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

General Information of Drug (ID: DR5143)
Drug Name
Cephaloglycin
Synonyms
CEG; Cefaloglicina; Cefaloglycin; Cefaloglycine; Cefaloglycinum; Cephaloglycine; Kafocin; Kefglycin; Cephaloglycinanhdyous; Cephaloglycin anhydrous; Cephaoglycin acid; Lilly 39435; Cefaloglicina [INN-Spanish]; Cefaloglycin (JAN); Cefaloglycine [INN-French]; Cefaloglycinum [INN-Latin]; Cephaloglycin (anhydrous); D-Cephaloglycine; D-(-)-Cephaloglycin; (6R,7R)-3-(acetoxymethyl)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(acetyloxy)methyl]-7-{[(2R)-2-amino-2-phenylacetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 3-((Acetyloxy)methyl)-7-((aminophenylacetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; 3-acetoxymethyl-7beta-[(2R)-2-amino-2-phenylacetamido]-3,4-didehydrocepham-4-carboxylic acid; 7-(2-Amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid acetate (ester); 7-(2-Amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)octane-2-carboxylic acid, acetate inner salt; 7-(2-D-alpha-Aminophenylacetamido)cephalosporanic acid; 7-(D-2-Amino-2-phenylacetamido)-3-acetoxymethyl-delta(sup 3)-cephem-4-carboxylic acid; 7-(D-2-Amino-2-phenylacetamido)-3-acetoxymethyl-delta(sup3)-cephem-4-carboxylic acid; 7-(D-alpha-Aminophenyl-acetamido)cephalosporanic acid
Indication Bacterial infection [ICD11: 1A00-1C4Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 405.4 Topological Polar Surface Area 164
Heavy Atom Count 28 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
19150
ChEBI ID
CHEBI:34613
CAS Number
3577-01-3
TTD Drug ID
D07WZH
Formula
C18H19N3O6S
Canonical SMILES
CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)SC1)C(=O)O
InChI
InChI=1S/C18H19N3O6S/c1-9(22)27-7-11-8-28-17-13(16(24)21(17)14(11)18(25)26)20-15(23)12(19)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1
InChIKey
FUBBGQLTSCSAON-PBFPGSCMSA-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
Benzoylformic Acid DM014948
11915
Unclear - Unclear 1 [3]
Deacetylcephaloglycin DM015249
192789
Unclear - Unclear 1 [4] , [3]
Benzoylformic Acid DM014948
11915
Unclear - Unclear 2 [3]
Deacetylcephaloglycin lactone(DACEG-L) DM016879 N. A. Unclear - Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007678 Cephaloglycin Deacetylcephaloglycin Unclear - Unclear Unclear [4], [3]
MR007681 Cephaloglycin Benzoylformic Acid Unclear - Unclear Unclear [3]
MR007679 Deacetylcephaloglycin Deacetylcephaloglycin lactone(DACEG-L) Unclear - Unclear Unclear [3]
MR007680 Deacetylcephaloglycin Benzoylformic Acid Unclear - Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Penicillin G acylase (pac) DMEN749 Escherichia coli Not Available Not Available [2]
References
1 Drug information of Cephaloglycin, 2008. eduDrugs.
2 Expression of penicillin G acylase gene from Bacillus megaterium ATCC 14945 in Escherichia coli and Bacillus subtilis
3 Chromatographic analysis and pharmacokinetic investigation of cephaloglycin and its metabolites in man
4 Cephaloglycin and its biologically active metabolite desacetylcephaloglycin

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