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

General Information of Drug (ID: DR2321)
Drug Name
Oxacillin
Synonyms
Ossacillina; Ossacillina [DCIT]; Oxacilina; Oxacilina (TN); Oxacilina [INN-Spanish]; Oxacillin (INN); Oxacillin [INN:BAN]; Oxacilline; Oxacilline [INN-French]; Oxacillinum; Oxacillinum [INN-Latin]; Oxazocillin; Oxazocilline; Prostaphlin; Prostaphlyn; Bactocill; Bactocill (TN); MPI-penicillin; MPi-PC; OXACILLIN SODIUM; Sodium oxacillin; (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (5-methyl-3-phenyl-4-isoxazolyl)penicillin; 2,2-dimethyl-6beta-(5-methyl-3-phenyl-1,2-oxazole-4-carboxamido)penam-3alpha-carboxylic acid; 5-Methyl-3-phenyl-4-isoxazolyl-penicillin; 6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid; Oxacillin, Monosodium Salt, Anhydrous; Penicillin, Methylphenylisoxazolyl
Indication Pseudomonas infection [ICD11: 1G40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 401.4 Topological Polar Surface Area 138
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
6196
PubChem SID
9541 ; 637164 ; 7980211 ; 8153886 ; 24398251 ; 29225194 ; 46505710 ; 48416356 ; 50050738 ; 57323249 ; 77266000 ; 96024994 ; 103215636 ; 104133798 ; 104311373 ; 124766053 ; 129432415 ; 134223022 ; 134337736 ; 134972946 ; 136357169 ; 137003784 ; 139694323 ; 144224285 ; 160964057 ; 175266996 ; 175443951 ; 177749334 ; 179296061 ; 223555599 ; 226395922 ; 250135015 ; 252553436
ChEBI ID
ChEBI:7809
CAS Number
66-79-5
TTD Drug ID
D0MB8I
Formula
C19H19N3O5S
Canonical SMILES
CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
InChI
1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1
InChIKey
UWYHMGVUTGAWSP-JKIFEVAISA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
Oxacillin M1 PDM007273
4128973
Hydrolysis - Hydrolysis of cyclic tertiary carboxamide 1 Human
Oxacillin M2 PDM007274 N. A. Conjugation - Glycine conjugation 1 Human
Oxacillin M3 PDM007275 N. A. Conjugation - alpha-N-Acetylation of peptide 1 Human
Oxacillin M4 PDM007276 N. A. Conjugation - O-Glucuronidation of aliphatic acid 1 Human
Oxacillin M5 PDM007277 N. A. Conjugation - Carnitine conjugation 1 Human
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
PenA beta-lactamase (penA1) DME1559 Burkholderia cepacia
O08350_BURCE
3.5.2.6
[2]
References
1 Oxacillin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterization of the penA and penR genes of Burkholderia cepacia 249 which encode the chromosomal class A penicillinase and its LysR-type transcriptional regulator. Antimicrob Agents Chemother. 1997 Nov;41(11):2399-405.

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