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MedKoo Cat#: 540064 | Name: Cefoperazone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cefoperazone is a penicillin binding protein inhibitor and mammalian mRNA splicing inhibitor that prevents peptidoglycan synthesis and bacterial cell wall formation.

Chemical Structure

Cefoperazone
Cefoperazone
CAS#62893-19-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 540064

Name: Cefoperazone

CAS#: 62893-19-0 (free acid)

Chemical Formula: C25H27N9O8S2

Exact Mass: 645.1424

Molecular Weight: 645.66

Elemental Analysis: C, 46.51; H, 4.22; N, 19.52; O, 19.82; S, 9.93

Price and Availability

Size Price Availability Quantity
1g USD 350.00 2 Weeks
5g USD 950.00 2 Weeks
20g USD 2,950.00 2 Weeks
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Related CAS #
62893-20-3 (sodium) 62893-19-0 (free acid)
Synonym
Cefobid; Cefozon; T1551; T-1551; T 1551; C06883; C-06883; C 06883 D07645; D-07645; D 07645
IUPAC/Chemical Name
(6R,7R)-7-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetamido)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
GCFBRXLSHGKWDP-XCGNWRKASA-N
InChi Code
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
SMILES Code
O=C(C(N12)=C(CSC3=NN=NN3C)CS[C@]2([H])[C@H](NC([C@H](NC(N4C(C(N(CC)CC4)=O)=O)=O)C5=CC=C(O)C=C5)=O)C1=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 645.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Gao C, Tong J, Yu K, Sun Z, An R, Du Z. Pharmacokinetics of cefoperazone/sulbactam in critically ill patients receiving continuous venovenous hemofiltration. Eur J Clin Pharmacol. 2016 Jul;72(7):823-30. doi: 10.1007/s00228-016-2045-x. Epub 2016 Mar 29. PubMed PMID: 27023465. 2: Koomanachai P, Tongsai S, Thamlikitkul V. Effectiveness and Safety of Generic Formulation of Cefoperazone/Sulbactam (Bacticep®) in Treatment of Infections at Siriraj Hospital. J Med Assoc Thai. 2016 Jan;99(1):8-14. PubMed PMID: 27455819. 3: Wang Q, Wu Y, Chen B, Zhou J. Drug concentrations in the serum and cerebrospinal fluid of patients treated with cefoperazone/sulbactam after craniotomy. BMC Anesthesiol. 2015 Mar 13;15:33. doi: 10.1186/s12871-015-0012-1. eCollection 2015. PubMed PMID: 25798070; PubMed Central PMCID: PMC4369365. 4: Ren J, Nettleship JE, Males A, Stuart DI, Owens RJ. Crystal structures of penicillin-binding protein 3 in complexes with azlocillin and cefoperazone in both acylated and deacylated forms. FEBS Lett. 2016 Jan;590(2):288-97. doi: 10.1002/1873-3468.12054. Epub 2016 Jan 23. PubMed PMID: 26823174; PubMed Central PMCID: PMC4764023. 5: Liu B, Bai Y, Liu Y, Di X, Zhang X, Wang R, Wang J. In vitro activity of tigecycline in combination with cefoperazone-sulbactam against multidrug-resistant Acinetobacter baumannii. J Chemother. 2015 Oct;27(5):271-6. doi: 10.1179/1973947814Y.0000000203. Epub 2014 Jul 28. PubMed PMID: 25068186. 6: Alasmari F, Rao PS, Sari Y. Effects of cefazolin and cefoperazone on glutamate transporter 1 isoforms and cystine/glutamate exchanger as well as alcohol drinking behavior in male alcohol-preferring rats. Brain Res. 2016 Mar 1;1634:150-7. doi: 10.1016/j.brainres.2016.01.007. Epub 2016 Jan 11. PubMed PMID: 26790351; PubMed Central PMCID: PMC4779704. 7: Xia J, Zhang D, Xu Y, Gong M, Zhou Y, Fang X. A retrospective analysis of carbapenem-resistant Acinetobacter baumannii-mediated nosocomial pneumonia and the in vitro therapeutic benefit of cefoperazone/sulbactam. Int J Infect Dis. 2014 Jun;23:90-3. doi: 10.1016/j.ijid.2014.01.017. Epub 2014 Apr 12. PubMed PMID: 24726664. 8: Hoang VD, Loan NT, Tho VT, Nguyen HM. UV spectrophotometric simultaneous determination of cefoperazone and sulbactam in pharmaceutical formulations by derivative, Fourier and wavelet transforms. Spectrochim Acta A Mol Biomol Spectrosc. 