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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:14:34 UTC
HMDB IDHMDB0015101
Secondary Accession Numbers
  • HMDB15101
Metabolite Identification
Common NameTelmisartan
DescriptionTelmisartan 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
ValueSource
4'-((1,4'-Dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl)methyl)-(1,1'-biphenyl)-2-carboxylic acidChEBI
4'-((4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylic acidChEBI
4'-[(1,4'-Dimethyl-2'propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic acidChEBI
4'-[(1,7'-Dimethyl-2'-propyl-1H,3'H-2,5'-bibenzimidazol-3'-yl)methyl]biphenyl-2-carboxylic acidChEBI
BIBR 277ChEBI
MicardisChEBI
4'-((1,4'-Dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl)methyl)-(1,1'-biphenyl)-2-carboxylateGenerator
4'-((4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylateGenerator
4'-[(1,4'-Dimethyl-2'propyl[2,6'-bi-1H-benzimidazol]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylateGenerator
4'-[(1,7'-Dimethyl-2'-propyl-1H,3'H-2,5'-bibenzimidazol-3'-yl)methyl]biphenyl-2-carboxylateGenerator
BIBR 277SeHMDB
PritorMeSH
BIBR-277MeSH
Chemical FormulaC33H30N4O2
Average Molecular Weight514.6169
Monoisotopic Molecular Weight514.236876224
IUPAC Name2-(4-{[4-methyl-6-(1-methyl-1H-1,3-benzodiazol-2-yl)-2-propyl-1H-1,3-benzodiazol-1-yl]methyl}phenyl)benzoic acid
Traditional Nametelmisartan
CAS Registry Number144701-48-4
SMILES
CCCC1=NC2=C(C=C(C=C2C)C2=NC3=CC=CC=C3N2C)N1CC1=CC=C(C=C1)C1=CC=CC=C1C(O)=O
InChI Identifier
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 KeyRMMXLENWKUUMAY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Benzimidazole
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • N-substituted imidazole
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point261 - 263 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0035 g/LNot Available
LogP7.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0035 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity164.49 m³·mol⁻¹ChemAxon
Polarizability58.61 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1391600000-b7b1d6d3189b5d2dfc57View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-5381490000-c37e35b281270dd6eedbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0020390000-96e1851c27d6f6e79183View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0000090000-219191b231632ae82938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0002490000-d9a86d68a321494f4172View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00li-0095500000-433f75bf696d30339ffeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0093100000-d1a212009af2d2b6d576View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-0093000000-dc77c406187bdc1b4750View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0000900000-2da316f976108d0ab57aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0000090000-fa13ab012f6c3edda644View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0fri-0094500000-fc4e746d5acf7c28974bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0093000000-739535a2fb80154ac329View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0093000000-7b45a183400fc2d5c56eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0079-0090000000-f2b72bb436b094188b4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0000090000-4193d926fb43b7e7650aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00ri-0090400000-4c927fd317a9c571c8c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0094000000-a362fb77a1bf330b4d4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0f79-0095000000-c9574b21fc223d1415ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000i-0090000000-0d0b0eddab1ab829b1c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-95cf0efe8a365f6e1b11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0000900000-3c8f5cf8f5d9a897d72dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0001790000-123c9048f032a4eb3562View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0002920000-85bfad8eb848e0c25b30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-3404900000-06f75fcbbe3bd8d84a55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000490000-a739d296c35c2238898eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0000940000-bc1ede93fed547acb308View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-1863900000-efee3f29c696a7b0d77bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00966 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00966 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00966
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID59391
KEGG Compound IDC07710
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTelmisartan
METLIN IDNot Available
PubChem Compound65999
PDB IDTLS
ChEBI ID9434
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':http://www.ncbi.nlm.nih.gov/pubmed/20502601
Material Safety Data Sheet (MSDS)Not Available
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. 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 ]
  3. 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 ]
  4. 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 ]

Enzymes

General function:
Involved in monooxygenase 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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Molecular weight:
41060.5
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 ]
General function:
Involved in DNA binding
Specific function:
Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular weight:
57619.6
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 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular weight:
174205.6
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 ]
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
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 ]
General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5
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 ]