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MedKoo Cat#: 596758 | Name: Cefcanel daloxate HCl
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Description:

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

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 HCl
Cefcanel daloxate HCl
CAS#92602-21-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 596758

Name: Cefcanel daloxate HCl

CAS#: 92602-21-6 (HCl)

Chemical Formula: C27H28ClN5O9S3

Exact Mass:

Molecular Weight: 698.18

Elemental Analysis: C, 46.45; H, 4.04; Cl, 5.08; N, 10.03; O, 20.62; S, 13.78

Price and Availability

Size Price Availability Quantity
1mg USD 150.00 Ready to ship
5mg USD 550.00 Ready to ship
10mg USD 950.00 Ready to ship
25mg USD 1,850.00 Ready to ship
50mg USD 2,950.00 Ready to ship
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Related CAS #
97275-40-6 (free base) 41952-52-7 92602-21-6 (HCl)
Synonym
Cefcanel daloxate hydrochloride; 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, hydrochloride
InChi Key
HFVATKYQUGKLGL-PCQLZLFJSA-N
InChi Code
InChI=1S/C27H27N5O9S3.ClH/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);1H/t12-,18+,20+,23+;/m0./s1
SMILES Code
O=C(C(N12)=C(CSC3=NN=C(C)S3)CS[C@]2([H])[C@H](NC([C@H](OC([C@H](C)N)=O)C4=CC=CC=C4)=O)C1=O)OCC5=C(C)OC(O5)=O.[H]Cl
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
Biological target:
Cefcanel daloxate, also known as KY-109, is a pro-drug to improve oral absorption of KY-087.
In vitro activity:
KY-087, which is the active form of KY-109, had broad antimicrobial spectrum against Gram-positive and Gram-negative organisms, but showed low antimicrobial activity against Enterobacter sp., Serratia, and Pseudomonas sp. The antimicrobial activities of KY-087 against clinically isolated Gram-positive organisms were superior to those of CEX and CCL. Reference: J Antibiot (Tokyo). 1988 Jul;41(7):949-58. https://pubmed.ncbi.nlm.nih.gov/3417567/
In vivo activity:
The in vivo efficacy of this prodrug (cefcanel daloxate) in comparison with cefaclor was assessed in a localized thigh infection model in mice. Both drugs caused a reduction in viable count by approx. 90% for all test organisms, while in the untreated animals the number of bacteria increased 4 to 10 times within 6 hours after challenge. Reference: Scand J Infect Dis Suppl. 1990;74:185-9. https://pubmed.ncbi.nlm.nih.gov/2097707/

Preparing Stock Solutions

The following data is based on the product molecular weight 698.18 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:
1. 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. 2. 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. 3. 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.
In vitro protocol:
1. 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.
In vivo protocol:
1. 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. 2. 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.
1: 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. 2: 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. 3: Holst E, Rollof J, Miörner H. In vitro activities of cefcanel and some other cephalosporins against Pasteurella multocida. Antimicrob Agents Chemother. 1989 Dec;33(12):2142-3. doi: 10.1128/AAC.33.12.2142. PMID: 2619280; PMCID: PMC172837. 4: Bergan T, da Fonseca J. Antibacterial activity of cefcanel. Chemotherapy. 1993 Mar-Apr;39(2):96-104. doi: 10.1159/000239109. PMID: 8458252. 5: Cazzola M. Novel oral cephalosporins. Expert Opin Investig Drugs. 2000 Feb;9(2):237-46. doi: 10.1517/13543784.9.2.237. PMID: 11060674. 6: Nord CE, Lindmark A, Persson I. Comparative antibacterial activity of the new cephalosporin cefcanel against anaerobic bacteria. Eur J Clin Microbiol Infect Dis. 1989 Jun;8(6):550-1. doi: 10.1007/BF01967478. PMID: 2548866. 7: 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. 8: 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. 9: Löwdin E, Tornqvist IO, Cars O. The postantibiotic effect of cefcanel on beta-hemolytic streptococci group A in vitro and in vivo. Scand J Infect Dis Suppl. 1990;74:190-4. PMID: 2097708. 10: Chin NX, Gu JW, Neu HC. In vitro activity of cefcanel versus other oral cephalosporins. Eur J Clin Microbiol Infect Dis. 1991 Aug;10(8):676-82. doi: 10.1007/BF01975825. PMID: 1748125. 11: Bergan T, da Fonseca J. Efficacy of cefcanel on staphylocci. Chemotherapy. 1991;37(1):43-9. doi: 10.1159/000238831. PMID: 2013241. 12: 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. 13: 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. 14: 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. 15: Odenholt-Tornqvist I, Löwdin E, Cars O. Pharmacodynamic effects of subinhibitory concentrations of beta-lactam antibiotics in vitro. Antimicrob Agents Chemother. 1991 Sep;35(9):1834-9. doi: 10.1128/AAC.35.9.1834. PMID: 1952854; PMCID: PMC245277. 16: 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. 17: 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. 18: 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. 19: 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.

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