2014;121:704-14. doi: 10.1016/j.saa.2013.11.095. Epub 2013 Nov 25. PubMed PMID: 24374557. 9: Rao PS, Goodwani S, Bell RL, Wei Y, Boddu SH, Sari Y. Effects of ampicillin, cefazolin and cefoperazone treatments on GLT-1 expressions in the mesocorticolimbic system and ethanol intake in alcohol-preferring rats. Neuroscience. 2015 Jun 4;295:164-74. doi: 10.1016/j.neuroscience.2015.03.038. Epub 2015 Mar 24. PubMed PMID: 25813713; PubMed Central PMCID: PMC4408259. 10: Xin X, Jian L, Xia X, Jia B, Huang W, Li C, Wang C, Zhou L, Sun X, Tang X, Huang Y, Zhu Y, Zhang W. A multicentre clinical study on the injection of ceftriaxone/sulbactam compared with cefoperazone/sulbactam in the treatment of respiratory and urinary tract infections. Ann Clin Microbiol Antimicrob. 2013 Dec 9;12:38. doi: 10.1186/1476-0711-12-38. PubMed PMID: 24321187; PubMed Central PMCID: PMC4029302. 11: Feßler AT, Turnidge J, Schwarz S. Quality control ranges for cefoperazone 30 μg disks for Staphylococcus aureus ATCC® 25923 and Escherichia coli ATCC® 25922. Vet Microbiol. 2014 Jul 16;171(3-4):284-9. doi: 10.1016/j.vetmic.2014.02.039. Epub 2014 Mar 12. PubMed PMID: 24685239. 12: Yuan Y, Fu S, Xu Q, Yang J, Hu X, Liu S. The fluorescence and resonance Rayleigh scattering spectral study and analytical application of cerium (IV) and cefoperazone system. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Jun 5;162:93-7. doi: 10.1016/j.saa.2016.03.001. Epub 2016 Mar 3. PubMed PMID: 26994317. 13: Patankar M, Sukumaran S, Chhibba A, Nayak U, Sequeira L. Comparative in-vitro activity of cefoperazone-tazobactam and cefoperazone-sulbactam combinations against ESBL pathogens in respiratory and urinary infections. J Assoc Physicians India. 2012 Nov;60:22-4. PubMed PMID: 23767198. 14: Feng J, Auwaerter PG, Zhang Y. Drug combinations against Borrelia burgdorferi persisters in vitro: eradication achieved by using daptomycin, cefoperazone and doxycycline. PLoS One. 2015 Mar 25;10(3):e0117207. doi: 10.1371/journal.pone.0117207. eCollection 2015. PubMed PMID: 25806811; PubMed Central PMCID: PMC4373819. 15: Pei G, Mao Y, Sun Y. In vitro activity of minocycline alone and in combination with cefoperazone-sulbactam against carbapenem-resistant Acinetobacter baumannii. Microb Drug Resist. 2012 Dec;18(6):574-7. doi: 10.1089/mdr.2012.0076. Epub 2012 Aug 28. PubMed PMID: 22928863. 16: Turk Dagi H, Kus H, Arslan U, Tuncer I. [In vitro synergistic activity of sulbactam in combination with imipenem, meropenem and cefoperazone against carbapenem-resistant Acinetobacter baumannii isolates]. Mikrobiyol Bul. 2014 Apr;48(2):311-5. Turkish. PubMed PMID: 24819268. 17: Poudyal N, Gyawali N, Gurung R, Bhattarai NR, Baral R, Khanal B, Shrestha S, Amatya R, Bhattacharya SK. In vitro activity of cefoperazone-sulbactam combination against gram negative bacilli. Nepal Med Coll J. 2012 Mar;14(1):5-8. PubMed PMID: 23441486. 18: Ovali F, Gursoy T, Sari I, Divrikli D, Aktas A. Use of cefoperazone/sulbactam in neonates. Pediatr Int. 2012 Feb;54(1):60-3. doi: 10.1111/j.1442-200X.2011.03458.x. Epub 2011 Oct 17. PubMed PMID: 21883691. 19: Wieczorek P, Sacha P, Ojdana D, Milewski R, Jurczak A, Kaczyńska K, Tryniszewska E. [In vitro resistance development in Acinetobacter baumannii to sulbactam and cefoperazone]. Med Dosw Mikrobiol. 2012;64(1):55-62. Polish. PubMed PMID: 22808730. 20: Xie J, Wang Y, Zheng X, Yang Q, Wang T, Zou Y, Xing J, Dong Y. Modeling and forecasting Acinetobacter baumannii resistance to set appropriate use of cefoperazone-sulbactam: Results from trend analysis of antimicrobial consumption and development of resistance in a tertiary care hospital. Am J Infect Control. 2015 Aug;43(8):861-4. doi: 10.1016/j.ajic.2015.04.197. Epub 2015 May 29. PubMed PMID: 26033693.