Cefaloridine

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MedKoo CAT#: 326867

CAS#: 50-59-9

Description: Cefaloridine, also known as Cephaloridine, Sch 11527, is a first generation semisynthetic derivative of cephalosporin C. It is unique among cephalosporins in that it exists as a zwitterion. Before the 1970s, cephaloridine was used to treat patients with urinary tract infections. Besides the drugs has been used successfully in the treatment of various lower respiratory tract infections. Cephaloridine was very effective to cure pneumococcal pneumonia. It has a high clinical and bacteriological rate of success in staphylococcal and streptococcal infections.


Chemical Structure

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Cefaloridine
CAS# 50-59-9

Theoretical Analysis

MedKoo Cat#: 326867
Name: Cefaloridine
CAS#: 50-59-9
Chemical Formula: C19H17N3O4S2
Exact Mass: 415.07
Molecular Weight: 415.482
Elemental Analysis: C, 54.93; H, 4.12; N, 10.11; O, 15.40; S, 15.43

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.
Note: Price will be listed if it is available in the future.

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Synonym: Sch 11527; Cephaloridine; Cefaloridine

IUPAC/Chemical Name: (6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

InChi Key: CZTQZXZIADLWOZ-CRAIPNDOSA-N

InChi Code: InChI=1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1

SMILES Code: O=C(N[C@H]1[C@@]2([H])SCC(C[N+]3=CC=CC=C3)=C(C([O-])=O)N2C1=O)CC4=CC=CS4

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:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 415.48 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: Kano T, Kato Y, Ito K, Ogihara T, Kubo Y, Tsuji A. Carnitine/organic cation transporter OCTN2 (Slc22a5) is responsible for renal secretion of cephaloridine in mice. Drug Metab Dispos. 2009 May;37(5):1009-16. doi: 10.1124/dmd.108.025015. Epub 2009 Feb 12. PubMed PMID: 19220985.

2: Rokushima M, Fujisawa K, Furukawa N, Itoh F, Yanagimoto T, Fukushima R, Araki A, Okada M, Torii M, Kato I, Ishizaki J, Omi K. Transcriptomic analysis of nephrotoxicity induced by cephaloridine, a representative cephalosporin antibiotic. Chem Res Toxicol. 2008 Jun;21(6):1186-96. doi: 10.1021/tx800008e. Epub 2008 May 23. PubMed PMID: 18500788.

3: Kohda Y, Matsunaga Y, Yonogi K, Kawai Y, Awaya A, Gemba M. Protective effect of serum thymic factor, FTS, on cephaloridine-induced nephrotoxicity in rats. Biol Pharm Bull. 2005 Nov;28(11):2087-91. PubMed PMID: 16272694.

4: Kawai Y, Kohda Y, Kodawara T, Gemba M. Protective effect of a protein kinase inhibitor on cellular injury induced by cephaloridine in the porcine kidney cell line LLC-PK(1). J Toxicol Sci. 2005 Aug;30(3):157-63. PubMed PMID: 16141650.

5: Guitton J, Conjard A, Eid A, Martin M, Boghossian M, Delage H, Baverel G, Ferrier B. Identification of novel targets of cephaloridine in rabbit renal proximal tubules synthesizing glutamine from alanine. Arch Toxicol. 2005 Oct;79(10):587-94. Epub 2005 Jul 1. PubMed PMID: 15991025.

6: Kohda Y, Gemba M. Cephaloridine induces translocation of protein kinase C delta into mitochondria and enhances mitochondrial generation of free radicals in the kidney cortex of rats causing renal dysfunction. J Pharmacol Sci. 2005 May;98(1):49-57. Epub 2005 May 7. PubMed PMID: 15879677.

7: Kohda Y, Hiramatsu J, Gemba M. Involvement of MEK/ERK pathway in cephaloridine-induced injury in rat renal cortical slices. Toxicol Lett. 2003 Jul 20;143(2):185-94. PubMed PMID: 12749822.

8: Kohda Y, Gemba M. Enhancement of protein kinase C activity and chemiluminescence intensity in mitochondria isolated from the kidney cortex of rats treated with cephaloridine. Biochem Pharmacol. 2002 Aug 1;64(3):543-9. PubMed PMID: 12147306.

9: Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H. Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. PubMed PMID: 12005172.

10: Chen CC, Herzberg O. Structures of the acyl-enzyme complexes of the Staphylococcus aureus beta-lactamase mutant Glu166Asp:Asn170Gln with benzylpenicillin and cephaloridine. Biochemistry. 2001 Feb 27;40(8):2351-8. PubMed PMID: 11327855.

11: Tsai TH, Kao HY, Chen CF. Measurement and pharmacokinetic analysis of unbound cephaloridine in rat blood by on-line microdialysis and microbore liquid chromatography. Biomed Chromatogr. 2001 Apr;15(2):79-82. PubMed PMID: 11268046.

12: Kohda Y, Gemba M. Modulation by cyclic AMP and phorbol myristate acetate of cephaloridine-induced injury in rat renal cortical slices. Jpn J Pharmacol. 2001 Jan;85(1):54-9. PubMed PMID: 11243575.

13: Kiyomiya K, Matsushita N, Matsuo S, Kurebe M. Roles of oxygen radical production and lipid peroxidation in the cytotoxicity of cephaloridine on cultured renal epithelial cells (LLC-PK1). J Vet Med Sci. 2000 Sep;62(9):977-81. PubMed PMID: 11039594.

14: Kiyomiya K, Matsushita N, Matsuo S, Kurebe M. Cephaloridine-induced inhibition of cytochrome c oxidase activity in the mitochondria of cultured renal epithelial cells (LLC-PK(1)) as a possible mechanism of its nephrotoxicity. Toxicol Appl Pharmacol. 2000 Sep 1;167(2):151-6. PubMed PMID: 10964766.

15: Takeda M, Tojo A, Sekine T, Hosoyamada M, Kanai Y, Endou H. Role of organic anion transporter 1 (OAT1) in cephaloridine (CER)-induced nephrotoxicity. Kidney Int. 1999 Dec;56(6):2128-36. PubMed PMID: 10594788.

16: Yokozawa T, Owada S. Effect of ginsenoside-Rd in cephaloridine-induced renal disorder. Nephron. 1999 Feb;81(2):200-7. PubMed PMID: 9933756.

17: Yokozawa T, Dong E, Liu ZW, Shibata T, Hasegawa M, Watanabe H, Oura H. Magnesium lithospermate B ameliorates cephaloridine-induced renal injury. Exp Toxicol Pathol. 1997 Dec;49(5):337-41. PubMed PMID: 9455678.

18: Valentovic M, Ball JG, Rogers BA, Meadows MK, Harmon RC, Moles J. Cephaloridine in vitro toxicity and accumulation in renal slices from normoglycemic and diabetic rats. Fundam Appl Toxicol. 1997 Aug;38(2):184-90. PubMed PMID: 9299192.

19: Bolon C, Gauthier C, Simonnet H, Baverel G. Advantages of a two-chamber culture system to test drug nephrotoxicity: the example of cephaloridine. Kidney Blood Press Res. 1997;20(4):264-70. Erratum in: Kidney Blood Press Res 1998;21(1):74. PubMed PMID: 9398033.

20: Morin JP, Marouillat S, Lendormi C, Monteil C. Comparative impact of cephaloridine on glutathione and related enzymes in LLC-PK1, LLC-RK1, and primary cultures of rat and rabbit proximal tubule cells. Cell Biol Toxicol. 1996 Dec;12(4-6):275-82. PubMed PMID: 9034621.