inc.
Dosage forms
FormRouteStrength
TabletOral20 mg
TabletOral20 mg/1
TabletOral40 mg/1
TabletOral80 mg/1
TabletOral40 mg
TabletOral80 mg
TabletOral
Tablet, multilayerOral
Prices
Unit descriptionCostUnit
Micardis 30 40 mg tablet Box110.11USD box
Micardis HCT 30 40-12.5 mg tablet Box106.34USD box
Micardis HCT 30 80-12.5 mg tablet Box106.18USD box
Micardis 30 80 mg tablet Box103.92USD box
Micardis HCT 30 80-25 mg tablet Box100.48USD box
Micardis 30 20 mg tablet Box99.7USD box
Micardis 20 mg tablet3.29USD tablet
Micardis hct 40-12.5 mg tablet3.29USD tablet
Micardis hct 80-12.5 mg tablet3.29USD tablet
Micardis hct 80-25 mg tablet3.29USD tablet
Micardis 40 mg tablet2.24USD tablet
Micardis 80 mg tablet2.24USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5591762No1994-01-072014-01-07Us
CA2060624No1999-12-212012-02-04Canada
US6358986No2000-01-102020-01-10Us
US7998953No2000-06-062020-06-06Us
US8003679No2002-10-062022-10-06Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)261-263 °CNot Available
water solubilityPractically insolubleNot Available
logP7.7Not Available
Caco2 permeability-4.82ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0035 mg/mLALOGPS
logP6.66ALOGPS
logP6.04ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)6.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.94 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity164.49 m3·mol-1ChemAxon
Polarizability58.61 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8794
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.6061
P-glycoprotein inhibitor INon-inhibitor0.5261
P-glycoprotein inhibitor IIInhibitor0.8653
Renal organic cation transporterNon-inhibitor0.6047
CYP450 2C9 substrateNon-substrate0.7876
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5255
CYP450 1A2 substrateInhibitor0.5699
CYP450 2C9 inhibitorNon-inhibitor0.5481
CYP450 2D6 inhibitorNon-inhibitor0.7796
CYP450 2C19 inhibitorNon-inhibitor0.5509
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.601
Ames testNon AMES toxic0.6432
CarcinogenicityNon-carcinogens0.9094
BiodegradationNot ready biodegradable0.9862
Rat acute toxicity2.8075 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9166
hERG inhibition (predictor II)Non-inhibitor0.7114
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03di-0000090000-219191b231632ae82938
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03di-0002490000-d9a86d68a321494f4172
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00li-0095500000-433f75bf696d30339ffe
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-000i-0093100000-d1a212009af2d2b6d576
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-000i-0093000000-dc77c406187bdc1b4750
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0000900000-2da316f976108d0ab57a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0000090000-fa13ab012f6c3edda644
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0fri-0094500000-fc4e746d5acf7c28974b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0093000000-739535a2fb80154ac329
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0093000000-7b45a183400fc2d5c56e
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0079-0090000000-f2b72bb436b094188b4b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0000090000-4193d926fb43b7e7650a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00ri-0090400000-4c927fd317a9c571c8c1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0094000000-a362fb77a1bf330b4d4b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0f79-0095000000-c9574b21fc223d1415ff
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0090000000-0d0b0eddab1ab829b1c1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0090000000-95cf0efe8a365f6e1b11
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-0000900000-3c8f5cf8f5d9a897d72d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01p9-0093450000-1dd7fd500cf0b3c0dc32
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0000090000-d2b14455bf61ea4f82a1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0000090000-6187f6c1620a7c2b51b1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0000090000-dc95af971f11219cb750
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014j-0000690000-92f9c219585dd2f6abdd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-002b-0091820000-b4160c5238973be1326b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0000900000-81da14e51168bd40dbc8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0000090000-e488353a2ab5a5ca95c8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0000090000-45ac38d5e068041afc7f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0051930000-355f3efe4c799be31eee
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0091000000-0119ca397b44d63c12e1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0190000000-c8f628b5d1752b565720
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03fr-0290000000-e1a994dd22ac9af9bd71
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0000090000-79a32c207900b92a8001
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0000090000-522439ae25d7e43446e5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-002b-0061930000-355af521f837490feefd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0091000000-28e6d3e6afd2cee22baf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0190000000-24d6dc729edb2e402cb5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03fr-0290000000-8ed1014ce3c441c09502
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0000900000-683d2b1a6727533bf2cc
MS/MS Spectrum - ESI-QTOF , positiveLC-MS/MSsplash10-014j-0000690000-e5484f50567b0ed1d402
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0011390000-909e49aea97bff3f66e6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0bt9-2596000000-b809729f5d533c915b79
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0020390000-96e1851c27d6f6e79183
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0bt9-0289000000-899a015c97aa18e79eb5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-06vi-3892000000-408ee10cb09fe63e849e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-016s-1493650000-7139ff8e100efd8f486c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-016r-0081290000-363d23081a66306a3f9e

Taxonomy

Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Benzoic acids / Benzimidazoles / Benzoyl derivatives / N-substituted imidazoles / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
show 3 more
Substituents
Biphenyl / Benzimidazole / Benzoic acid or derivatives / Benzoic acid / Benzoyl / N-substituted imidazole / Imidazole / Azole / Heteroaromatic compound / Azacycle
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
biphenyls, benzimidazoles (CHEBI:9434)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.
