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

• ChemBase ID: 1384
• Molecular Formular: C15H16N2O6S2
• Molecular Mass: 384.42734
• Monoisotopic Mass: 384.04497824
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)[C@@H](c1ccsc1)C(=O)O
• 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
• InChI: InChI=1S/C15H16N2O6S2/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)/t7-,8-,9+,12-/m1/s1
• InChIKey: OHKOGUYZJXTSFX-KZFFXBSXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[(2R)-2-carboxy-2-(thiophen-3-yl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: ticarcillin
• Synonyms: Ticarcilina [inn-spanish]; Ticarcillin supplement; Ticarcilline [inn-french]; Ticarcillinum [inn-latin]; Ticarcillin; Ticarcillin; Ticarcillin Supplement; 替卡西林; 替卡西林添加剂

Database IDs

• CAS Number: 34787-01-4
• EC Number: 252-213-5
• MDL Number: MFCD00864998
• PubChem SID: 24850647; 46505959; 160964844
• PubChem CID: 36921

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0920584
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -3.1756372
• LogD (pH = 7.4): -5.9742513
• Log P: 0.5957988
• Molar Refractivity: 87.9253 cm^3
• Polarizability: 34.58174 Å^3
• Polar Surface Area: 124.01 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.99
• LOG S: -3.73
• Solubility (Water): 7.16e-02 g/l

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• 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

• Grade: for microbiology
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C15H16N2O6S2

DETAILS

DrugBank - DB01607

• Drug Groups: approved
• Description: An antibiotic derived from penicillin similar to carbenicillin in action.
• Indication: For the treatment of bacterial infections.
• Pharmacology: Ticarcillin is a semisynthetic antibiotic with a broad spectrum of bactericidal activity against many gram-positive and gram-negative aerobic and anaerobic bacteria. Ticarcillin is, however, susceptible to degradation by ?-lactamases, and therefore, the spectrum of activity does not normally include organisms which produce these enzymes.
• Toxicity: As with other penicillins, neurotoxic reactions may arise when very high doses of ticarcillin are administered, especially in patients with impaired renal function.
• Affected Organisms: Enteric bacteria and other eubacteria
• Half Life: 1.1 hours
• Protein Binding: 45%
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 17778

Components
Composition (per vial; sufficient for 1000 mL medium): Ticarcillin 1.00 mg
Application
An antibiotic supplement recommended for the selective enrichment of Yersinia enterocolitica.