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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:37 UTC
HMDB IDHMDB0014420
Secondary Accession Numbers
  • HMDB14420
Metabolite Identification
Common NameOlmesartan
DescriptionOlmesartan, also known as DE-092, 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. In humans, olmesartan is involved in the olmesartan action pathway. Olmesartan is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Olmesartan.
Structure
Data?1582753177
Synonyms
ValueSource
4-(1-Hydroxy-1-methylethyl)-2-propyl-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acidChEBI
4-(Hydroxy-1-methylethyl)-2-propyl-1-{[2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acidChEBI
4-(1-Hydroxy-1-methylethyl)-2-propyl-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylateGenerator
4-(Hydroxy-1-methylethyl)-2-propyl-1-{[2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylateGenerator
DE-092HMDB
Olmesartan medoximilHMDB
Olmesartan medoxomilHMDB
OmesartanHMDB
4-(Hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl)-1H-imidazole-5-carboxylic acidHMDB
Chemical FormulaC24H26N6O3
Average Molecular Weight446.5016
Monoisotopic Molecular Weight446.206638728
IUPAC Name4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylic acid
Traditional Nameolmesartan
CAS Registry Number144689-63-4
SMILES
CCCC1=NC(=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1)C(O)=O)C(C)(C)O
InChI Identifier
InChI=1S/C24H26N6O3/c1-4-7-19-25-21(24(2,3)33)20(23(31)32)30(19)14-15-10-12-16(13-11-15)17-8-5-6-9-18(17)22-26-28-29-27-22/h5-6,8-13,33H,4,7,14H2,1-3H3,(H,31,32)(H,26,27,28,29)
InChI KeyVTRAEEWXHOVJFV-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Phenyltetrazole
  • 1,2,4,5-tetrasubstituted imidazole
  • Imidazole-4-carbonyl group
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tertiary alcohol
  • Tetrazole
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175 - 180 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.01 g/LNot Available
LogP5.9Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP2.98ALOGPS
logP2.14ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)0.91ChemAxon
pKa (Strongest Basic)5.57ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area129.81 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity137.32 m³·mol⁻¹ChemAxon
Polarizability47.46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available201.00531661259
DarkChem[M-H]-PredictedNot Available204.2431661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Olmesartan,1TMS,#13708.6226https://arxiv.org/abs/1905.12712
Olmesartan,1TMS,#23746.723https://arxiv.org/abs/1905.12712
Olmesartan,1TMS,#33862.583https://arxiv.org/abs/1905.12712
Olmesartan,2TMS,#13684.3345https://arxiv.org/abs/1905.12712
Olmesartan,2TMS,#23824.444https://arxiv.org/abs/1905.12712
Olmesartan,2TMS,#33838.385https://arxiv.org/abs/1905.12712
Olmesartan,1TBDMS,#13912.133https://arxiv.org/abs/1905.12712
Olmesartan,1TBDMS,#23943.2021https://arxiv.org/abs/1905.12712
Olmesartan,1TBDMS,#34041.1135https://arxiv.org/abs/1905.12712
Olmesartan,2TBDMS,#14012.6128https://arxiv.org/abs/1905.12712
Olmesartan,2TBDMS,#24154.1445https://arxiv.org/abs/1905.12712
Olmesartan,2TBDMS,#34193.351https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-003i-3062900000-66da1fa4f726bf91355c2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-1000090000-53c6343e73cdd95381622017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a6r-0692700000-11f020dfbb889ac85e4e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a6r-0692700000-11f020dfbb889ac85e4e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0uxs-0401900000-cd5b861ab18adf045ab02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-0390100000-54b0de6532b2a6606a522021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0010900000-7248e647ec2c980aaf5f2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-0173900000-939a2f46d78608eb934c2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-6290000000-5391e796fbd1525a89622017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0113900000-aad428450b97d41a976f2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0wml-0739700000-8723aec4a7e22bb975e62017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbd-1911000000-8ea914bbddbfc4679a392017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0010900000-8fdf38f12572465f17612021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0550-0293200000-05222f637eae756fc82d2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0590000000-56c8def2e6618cb2cf2c2021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00275 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00275 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00275
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID139674
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOlmesartan
METLIN IDNot Available
PubChem Compound158781
PDB IDNot Available
ChEBI ID48416
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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. Koike H, Sada T, Mizuno M: In vitro and in vivo pharmacology of olmesartan medoxomil, an angiotensin II type AT1 receptor antagonist. J Hypertens Suppl. 2001 Jun;19(1):S3-14. [PubMed:11451212 ]
  3. Ochiai K, Hu Q, Lee J, Mansoor A, Liu J, Wang X, Gong G, Murakami Y, Ishibashi Y, Shimada T, Zhang J: Functional and bioenergetic consequences of AT1 antagonist olmesartan medoxomil in hearts with postinfarction LV remodeling. J Cardiovasc Pharmacol. 2006 May;47(5):686-94. [PubMed:16775509 ]
  4. Warner GT, Jarvis B: Olmesartan medoxomil. Drugs. 2002;62(9):1345-53; discussion 1354-6. [PubMed:12076183 ]
  5. Mire DE, Silfani TN, Pugsley MK: A review of the structural and functional features of olmesartan medoxomil, an angiotensin receptor blocker. J Cardiovasc Pharmacol. 2005 Nov;46(5):585-93. [PubMed:16220064 ]
  6. Kreutz R, Bolbrinker J, Huber M: Pharmacokinetics of olmesartan medoxomil plus hydrochlorothiazide combination in healthy subjects. Clin Drug Investig. 2006;26(1):29-34. [PubMed:17163232 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular weight:
77402.2
References
  1. Nakagomi-Hagihara R, Nakai D, Kawai K, Yoshigae Y, Tokui T, Abe T, Ikeda T: OATP1B1, OATP1B3, and mrp2 are involved in hepatobiliary transport of olmesartan, a novel angiotensin II blocker. Drug Metab Dispos. 2006 May;34(5):862-9. Epub 2006 Feb 24. [PubMed:16501004 ]
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Nakagomi-Hagihara R, Nakai D, Kawai K, Yoshigae Y, Tokui T, Abe T, Ikeda T: OATP1B1, OATP1B3, and mrp2 are involved in hepatobiliary transport of olmesartan, a novel angiotensin II blocker. Drug Metab Dispos. 2006 May;34(5):862-9. Epub 2006 Feb 24. [PubMed:16501004 ]
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 ]
  2. Nakagomi-Hagihara R, Nakai D, Kawai K, Yoshigae Y, Tokui T, Abe T, Ikeda T: OATP1B1, OATP1B3, and mrp2 are involved in hepatobiliary transport of olmesartan, a novel angiotensin II blocker. Drug Metab Dispos. 2006 May;34(5):862-9. Epub 2006 Feb 24. [PubMed:16501004 ]