Gene Name
AGTR1
Uniprot ID
P30556
Uniprot Name
Type-1 angiotensin II receptor
Molecular Weight
41060.53 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Karlberg BE, Lins LE, Hermansson K: Efficacy and safety of telmisartan, a selective AT1 receptor antagonist, compared with enalapril in elderly patients with primary hypertension. TEES Study Group. J Hypertens. 1999 Feb;17(2):293-302. [PubMed:10067800]
  3. Balt JC, Mathy MJ, Nap A, Pfaffendorf M, van Zwieten PA: Effect of the AT1-receptor antagonists losartan, irbesartan, and telmisartan on angiotensin II-induced facilitation of sympathetic neurotransmission in the rat mesenteric artery. J Cardiovasc Pharmacol. 2001 Jul;38(1):141-8. [PubMed:11444497]
  4. Gohlke P, Weiss S, Jansen A, Wienen W, Stangier J, Rascher W, Culman J, Unger T: AT1 receptor antagonist telmisartan administered peripherally inhibits central responses to angiotensin II in conscious rats. J Pharmacol Exp Ther. 2001 Jul;298(1):62-70. [PubMed:11408526]
  5. Strohmenger HU, Lindner KH, Wienen W, Vogt J: Effects of the AT1-selective angiotensin II antagonist, telmisartan, on hemodynamics and ventricular function after cardiopulmonary resuscitation in pigs. Resuscitation. 1997 Aug;35(1):61-8. [PubMed:9259062]
  6. Fujimoto M, Masuzaki H, Tanaka T, Yasue S, Tomita T, Okazawa K, Fujikura J, Chusho H, Ebihara K, Hayashi T, Hosoda K, Nakao K: An angiotensin II AT1 receptor antagonist, telmisartan augments glucose uptake and GLUT4 protein expression in 3T3-L1 adipocytes. FEBS Lett. 2004 Oct 22;576(3):492-7. [PubMed:15498586]
  7. Sharpe M, Jarvis B, Goa KL: Telmisartan: a review of its use in hypertension. Drugs. 2001;61(10):1501-29. [PubMed:11558835]
  8. McClellan KJ, Markham A: Telmisartan. Drugs. 1998 Dec;56(6):1039-44; discussion 1045-6. [PubMed:9878991]
  9. Galzerano D, Capogrosso C, Di Michele S, Galzerano A, Paparello P, Lama D, Gaudio C: New standards in hypertension and cardiovascular risk management: focus on telmisartan. Vasc Health Risk Manag. 2010 Mar 24;6:113-33. [PubMed:20448797]
  10. Tagami T, Yamamoto H, Moriyama K, Sawai K, Usui T, Shimatsu A, Naruse M: A selective peroxisome proliferator-activated receptor-gamma modulator, telmisartan, binds to the receptor in a different fashion from thiazolidinediones. Endocrinology. 2009 Feb;150(2):862-70. doi: 10.1210/en.2008-0502. Epub 2009 Jan 15. [PubMed:19147680]
  11. Imayama I, Ichiki T, Inanaga K, Ohtsubo H, Fukuyama K, Ono H, Hashiguchi Y, Sunagawa K: Telmisartan downregulates angiotensin II type 1 receptor through activation of peroxisome proliferator-activated receptor gamma. Cardiovasc Res. 2006 Oct 1;72(1):184-90. Epub 2006 Jul 21. [PubMed:16938288]
  12. Kurtz TW: Beyond the classic angiotensin-receptor-blocker profile. Nat Clin Pract Cardiovasc Med. 2008 Jul;5 Suppl 1:S19-26. doi: 10.1038/ncpcardio0805. [PubMed:18580862]
  13. Yamagishi S, Takeuchi M: Telmisartan is a promising cardiometabolic sartan due to its unique PPAR-gamma-inducing property. Med Hypotheses. 2005;64(3):476-8. [PubMed:15617852]
