Desfuroylceftiofur
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MedKoo CAT#: 465408

CAS#: 120882-22-6

Description: Desfuroylceftiofur is an active metabolite of the broad-spectrum cephalosporin antibiotic ceftiofur. It is formed from ceftiofur by bovine kidney and liver esterases. Desfuroylceftiofur is active against 539 veterinary isolates of Gram-negative bacteria and Gram-positive cocci bacteria (MIC50s = 0.0078-1 and 0.015-4 µg/ml, respectively).

Chemical Structure

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Desfuroylceftiofur
CAS# 120882-22-6
Instruction

Theoretical Analysis

MedKoo Cat#: 465408
Name: Desfuroylceftiofur
CAS#: 120882-22-6
Chemical Formula: C14H15N5O5S3
Exact Mass: 429.02
Molecular Weight: 429.484
Elemental Analysis: C, 39.15; H, 3.52; N, 16.31; O, 18.63; S, 22.39

Price and Availability

Size Price Availability Quantity
1mg USD 450 2 Weeks
5mg USD 1250 2 Weeks
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Synonym: Desfuroylceftiofur;

IUPAC/Chemical Name: (6R,7R)-7-((Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChi Key: OITCOWCNESRWSM-GHXIOONMSA-N

InChi Code: InChI=1S/C14H15N5O5S3/c1-24-18-7(6-4-27-14(15)16-6)10(20)17-8-11(21)19-9(13(22)23)5(2-25)3-26-12(8)19/h4,8,12,25H,2-3H2,1H3,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1

SMILES Code: SCC1=C(N2[C@]([H])(SC1)[C@@H](C2=O)NC(/C(C3=CSC(N)=N3)=N\OC)=O)C(O)=O

Appearance: Solid powder

Purity: >80% (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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 429.48 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Gaire TN, Salas J, Dunmire KM, Paulk CB, Tokach MD, Nagaraja TG, Volkova VV. Faecal concentrations of ceftiofur metabolites in finisher pigs administered intramuscularly with ceftiofur. Vet Med Sci. 2021 May 15. doi: 10.1002/vms3.520. Epub ahead of print. PMID: 33991410.

2: Adil M, Omer MO, Javeed A, Ghafoor A, Ashraf M, Khan AM. Isocratic High Performance Liquid Chromatography Assay for Quantification of Ceftiofur Hydrochloride in Bubaline Plasma. Acta Chim Slov. 2019 Dec;66(4):859-864. PMID: 34057479.

3: Wang J, Schneider BK, Xue J, Sun P, Qiu J, Mochel JP, Cao X. Pharmacokinetic Modeling of Ceftiofur Sodium Using Non-linear Mixed-Effects in Healthy Beagle Dogs. Front Vet Sci. 2019 Oct 17;6:363. doi: 10.3389/fvets.2019.00363. PMID: 31681816; PMCID: PMC6811611.

4: Zhang M, Yang F, Yu HJ, Kang TJ, Ding YH, Yu ML, Wang QK, Zhu YX, Yang F. Pharmacokinetics of ceftiofur sodium in cats following a single intravenous and subcutaneous injection. J Vet Pharmacol Ther. 2019 Nov;42(6):602-608. doi: 10.1111/jvp.12814. Epub 2019 Sep 17. PMID: 31529627.

5: Li XD, Chi SQ, Wu LY, Liu C, Sun T, Hong J, Chen X, Chen XG, Wang GS, Yu DJ. PK/PD modeling of Ceftiofur Sodium against Haemophilus parasuis infection in pigs. BMC Vet Res. 2019 Aug 1;15(1):272. doi: 10.1186/s12917-019-2008-4. PMID: 31370843; PMCID: PMC6676638.

6: Fayette MA, Rose JB, Hunter RP, Bowman MR, Proudfoot JS. NAÏVE-POOLED PHARMACOKINETICS OF CEFTIOFUR CRYSTALLINE FREE ACID AFTER SINGLE INTRAMUSCULAR ADMINISTRATION IN SMOOTH DOGFISH (MUSTELUS CANIS). J Zoo Wildl Med. 2019 Jun 13;50(2):466-469. doi: 10.1638/2018-0104. PMID: 31260216.

7: Xiong J, Zhu Q, Lei Z, Yang S, Chen P, Zhao Y, Cao J, Qiu Y. Bioequivalence evaluation of two 5% ceftiofur hydrochloride sterile suspension in pigs. J Vet Med Sci. 2018 Dec 11;80(12):1847-1852. doi: 10.1292/jvms.18-0470. Epub 2018 Nov 1. PMID: 30381675; PMCID: PMC6305520.

8: Altan F, Uney K, Er A, Cetin G, Dik B, Yazar E, Elmas M. Pharmacokinetics of ceftiofur in healthy and lipopolysaccharide-induced endotoxemic newborn calves treated with single and combined therapy. J Vet Med Sci. 2017 Jul 19;79(7):1245-1252. doi: 10.1292/jvms.16-0641. Epub 2017 Jun 5. PMID: 28579597; PMCID: PMC5559372.

