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Showing metabocard for Fexofenadine (HMDB0005030)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-10-17 09:48:25 UTC
Update Date2019-01-11 19:18:33 UTC
HMDB IDHMDB0005030
Secondary Accession Numbers
  • HMDB05030
Metabolite Identification
Common NameFexofenadine
DescriptionFexofenadine is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine, an antihistamine with potentially fatal contraindications. Fexofenadine, like other second-generation antihistamines, does not readily enter the brain from the blood, and so causes less drowsiness than first generation histamine receptor antagonists; Fexofenadine hydrochloride (brand names include Allegra and Telfast) is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms. It was developed as a successor of and alternative to terfenadine, an antihistamine with potentially fatal contraindications. Fexofenadine, like other second generation antihistamines, does not readily enter the brain from the blood, and so causes less drowsiness than first-generation histamine-receptor antagonists.
Structure
Data?1547234313
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acidChEBI
CarboxyterfenadineChEBI
Terfenadine acid metaboliteChEBI
Terfenadine carboxylateChEBI
Terfenadine-COOHChEBI
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetateGenerator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetic acidGenerator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetateGenerator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetateGenerator
4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetic acidGenerator
Terfenadine carboxylic acidGenerator
AllegraHMDB
Fexofenadine hydrochlorideHMDB
TelfastHMDB
Aventis pharma brand OF fexofenadine hydrochlorideMeSH
MDL 16,455aMeSH
alpha-(4-(1-Carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanolMeSH
Aventis behring brand OF fexofenadine hydrochlorideMeSH
Aventis brand OF fexofenadine hydrochlorideMeSH
Hoechst brand OF fexofenadine hydrochlorideMeSH
Chemical FormulaC32H39NO4
Average Molecular Weight501.6564
Monoisotopic Molecular Weight501.287908741
IUPAC Name2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid
Traditional Namefexofenadine
CAS Registry Number83799-24-0
SMILES
CC(C)(C(O)=O)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)
InChI KeyRWTNPBWLLIMQHL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylbutylamine
  • Phenylpropane
  • Aralkylamine
  • Piperidine
  • Tertiary alcohol
  • Amino acid or derivatives
  • Secondary alcohol
  • Amino acid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Carbonyl group
  • Aromatic alcohol
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0027 g/LALOGPS
logP5.02ALOGPS
logP2.94ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.04ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area81 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity147.98 m³·mol⁻¹ChemAxon
Polarizability57.42 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0912400000-d47ca5514638bcd48093View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1931153000-7fd2e3b3cc17ae068da6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a6r-0005900000-17ae091cc3d9ba9c62f3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a6r-0396000000-be2d6fedab983b50c280View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-1970000000-c78b1c745afc54f58e01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4r-0920000000-9ad3dc88e743866c23caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0btj-0900000000-66a31911b29382b93745View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-1900000000-ce2d00bbddc284806cb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0000090000-2622c1f2ddb4bff3f93dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0159-0000910000-0afa1079fbe9a822e35cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00xr-1920200000-1163d721ce08480aea71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-1910000000-c593678096415da5efb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002f-2900000000-01de1f32826ab5569301View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002f-3900000000-72f624b2d6e05d29cb72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0001930000-b9b7ff78564293a249b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0541-0212900000-ab3069ba65212a7da302View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-1985500000-f990cf713f3191736f10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100690000-e140f2c9a1bcece115e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zj0-4223930000-8c8b81776964fc2cb368View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004u-9651000000-b823e5714fa6afb8f50fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Kidney
  • Liver
  • Skin
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    		 details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal    		 details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      		 details
      Abnormal Concentrations
      Not Available
      Predicted Concentrations
      BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
      Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
      Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDDB00950
      Phenol Explorer Compound IDNot Available
      FoodDB IDFDB023597
      KNApSAcK IDNot Available
      Chemspider ID3231
      KEGG Compound IDC06999
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkFexofenadine
      METLIN ID2766
      PubChem Compound3348
      PDB IDNot Available
      ChEBI ID5050
      References
      Synthesis ReferenceCarr, Albert A.; Dolfini, Joseph E.; Wright, George J. Piperidine derivatives with antihistamine action. Ger. Offen. (1980), 39 pp. CODEN: GWXXBX DE 3007498 19801023 CAN 94:156758 AN 1981:156758
      Material Safety Data Sheet (MSDS)Download (PDF)
      General References
      1. Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612 ]
      2. Tashiro M, Sakurada Y, Iwabuchi K, Mochizuki H, Kato M, Aoki M, Funaki Y, Itoh M, Iwata R, Wong DF, Yanai K: Central effects of fexofenadine and cetirizine: measurement of psychomotor performance, subjective sleepiness, and brain histamine H1-receptor occupancy using 11C-doxepin positron emission tomography. J Clin Pharmacol. 2004 Aug;44(8):890-900. [PubMed:15286093 ]
      3. Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83. [PubMed:12417888 ]
      4. Purohit A, Duvernelle C, Melac M, Pauli G, Frossard N: Twenty-four hours of activity of cetirizine and fexofenadine in the skin. Ann Allergy Asthma Immunol. 2001 Apr;86(4):387-92. [PubMed:11345280 ]
      5. Inoue T, Katoh N, Kishimoto S, Matsunaga K: Inhibitory effects of oral prednisolone and fexofenadine on skin responses by prick tests with histamine and compound 48/80. J Dermatol Sci. 2002 Dec;30(3):180-4. [PubMed:12443840 ]

      Enzymes

      Enzyme Details
      1. Cytochrome P450 3A4
      General function:
      Involved in monooxygenase activity
      Specific function:
      Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
      Gene Name:
      CYP3A4
      Uniprot ID:
      P08684
      Molecular weight:
      57255.585
      Enzyme Details
      2. Histamine H1 receptor
      General function:
      Involved in G-protein coupled receptor protein signaling pathway
      Specific function:
      In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
      Gene Name:
      HRH1
      Uniprot ID:
      P35367
      Molecular weight:
      55783.6