(2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 460
• Molecular Formular: C17H18N2O6S
• Molecular Mass: 378.39962
• Monoisotopic Mass: 378.08855731
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)C(c1ccccc1)C(=O)O
• Canonical SMILES: O=C(C(c1ccccc1)C(=O)O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1
• InChIKey: FPPNZSSZRUTDAP-UWFZAAFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-(2-carboxy-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: carbenicillin
• Brand Name: Geopen; Pyopen
• Synonyms: Carboxybenzylpenicillin acid; Carboxybenzylpenicillin; Carbenicillinum [INN-Latin]; Carbenicilline [INN-French]; Carbenicillina [DCIT]; Carbenicilina [INN-Spanish]; alpha-Carboxybenzylpencillin; Carbenicillin; α-Carboxybenzylpenicillin solution; Carbenicillin; Carbenicillin; Klebsiella Selective Supplement; α-Carboxybenzylpenicillin 溶液; 羧苄青霉素; 羧苄青霉素; 克雷伯氏菌选择性添加剂

Database IDs

• CAS Number: 4697-36-3
• EC Number: 225-171-0
• MDL Number: MFCD00242604
• PubChem SID: 160963923; 46505653; 24892425
• PubChem CID: 20824

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.1068087
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -3.1951313
• LogD (pH = 7.4): -5.9115877
• Log P: 0.81535685
• Molar Refractivity: 90.8195 cm^3
• Polarizability: 35.8031 Å^3
• Polar Surface Area: 124.01 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.13
• LOG S: -2.99
• Solubility (Water): 3.90e-01 g/l

PROPERTIES

Physical Property

• Solubility: 451 mg/L
• Flash Point: 104 °F; 40 °C
• Hydrophobicity(logP): 1.8

Safety Information

• RTECS: ON9104700
• European Hazard Symbols: Harmful (Xn)
• UN Number: 1170
• German water hazard class: 2; 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10-42/43; 42/43
• Safety Statements: 22-36/37-45; 23-36/37-45
• GHS Pictograms: GHS02; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H317-H334; H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Concentration: 100 mg/mL in ethanol/water
• Grade: for microbiology
• Sterility: 0.2 μm filtered
• Shelf Life: (limited shelf life, expiry date on the label)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C17H18N2O6S

DETAILS

DrugBank - DB00578

• Drug Groups: approved
• Description: Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function. [PubChem]
• Indication: For the treatment of acute and chronic infections of the upper and lower urinary tract and in asymptomatic bacteriuria due to susceptible strains of bacteria.
• Pharmacology: Carbenicillin is a semisynthetic penicillin. Though carbenicillin provides substantial in vitro activity against a variety of both gram-positive and gram-negative microorganisms, the most important aspect of its profile is in its antipseudomonal and antiproteal activity. Because of the high urine levels obtained following administration, carbenicillin has demonstrated clinical efficacy in urinary infections due to susceptible strains of: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Morganella morganii, Pseudomonas species, Providencia rettgeri, Enterobacter species, and Enterococci (S. faecalis).
• Toxicity: Carbenicillin blood levels achievable are very low, and toxic reactions as a function of overdosage should not occur systematically. The oral LD₅₀ in mice is 3,600 mg/kg, in rats 2,000 mg/kg, and in dogs is in excess of 500 mg/kg. The lethal human dose is not known. Symptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Minimal.
• Absorption: Rapidly absorbed from the small intestine following oral administration. Oral bioavailability is 30 to 40%.
• Half Life: 1 hour
• Protein Binding: 30 to 60%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - C1613

Application
Used for selection of ampr transformed cells. Use to study the role of penicillin-sensitive transpeptidases in cell wall biosynthesis.
Biochem/physiol Actions
The antibiotic carbenicillin, an ampicillin analog, is a commonly used selection agent that binds and inhibits enzymes involved in the synthesis of the bacterial cell wall. It is active against most isolates of Pseudomonas aerogenosa and certain indole-positive Proteus strains that are resistant to ampicillin. The gene conferring resistance to ampicillin and its analogs, ampr, codes for the enzyme β-lactamase. Carbenicillin is less sensitive to β-lactamase than ampicillin. In addition it has a superior stability at low pH. Experiments have shown that the use of carbenicillin in place of ampicillin helps prevent overgrowth of satellite colonies. Effective concentration: 50 to 100 μg/ml.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 15821

Components
(per vial, sufficient for 500 ml medium)Carbenicillin 25 mg
Application
For selective isolation and detection of Klebsiella species.
Biochem/physiol Actions
The antibiotic carbenicillin, an ampicillin analog, is a commonly used selection agent that binds and inhibits enzymes involved in the synthesis of the bacterial cell wall. It is active against most isolates of Pseudomonas aerogenosa and certain indole-positive Proteus strains that are resistant to ampicillin. The gene conferring resistance to ampicillin and its analogs, ampr, codes for the enzyme β-lactamase. Carbenicillin is less sensitive to β-lactamase than ampicillin. In addition it has a superior stability at low pH. Experiments have shown that the use of carbenicillin in place of ampicillin helps prevent overgrowth of satellite colonies. Effective concentration: 50 to 100 μg/ml.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 15821.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.