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Cephapirin, Sodium

Synopsis, Chemistry

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Also known as: Cefapirin, Cephapirine, Cefaprin, 21593-23-7, Cefadyl, Cefapirina

Molecular Formula

C₁₇H₁₇N₃O₆S₂

Molecular Weight

423.5 g/mol

InChI Key

UQLLWWBDSUHNEB-CZUORRHYSA-N

FDA UNII

89B59H32VN

Cephalosporin antibiotic, partly plasma-bound, that is effective against gram-negative and gram-positive organisms.

1 2D Structure

Cephapirin, Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1

2.1.3 InChI Key

UQLLWWBDSUHNEB-CZUORRHYSA-N

2.1.4 Canonical SMILES

CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O

2.1.5 Isomeric SMILES

CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

89B59H32VN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bl P 1322

2. Bl-p 1322

3. Blp 1322

4. Brisfirina

5. Cfaloject

6. Cefadyl

7. Cefapirin

8. Cephapirin Monosodium Salt

9. Cephapirin Sodium

10. Cephapirin, Sodium

11. Monosodium Salt, Cephapirin

12. Salt, Cephapirin Monosodium

13. Sodium Cephapirin

2.3.2 Depositor-Supplied Synonyms

1. Cefapirin

2. Cephapirine

3. Cefaprin

4. 21593-23-7

5. Cefadyl

6. Cefapirina

7. Cefapirine

8. Cefapirinum

9. Cepr

10. Cefapirine [inn-french]

11. Cefapirinum [inn-latin]

12. Cefapirina [inn-spanish]

13. Cefatrexyl

14. Ambrocef

15. Cefatrex

16. Chebi:554446

17. 7-(2-(4-pyridylthio)acetamido)cephalosporanic Acid

18. Cefa

19. 89b59h32vn

20. Cefaprin Sodium

21. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-(2-(pyridin-4-ylthio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

22. (6r,7r)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

23. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridinylthio)acetyl)amino)-, (6r-trans)-

24. Cefapirin [inn:ban]

25. Antibiotic Bl-p1322

26. Cefapirin (ban)

27. Metricure (tn)

28. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

29. 24356-60-3

30. Cefapilin

31. 356c603

32. Cefa-lak

33. Hsdb 3215

34. Cefa -ak

35. Einecs 244-466-5

36. Brn 1095157

37. Nsc179171

38. Spectrum_000112

39. Cefapirin [inn]

40. Cephapirin [mi]

41. Cefapirin [hsdb]

42. Prestwick0_000851

43. Prestwick1_000851

44. Prestwick2_000851

45. Spectrum2_000103

46. Spectrum3_000333

47. Spectrum4_000270

48. Spectrum5_000671

49. Cephapirin [vandf]

50. Epitope Id:116226

51. Cefapirin [who-dd]

52. Schembl3205

53. Chembl1599

54. Lopac0_000279

55. Bspbio_001965

56. Kbiogr_000740

57. Kbioss_000552

58. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure

59. 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamidol-5-thia-1-azabicyclo(4.2.0)oct-2-en-2carbonsaeure Acetat

60. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-, Acetate (ester)

61. Divk1c_000042

62. Unii-89b59h32vn

63. Spbio_000086

64. Spbio_002782

65. Cephalosporanic Acid, 7-(2-(4-pyridylthio)acetamido)-

66. Dtxsid9022784

67. Gtpl12191

68. Kbio1_000042

69. Kbio2_000552

70. Kbio2_003120

71. Kbio2_005688

72. Kbio3_001185

73. Ninds_000042

74. Hy-a0153

75. Zinc3830511

76. Bdbm50370592

77. Akos015896499

78. Db01139

79. Idi1_000042

80. (6r,7r)-3-[(acetyloxy)methyl]-8-oxo-7-{[(pyridin-4-ylthio)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

81. (6r,7r)-3-acetoxymethyl-7-[(pyridin-4-ylsulfanyl)acetamido]-3,4-didehydrocepham-4-carboxylic Acid

82. Sbi-0050267.p004

83. Cs-0017478

84. C06896

85. D07636

86. Q549803

87. J-014163

88. 7-(.alpha.-(4-pyridylthio)acetamido)cephalosporanic Acid

89. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-(2-(pyridin-4-ylthio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid

90. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-[[2-(4-pyridylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

91. (6r,7r)-3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate Acetate (ester)

92. (6r,7r)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

93. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 3-[(acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-, (6r,7r)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₇N₃O₆S₂
Molecular Weight	423.5 g/mol
XLogP3	-1.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	8
Exact Mass	423.05587762 g/mol
Monoisotopic Mass	423.05587762 g/mol
Topological Polar Surface Area	177 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	707
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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)

Cephalosporins are still useful as alternatives to penicillins for a variety of infections in patients who can't tolerate penicillins. These include streptococcal and staphylococcal infections.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1091

BACTERIA SUSCEPTIBLE TO CEPHALOTHIN /BOTH GRAM POSITIVE & GRAM-NEGATIVE MICROORGANISMS/ ARE SENSITIVE OVER APPROX SAME RANGE OF CONCN TO ... CEPHAPIRIN. ... CEPHAPIRIN IS SOMEWHAT MORE INHIBITORY THAN CEPHALOTHIN FOR GROUP-A STREP PYOGENES & PNEUMOCOCCUS.

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

CEPHAPIRIN IS ONE OF NEWEST SEMISYNTHETIC CEPHALOSPORINS. ... LIKE OTHER CEPHALOSPORINS, CEPHAPIRIN SHOULD BE RESERVED FOR THOSE INSTANCES IN WHICH ORGANISM IS SENSITIVE TO IT & PATIENT IS HYPERSENSITIVE TO PENICILLIN.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 719

For more Therapeutic Uses (Complete) data for CEPHAPIRIN (10 total), please visit the HSDB record page.

4.2 Drug Warning

SINCE ... CEPHAPIRIN ... ADMIN AS ... SODIUM SALTS, CARE SHOULD BE EXERCISED IN USE OF LARGE DOSES IN PERSONS WITH IMPAIRED CAPACITY TO EXCRETE THIS CATION. ... SUPRAINFECTIONS, USUALLY DUE TO GRAM NEGATIVE BACTERIA, MAY OCCUR WHEN THESE ANTIBIOTICS ARE EMPLOYED.

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

TYPICAL DOSAGE SCHEDULES ... FOR MOST OF CEPHALOSPORINS MUST BE MODIFIED FOR PATIENTS WITH IMPAIRED RENAL FUNCTION. /CEPHALOSPORINS/

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

... HYPERSENSITIVITY REACTIONS TO CEPHALOSPORINS IS HIGHER IN PATIENTS WHO HAVE SHOWN ALLERGIC MANIFESTATIONS FOLLOWING ADMIN OF PENICILLIN. THIS APPEARS TO BE RELATED TO SENSITIZATION TO BETA-LACTAM RING COMMON TO BOTH THESE DRUGS. /CEPHALOSPORINS/

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

... ENTEROCOCCAL ENDOCARDITIS CANNOT BE CURED WITH CEPHALOSPORIN EVEN WHEN ... GIVEN CONCURRENTLY WITH GENTAMICIN OR STREPTOMYCIN. ... ENTEROBACTER (AEROBACTER) INFECTIONS ARE, AS A RULE, RESISTANT TO THESE CMPD. /CEPHALOSPORINS/

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

For more Drug Warnings (Complete) data for CEPHAPIRIN (10 total), please visit the HSDB record page.

4.3 Drug Indication

For treatment of infections caused by susceptible bacteria.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cephapirin is a first-generation cephalosporin that has a wide spectrum of activity against gram-positive and gram-negative organisms. Cephapirin is more resistant to beta-lactamases than are the penicillins and so is effective against staphylococci, with the exception of methicillin-resistant staphylococci.

