disodium (2S,5R,6R)-6-(2-carboxylato-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 105918
• Molecular Formular: C17H16N2Na2O6S
• Molecular Mass: 422.36328
• Monoisotopic Mass: 422.0524458
• SMILES: [Na+].[Na+].O=C([O-])[C@@H]1N2C(=O)[C@@H](NC(=O)C(c3ccccc3)C(=O)[O-])[C@H]2SC1(C)C
• 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.[Na+].[Na+]
• InChI: InChI=1S/C17H18N2O6S.2Na/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);;/q;2*+1/p-2/t9?,10-,11+,14-;;/m1../s1
• InChIKey: RTYJTGSCYUUYAL-YCAHSCEMSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S,5R,6R)-6-(2-carboxylato-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: disodium carbenicillin(2-)
• Synonyms: (2S,5R,6R)-6-[(2-Carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt; N-(2-Carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-2-phenylmalonamic Acid Disodium Salt; Anabactyl; BRL 2064; Carbapen; Carbecin; Carbenicillin Sodium; Carbenicilline Disodium; Carboxybenzylpenicillin Sodium; Disodium (α-Carboxybenzyl)penicillin; Disodium Carbenicillin; Fugacillin; Geocillin; Geopen; Gripenin; Hyoper; Microcillin; NSC 111071; Piopen; Pyopen; Pyopene; Sodium carbenicillin; α-Carboxybenzylpenicillin Sodium Salt; Carbenicillin Disodium; Carbenicillin disodium; Carbenicillin disodium salt; α-Carboxybenzylpenicillin; CARBENICILLIN DISODIUM SALT; α-Carboxybenzylpenicillin disodium salt; 羧苄青霉素 二钠盐; 羧苄青霉素 二钠; α-Carboxybenzylpenicillin disodium salt 二钠盐; 羧苄青霉素 二钠盐

Database IDs

• CAS Number: 4800-94-6
• EC Number: 225-360-8
• MDL Number: MFCD00077683
• Beilstein Number: 5722128
• PubChem SID: 24892613; 24892409; 162092623; 24893142
• PubChem CID: 20933

CALCULATED PROPERTIES

• Acid pKa: 3.1068087
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -3.1951313
• LogD (pH = 7.4): -5.9115877
• Log P: 0.81535685
• Molar Refractivity: 112.4937 cm^3
• Polarizability: 35.574165 Å^3
• Polar Surface Area: 129.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohol: soluble; H2O: soluble (solutions are stable 24 hr at room temp, 72 hr at 2-8°C.); H2O: soluble50 mg/mL

Safety Information

• Storage Condition: 2-8°C
• RTECS: ON9105000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (anhydrous basis); 89.0-100.5% anhydrous basis
• Suitability: meets USP testing specifications; plant cell culture tested
• Empirical Formula (Hill Notation): C17H16N2Na2O6S

DETAILS

MP Biomedicals - 02195092

Disodium Salt

Sigma Aldrich - C3416

Analysis Note
Stable at 37 °C for 3 days
Application
Recommended for antibacterial use in cell culture media at 100 μg/ml and for selection of ampr transformed cells.
Biochem/physiol Actions
Carboxypenicillin antibiotic that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Analog to ampicillin. Antimicrobial spectrum: Gram-positive and Gram-negative bacteria, Pseudomonas.
Physical form
Hygroscopic powder
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 21800

Analysis Note
Stable at 37 °C for 3 days
Biochem/physiol Actions
Carboxypenicillin antibiotic that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Analog to ampicillin. Antimicrobial spectrum: Gram-positive and Gram-negative bacteria, Pseudomonas.
Other Notes
Parenteral antibiotic active against Pseudomonas aeruginosa.; Characterization of two chromosome-encoded β-lactamases from Citrobacter diversus ULA-271

Sigma Aldrich - C1389

Analysis Note
Stable at 37 °C for 3 days
Application
Used for selection of ampr transformed cells and to study the role of penicillin-sensitive transpeptidases in cell wall biosynthesis.
Biochem/physiol Actions
Carboxypenicillin antibiotic that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Analog to ampicillin. Antimicrobial spectrum: Gram-positive and Gram-negative bacteria, Pseudomonas.

Sigma Aldrich - C9231

Analysis Note
Stable at 37 °C for 3 days
Application
Used for selection of ampr transformed cells. Used to study the role of penicillin-sensitive transpeptidases in cell wall biosynthesis.
Biochem/physiol Actions
Carboxypenicillin antibiotic that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Analog to ampicillin. Antimicrobial spectrum: Gram-positive and Gram-negative bacteria, Pseudomonas.

Toronto Research Chemicals - C176080

Semi-synthetic antibiotic related to Penicillin (P223500). Antibacterial.

REFERENCES

• Naumann, K., et al.: Arzneim. Forsch., 19, 1222 (1969)
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1969)