Cefcanel daloxate

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MedKoo CAT#: 596758

CAS#: 97275-40-6

Description: Cefcanel daloxate, also known as KY-109, is a pro-drug to improve oral absorption of KY-087. The antimicrobial activities of KY-087 against clinically isolated Gram-positive organisms were superior to those of CEX and CCL. The antimicrobial activities of KY-087 against Gram-negative organisms, such as Enterobacter sp., Serratia, and Pseudomonas sp., were less active. KY-087 showed dose-related bactericidal activity against Staphylococcus aureus and Escherichia coli. The therapeutic efficacy of KY-109 against experimental intraperitoneal infections caused by Gram-positive and Gram-negative organisms in mice was comparable to that of CEX but inferior to that of CCL. In experimental granuloma pouch models in rats and kidney infection in rabbits, therapeutic efficacy of KY-109 was either comparable or superior to that of CEX and CCL.

Chemical Structure

Cefcanel daloxate
CAS# 97275-40-6

Theoretical Analysis

MedKoo Cat#: 596758
Name: Cefcanel daloxate
CAS#: 97275-40-6
Chemical Formula: C27H27N5O9S3
Exact Mass: 661.0971
Molecular Weight: 661.72
Elemental Analysis: C, 49.01; H, 4.11; N, 10.58; O, 21.76; S, 14.53

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
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Related CAS #: 97275-40-6 (free base)   41952-52-7   92602-21-6 (HCl)    

Synonym: Cefcanel daloxate; Cefcanel daloxate HCl; KY-109; KY109; KY 109;

IUPAC/Chemical Name: (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (6R,7R)-7-((R)-2-((L-alanyl)oxy)-2-phenylacetamido)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate


InChi Code: InChI=1S/C27H27N5O9S3/c1-12(28)24(35)41-20(15-7-5-4-6-8-15)21(33)29-18-22(34)32-19(25(36)38-9-17-13(2)39-27(37)40-17)16(10-42-23(18)32)11-43-26-31-30-14(3)44-26/h4-8,12,18,20,23H,9-11,28H2,1-3H3,(H,29,33)/t12-,18+,20+,23+/m0/s1

SMILES Code: N[C@@H](C)C(O[C@H](C1=CC=CC=C1)C(N[C@H]2[C@@]3([H])SCC(CSC4=NN=C(C)S4)=C(C(OCC5=C(C)OC(O5)=O)=O)N3C2=O)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 661.72 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

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1: Cazzola M. Novel oral cephalosporins. Expert Opin Investig Drugs. 2000 Feb;9(2):237-46. doi: 10.1517/13543784.9.2.237. PMID: 11060674.

2: Köhler W, Schenk P. Cephalosporinbehandlung der Sinusitis maxillaris [Cephalosporin treatment of maxillary sinusitis]. Laryngorhinootologie. 1995 Jun;74(6):355-60. German. doi: 10.1055/s-2007-997757. PMID: 7662079.

3: Grunfeld A, Sinclair P, Nicolle L; Canadian Tonsillitis Study Group. Cefcanel daloxate versus penicillin in acute streptococcal pharyngotonsillitis. Can J Infect Dis. 1994 May;5(3):119-24. doi: 10.1155/1994/531572. PMID: 22346486; PMCID: PMC3250823.

4: Edwall B, Slettevold L, Thurmann-Nielsen E, Walstad R, Torrång A, Dahl K. Pharmacokinetics of oral cefcanel daloxate hydrochloride in healthy volunteers and patients with various degrees of impaired renal function. J Antimicrob Chemother. 1994 Feb;33(2):281-8. doi: 10.1093/jac/33.2.281. PMID: 8182009.

5: Nicolle LE, Hoepelman AI, Floor M, Verhoef J, Norgard K. Comparison of three days' therapy with cefcanel or amoxicillin for the treatment of acute uncomplicated urinary tract infection. Scand J Infect Dis. 1993;25(5):631-7. doi: 10.3109/00365549309008553. PMID: 8284649.

6: Edwall B, Arvidsson A, Lake-Bakaar D, Lanbeck-Vallén K, Yisak W. Disposition of oral [14C]cefcanel daloxate hydrochloride in healthy male subjects. Drug Metab Dispos. 1993 Jan-Feb;21(1):171-7. PMID: 8095213.

7: Lanbeck-Vallén K, Carlqvist J. Determination of cefcanel in plasma and urine by high-performance liquid chromatography using coupled columns, after administration of the new cephalosporin prodrug cefcanel daloxate hydrochloride. J Chromatogr. 1992 Jul 1;578(1):71-6. doi: 10.1016/0378-4347(92)80226-g. PMID: 1400788.

8: Magni L, Lionell C. In vivo efficacy of cefcanel daloxate in comparison with cefaclor. Scand J Infect Dis Suppl. 1990;74:185-9. PMID: 2097707.

9: Nishizawa S, Yoshimi A, Muro H, Kasai M, Hatano S, Hashizume H, Yamada T, Hashimoto E, Nishimura K, Kakeya N. [Study on orally active cephalosporin pro- drug. Synthesis, oral absorption and antibacterial activity of (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 7-[D-O-(aminoacyl)mandelamido]-3-[[(5-methyl-1,3,4-thiadiazol -2-yl)-thio]methyl]-3-cephem-4-carboxylates]. Yakugaku Zasshi. 1988 Aug;108(8):745-53. Japanese. doi: 10.1248/yakushi1947.108.8_745. PMID: 3246644.

10: Obana Y, Hashizume H, Yoshimi A, Nishino T. In vitro and in vivo antibacterial activity of KY-109, a new orally active cephalosporin. J Antibiot (Tokyo). 1988 Jul;41(7):949-58. doi: 10.7164/antibiotics.41.949. PMID: 3417567.

11: Nishimura K, Nishizawa S, Yoshimi A, Nakamura S, Nishimura M, Kakeya N. KY-109, a new bifunctional prodrug of cephalosporin. II. Mechanism of oral absorption. Chem Pharm Bull (Tokyo). 1988 Jun;36(6):2128-34. doi: 10.1248/cpb.36.2128. PMID: 3240449.

12: Kakeya N, Nishizawa S, Nishimura K, Yoshimi A, Tamaki S, Mori T, Kitao K. KY-109, a new bifunctional pro-drug of a cephalosporin. Chemistry, physico- chemical and biological properties. J Antibiot (Tokyo). 1985 Mar;38(3):380-9. doi: 10.7164/antibiotics.38.380. PMID: 3839226.