ContaminantDB: Fexofenadine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:01 UTC

Update Date

2026-05-14 16:53:55 UTC

Accession Number

CHEM002309

Identification

Common Name

Fexofenadine

Class

Small Molecule

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.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Anti-Allergic Agent
Drug
Food Toxin
Histamine Antagonist
Histamine H1 Antagonist, Non-Sedating
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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
Telfast	Kegg
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, MeSH
Fexofenadine hydrochloride	HMDB, MeSH
Aventis pharma brand OF fexofenadine hydrochloride	MeSH, HMDB
MDL 16,455a	MeSH, HMDB
alpha-(4-(1-Carboxy-1-methylethyl)phenyl)-4-hydroxydiphenylmethyl-1-piperidinebutanol	MeSH, HMDB
Aventis behring brand OF fexofenadine hydrochloride	MeSH, HMDB
Aventis brand OF fexofenadine hydrochloride	MeSH, HMDB
Hoechst brand OF fexofenadine hydrochloride	MeSH, HMDB

Chemical Formula

C₃₂H₃₉NO₄

Average Molecular Mass

501.656 g/mol

Monoisotopic Mass

501.288 g/mol

CAS Registry Number

83799-24-0

IUPAC Name

2-(4-{1-hydroxy-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butyl}phenyl)-2-methylpropanoic acid

Traditional Name

fexofenadine

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 Key

RWTNPBWLLIMQHL-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:5050 )
tertiary amine (CHEBI:5050 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Brain
Kidney
Liver
Skin

Pathways

Not Available

Applications

Biological Roles

H1-receptor antagonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	142.5°C
Boiling Point	Not Available
Solubility	Slightly soluble

Predicted Properties

Property	Value	Source
Water Solubility	0.0027 g/L	ALOGPS
logP	5.02	ALOGPS
logP	2.94	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	81 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	147.98 m³·mol⁻¹	ChemAxon
Polarizability	57.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0912400000-d47ca5514638bcd48093	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-001i-1931153000-7fd2e3b3cc17ae068da6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a6r-0005900000-17ae091cc3d9ba9c62f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a6r-0396000000-be2d6fedab983b50c280	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-1970000000-c78b1c745afc54f58e01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4r-0920000000-9ad3dc88e743866c23ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0btj-0900000000-66a31911b29382b93745	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-1900000000-ce2d00bbddc284806cb0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-0000090000-2622c1f2ddb4bff3f93d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0159-0000910000-0afa1079fbe9a822e35c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00xr-1920200000-1163d721ce08480aea71	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-1910000000-c593678096415da5efb2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-002f-2900000000-01de1f32826ab5569301	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-002f-3900000000-72f624b2d6e05d29cb72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0a6r-0296000000-08bc8f52b1adac426d92	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0a4i-1970000000-7a763967a0e22ba5aee4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0a6r-0004900000-264e1e3683f099cd4d18	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00xr-1920200000-f89d210776b04ca1a4f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0159-0000910000-e86af4100fbcd4806c84	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0udi-0000090000-9d409ff3e4f83806f5ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0001930000-b9b7ff78564293a249b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0541-0212900000-ab3069ba65212a7da302	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000g-1985500000-f990cf713f3191736f10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0100690000-e140f2c9a1bcece115e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zj0-4223930000-8c8b81776964fc2cb368	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004u-9651000000-b823e5714fa6afb8f50f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0000980000-811ef09a2d84417ca55c	Spectrum

Toxicity Profile

Route of Exposure

Oral. 33%

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.

Metabolism

Approximately 5% of the total dose is metabolized, by cytochrome P450 3A4 and by intestinal microflora. Half Life: 14.4 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

An antihistamine drug used in the treatment of hayfever and similar allergy symptoms.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Side effects include dizziness, drowsiness, and dry mouth.

Treatment

In the event of overdose, consider standard measures to remove any unabsorbed drug. Symptomatic and supportive treatment is recommended. (12)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Fexofenadine

Chemspider ID

3231

ChEBI ID

5050

PubChem Compound ID

Not Available

Kegg Compound ID

C06999

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Federico Milla, “Processes for the production of fexofenadine.” U.S. Patent US20030166682, issued September 04, 2003.

MSDS

Link

General References

Not Available

Fexofenadine (CHEM002309)

Structure for CHEM002309: Fexofenadine