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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014816
Secondary Accession Numbers
  • HMDB14816
Metabolite Identification
Common NameLosartan
DescriptionLosartan is an angiotensin-receptor blocker (ARB) that may be used alone or with other agents to treat hypertension. Losartan and its longer acting metabolite, E-3174, lower blood pressure by antagonizing the renin-angiotensin-aldosterone system (RAAS); they compete with angiotensin II for binding to the type-1 angiotensin II receptor (AT1) subtype and prevents the blood pressure increasing effects of angiotensin II. Unlike angiotensin-converting enzyme (ACE) inhibitors, ARBs do not have the adverse effect of dry cough. Losartan may be used to treat hypertension, isolated systolic hypertension, left ventricular hypertrophy and diabetic nephropathy. It may also be used as an alternative agent for the treatment of systolic dysfunction, myocardial infarction, coronary artery disease, and heart failure.
Structure
Data?1582753223
Synonyms
ValueSource
(2-Butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)methanolChEBI
2-N-Butyl-4-chloro-5-hydroxymethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]imidazoleChEBI
LosarticKegg
DUP 89HMDB
Losartan potassiumHMDB
DuP 753HMDB
Potassium, losartanHMDB
2-Butyl-4-chloro-1-((2'-(1H-etrazol-5-yl) (1,1'-biphenyl)-4-yl)methyl)-1H-imidazole-5-methanolHMDB
DuP-753HMDB
CozaarHMDB
Losartan monopotassium saltHMDB
Monopotassium salt, losartanHMDB
Salt, losartan monopotassiumHMDB
Chemical FormulaC22H23ClN6O
Average Molecular Weight422.911
Monoisotopic Molecular Weight422.162187095
IUPAC Name[2-butyl-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-5-yl]methanol
Traditional Namelosartan
CAS Registry Number114798-26-4
SMILES
CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1
InChI Identifier
InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)
InChI KeyPSIFNNKUMBGKDQ-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
  • Aryl chloride
  • Aryl halide
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Tetrazole
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic alcohol
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183.5 - 184.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0047 g/LNot Available
LogP6.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM200.330932474
[M+H]+Not Available199.228http://allccs.zhulab.cn/database/detail?ID=AllCCS00000749
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0047 g/LALOGPS
logP4.5ALOGPS
logP5.08ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)7.4ChemAxon
pKa (Strongest Basic)4.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.51 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity131.85 m³·mol⁻¹ChemAxon
Polarizability44.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+197.22230932474
DeepCCS[M-H]-194.84730932474
DeepCCS[M-2H]-229.15530932474
DeepCCS[M+Na]+204.88830932474
AllCCS[M+H]+201.532859911
AllCCS[M+H-H2O]+199.132859911
AllCCS[M+NH4]+203.832859911
AllCCS[M+Na]+204.432859911
AllCCS[M-H]-199.532859911
AllCCS[M+Na-2H]-199.732859911
AllCCS[M+HCOO]-200.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LosartanCCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N14513.0Standard polar33892256
LosartanCCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N13657.5Standard non polar33892256
LosartanCCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N13930.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Losartan,1TMS,isomer #1CCCCC1=NC(Cl)=C(CO[Si](C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=N[NH]N=N2)C=C13623.1Semi standard non polar33892256
Losartan,1TMS,isomer #2CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C13781.5Semi standard non polar33892256
Losartan,2TMS,isomer #1CCCCC1=NC(Cl)=C(CO[Si](C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C13785.9Semi standard non polar33892256
Losartan,2TMS,isomer #1CCCCC1=NC(Cl)=C(CO[Si](C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C13723.0Standard non polar33892256
Losartan,2TMS,isomer #1CCCCC1=NC(Cl)=C(CO[Si](C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C)N=N2)C=C14606.0Standard polar33892256
Losartan,1TBDMS,isomer #1CCCCC1=NC(Cl)=C(CO[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=N[NH]N=N2)C=C13792.0Semi standard non polar33892256
Losartan,1TBDMS,isomer #2CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C13906.6Semi standard non polar33892256
Losartan,2TBDMS,isomer #1CCCCC1=NC(Cl)=C(CO[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C14050.6Semi standard non polar33892256
Losartan,2TBDMS,isomer #1CCCCC1=NC(Cl)=C(CO[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C14171.2Standard non polar33892256
