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Cephaloglycin

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Also known as: Cefaloglycin, Cephaloglycine, D-cephaloglycine, Cephaoglycin acid, Cephaloglycin anhydrous, 3577-01-3

Molecular Formula

C₁₈H₁₉N₃O₆S

Molecular Weight

405.4 g/mol

InChI Key

FUBBGQLTSCSAON-PBFPGSCMSA-N

FDA UNII

HD2D469W6U

A cephalorsporin antibiotic.

1 2D Structure

Cephaloglycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC 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

2.1.2 InChI

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

2.1.3 InChI Key

FUBBGQLTSCSAON-PBFPGSCMSA-N

2.1.4 Canonical SMILES

CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)N)SC1)C(=O)O

2.1.5 Isomeric SMILES

CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)SC1)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

HD2D469W6U

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cefaloglycin

2. Cephaloglycin Dihydrate

3. Cephaloglycine

4. Dihydrate, Cephaloglycin

2.3.2 Depositor-Supplied Synonyms

1. Cefaloglycin

2. Cephaloglycine

3. D-cephaloglycine

4. Cephaoglycin Acid

5. Cephaloglycin Anhydrous

6. 3577-01-3

7. Cefaloglycine

8. Cefaloglicina

9. Cefaloglycinum

10. D-(-)-cephaloglycin

11. 7-(d-alpha-aminophenyl-acetamido)cephalosporanic Acid

12. 7-(2-d-alpha-aminophenylacetamido)cephalosporanic Acid

13. Cefaloglycin (jan)

14. Cefaloglycin [inn]

15. Chebi:34613

16. Kefglycin

17. (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

18. Ceg

19. Cephaloglycin Dihydrate

20. Hd2d469w6u

21. Kefocin

22. 7-(d-2-amino-2-phenylacetamido)-3-acetoxymethyl-delta(sup3)-cephem-4-carboxylic Acid

23. Cefaloglycin [jan]

24. Cefaloglycin Dihydrate

25. Cefaloglycine [inn-french]

26. Cefaloglycinum [inn-latin]

27. Cefaloglicina [inn-spanish]

28. Lilly 39435

29. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,3-[(acetyloxy)methyl]-7-[[(2r)-aminophenylacetyl]amino]-8-oxo-,(6r,7r)-

30. Hsdb 3214

31. Einecs 222-696-7

32. Cephaloglycin Anhdyous

33. 7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid Acetate (ester)

34. Cephaloglycin [mi]

35. Epitope Id:174844

36. Schembl2947

37. 7-(d-2-amino-2-phenylacetamido)-3-acetoxymethyl-delta(sup 3)-cephem-4-carboxylic Acid

38. Cephaloglycin [hsdb]

39. Unii-hd2d469w6u

40. 3-((acetyloxy)methyl)-7-((aminophenylacetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

41. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-((acetyloxy)methyl)-7-((aminophenylacetyl)amino)-8-oxo-, (6r-(6alpha,7beta(r*)))-

42. 7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)octane-2-carboxylic Acid, Acetate Inner Salt

43. Cefaloglycin [who-dd]

44. Chembl1200971

45. Dtxsid4022781

46. Gtpl12193

47. Zinc3830503

48. Db00689

49. 3-acetoxymethyl-7beta-[(2r)-2-amino-2-phenylacetamido]-3,4-didehydrocepham-4-carboxylic Acid

50. Ncgc00521078-02

51. (6r,7r)-3-(acetoxymethyl)-7-{[(2r)-2-amino-2-phenylacetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

52. (6r,7r)-3-[(acetyloxy)methyl]-7-{[(2r)-2-amino-2-phenylacetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

53. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-, Acetate (ester), D-

54. Hy-16137

55. Cs-0006156

56. D01949

57. Q5057214

58. (6r,7r)-3-[(acetyloxy)methyl]-7-[(2r)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

59. (6r,7r)-7-((r)-2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid Acetate (ester)

60. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic Acid, 3-((acetyloxy)methyl)-7-((aminophenylacetyl)amino)-8-oxo-, (6r-(6.alpha.,7.beta.(r*)))

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₉N₃O₆S
Molecular Weight	405.4 g/mol
XLogP3	-3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	405.09945651 g/mol
Monoisotopic Mass	405.09945651 g/mol
Topological Polar Surface Area	164 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	718
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Cephalosporins

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

...BECAUSE CEPHALOGLYCIN IS CONCENTRATED IN URINE, IT MAY BE EFFECTIVE IN TREATMENT OF URINARY TRACT INFECTIONS... /DIHYDRATE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1120

MOST OF CEPHALOGLYCIN...IS EXCRETED IN URINE AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE. URINARY CONCN OF METABOLITE AVG 350 UG/ML OVER 8-HR PERIOD FOLLOWING ADMIN OF 500 MG OF CEPHALOGLYCIN; THIS IS SUFFICIENT TO INHIBIT MOST STRAINS OF E COLI, MIRABILIS, & KLEBSIELLA-ENTEROBACTER (AEROBACTER) GROUP.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162

ITS IN VITRO SPECTRUM IS SIMILAR TO THAT OF OTHER CEPHALOSPORINS...& INCL MANY PATHOGENS THAT INFECT URINARY TRACT (EG, ESCHERICHIA COLI, CERTAIN SPECIES OF KLEBSIELLA, STAPHYLOCOCCUS AUREUS). /DIHYDRATE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 722

For more Therapeutic Uses (Complete) data for CEPHALOGLYCIN (7 total), please visit the HSDB record page.

