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

General Information of Drug (ID: DR1189)
Drug Name
Oleandomycin
Synonyms
Oleandomycin A; Amimycin; Landomycin; Matromycin; Antibiotic PA 105; LMPK04000007; P8ZQ646136; PA 105; Prestwick3_000152; RZPAKFUAFGMUPI-QESOVKLGSA-N; Romicil; SCHEMBL3717; ZINC85432018; oleandomycin; 3922-90-5; AB00513809; AC1L2I65; BDBM234401; BPBio1_000314; BSPBio_000284; C01946; CHEBI:16869; CHEMBL606258; CS-0063452; E704; HY-116010; NCGC00179617-01; UNII-P8ZQ646136
Indication Acute upper respiratory infection [ICD11: CA07] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 687.9 Topological Polar Surface Area 166
Heavy Atom Count 48 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 13
Cross-matching ID
PubChem CID
72493
ChEBI ID
CHEBI:16869
CAS Number
3922-90-5
Formula
C35H61NO12
Canonical SMILES
CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
InChI
1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1
InChIKey
RZPAKFUAFGMUPI-QESOVKLGSA-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
Cytochrome P-450-metabolite complexes DM002724 N. A. Unclear 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001816 Oleandomycin Cytochrome P-450-metabolite complexes Unclear CYP [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
References
1 National Center for Advancing Translational Science-Inxight: drug (P8ZQ646136)
2 Inversion of the anomeric configuration of the transferred sugar during inactivation of the macrolide antibiotic oleandomycin catalyzed by a macrolide glycosyltransferase. FEBS Lett. 2000 Jul 7;476(3):186-9.
3 Formation of inactive cytochrome P-450 Fe(II)-metabolite complexes with several erythromycin derivatives but not with josamycin and midecamycin in rats Biochem Pharmacol. 1983 May 1;32(9):1487-93. doi: 10.1016/0006-2952(83)90470-7.
4 Self-induction by oleandomycin of its own transformation into a metabolite forming an inactive complex with reduced cytochrome P-450. Comparison with troleandomycin J Pharmacol Exp Ther. 1982 Apr;221(1):215-21.

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