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

General Information of Drug (ID: DR5725)
Drug Name
Ceftazidime
Synonyms
Ceftazidima; Ceftazidimum; Ceptaz; Fortaz; Ceftazidime Sodium In Plastic Container; Ceftazidime anhydrous; Ceftazidime pentahydrate; Fortaz In Plastic Container; SN 401; CEFTAZIDIME (ARGININE FORMULATION); Ceftazidima [INN-Spanish]; Ceftazidime (INN); Ceftazidime (TN); Ceftazidimum [INN-Latin]; Cefzim (TN); Ceptaz (TN); Fortaz (TN); Fortum (TN); (6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetyl}amino)-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(1-hydroxy-2-methyl-1-oxopropan-2-yl)oxyiminoacetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(1-hydroxy-2-methyl-1-oxopropan-2-yl)oxyiminoacetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(1-hydroxy-2-methyl-1-oxopropan-2-yl)oxyiminoacetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; 7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(1-hydroxy-2-methyl-1-oxopropan-2-yl)oxyiminoacetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate; 7beta-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-3-(pyridinium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylate
Indication Bacterial infection [ICD11: 1A00-1C4Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 546.6 Topological Polar Surface Area 245
Heavy Atom Count 37 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
5481173
ChEBI ID
CHEBI:3508
CAS Number
72558-82-8
TTD Drug ID
D0PH5Z
Formula
C22H22N6O7S2
Canonical SMILES
CC(C)(C(=O)O)O/N=C(/C1=CSC(=N1)N)\\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]
InChI
InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1
InChIKey
ORFOPKXBNMVMKC-DWVKKRMSSA-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
Ceftazidime M1 PDM013425 N. A. Hydrolysis - Hydrolysis of cyclic tertiary carboxamide 1 Human
Ceftazidime M2 PDM013426 N. A. Conjugation - Glycine conjugation 1 Human
Ceftazidime M3 PDM013427 N. A. Conjugation - O-Glucuronidation of aliphatic acid 1 Human
Ceftazidime M4 PDM013428 N. A. Conjugation - Glucuronidation of primary aromatic amine 1 Human
Ceftazidime M5 PDM013429 N. A. Conjugation - Carnitine conjugation 1 Human
Ceftazidime M6 PDM013430 N. A. Reduction - Reduction of alpha,beta-unsaturated carbon-carbon double bond adjacent to electron withdrawing group 1 Gut microbial environment
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase (bla ADC-1) DMEN846 . Not Available Not Available [2]
Beta-lactamase (bla ADC-33) DMEN851 . Not Available Not Available [3]
Beta-lactamase (bla ADC-7) DMEN849 Acinetobacter sp. Not Available Not Available [4]
Beta-lactamase (bla OXA-17) DMEN835 Pseudomonas aeruginosa Not Available Not Available [5]
Beta-lactamase (bla OXA-2) DMEN847 . Not Available Not Available [6]
Beta-lactamase (bla OXA-48) DMEN845 Klebsiella pneumoniae
Q6XEC0_KLEPN
3.5.2.6
[7]
Beta-lactamase (bla TEM-10) DMEN844 Klebsiella pneumoniae Not Available Not Available [8]
Beta-lactamase (bla TEM-43) DMEN843 Klebsiella pneumoniae
O34176_KLEPN
3.5.2.6
[8]
Beta-lactamase (dha-1) DMEN852 Escherichia coli
X2L3Y0_ECOLX
3.5.2.6
[9]
beta-lactamase CTX-M-1 (bla) DMEN848 Escherichia coli
BLC1_ECOLX
3.5.2.6
[10]
Class A carbapenemase (bla KPC-2) DMEN850 Klebsiella pneumoniae
C0KUK0_KLEPN
Not Available [11]
extended-spectrum -lactamase 1 (PME-1) DMEN834 Pseudomonas aeruginosa Not Available Not Available [12]
⏷ Show the Full List of 12  DME(s)
References
1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 New mutations in ADC-type -lactamases from Acinetobacter spp. affect cefoxitin and ceftazidime hydrolysis
3 Extended-spectrum cephalosporinase in Acinetobacter baumannii
4 Structural Insights into Inhibition of the Acinetobacter-Derived Cephalosporinase ADC-7 by Ceftazidime and Its Boronic Acid Transition State Analog
5 OXA-17, a further extended-spectrum variant of OXA-10 beta-lactamase, isolated from Pseudomonas aeruginosa
6 Reduced ceftazidime and ertapenem susceptibility due to production of OXA-2 in Klebsiella pneumoniae ST258
7 OXA-48-Mediated Ceftazidime-Avibactam Resistance Is Associated with Evolutionary Trade-Offs
8 Ceftazidime-resistant Klebsiella pneumoniae and Escherichia coli isolates producing TEM-10 and TEM-43 beta-lactamases from St. Louis, Missouri
9 Genetic and kinetic characterization of the novel AmpC -lactamases DHA-6 and DHA-7
10 Antagonism between substitutions in -lactamase explains a path not taken in the evolution of bacterial drug resistance
11 Natural Variants of the KPC-2 Carbapenemase have Evolved Increased Catalytic Efficiency for Ceftazidime Hydrolysis at the Cost of Enzyme Stability
12 PME-1, an extended-spectrum -lactamase identified in Pseudomonas aeruginosa

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