Details of the Drug

General Information of Drug (ID: DMTBKF3)

Drug Name

Piperacillin

Synonyms

PIPC; Peperacillin; Peracin; Pipercillin; Pipracil; Pipril; PIPERACILLIN SODIUM; Piperacillin Monosodium Salt; Piperacillin anhydrous; Cl-227193; Peracin (TN); Piperacillin (INN); Piperacillin (anhydrous); Pipracil, Piper; 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

Indication

Disease Entry	ICD 11	Status	REF
Acute gonococcal cervicitis	N.A.	Approved	[1]
Appendicitis	DB10	Approved	[1]
Bacteremia	1A73	Approved	[1]
Bacterial infection	1A00-1C4Z	Approved	[2]
Peritonitis	N.A.	Approved	[1]
Pseudomonas aeruginosa infectious disease	N.A.	Approved	[1]
Staphylococcus aureus infection	N.A.	Approved	[1]
Urinary tract infection	GC08	Approved	[1]
Pelvic inflammatory disease	GA05	Investigative	[1]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

517.6

Logarithm of the Partition Coefficient (xlogp)

0.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is not absorbed after oral administration []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 4 mL/min/kg [4]
Elimination: 71% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 36 - 72 minutes [4]
Metabolism: The drug is not metabolised []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 772.84985 micromolar/kg/day [5]
Unbound Fraction: The unbound fraction of drug in plasma is 0.5% [4]
Vd: The volume of distribution (Vd) of drug is 0.101 L/kg []
Water Solubility: The ability of drug to dissolve in water is measured as 714.3 mg/mL [3]

Chemical Identifiers

Formula: C23H27N5O7S
IUPAC Name: (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
Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChI: 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

Cross-matching ID

PubChem CID: 43672
ChEBI ID: CHEBI:8232
CAS Number: 61477-96-1
DrugBank ID: DB00319
TTD ID: D04ZAH
VARIDT ID: DR00857
INTEDE ID: DR2410

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Penicillin binding protein (Bact PBP)	TTJP4SM	NOUNIPROTAC	Binder	[6]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Peptide transporter 1 (SLC15A1)	DT9G7XN	S15A1_HUMAN	Substrate	[7]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Beta-lactamase (blaB)	DET9I1W	BLAC_BACUN	Substrate	[8]
Beta-lactamase (blaB)	DEYIEO5	AMPC_SERMA	Substrate	[9]
Beta-lactamase (blaB)	DEEZ5CV	BLO1_KLEOX	Substrate	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Piperacillin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Anisindione	DM2C48U	Moderate	Increased risk of bleeding by the combination of Piperacillin and Anisindione.	Coagulation defect [3B10]	[11]
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Piperacillin due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[12]
Probenecid	DMMFWOJ	Minor	Decreased elimination of Piperacillin caused by Probenecid mediated competitive inhibition of renal tubular secretion.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[13]
Methotrexate	DM2TEOL	Major	Decreased elimination of Piperacillin caused by Methotrexate mediated competitive inhibition of renal tubular secretion.	Leukaemia [2A60-2B33]	[14]
Warfarin	DMJYCVW	Moderate	Increased risk of bleeding by the combination of Piperacillin and Warfarin.	Supraventricular tachyarrhythmia [BC81]	[11]
Mycophenolate mofetil	DMPQAGE	Moderate	Altered absorption of Piperacillin due to GI flora changes caused by Mycophenolate mofetil.	Transplant rejection [NE84]	[12]
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References

1	Piperacillin FDA Label
2	Zosyn (piperacillin/tazobactam) reformulation: Expanded compatibility and coadministration with lactated Ringer's solutions and selected aminoglycosides. Ther Clin Risk Manag. 2008 Apr;4(2):303-14.
3	BDDCS applied to over 900 drugs
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	In vitro antienterococcal activity explains associations between exposures to antimicrobial agents and risk of colonization by multiresistant enter... J Infect Dis. 2004 Dec 15;190(12):2162-6.
7	Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. J Med Chem. 2005 Jun 30;48(13):4410-9.
8	Purification and characterization of a new beta-lactamase from Bacteroides uniformis. Antimicrob Agents Chemother. 1995 Jul;39(7):1458-61.
9	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.
10	Characterization of piperacillin/tazobactam-resistant klebsiella oxytoca recovered from a nosocomial outbreak. PLoS One. 2015 Nov 5;10(11):e0142366.
11	Alexander DP, Russo ME, Fohrman DE, Rothstein G "Nafcillin-induced platelet dysfunction and bleeding." Antimicrob Agents Chemother 23 (1983): 59-62. [PMID: 6830209]
12	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
13	Allen MB, Fitzpatrick RW, Barratt A, Cole RB "The use of probenecid to increase the serum amoxycillin levels in patients with bronchiectasis." Respir Med 84 (1990): 143-6. [PMID: 2371437]
14	Kwon OC, Lee JS, Kim YG, Lee CK, Yoo B, Hong S. Safety of the concomitant use of methotrexate and a prophylactic dose of trimethoprim-sulfamethoxazole.?Clin Rheumatol. 2018;37(12):3215-3220. [PMID: 29383453]