4.2 Drug Warning

...CEPHALOGLYCIN IS NOT DRUG OF CHOICE FOR TREATING URINARY TRACT INFECTIONS... IS NOT EVEN A CEPHALOSPORIN OF 1ST CHOICE FOR SEVERE URINARY TRACT INFECTIONS. AVAILABILITY OF...CEPHALOSPORINS...EXCRETED BY KIDNEY...ACHIEVING HIGHER BACTERICIDAL CONCN IN URINE THAN CEPHALOGLYCIN...RENDERED CEPHALOGLYCIN OBSOLETE. /DIHYDRATE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 722

CEPHALOGLYCIN IS INEFFECTIVE AGAINST PSEUDOMONAS, & MOST SPECIES OF ENTEROCOCCI, ENTEROBACTER, & INDOLE-POSITIVE PROTENS. BECAUSE OF LIMITED ABSORPTION, SERUM LEVELS OF DRUG ADEQUATE TO TREAT SYSTEMIC INFECTIONS CANNOT BE ATTAINED CLINICALLY. /DIHYDRATE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 722

SUPRAINFECTIONS, USUALLY DUE TO GRAM-NEGATIVE BACTERIA, MAY OCCUR WHEN THESE ANTIBIOTICS ARE EMPLOYED. /CEPHALOSPORINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1163

Hypersensitivity reactions to the cephalosporins are the most common side effects...the reactions appear to be identical to those caused by the penicillins. /Cephalosporins/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1095

For more Drug Warnings (Complete) data for CEPHALOGLYCIN (12 total), please visit the HSDB record page.

4.3 Drug Indication

For treatment of severe infections caused by susceptible bacteria.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cephaloglycin is an antibiotic related to cephalosporin but no longer in common use. It is an orally absorbed derivative of cephalosporin C.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.3 Absorption, Distribution and Excretion

Absorption

Well absorbed following oral administration.

MOST OF CEPHALOGLYCIN THAT IS ABSORBED IS EXCRETED IN URINE AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE. URINARY CONCN OF METABOLITE AVG 350 UG/ML OVER 8-HR PERIOD FOLLOWING ADMIN OF 500 MG OF CEPHALOGLYCIN...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162

CEPHALOGLYCIN IS NOT DESTROYED IN GASTRIC ACID, BUT IT GRADUALLY DECOMP IN NEUTRAL & ALKALINE SECRETIONS OF INTESTINES. ONLY 1/4 TO 1/3 IS ABSORBED. /DIHYDRATE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1120

...CEPHALOSPORINS ARE UNPREDICTABLE IN MANNER IN WHICH THEY CROSS BLOOD-BRAIN BARRIER & THEY PENETRATE POORLY INTO CEREBROSPINAL FLUID... /CEPHALOSPORINS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 713

5.4 Metabolism/Metabolites

MOST OF CEPHALOGLYCIN THAT IS ABSORBED IS EXCRETED...AS DEACETYLCEPHALOGLYCIN, AN ANTIMICROBIALLY ACTIVE METABOLITE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162

5.5 Biological Half-Life

THIS ANTIBIOTIC IS PARTIALLY ABSORBED FROM GI TRACT... PLASMA CONCN REACH PEAK OF ONLY 2-6 UG/ML @ ABOUT 2 HR FOLLOWING SINGLE DOSE OF 0.5 G; DRUG IS NO LONGER DETECTABLE IN PLASMA 8 HR AFTER THIS DOSE. HALF-LIFE...IS ABOUT 4 HR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1162

PLASMA LEVELS AFTER ORAL ADMIN VARY WIDELY AMONG PT. PEAK LEVEL OF AT LEAST 0.6 UG/ML IS USUALLY ACHIEVED WITH ORAL DOSE OF 500 MG, & IT MAY REACH 6 UG/ML IN FAIR PROP OF CASES. FOOD IN STOMACH INTERFERES WITH ABSORPTION. HALF-LIFE IN PLASMA...ABOUT 3-5 HR, BUT WHEN...SEVERE RENAL IMPAIRMENT...MAY BE 9-20 HR. /DIHYDRATE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1120

5.6 Mechanism of Action

The bactericidal activity of cephaloglycin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).

CEPHALOTHIN & ITS CONGENERS INHIBIT BACTERIAL CELL-WALL SYNTHESIS IN MANNER SIMILAR TO THAT OF PENICILLIN. /CEPHALOTHIN & ITS CONGENERS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1160

/PENICILLINS & CEPHALOSPORINS/...HAVE SIMILAR MECHANISM OF ANTIBACTERIAL ACTION; BOTH INTERFERE WITH TERMINAL STEP IN BACTERIAL CELL WALL SYNTH BY INACTIVATING TRANSPEPTIDASE, THEREFORE PREVENTING CROSS-LINKAGE OF PEPTIDOGLYCAN CHAINS. /PENICILLINS & CEPHALOSPORINS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 712

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