9: Di Rocco M, Moloney M, O'Beirne T, Earley S, Berendsen B, Furey A, Danaher M. Development and validation of a quantitative confirmatory method for 30 β-lactam antibiotics in bovine muscle using liquid chromatography coupled to tandem mass spectrometry. J Chromatogr A. 2017 Jun 2;1500:121-135. doi: 10.1016/j.chroma.2017.04.022. Epub 2017 Apr 12. PMID: 28449875.

10: Macpherson ML, Giguère S, Pozor MA, Runcan E, Vickroy TW, Benson SA, Troedsson MHT, Hatzel JN, Larson J, Vanden Berg E, Kelleman AA, Sanchez LC, LeBlanc MM. Pharmacokinetics of ceftiofur sodium in equine pregnancy. J Vet Pharmacol Ther. 2017 Dec;40(6):656-662. doi: 10.1111/jvp.12399. Epub 2017 Mar 19. PMID: 28317126.

11: Waraich GS, Sidhu PK, Daundkar PS, Kaur G, Sharma SK. Pharmacokinetic and pharmacodynamic characterization of ceftiofur crystalline-free acid following subcutaneous administration in domestic goats. J Vet Pharmacol Ther. 2017 Oct;40(5):429-438. doi: 10.1111/jvp.12373. Epub 2016 Dec 12. PMID: 27943295.

12: Cox KS, Nelson BB, Wittenburg L, Gold JR. Plasma, subcutaneous tissue and bone concentrations of ceftiofur sodium after regional limb perfusion in horses. Equine Vet J. 2017 May;49(3):341-344. doi: 10.1111/evj.12614. Epub 2016 Aug 24. PMID: 27458113.

13: Woodrow JS, Caldwell M, Cox S, Hines M, Credille BC. Comparative plasma pharmacokinetics of ceftiofur sodium and ceftiofur crystalline-free acid in neonatal calves. J Vet Pharmacol Ther. 2016 Jun;39(3):271-6. doi: 10.1111/jvp.12275. Epub 2015 Nov 6. PMID: 26542633.

14: Beyer A, Baumann S, Scherz G, Stahl J, von Bergen M, Friese A, Roesler U, Kietzmann M, Honscha W. Effects of ceftiofur treatment on the susceptibility of commensal porcine E.coli--comparison between treated and untreated animals housed in the same stable. BMC Vet Res. 2015 Oct 15;11:265. doi: 10.1186/s12917-015-0578-3. PMID: 26472561; PMCID: PMC4608134.

15: Mompelat S, Fourmond MP, Laurentie M, Verdon E, Hurtaud-Pessel D, Abjean JP. Validation of a liquid chromatography-high-resolution mass spectrometry method for the analysis of ceftiofur in poultry muscle, kidneys and plasma: A unique accuracy profile for each and every matrix. J Chromatogr A. 2015 Aug 14;1407:119-29. doi: 10.1016/j.chroma.2015.06.043. Epub 2015 Jun 23. PMID: 26152526.

16: Chiesa OA, Feng S, Kijak P, Smith EA, Li H, Qiu J. Plasma pharmacokinetics of ceftiofur metabolite desfuroylceftiofur cysteine disulfide in holstein steers: application of nonlinear mixed-effects modeling. J Vet Pharmacol Ther. 2016 Apr;39(2):149-56. doi: 10.1111/jvp.12245. Epub 2015 Jun 26. PMID: 26112893.

17: Kottwitz J, Blue-McLendon A, Monarski C, Jensen J, Boothe D. DISPOSITION OF CEFTIOFUR AND ITS ACTIVE METABOLITES IN FALLOW DEER (DAMA DAMA) FOLLOWING SINGLE-DOSE INTRAVENOUS AND INTRAMUSCULAR ADMINISTRATION. J Zoo Wildl Med. 2015 Jun;46(2):255-61. doi: 10.1638/2014-0250R.1. PMID: 26056876.

18: McGrath TF, McClintock L, Dunn JS, Husar GM, Lochhead MJ, Sarver RW, Klein FE, Rice JA, Campbell K, Elliott CT. Development of a rapid multiplexed assay for the direct screening of antimicrobial residues in raw milk. Anal Bioanal Chem. 2015 Jun;407(15):4459-72. doi: 10.1007/s00216-015-8526-4. Epub 2015 Feb 21. PMID: 25701420.

19: Fultz L, Giguère S, Berghaus LJ, Grover GS, Merritt DA. Pulmonary pharmacokinetics of desfuroylceftiofur acetamide after nebulisation or intramuscular administration of ceftiofur sodium to weanling foals. Equine Vet J. 2015 Jul;47(4):473-7. doi: 10.1111/evj.12316. Epub 2014 Sep 5. PMID: 24975449.

20: Feng S, Chiesa OA, Kijak P, Chattopadhaya C, Lancaster V, Smith EA, Girard L, Sklenka S, Li H. Determination of ceftiofur metabolite desfuroylceftiofur cysteine disulfide in bovine tissues using liquid chromatography-tandem mass spectrometry as a surrogate marker residue for ceftiofur. J Agric Food Chem. 2014 Jun 4;62(22):5011-9. doi: 10.1021/jf405423e. Epub 2014 May 21. PMID: 24819974.