sodium (2S,5R,6R)-6-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 204
• Molecular Formular: C23H26N5NaO7S
• Molecular Mass: 539.53661
• Monoisotopic Mass: 539.14506348
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)NC(=O)[C@@H](c1ccccc1)NC(=O)N1C(=O)C(=O)N(CC1)CC.[Na+]
• Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)c1ccccc1.[Na+]
• InChI: InChI=1S/C23H27N5O7S.Na/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);/q;+1/p-1/t13-,14-,15+,20-;/m1./s1
• InChIKey: WCMIIGXFCMNQDS-IDYPWDAWSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: potassium (2S,5R,6R)-6-[(2R)-2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; sodium piperacillin(1-)
• Brand Name: Pipracil
• Synonyms: Piperacillin sodium salt; Piperacillin Anhydrous; Piperacillin; Sodium Piperacillin; Pipracil; Pipril; PIPERACILLIN SODIUM SALT

Database IDs

• CAS Number: 66258-76-2; 59703-84-3
• EC Number: 261-868-6
• MDL Number: MFCD00917471
• Beilstein Number: 5373920
• PubChem SID: 160963667
• PubChem CID: 23666879

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4850655
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -2.2645185
• LogD (pH = 7.4): -3.6383073
• Log P: -0.25849018
• Molar Refractivity: 137.1338 cm^3
• Polarizability: 49.18091 Å^3
• Polar Surface Area: 159.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.21
• LOG S: -3.2
• Solubility (Water): 3.40e-01 g/l

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless to faintly yellow
• Hydrophobicity(logP): 0.3

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: XI0180000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (TLC)
• Impurities: ≤3% water
• Empirical Formula (Hill Notation): C23H26N5NaO7S

DETAILS

MP Biomedicals - 02156268

Sodium Salt

DrugBank - DB00319

• Drug Groups: approved
• Description: Semisynthetic, broad-spectrum, ampicillin derived ureidopenicillin antibiotic proposed for pseudomonas infections. It is also used in combination with other antibiotics. [PubChem]
• Indication: For the treatment of polymicrobial infections.
• Pharmacology: Piperacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Piperacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Piperacillin results from the inhibition of cell wall synthesis and is mediated through Piperacillin binding to penicillin binding proteins (PBPs). Piperacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Largely not metabolized.
• Absorption: Not absorbed following oral administration.
• Half Life: 36-72 minutes
• Elimination: As with other penicillins, PIPRACIL is eliminated primarily by glomerular filtration and tubular secretion; it is excreted rapidly as unchanged drug in high concentrations in the urine. Because PIPRACIL is excreted by the biliary route as well as by the renal route, it can be used safely in appropriate dosage in patients with severely restricted kidney function.
• Distribution: * 101 mL/kg [intravenous administration of 50 mg/kg (5-minute infusion) in neonates]
• Clearance: * 32?-?41 mL/min/1.73?m2; * 124?-?160 mL/min/1.73?m2 [older pediatric patients]
• References: Lau WK, Mercer D, Itani KM, Nicolau DP, Kuti JL, Mansfield D, Dana A: Randomized, open-label, comparative study of piperacillin-tazobactam administered by continuous infusion versus intermittent infusion for treatment of hospitalized patients with complicated intra-abdominal infection. Antimicrob Agents Chemother. 2006 Nov;50(11):3556-61. Epub 2006 Aug 28. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - P8396

Application
Piperacillin is a semisynthetic, broad-spectrum ureidopenicillin antibiotic. It is derived from ampicillin. It has been used in pharmacokinetic studies in order to optimize antimicrobial therapy in patients with sepsis1. It is used to study piperacillin hypersensitivity reactions2 and to study multidrug-resistant organisms3.
Biochem/physiol Actions
Piperacillin inhibits the final stage of bacterial cell wall biosynthesis at the level of PBP binding.
Piperacillin inhibits the last stage of bacterial cell wall synthesis by binding to certain penicillin-binding proteins (PBPs), which results in cell lysis. Cell lysis is mediated by bacterial cell wall autolytic enzymes. Piperacillin may interfere with autolysin inhibitors.

REFERENCES

• Lau WK, Mercer D, Itani KM, Nicolau DP, Kuti JL, Mansfield D, Dana A: Randomized, open-label, comparative study of piperacillin-tazobactam administered by continuous infusion versus intermittent infusion for treatment of hospitalized patients with complicated intra-abdominal infection. Antimicrob Agents Chemother. 2006 Nov;50(11):3556-61. Epub 2006 Aug 28. Pubmed