Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:28:01 UTC |
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Update Date | 2014-12-24 20:25:53 UTC |
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Accession Number | T3D2938 |
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Identification |
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Common Name | Fexofenadine |
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Class | Small Molecule |
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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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Compound Type | - Amine
- Anti-Allergic Agent
- Drug
- Food Toxin
- Histamine Antagonist
- Histamine H1 Antagonist, Non-Sedating
- Metabolite
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 4-(1-Hydroxy-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl)-alpha,alpha-dimethylbenzeneacetic acid | Allegra | Carboxyterfenadine | Fastofen | Fexidine | Fexofenadine hydrochloride | Telfast | Terfenadine acid metabolite | Terfenadine carboxylate | Terfenadine-COOH | Vifas |
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Chemical Formula | C32H39NO4 |
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Average Molecular Mass | 501.656 g/mol |
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Monoisotopic Mass | 501.288 g/mol |
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CAS Registry Number | 83799-24-0 |
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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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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=1/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 | InChIKey=RWTNPBWLLIMQHL-UHFFFAOYNA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes 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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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 142.5°C | Boiling Point | Not Available | Solubility | Slightly soluble | LogP | 5.6 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-0912400000-d47ca5514638bcd48093 | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-001i-1931153000-7fd2e3b3cc17ae068da6 | 2017-10-06 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a6r-0005900000-17ae091cc3d9ba9c62f3 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a6r-0396000000-be2d6fedab983b50c280 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a4i-1970000000-c78b1c745afc54f58e01 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a4r-0920000000-9ad3dc88e743866c23ca | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0btj-0900000000-66a31911b29382b93745 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0a4i-1900000000-ce2d00bbddc284806cb0 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0udi-0000090000-2622c1f2ddb4bff3f93d | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-0159-0000910000-0afa1079fbe9a822e35c | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-00xr-1920200000-1163d721ce08480aea71 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-00di-1910000000-c593678096415da5efb2 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-002f-2900000000-01de1f32826ab5569301 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-002f-3900000000-72f624b2d6e05d29cb72 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0a6r-0296000000-08bc8f52b1adac426d92 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 45V, Negative | splash10-0a4i-1970000000-7a763967a0e22ba5aee4 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 15V, Negative | splash10-0a6r-0004900000-264e1e3683f099cd4d18 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-00xr-1920200000-f89d210776b04ca1a4f1 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0159-0000910000-e86af4100fbcd4806c84 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-0udi-0000090000-9d409ff3e4f83806f5ac | 2021-09-20 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f89-0001930000-b9b7ff78564293a249b0 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0541-0212900000-ab3069ba65212a7da302 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000g-1985500000-f990cf713f3191736f10 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0100690000-e140f2c9a1bcece115e3 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zj0-4223930000-8c8b81776964fc2cb368 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004u-9651000000-b823e5714fa6afb8f50f | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ue9-0000980000-811ef09a2d84417ca55c | 2021-09-22 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral. 33% |
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Mechanism of Toxicity | Like other H1-blockers, Fexofenadine competes with free histamine for binding at H1-receptors in the GI tract, large blood vessels, and bronchial smooth muscle. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine. Fexofenadine exhibits no anticholinergic, antidopaminergic, alpha1-adrenergic or beta-adrenergic-receptor blocking effects. |
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Metabolism | Approximately 5% of the total dose is metabolized, by cytochrome P450 3A4 and by intestinal microflora.
Half Life: 14.4 hours |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | An antihistamine drug used in the treatment of hayfever and similar allergy symptoms. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Side effects include dizziness, drowsiness, and dry mouth. |
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Treatment | In the event of overdose, consider standard measures to remove any unabsorbed drug. Symptomatic and supportive treatment is recommended. (12) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00950 |
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HMDB ID | HMDB05030 |
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PubChem Compound ID | 3348 |
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ChEMBL ID | CHEMBL914 |
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ChemSpider ID | 3231 |
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KEGG ID | C06999 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 5050 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Fexofenadine |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Fexofenadine |
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References |
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Synthesis Reference | Federico Milla, “Processes for the production of fexofenadine.” U.S. Patent US20030166682, issued September 04, 2003. |
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MSDS | Link |
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General References | - Smith SM, Gums JG: Fexofenadine: biochemical, pharmacokinetic and pharmacodynamic properties and its unique role in allergic disorders. Expert Opin Drug Metab Toxicol. 2009 Jul;5(7):813-22. doi: 10.1517/17425250903044967. [19545214 ]
- Bachert C: A review of the efficacy of desloratadine, fexofenadine, and levocetirizine in the treatment of nasal congestion in patients with allergic rhinitis. Clin Ther. 2009 May;31(5):921-44. doi: 10.1016/j.clinthera.2009.05.017. [19539095 ]
- Markham A, Wagstaff AJ: Fexofenadine. Drugs. 1998 Feb;55(2):269-74; discussion 275-6. [9506246 ]
- Golightly LK, Greos LS: Second-generation antihistamines: actions and efficacy in the management of allergic disorders. Drugs. 2005;65(3):341-84. [15669879 ]
- Molimard M, Diquet B, Benedetti MS: Comparison of pharmacokinetics and metabolism of desloratadine, fexofenadine, levocetirizine and mizolastine in humans. Fundam Clin Pharmacol. 2004 Aug;18(4):399-411. [15312146 ]
- 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. [10421612 ]
- 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. [12417888 ]
- 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. [15286093 ]
- 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. [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. [12443840 ]
- Drugs.com [Link]
- RxList: The Internet Drug Index (2009). [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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