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Record Information |
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Version | 4.0 |
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Status | Detected but not Quantified |
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Creation Date | 2006-10-17 09:48:25 UTC |
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Update Date | 2019-01-11 19:18:33 UTC |
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HMDB ID | HMDB0005030 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Fexofenadine |
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Description | Fexofenadine 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. |
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Structure | |
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Synonyms | Value | Source |
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4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid | ChEBI | Carboxyterfenadine | ChEBI | Terfenadine acid metabolite | ChEBI | Terfenadine carboxylate | ChEBI | Terfenadine-COOH | ChEBI | 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetate | Generator | 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-a,a-dimethylbenzeneacetic acid | Generator | 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetate | Generator | 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetate | Generator | 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-α,α-dimethylbenzeneacetic acid | Generator | Terfenadine carboxylic acid | Generator | Allegra | HMDB | Fexofenadine hydrochloride | HMDB | Telfast | HMDB | Aventis pharma brand OF fexofenadine hydrochloride | MeSH | MDL 16,455a | MeSH | alpha-(4-(1-Carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol | MeSH | Aventis behring brand OF fexofenadine hydrochloride | MeSH | Aventis brand OF fexofenadine hydrochloride | MeSH | Hoechst brand OF fexofenadine hydrochloride | MeSH |
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Chemical Formula | C32H39NO4 |
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Average Molecular Weight | 501.6564 |
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Monoisotopic Molecular Weight | 501.287908741 |
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IUPAC Name | 2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid |
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Traditional Name | fexofenadine |
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CAS Registry Number | 83799-24-0 |
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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 |
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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) |
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InChI Key | RWTNPBWLLIMQHL-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | This 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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Diphenylmethanes |
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Direct Parent | Diphenylmethanes |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 142.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-0912400000-d47ca5514638bcd48093 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-001i-1931153000-7fd2e3b3cc17ae068da6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a6r-0005900000-17ae091cc3d9ba9c62f3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a6r-0396000000-be2d6fedab983b50c280 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a4i-1970000000-c78b1c745afc54f58e01 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a4r-0920000000-9ad3dc88e743866c23ca | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0btj-0900000000-66a31911b29382b93745 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a4i-1900000000-ce2d00bbddc284806cb0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0udi-0000090000-2622c1f2ddb4bff3f93d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0159-0000910000-0afa1079fbe9a822e35c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-00xr-1920200000-1163d721ce08480aea71 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-00di-1910000000-c593678096415da5efb2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-002f-2900000000-01de1f32826ab5569301 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-002f-3900000000-72f624b2d6e05d29cb72 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f89-0001930000-b9b7ff78564293a249b0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0541-0212900000-ab3069ba65212a7da302 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000g-1985500000-f990cf713f3191736f10 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0100690000-e140f2c9a1bcece115e3 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zj0-4223930000-8c8b81776964fc2cb368 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004u-9651000000-b823e5714fa6afb8f50f | View in MoNA |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | | Not Available | Not Available | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Expected but not Quantified | | Not Available | Not Available | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00950 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB023597 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 3231 |
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KEGG Compound ID | C06999 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Fexofenadine |
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METLIN ID | 2766 |
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PubChem Compound | 3348 |
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PDB ID | Not Available |
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ChEBI ID | 5050 |
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References |
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Synthesis Reference | Carr, 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 |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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