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

• ChemBase ID: 155569
• Molecular Formular: C15H14N2Na2O6S2
• Molecular Mass: 428.391
• Monoisotopic Mass: 428.00886674
• SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c1ccsc1)C(=O)[O-])C(=O)[O-])C.[Na+].[Na+]
• Canonical SMILES: O=C([C@@H](c1cscc1)C(=O)[O-])N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C.[Na+].[Na+]
• InChI: InChI=1S/C15H16N2O6S2.2Na/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6;;/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23);;/q;2*+1/p-2/t7-,8-,9+,12-;;/m1../s1
• InChIKey: ZBBCUBMBMZNEME-QBGWIPKPSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S,5R,6R)-6-[(2R)-2-carboxylato-2-(thiophen-3-yl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: disodium ticarcillin(2-)
• Synonyms: (2S,5R,6R)-6-[[(2R)-Carboxy-3-thienylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt; Ticarcillin disodium salt; 替卡西林 二钠盐

Database IDs

• CAS Number: 4697-14-7
• MDL Number: MFCD07787410
• PubChem SID: 24900306; 162249707
• PubChem CID: 470375

CALCULATED PROPERTIES

• Acid pKa: 3.0920584
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -3.1756372
• LogD (pH = 7.4): -5.9742513
• Log P: 0.5957988
• Molar Refractivity: 109.5995 cm^3
• Polarizability: 34.349667 Å^3
• Polar Surface Area: 129.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: XM9410000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38-42-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H334-H335
• GHS Precautionary statements: P261-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C15H14N2Na2O6S2

DETAILS

Sigma Aldrich - T5639

Other Notes
β-Lactam antibiotic
Application
Ticarcillin is a semisynthetic antibiotic with a broad spectrum of bactericidal activity against many gram-positive and gram-negative aerobic and anaerobic bacteria. It is commonly used in combination with clavulanate in order to improve it′s efficacy1. It is used to study appropriate dosing in pediatric patients who have cystic fibrosis2.
Biochem/physiol Actions
Ticarcillin is a β-Lactam antibiotic that prevents bacterial cell wall biosynthesis at the level of peptidogylcan cross-linking by inhibiting peptidoglycan transpeptidases. It is derived from penicillin and is similar to carbenicillin in action. Ticarcillin is susceptible to degradation by β-lactamases1.