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

General Information of Drug (ID: DR0336)
Drug Name
Clarithromycin
Synonyms
Clacee; Clacid; Clacine; Clambiotic; Clarem; Claribid; Claricide; Claridar; Claripen; Clarith; Clarithromycine; Clarithromycinum; Claritromicina; Clathromycin; Crixan; Cyllid; Erythromycin, 6-O-methyl-; Fromilid; Heliclar; Klabax; Astromen; Biaxin; Biaxin HP; Biaxin filmtab; Biaxin xl filmtab; Bicrolid; Klacid; Klaciped; Klaricid; Klarid; Klarin; Kofron; Mabicrol; Macladin; Maclar; TE-031; Veclam; Zeclar; clarithromycin; 6-O-Methylerythromycin; 6-O-Methylerythromycin a; 81103-11-9; A-56268; Abbotic; Abbott-56268; Adel; Helas; Klax; Mavid; Naxy
Indication Pneumocystis pneumonia [ICD11: CA40] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 748 Topological Polar Surface Area 183
Heavy Atom Count 52 Rotatable Bond Count 8
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 14
Cross-matching ID
PubChem CID
84029
ChEBI ID
CHEBI:3732
CAS Number
81103-11-9
TTD Drug ID
D0Z1ZM
Formula
C38H69NO13
Canonical SMILES
CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)O)(C)O
InChI
1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
InChIKey
AGOYDEPGAOXOCK-KCBOHYOISA-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
14-hydroxyclarithromycin DM006062
84020
Oxidation - Hydrolyzationn 1 [5]
Cladinose DM006065
10012435
Hydrolysis - Hydrolysis 1 [6]
Decladinose Clarithromycin DM006064
10579285
Hydrolysis - Hydrolysis 1 [6]
N-desmethylclarithromycin DM006063
11072636
Oxidation - N-demethylation 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006528 Clarithromycin 14-hydroxyclarithromycin Oxidation - Hydrolyzationn CYP3A4 [5]
MR006529 Clarithromycin N-desmethylclarithromycin Oxidation - N-demethylation CYP3A4 [5]
MR006530 Clarithromycin Decladinose Clarithromycin Hydrolysis - Hydrolysis Unclear [6]
MR006531 Clarithromycin Cladinose Hydrolysis - Hydrolysis Unclear [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
References
1 Clarithromycin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetic variability of clarithromycin and differences in CYP3A4 activity in patients with cystic fibrosis. J Cyst Fibros. 2014 Mar;13(2):179-85.
3 Drug Interactions Flockhart Table
4 Influence of CYP2C19 polymorphism and Helicobacter pylori genotype determined from gastric tissue samples on response to triple therapy for H pylori infection. Clin Gastroenterol Hepatol. 2005 Jun;3(6):564-73.
5 Aquatic toxicity of the macrolide antibiotic clarithromycin and its metabolites
6 Quantification of clarithromycin, its 14-hydroxy and decladinose metabolites in rat plasma, gastric juice and gastric tissue using high-performance liquid chromatography with electrochemical detection

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.