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

General Information of Drug (ID: DR2410)
Drug Name
Piperacillin
Synonyms
Peperacillin; Peracin; Peracin (TN); Piperacillin (INN); Piperacillin (anhydrous); Piperacillin Monosodium Salt; Piperacillin anhydrous; Pipercillin; Pipracil; Pipracil, Piper; Pipril; PIPERACILLIN SODIUM; T-1220; Zobactin (TN); (2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S-(2alpha,5alpha,6beta(S*)))-6-(((((4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 4-ethyl-2,3-dioxopiperazine carbonyl ampicillin; 6-(D-(-)-alpha-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)phenylacetamido)penicillanicacid; 6beta-{(2R)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3alpha-carboxylic acid; Cl-227193; PIPC
Indication Pneumocystis pneumonia [ICD11: CA40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 517.6 Topological Polar Surface Area 182
Heavy Atom Count 36 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
43672
PubChem SID
854275 ; 7835955 ; 7980328 ; 8178297 ; 11466783 ; 11467903 ; 11486445 ; 14860547 ; 14885009 ; 34709064 ; 46504757 ; 47216691 ; 47736382 ; 47959647 ; 48035016 ; 48416441 ; 50050723 ; 50953976 ; 53786998 ; 57312854 ; 58106750 ; 85788489 ; 92309155 ; 93166325 ; 96025066 ; 104098277 ; 104234163 ; 104342936 ; 117541876 ; 124766128 ; 126685780 ; 127341075 ; 127341076 ; 127341077 ; 131465223 ; 134338409 ; 135006048 ; 135951164 ; 137248591 ; 140093228 ; 142043554 ; 163403896 ; 163846739 ; 164232663 ; 164814522 ; 175266788 ; 175442177 ; 176484439 ; 179116854 ; 185975394
ChEBI ID
ChEBI:8232
CAS Number
66258-76-2
TTD Drug ID
D04ZAH
Formula
C23H27N5O7S
Canonical SMILES
CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
InChI
1S/C23H27N5O7S/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34)/t13-,14-,15+,20-/m1/s1
InChIKey
IVBHGBMCVLDMKU-GXNBUGAJSA-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
Desethyl-piperacillin DM002862
10051220
Oxidation - N-Dealkylation 1 [5] , [2] , [6]
Desethyl-piperacillin glucuronide DM002863 N. A. Unclear 2 [5] , [2] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002057 Piperacillin Desethyl-piperacillin Oxidation - N-Dealkylation blaB [5], [2], [6]
MR002056 Desethyl-piperacillin Desethyl-piperacillin glucuronide Unclear Unclear [5], [2], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase (blaB) DME1231 Serratia marcescens
AMPC_SERMA
3.5.2.6
[2]
Beta-lactamase (blaB) DME1226 Klebsiella oxytoca
BLO1_KLEOX
3.5.2.6
[3]
Beta-lactamase (blaB) DME1026 Bacteroides uniformis
BLAC_BACUN
3.5.2.6
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Beta-lactamase (blaB) DME1026 Km = 0.58 microM
BLAC_BACUN
[4]
References
1 Piperacillin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Determination of the antibiotic resistance rates of Serratia marcescens isolates obtained from various clinical specimens. Niger J Clin Pract. 2019 Jan;22(1):125-130.
3 Characterization of piperacillin/tazobactam-resistant klebsiella oxytoca recovered from a nosocomial outbreak. PLoS One. 2015 Nov 5;10(11):e0142366.
4 Purification and characterization of a new beta-lactamase from Bacteroides uniformis. Antimicrob Agents Chemother. 1995 Jul;39(7):1458-61.
5 The formation of desethyl-piperacillin from piperacillin by human liver S9 in vitro Biopharm Drug Dispos. 1997 Apr;18(3):185-90. doi: 10.1002/(sici)1099-081x(199704)18:3<185::aid-bdd10>3.0.co;2-u.
6 In vitro and in vivo determination of piperacillin metabolism in humans Drug Metab Dispos. 2007 Mar;35(3):345-9. doi: 10.1124/dmd.106.012278.

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