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

General Information of Drug (ID: DR1448)
Drug Name
Roxithromycin
Synonyms
Roxithromycine; Roxithromycine [French]; Roxithromycinum; Roxithromycinum [Latin]; Roxitromicina; Roxitromicina [Spanish]; Rulide; Rulide (TN); RU 28965; RU 965; RU-28965; RU-965; SR-05000001850; roxithromycin; (E)-roxithromycin; 21KOF230FA; 80214-83-1; 9-(O-((2-Methoxyethoxy)methyl)oxime)erythromycin; BRN 4286925; CCRIS 3461; CHEBI:48844; CHEBI:48935; Erythromycin 9-(O-((2-methoxyethoxy)methyl)oxime); Erythromycin, 9-(O-((2-methoxyethoxy)methyl)oxime); Erythromycin, 9-(O-((2-methoxyethoxy)methyl)oxime), (9E)-; UNII-21KOF230FA
Indication Acute lower respiratory infection [ICD11: CA4Z] Phase 4 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 837 Topological Polar Surface Area 217
Heavy Atom Count 58 Rotatable Bond Count 13
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 17
Cross-matching ID
PubChem CID
6915744
PubChem SID
585237 ; 602768 ; 7848773 ; 7890303 ; 8149971 ; 14791576 ; 14816129 ; 17193218 ; 26612461 ; 26681158 ; 43527885 ; 46507676 ; 47500552 ; 48020029 ; 48020030 ; 49658614 ; 49658887 ; 49835235 ; 50123162 ; 50599965 ; 53787485 ; 56314318 ; 57288831 ; 57371618 ; 81093210 ; 88283688 ; 92124863 ; 92307881 ; 99301470 ; 104240364 ; 114784612 ; 124637170 ; 135013062 ; 137003693 ; 137241413 ; 144075595 ; 152109149 ; 162107641 ; 176251435 ; 179038902 ; 179113863 ; 210279582 ; 210281905 ; 226447059 ; 252401199
ChEBI ID
ChEBI:48935
CAS Number
80214-83-1
TTD Drug ID
D0Y4FL
Formula
C41H76N2O15
Canonical SMILES
CCC1C(C(C(C(=NOCOCCOC)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)O)C)C)O)(C)O
InChI
1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1
InChIKey
RXZBMPWDPOLZGW-XMRMVWPWSA-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
Descladinose roxithromycin DM004868
131769961
Unclear 1 [3]
N-di-demethyl roxithromycin DM004869
131769919
Oxidation - N-demethylation 1 [4] , [3]
N-mono roxithromycin DM004870
101642065
Oxidation - N-demethylation 1 [4] , [3]
Roxithromycin metabolite M2 DM004863
5483652
Oxidation - O-dealkylation 1 [4] , [3]
Roxithromycin metabolite M4 DM004866 N. A. Oxidation - O-demethylation 1 [3]
Roxithromycin metabolite M5 DM004864 N. A. Oxidation - N-demethylation 2 [4] , [3]
Roxithromycin metabolite M6 DM004867 N. A. Oxidation - N-demethylation 2 [3]
Roxithromycin metabolite M7 DM004865 N. A. Oxidation - N-demethylation 3 [4] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005239 Roxithromycin Roxithromycin metabolite M2 Oxidation - O-dealkylation Unclear [4], [3]
MR005242 Roxithromycin Roxithromycin metabolite M4 Oxidation - O-demethylation Unclear [3]
MR005244 Roxithromycin Descladinose roxithromycin Unclear Unclear [3]
MR005245 Roxithromycin N-di-demethyl roxithromycin Oxidation - N-demethylation Unclear [4], [3]
MR005246 Roxithromycin N-mono roxithromycin Oxidation - N-demethylation Unclear [4], [3]
MR005240 Roxithromycin metabolite M2 Roxithromycin metabolite M5 Oxidation - N-demethylation Unclear [4], [3]
MR005243 Roxithromycin metabolite M4 Roxithromycin metabolite M6 Oxidation - N-demethylation Unclear [3]
MR005241 Roxithromycin metabolite M5 Roxithromycin metabolite M7 Oxidation - N-demethylation Unclear [4], [3]
⏷ Show the Full List of 8 MR(s)
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]
References
1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 Hepatic veno-occlusive disease associated with immunosuppressive cyclophosphamide dosing and roxithromycin. Ann Pharmacother. 2006 Apr;40(4):767-70.
3 Identification of the metabolites of roxithromycin in humans
4 Metabolism of roxithromycin in phenobarbital-treated rat liver microsomes

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