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

General Information of Drug (ID: DR5208)
Drug Name
Azlocillin
Synonyms
Azlocilina; Azlocilline; Azlocillinum; Securopen; Bayer Brand of Azlocillin; Azlocilina [INN-Spanish]; Azlocillin Sodium (Sterile); Azlocilline [INN-French]; Azlocillinum [INN-Latin]; Bay-e 6905; Azlocillin (USAN/INN); Azlocillin [USAN:BAN:INN]; (2R,5R,6S)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2R,5S,6S)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-((R)-2-(2-oxo-1-imidazolidinecarboxamido)-2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2S)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2S)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5S,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2r,5s,6s)-3,3-dimethyl-7-oxo-6-{[(2r)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (6R)-3,3-dimethyl-7-oxo-6-[[2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 2,2-dimethyl-6beta-[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]penam-3alpha-carboxylic acid; 3,3-dimethyl-7-oxo-6-[[2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 3,3-dimethyl-7-oxo-6-{[{[(2-oxoimidazolidin-1-yl)carbonyl]amino}(phenyl)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-((R)-2-(2-Oxoimidazolidin-1-carboxamido)-2-phenylacetamido)penicillansaeure
Indication Pseudomonas infection [ICD11: 1B92] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 461.5 Topological Polar Surface Area 173
Heavy Atom Count 32 Rotatable Bond Count 5
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
6479523
ChEBI ID
CHEBI:2956
CAS Number
37091-66-0
TTD Drug ID
D0PA2N
Formula
C20H23N5O6S
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C
InChI
InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1
InChIKey
JTWOMNBEOCYFNV-NFFDBFGFSA-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
Penicilloate DM015115
98994
Unclear - Unclear 1 [2]
Penilloic acid DM015262
255293
Reduction - Decarboxylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008092 Azlocillin Penicilloate Unclear - Unclear Unclear [2]
MR008093 Penicilloate Penilloate Reduction - Decarboxylation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase PSE-1 (pse1) DMEN870 Pseudomonas aeruginosa
BLP1_PSEAI
3.5.2.6
[2]
VIM-1 metallo-beta-lactamase (blaVIM) DMEN871 Pseudomonas aeruginosa
Q9XAY4_PSEAI
Not Available [3]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Degradation of azlocillin in human serum
3 Purification and biochemical characterization of the VIM-1 metallo-beta-lactamase

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