Cefoperazone

CAS# 62893-19-0

Cefoperazone

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Chemical structure

Cefoperazone

3D structure

Chemical Properties of Cefoperazone

Cas No. 62893-19-0 SDF Download SDF
PubChem ID 44187 Appearance Powder
Formula C25H27N9O8S2 M.Wt 645.66
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (154.88 mM)
H2O : < 0.1 mg/mL (insoluble)
*"≥" means soluble, but saturation unknown.
Chemical Name (6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=C(C=C2)O)C(=O)NC3C4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
Standard InChIKey GCFBRXLSHGKWDP-XCGNWRKASA-N
Standard InChI InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Cefoperazone

DescriptionCefoperazone is a cephalosporin antibiotic for inhibition of rMrp2-mediated [3H]E217βG uptake with IC50 of 199 μM. Target: Antibacterial Cefoperazone is a sterile, semisynthetic, broad-spectrum, parenteral cephalosporin antibiotic for intravenous or intramuscular administration. After intravenous administration of 2 g of Cefoperazone, levels in serum rang from 202μg/mL to 375 μg/mL depending on the period of drug administration. After intramuscular injection of 2 g of Cefoperazone, the mean peak serum level is 111 μg/mL at 1.5 hours. At 12 hours after dosing, mean serum levels are still 2 to 4 μg/mL. Cefoperazone is 90% bound to serum proteins.

References:
[1]. Kato, Y., et al., Involvement of multidrug resistance-associated protein 2 (Abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics. Drug Metab Dispos, 2008. 36(6): p. 1088-96. [2]. Craig, W.A. and A.U. Gerber, Pharmacokinetics of cefoperazone: a review. Drugs, 1981. 22 Suppl 1: p. 35-45.

Cefoperazone Dilution Calculator

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Cefoperazone Molarity Calculator

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Preparing Stock Solutions of Cefoperazone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5488 mL 7.744 mL 15.488 mL 30.9761 mL 38.7201 mL
5 mM 0.3098 mL 1.5488 mL 3.0976 mL 6.1952 mL 7.744 mL
10 mM 0.1549 mL 0.7744 mL 1.5488 mL 3.0976 mL 3.872 mL
50 mM 0.031 mL 0.1549 mL 0.3098 mL 0.6195 mL 0.7744 mL
100 mM 0.0155 mL 0.0774 mL 0.1549 mL 0.3098 mL 0.3872 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Cefoperazone

Cefoperazone is an antimicrobial agent that possesses potent LACTB (β-lactamase) inhibitory properties.

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References on Cefoperazone

Cefoperazone-treated Mouse Model of Clinically-relevant Clostridium difficile Strain R20291.[Pubmed:28060346]

J Vis Exp. 2016 Dec 10;(118).

Clostridium difficile is an anaerobic, gram-positive, spore-forming enteric pathogen that is associated with increasing morbidity and mortality and consequently poses an urgent threat to public health. Recurrence of a C. difficile infection (CDI) after successful treatment with antibiotics is high, occurring in 20-30% of patients, thus necessitating the discovery of novel therapeutics against this pathogen. Current animal models of CDI result in high mortality rates and thus do not approximate the chronic, insidious disease manifestations seen in humans with CDI. To evaluate therapeutics against C. difficile, a mouse model approximating human disease utilizing a clinically-relevant strain is needed. This protocol outlines the Cefoperazone mouse model of CDI using a clinically-relevant and genetically-tractable strain, R20291. Techniques for clinical disease monitoring, C. difficile bacterial enumeration, toxin cytotoxicity, and histopathological changes throughout CDI in a mouse model are detailed in the protocol. Compared to other mouse models of CDI, this model is not uniformly lethal at the dose administered, allowing for the observation of a prolonged clinical course of infection concordant with the human disease. Therefore, this Cefoperazone mouse model of CDI proves a valuable experimental platform to assess the effects of novel therapeutics on the amelioration of clinical disease and on the restoration of colonization resistance against C. difficile.

Antimicrobial activity of tigecycline and cefoperazone/sulbactam tested against 18,386 Gram-negative organisms from Europe and the Asia-Pacific region (2013-2014).[Pubmed:28341098]

Diagn Microbiol Infect Dis. 2017 Jun;88(2):177-183.

A total of 18,386 organisms, including 13,224 Enterobacteriaceae, 3536 Pseudomonas aeruginosa, 1254 Acinetobacter spp., and 372Stenotrophomonas maltophilia were collected from Western Europe (WEU; n=10,021), Eastern Europe (EEU; n=4957), and the Asia-Pacific region (APAC; n=3408 [1052 from China]) in 2013-2014 as part of the SENTRY Antimicrobial Surveillance Program and tested by a reference broth microdilution method for susceptibility against tigecycline, Cefoperazone/sulbactam, and comparator agents. Overall, 95.3% of Enterobacteriaceae were susceptible (Cefoperazone/sulbactam inhibited 94.6/83.5/91.5% of Enterobacteriaceae at

Acute localized exanthematous pustulosis caused by cefoperazone and sodium sulbactam.[Pubmed:28099605]

An Bras Dermatol. 2016 Nov-Dec;91(6):808-810.

Acute localized exanthematous pustulosis is a localized variant of acute generalized exanthematous pustulosis, which is characterized by the eruption of multiple scattered pustules following drug administration. A 72-year-old woman presented with multiple erythematous pustules on her face, which had appeared two days after using Cefoperazone and sodium sulbactam. Histopathological findings showed subcorneal pustules and mixed inflammatory cell infiltration in the dermis. The pustules resolved within about two weeks after the patient discontinued the antibiotics. This report discusses the case of a woman with a cutaneous drug reaction consistent with acute localized exanthematous pustulosis that occurred after Cefoperazone and sodium sulbactam were administered.

Description

Cefoperazone is a cephalosporin antibiotic for inhibition of rMrp2-mediated [3H]E217βG uptake with IC50 of 199 μM.

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