Cefaloglycin
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MedKoo CAT#: 317457

CAS#: 3577-01-3

Description: Cefaloglycin is a first-generation semisynthetic cephalosporin with antibacterial activity. Cephaloglycin binds to and inactivates penicillin-binding proteins located on the inner membrane of the bacterial cell wall. This results in the weakening of the bacterial cell wall and causes cell lysis.


Chemical Structure

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Cefaloglycin
CAS# 3577-01-3

Theoretical Analysis

MedKoo Cat#: 317457
Name: Cefaloglycin
CAS#: 3577-01-3
Chemical Formula: C18H19N3O6S
Exact Mass:
Molecular Weight: 405.42
Elemental Analysis: C, 53.32; H, 4.72; N, 10.36; O, 23.68; S, 7.91

Price and Availability

Size Price Availability Quantity
50.0mg USD 320.0 2 Weeks
1.0g USD 3250.0 2 Weeks
2.0g USD 5650.0 2 Weeks
5.0g USD 9650.0 2 Weeks
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Related CAS #: 22202-75-1 (dihydrate)   3577-01-3  

Synonym: Cefaloglycin; cephaloglycin. Kafocin, Kefglycin, Lilly 39435

IUPAC/Chemical Name: (6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChi Key: FUBBGQLTSCSAON-PBFPGSCMSA-N

InChi Code: InChI=1S/C18H19N3O6S/c1-9(22)27-7-11-8-28-17-13(16(24)21(17)14(11)18(25)26)20-15(23)12(19)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1

SMILES Code: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)N)SC1)C(=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, not in water

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

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 405.42 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: Tune BM, Fravert D, Hsu CY. Oxidative and mitochondrial toxic effects of cephalosporin antibiotics in the kidney. A comparative study of cephaloridine and cephaloglycin. Biochem Pharmacol. 1989 Mar 1;38(5):795-802. PubMed PMID: 2930580.

2: Tune BM, Fravert D. Cephalosporin nephrotoxicity. Transport, cytotoxicity and mitochondrial toxicity of cephaloglycin. J Pharmacol Exp Ther. 1980 Oct;215(1):186-90. PubMed PMID: 7452482.

3: Haginaka J, Nakagawa T, Uno T. Chromatographic analysis and pharmacokinetic investigation of cephaloglycin and its metabolites in man. J Antibiot (Tokyo). 1980 Feb;33(2):236-43. PubMed PMID: 7380734.

4: Haginaka J, Nakagawa T, Uno T. Acidic degredation of cephaloglycin and high performance liquid chromatographic determination of deacetylcephaloglycin in human urine. J Antibiot (Tokyo). 1979 May;32(5):462-7. PubMed PMID: 43318.

5: Tune BM, Hsu CY. The renal mitochondrial toxicity of beta-lactam antibiotics: in vitro effects of cephaloglycin and imipenem. J Am Soc Nephrol. 1990 Nov;1(5):815-21. PubMed PMID: 2133431.

6: Naito T, Okumura J, Kasai K, Masuko K, Hoshi H. Cephalosporins. I. Cephaloglycin analogs with six-membered heterocycles in the C-3 side chain. J Antibiot (Tokyo). 1977 Sep;30(9):691-7. PubMed PMID: 924890.

7: WICK WE, BONIECE WS. IN VITRO AND IN VIVO LABORATORY EVALUATION OF CEPHALOGLYCIN AND CEPHALORIDINE. Appl Microbiol. 1965 Mar;13:248-53. PubMed PMID: 14325888; PubMed Central PMCID: PMC1058230.

8: Barbhaiya RH, Turner P. Fluorimetric assay of cephradine, cephalexin and cephaloglycin. Br J Clin Pharmacol. 1977 Aug;4(4):427-31. PubMed PMID: 901733; PubMed Central PMCID: PMC1429050.

9: Tune BM, Fravert D. Mechanisms of cephalosporin nephrotoxicity: a comparison of cephaloridine and cephaloglycin. Kidney Int. 1980 Nov;18(5):591-600. PubMed PMID: 7463955.

10: Tune BM, Hsu CY, Fravert D. Cephalosporin and carbacephem nephrotoxicity. Roles of tubular cell uptake and acylating potential. Biochem Pharmacol. 1996 Feb 23;51(4):557-61. PubMed PMID: 8619902.

11: Nelson JD, Haltalin KC. In vitro effectiveness of four cephalosporins against Shigellae and clinical ineffectiveness of cephaloglycin. Chemotherapy. 1972;17(1):40-50. PubMed PMID: 4550565.

12: Whitin JC, Tham DM, Bhamre S, Ornt DB, Scandling JD, Tune BM, Salvatierra O, Avissar N, Cohen HJ. Plasma glutathione peroxidase and its relationship to renal proximal tubule function. Mol Genet Metab. 1998 Nov;65(3):238-45. PubMed PMID: 9851889.

13: Marrelli LP. Colorimetric estimation of cephalexin, cephaloglycin, and related compounds. J Pharm Sci. 1972 Oct;61(10):1647-8. PubMed PMID: 5072420.

14: Shapera RM, Matsen JM. New antibiotics clindamycin, cephaloglycin, carbenicillin. Postgrad Med. 1971 Jun;49(6):120-5. PubMed PMID: 5162357.

15: Halpin TC Jr, Perkins RL, Greenberger NJ. 14C-cephalexin and 14C-cephaloglycin: comparative intestinal absorption and biliary excretion. Pharmacol Res Commun. 1980 Sep;12(8):726-38. PubMed PMID: 7443759.

16: Bundgaard H. Chemical studies related to cephalosporin allergy. II. Competitive amine-catalyzed intra- and intermolecular aminolysis of cephalexin and cephaloglycin in aqueous solution. Acta Pharm Suec. 1976;13(4):299-312. PubMed PMID: 11639.

17: Ries KM, Cobbs GC, Gillenwater JY, Levison ME, Mandell GL, Kaye D. Comparison of carbenicillin indanyl sodium, ampicillin, and cephaloglycin in treatment of urinary-tract infection. J Infect Dis. 1973 May;127:Suppl:148-53. PubMed PMID: 4695479.

18: Applestein JM, Crosby EB, Johnson WD, Kaye D. In vitro antimicrobial activity and human pharmacology of cephaloglycin. Appl Microbiol. 1968 Jul;16(7):1006-10. PubMed PMID: 4385749; PubMed Central PMCID: PMC547578.

19: Braun P, Tillotson JR, Wilcox C, Finland M. Cephalexin and cephaloglycin activity in vitro and absorption and urinary excretion of single oral doses in normal young adults. Appl Microbiol. 1968 Nov;16(11):1684-94. PubMed PMID: 4387222; PubMed Central PMCID: PMC547740.

20: Wick WE, Wright WE, Kuder HV. Cephaloglycin and its biologically active metabolite desacetylcephaloglycin. Appl Microbiol. 1971 Mar;21(3):426-34. PubMed PMID: 4994901; PubMed Central PMCID: PMC377197.