Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1558)
Drug Name
Terfenadine
Prodrug Info Terfenadine is the prodrug of Fexofenadine
Synonyms
Teldane; Teldanex; Terdin; Terfen; Terfenadina; Terfenadina [INN-Spanish]; Terfenadinum; Terfenadinum [INN-Latin]; Terfex; Ternadin; Triludan; Aldaban; Allerplus; Cyater; GUGOEEXESWIERI-UHFFFAOYSA-N; MDL 9918; MDL-9918; RMI 9918; RMI-9918; Seldane; terfenadine; 50679-08-8; BRN 5857899; C32H41NO2; CHEBI:9453; CHEMBL17157; EINECS 256-710-8; HSDB 6508; MFCD00079622; MLS000028499; alpha-(p-tert-Butylphenyl)-4-(hydroxydiphenylmethyl)-1-piperidinebutanol; alpha-[4-(1,1-Dimethylethyl)phenyl]-4-(hydroxydiphenylmethyl)-1-piperidinebutanol
Indication Allergy [ICD11: 4A80] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 471.7 Topological Polar Surface Area 43.7
Heavy Atom Count 35 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5405
PubChem SID
9666 ; 511394 ; 855647 ; 3154381 ; 5639782 ; 7847587 ; 7980761 ; 8150039 ; 8153324 ; 10321465 ; 10524514 ; 11336186 ; 11361425 ; 11427139 ; 11462397 ; 11466166 ; 11467286 ; 11485891 ; 12013836 ; 14907543 ; 17405767 ; 24277779 ; 26752308 ; 29224457 ; 46507007 ; 47662382 ; 47662383 ; 47736580 ; 47810839 ; 47810840 ; 48035221 ; 48110535 ; 48416601 ; 49698808 ; 49703451 ; 50015354 ; 50105228 ; 50105229 ; 53778319 ; 53787217 ; 56422373 ; 57322760 ; 79821290 ; 85089724 ; 85209594 ; 85231279 ; 85787897 ; 90341346 ; 92125182 ; 92303330
ChEBI ID
CHEBI:9453
CAS Number
50679-08-8
TTD Drug ID
D08SOF
Formula
C32H41NO2
Canonical SMILES
CC(C)(C)C1=CC=C(C=C1)C(CCCN2CCC(CC2)C(C3=CC=CC=C3)(C4=CC=CC=C4)O)O
InChI
1S/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3
InChIKey
GUGOEEXESWIERI-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Azacyclonol DM005773
15723
Oxidation - N-dealkylation 1 [6]
Terfenadine alcohol DM005771
44296949
Oxidation - Hydrolyzationn 1 [6]
Terfenadine glucuronide DM005775 N. A. Conjugation - Glucuronidation 1 [7]
Terfenadine phosphate DM005774 N. A. Conjugation - Phosphorylation 1 [7]
Fexofenadine DM005772
3348
Oxidation - Oxidationn 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006164 Terfenadine Terfenadine alcohol Oxidation - Hydrolyzationn CYP3A4 [6]
MR006166 Terfenadine Azacyclonol Oxidation - N-dealkylation CYP3A4 [6]
MR006167 Terfenadine Terfenadine phosphate Conjugation - Phosphorylation Unclear [7]
MR006168 Terfenadine Terfenadine glucuronide Conjugation - Glucuronidation Unclear [7]
MR006165 Terfenadine alcohol Fexofenadine Oxidation - Oxidationn CYP3A4 [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
References
1 Comparative tolerability of second generation antihistamines. Drug Saf. 1999 May;20(5):385-401.
2 Effects of serum albumin and liver cytosol on CYP2C9- and CYP3A4-mediated drug metabolism. Drug Metab Pharmacokinet. 2002;17(6):522-31.
3 Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92.
4 Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin Pharmacokinet. 2005;44(3):279-304.
5 Drug Interactions Flockhart Table
6 Analysis of hydroxylated and N-dealkylated metabolites of terfenadine in microsomal incubates by liquid chromatography--mass spectrometry
7 Distribution of terfenadine and its metabolites in locusts studied by desorption electrospray ionization mass spectrometry imaging

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