Losartan,2TBDMS,isomer #1CCCCC1=NC(Cl)=C(CO[Si](C)(C)C(C)(C)C)N1CC1=CC=C(C2=CC=CC=C2C2=NN([Si](C)(C)C(C)(C)C)N=N2)C=C14609.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Losartan GC-MS (Non-derivatized) - 70eV, Positivesplash10-002r-4089100000-3b72c4e0ebc46e6402a92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Losartan GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9002300000-8cb18ee6a14e321f81eb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Losartan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-00di-0000900000-657db16bb4bfe91841142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-056r-0900000000-43bb8508cd1dbc71bcee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-004i-0900000000-55368087829d113fdb7b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-004i-0900000000-af470646c547613f82a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-004i-0900000000-746dcf7a43a3f8839c1d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-004i-0900000000-0bee80f7ccbc4b68eee02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-004i-0900000000-d845ae166a10faff242a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-004i-2900000000-d39a309c02e1aaa956b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-004i-7900000000-d27d10ab008deb157e7a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-00fr-0900700000-fef78a7f52d4aa515bb42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , negative-QTOFsplash10-00fr-0900600000-c62f0db44e17f79e0c702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOFsplash10-0a4i-0034900000-22ba49ec64d374c8965e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOFsplash10-0a4i-0191000000-8ff1b5a21f6ef4a462cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOFsplash10-0a4i-0590000000-9841ff7f881c3e9c11b92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOFsplash10-0a59-0960000000-a24e287a018dae01dd0d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOFsplash10-0a5c-0930000000-ff3e675bd445225bf04e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOFsplash10-0pxu-0920000000-9adf4aef59fc1545fea62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOFsplash10-0v00-1900000000-3591888cf5831cbe3d112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Losartan LC-ESI-QFT , positive-QTOFsplash10-0wmi-2900000000-ab9304c8cebc201d01782017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Losartan 10V, Positive-QTOFsplash10-05fr-0021900000-2c231055acd0a8f296d32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Losartan 20V, Positive-QTOFsplash10-052r-0195400000-b093eaecc05008eba3de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Losartan 40V, Positive-QTOFsplash10-01p9-8392000000-dc1eae529c5259d2591b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Losartan 10V, Negative-QTOFsplash10-00di-0304900000-071c5333315e558faa092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Losartan 20V, Negative-QTOFsplash10-0a73-0709200000-be33ec2e3b5adaf0fb632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Losartan 40V, Negative-QTOFsplash10-0v03-2900000000-2cc4dbb7931105738ba52016-08-03Wishart LabView 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 DB00678 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00678 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00678
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3824
KEGG Compound IDC07072
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLosartan
METLIN IDNot Available
PubChem Compound3961
PDB IDNot Available
ChEBI ID6541
Food Biomarker OntologyNot Available
VMH IDLSTN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. [PubMed:16029066 ]
  2. Dahlof B, Devereux RB, Kjeldsen SE, Julius S, Beevers G, de Faire U, Fyhrquist F, Ibsen H, Kristiansson K, Lederballe-Pedersen O, Lindholm LH, Nieminen MS, Omvik P, Oparil S, Wedel H: Cardiovascular morbidity and mortality in the Losartan Intervention For Endpoint reduction in hypertension study (LIFE): a randomised trial against atenolol. Lancet. 2002 Mar 23;359(9311):995-1003. [PubMed:11937178 ]
  3. Guo ZX, Qiu MC: [Losartan downregulates the expression of transforming growth factor beta type I and type II receptors in kidney of diabetic rat]. Zhonghua Nei Ke Za Zhi. 2003 Jun;42(6):403-8. [PubMed:12895325 ]
  4. Habashi JP, Judge DP, Holm TM, Cohn RD, Loeys BL, Cooper TK, Myers L, Klein EC, Liu G, Calvi C, Podowski M, Neptune ER, Halushka MK, Bedja D, Gabrielson K, Rifkin DB, Carta L, Ramirez F, Huso DL, Dietz HC: Losartan, an AT1 antagonist, prevents aortic aneurysm in a mouse model of Marfan syndrome. Science. 2006 Apr 7;312(5770):117-21. [PubMed:16601194 ]
  5. (). Bader, M. (2004). Renin-angiotensin-aldosterone system. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology_ (pp. 810-814). Berlin, Germany: Springer. . .
  6. (). FDA label . .
  7. (). Stanfield, C.L., & Germann, W.J. (2008). Principles of human physiology (3rd ed.). San Francisco, CA: Pearson Education, Inc.. .