General Information of Drug (ID: DR0977)
Drug Name
Loratadine
Synonyms
Lertamine; Lesidas; Lisino; Loracert; Loradex; Loradif; Loranox; Lorantis; Lorastine; Loratidine; Loratyne; Loraver; Lorfast; Loritine; Lowadina; Nularef; Optimin; Polaratyne; Restamine; Rhinase; Rinomex; Sanelor; Sch 29851; Sensibit; Aerotina; Alarin; Alavert; Alerpriv; Allertidin; Anhissen; Bedix Loratadina; Biloina; Bonalerg; Civeran; Claratyne; Clarinase; Claritin; Claritin Reditabs; Claritine; Clarityn; Clarityne; Fristamin; Histaloran; Sinhistan Dy; Sohotin; Tadine; Talorat Dy; Velodan; Versal; loratadine; 79794-75-5; Lergy; Pylor; Zeos
Indication Allergic rhinitis [ICD11: CA08] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 382.9 Topological Polar Surface Area 42.4
Heavy Atom Count 27 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3957
PubChem SID
535878 ; 855843 ; 1197563 ; 4964188 ; 7847430 ; 7979793 ; 8150042 ; 8152484 ; 11111394 ; 11113345 ; 11335967 ; 11361206 ; 11364390 ; 11366952 ; 11369514 ; 11371620 ; 11373832 ; 11377676 ; 11445825 ; 11462178 ; 11485284 ; 11489400 ; 11490556 ; 11491992 ; 11495310 ; 11528699 ; 12013131 ; 14804759 ; 17405241 ; 24278525 ; 25623638 ; 26612522 ; 26680506 ; 26719690 ; 26747010 ; 26751528 ; 29223071 ; 46386837 ; 46507853 ; 47365230 ; 48035159 ; 48110481 ; 48110482 ; 48259268 ; 48416183 ; 49835216 ; 49846690 ; 50100268 ; 50104102 ; 50104103
ChEBI ID
CHEBI:6538
CAS Number
79794-75-5
TTD Drug ID
D06ABF
Formula
C22H23ClN2O2
Canonical SMILES
CCOC(=O)N1CCC(=C2C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)CC1
InChI
1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
InChIKey
JCCNYMKQOSZNPW-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
Desloratadine DM004871
124087
Oxidation - Oxidationn 1 [7]
3-hydroxydesloratadine DM000782
10359050
Oxidation - 3-hydroxylation 2 [7]
Desloratadine glucuronide DM006423 N. A. Conjugation - Glucuronidation 2 [8]
3-Hydroxydesloratadine b-D-glucuronide DM000783
29918869
Conjugation - Glucuronidation 3 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006901 Loratadine Desloratadine Oxidation - Oxidationn CYP3A4 ... [7]
MR006904 Desloratadine Desloratadine glucuronide Conjugation - Glucuronidation UGT2B10 [8]
MR006902 Desloratadine glucuronide 3-Hydroxydesloratadine Oxidation - 3-hydroxylation CYP2C8 [7]
MR006903 3-Hydroxydesloratadine 3-hydroxydesloratadine O-glucuronide Conjugation - Glucuronidation UGT1A1 ... [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[7]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[7]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[7]
UDP-glucuronosyltransferase 2B10 (UGT2B10) DME0205 Homo sapiens
UDB10_HUMAN
2.4.1.17
[8]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[7]
⏷ Show the Full List of 12  DME(s)
References
1 Loratadine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of loratadine and further characterization of its in vitro metabolites. Drug Metab Lett. 2009 Aug;3(3):162-70.
3 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
4 In vitro inhibition of human liver drug metabolizing enzymes by second generation antihistamines. Chem Biol Interact. 1999 Nov 15;123(1):63-79.
5 In vitro characterization of the inhibition profile of loratadine, desloratadine, and 3-OH-desloratadine for five human cytochrome P-450 enzymes. Drug Metab Dispos. 2001 Sep;29(9):1173-5.
6 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
7 Advances in high-resolution MS and hepatocyte models solve a long-standing metabolism challenge: the loratadine story. Bioanalysis. 2016 Aug;8(16):1645-62.
8 A long-standing mystery solved: the formation of 3-hydroxydesloratadine is catalyzed by CYP2C8 but prior glucuronidation of desloratadine by UDP-glucuronosyltransferase 2B10 is an obligatory requirement Drug Metab Dispos. 2015 Apr;43(4):523-33. doi: 10.1124/dmd.114.062620.

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