Ticillin Disodium Salt

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Ticillin Disodium Salt
Category Antibiotics
Catalog number BBF-04022
CAS 4697-14-7
Molecular Weight 428.39
Molecular Formula C15H14N2Na2O6S2
Purity 96%

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Description

Ticarcillin disodium is a carboxypenicillin belonging to the beta-lactam class of antibiotics. It is used to prevent cross-linking of peptidoglycan during cell wall synthesis, when the bacteria try to divide, causing cell death.

Specification

Related CAS 3973-04-4 (free acid)
Synonyms (2S,5R,6R)-6-[[2-Carboxy-3-thienylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Disodium Salt; N-(2-Carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-3-thiophenemalonamic Acid Disodium Salt; [2S-(2α,5α,6β)]-6-[(Carboxy-3-thienylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Disodium Salt; Aerugipen Disodium Salt; Neoanabactyl; CSL Ticillin,Tarcil; Timentin sodium; Ticalpenin; ticarpen; TICAR
Shelf Life As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Storage Store at -20°C under inert atmosphere
IUPAC Name disodium;(2S,5R,6R)-6-[[(2R)-2-carboxylato-2-thiophen-3-ylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Canonical SMILES CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CSC=C3)C(=O)[O-])C(=O)[O-])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
InChI Key ZBBCUBMBMZNEME-QBGWIPKPSA-L
Source Semi-synthetic

Properties

Appearance White to Off-white Solid
Application Antibiotic
Boiling Point 768.3°C at 760 mmHg
Melting Point >173°C (dec.)
Solubility Soluble in DMSO (Slightly), Methanol (Slightly), Water (Slightly)

Reference Reading

1.Aeromonas spp.: An Emerging Nosocomial Pathogen.
Batra P1, Mathur P1, Misra MC2. J Lab Physicians. 2016 Jan-Jun;8(1):1-4. doi: 10.4103/0974-2727.176234.
Aeromonads are hallophillic, nonacid fast, nonspore forming, Gram-negative rods which are widely distributed in the soil, foodstuffs, and aquatic environment. Since times immemorial, they are important zoonotic pathogens of poikilotherms but are now emerging as important human pathogens. These emerging enteric pathogens flourish in the water distribution system by forming biofilms. They possess large number of virulence factors including inherent resistance to various antibiotics and ability to form biofilms using quorum sensing. These properties make them easy pathogens for human infections. Aeromonads are important enteric pathogens, but, with the growing level of immunosuppression in the population, they have been associated with various extraintestinal infections, such as skin and soft-tissue infections, traumatic wound infections, and lower respiratory tract/urinary tract infections. The average annual incidence of bacteremia in Southern Taiwan due to Aeromonas spp.
2.Antimicrobial resistance, integron carriage, and gyrA and gyrB mutations in Pseudomonas aeruginosa isolated from dogs with otitis externa and pyoderma in Brazil.
Arais LR1, Barbosa AV1, Carvalho CA1, Cerqueira AM1. Vet Dermatol. 2016 Apr;27(2):113-e31. doi: 10.1111/vde.12290. Epub 2016 Feb 1.
BACKGROUND: Pseudomonas aeruginosa is associated with otitis and pyoderma in dogs and is frequently resistant to several antimicrobial drugs. Resistance genes can be carried by integrons with quinolone resistance mainly due to mutations in DNA topoisomerases II and IV.
3.Intra- and Interspecies Effects of Outer Membrane Vesicles from Stenotrophomonas maltophilia on β-Lactam Resistance.
Devos S1, Stremersch S2, Raemdonck K2, Braeckmans K2, Devreese B3. Antimicrob Agents Chemother. 2016 Mar 25;60(4):2516-8. doi: 10.1128/AAC.02171-15. Print 2016 Apr.
The treatment ofStenotrophomonas maltophiliainfection with β-lactam antibiotics leads to increased release of outer membrane vesicles (OMVs), which are packed with two chromosomally encoded β-lactamases. Here, we show that these β-lactamase-packed OMVs are capable of establishing extracellular β-lactam degradation. We also show that they dramatically increase the apparent MICs of imipenem and ticarcillin for the cohabituating speciesPseudomonas aeruginosaandBurkholderia cenocepacia.
4.Activity of temocillin in a lethal murine model of infection of intra-abdominal origin due to KPC-producing Escherichia coli.
Alexandre K1, Chau F2, Guérin F3, Massias L4, Lefort A5, Cattoir V3, Fantin B6. J Antimicrob Chemother. 2016 Mar 29. pii: dkw066. [Epub ahead of print]
OBJECTIVES: Temocillin is a 6-α-methoxy derivative of ticarcillin that shows in vitro activity against Enterobacteriaceae producing Klebsiella pneumoniae carbapenemase (KPC). Our objective was to assess in vivo temocillin activity against KPC-producing Escherichia coli.

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