  14. Yamagishi S, Nakamura K, Matsui T: Potential utility of telmisartan, an angiotensin II type 1 receptor blocker with peroxisome proliferator-activated receptor-gamma (PPAR-gamma)-modulating activity for the treatment of cardiometabolic disorders. Curr Mol Med. 2007 Aug;7(5):463-9. [PubMed:17691961]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Partial agonist
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Tagami T, Yamamoto H, Moriyama K, Sawai K, Usui T, Shimatsu A, Naruse M: A selective peroxisome proliferator-activated receptor-gamma modulator, telmisartan, binds to the receptor in a different fashion from thiazolidinediones. Endocrinology. 2009 Feb;150(2):862-70. doi: 10.1210/en.2008-0502. Epub 2009 Jan 15. [PubMed:19147680]
  2. Imayama I, Ichiki T, Inanaga K, Ohtsubo H, Fukuyama K, Ono H, Hashiguchi Y, Sunagawa K: Telmisartan downregulates angiotensin II type 1 receptor through activation of peroxisome proliferator-activated receptor gamma. Cardiovasc Res. 2006 Oct 1;72(1):184-90. Epub 2006 Jul 21. [PubMed:16938288]
  3. Kurtz TW: Beyond the classic angiotensin-receptor-blocker profile. Nat Clin Pract Cardiovasc Med. 2008 Jul;5 Suppl 1:S19-26. doi: 10.1038/ncpcardio0805. [PubMed:18580862]
  4. Yamagishi S, Takeuchi M: Telmisartan is a promising cardiometabolic sartan due to its unique PPAR-gamma-inducing property. Med Hypotheses. 2005;64(3):476-8. [PubMed:15617852]
  5. Kurtz TW: Treating the metabolic syndrome: telmisartan as a peroxisome proliferator-activated receptor-gamma activator. Acta Diabetol. 2005 Apr;42 Suppl 1:S9-16. [PubMed:15868121]
  6. Yamagishi S, Nakamura K, Matsui T: Potential utility of telmisartan, an angiotensin II type 1 receptor blocker with peroxisome proliferator-activated receptor-gamma (PPAR-gamma)-modulating activity for the treatment of cardiometabolic disorders. Curr Mol Med. 2007 Aug;7(5):463-9. [PubMed:17691961]
  7. Yamagishi S, Takenaka K, Inoue H: Role of insulin-sensitizing property of telmisartan, a commercially available angiotensin II type 1 receptor blocker in preventing the development of atrial fibrillation. Med Hypotheses. 2006;66(1):118-20. Epub 2005 Sep 12. [PubMed:16154710]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. telmisartan - Drug Summary [Link]
  3. CTEP.gov CYP2C19 document [File]
  4. EMA label, Telmisartan [File]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Weiss J, Sauer A, Divac N, Herzog M, Schwedhelm E, Boger RH, Haefeli WE, Benndorf RA: Interaction of angiotensin receptor type 1 blockers with ATP-binding cassette transporters. Biopharm Drug Dispos. 2010 Mar;31(2-3):150-61. doi: 10.1002/bdd.699. [PubMed:20222053]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Weiss J, Sauer A, Divac N, Herzog M, Schwedhelm E, Boger RH, Haefeli WE, Benndorf RA: Interaction of angiotensin receptor type 1 blockers with ATP-binding cassette transporters. Biopharm Drug Dispos. 2010 Mar;31(2-3):150-61. doi: 10.1002/bdd.699. [PubMed:20222053]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Weiss J, Sauer A, Divac N, Herzog M, Schwedhelm E, Boger RH, Haefeli WE, Benndorf RA: Interaction of angiotensin receptor type 1 blockers with ATP-binding cassette transporters. Biopharm Drug Dispos. 2010 Mar;31(2-3):150-61. doi: 10.1002/bdd.699. [PubMed:20222053]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on October 15, 2018 04:36