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 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DB - First-generation cephalosporins

J01DB08 - Cefapirin

5.4 Absorption, Distribution and Excretion

... PENETRATION OF CEPHALOSPORINS INTO /CEREBROSPINAL FLUID/ IS POOR. /CEPHALOSPORINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1164

CLOSE TO 50% OF CEPHAPIRIN IS BOUND TO PLASMA PROTEIN. HALF-LIFE ... IN NORMAL INDIVIDUALS IS ABOUT 40 MIN & IS DEPENDENT ON RENAL FUNCTION. SIGNIFICANT AMT ... PRESENT IN BLOOD IS REMOVED BY HEMODIALYSIS. ... EXCRETED MAINLY BY KIDNEY; ONLY 1% PRESENT IN BILE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

... /CEPHAPIRIN/ NOT ABSORBED FROM GI TRACT. IM INJECTION OF 0.5 G OF CEPHAPIRIN PRODUCES MAX PLASMA CONCN OF ABOUT 10 UG/ML @ 45 MIN; 1 G ABOUT 16 UG/ML. PLASMA CONCN ... EFFECTIVE AGAINST MANY SENSITIVE MICROORGANISMS ARE STILL DETECTABLE 6 HR AFTER SINGLE IM DOSE OF 1 G.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

ABOUT 30% OF IM DOSE OF CEPHAPIRIN IS EXCRETED IN URINE IN EACH OF 1ST 2 HR PERIODS AFTER INJECTION.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

For more Absorption, Distribution and Excretion (Complete) data for CEPHAPIRIN (8 total), please visit the HSDB record page.

5.5 Metabolism/Metabolites

Major metabolite detected is desacetylcephapirin.

MAJOR METABOLITE OF CEPHAPIRIN IS DEACETYLCEPHAPIRIN, WHICH IS ABOUT ONE HALF OF ANTIMICROBIAL ACTIVITY OF PARENT CMPD; 20% OF ANTIBIOTIC ACTIVITY IN PLASMA IS DUE TO DEACETYLATED CMPD.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1161

Cephapirin is partially metabolized in the plasma, liver and kidneys to diacetyl cephapirin, which has about 50% of the antibacterial activity of the parent cmpd. ... Up to 20% of the antibiotic activity in serum is due to the desacetyl metabolite.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 157

5.6 Biological Half-Life

EIGHT HEALTHY ADULTS RECEIVED 1 G, IV AND IM. BIOLOGICAL HALF-LIFE OF CEPHAPIRIN WAS 43 MIN. ABSORPTION HALF-LIFE OF CEPHAPIRIN FROM IM ADMIN WAS 1.25 HR.

PMID:1206478 CABANA BE ET AL; J PHARMACOKINET BIOPHARM 3: 419-38 (1975)

IV SODIUM CEPHAPIRIN SHOWED BIEXPONENTIAL DISPOSITION CHARACTERISTICS IN SERUM & SUBCHONDRAL BONE, REACHING DISTRIBUTION EQUIL WITHIN 20 MIN. RAPIDLY ELIMINATED, WITH BETA HALF-LIFE OF ABOUT 0.3 HR & BODY CLEARANCE OF 400 ML/MIN.

PMID:821720 SCHURMAN DJ ET AL; CURR THER RES CLIN EXP 20: 194-203 (1976)

Serum half-life is 0.6 hr /From table/

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 334

5.7 Mechanism of Action

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

... VERY RESISTANT TO ACTION OF PENICILLINASE, FOR WHICH IT IS BOTH COMPETITIVE & NONCOMPETITIVE INHIBITOR ... IT DOES NOT SUPPRESS BREAKDOWN OF PENICILLIN G BY STAPHYLOCOCCAL PENICILLINASE. CEPHALOSPORIN C & ITS SEMISYNTHETIC CONGENERS INDUCE SYNTH OF PENICILLINASE BY B CEREUS & STAPH AUREUS. /CEPHALOSPORIN C/

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

... ENZYME ACTING SPECIFICALLY ON CEPHALOSPORIN C TO DESTROY ITS ANTIBACTERIAL ACTIVITY. THIS SUBSTANCE, CEPHALOSPORINASE IS ALSO BETA-LACTAMASE. MOST PREPN OF ENZYME ALSO EXHIBIT PENICILLINASE ACTIVITY, & SOME MICROORGANISMS PRODUCE ONE BETA-LACTAMASE THAT ACTS ON BOTH PENICILLIN & CEPHALOSPORINS. /CEPHALOSPORIN C/

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

Bactericidal; action depends on ability to reach and bind pencillin-binding proteins located in bacterial cytoplasmic membranes; cephalosporins inhibit bacterial septum and cell wall synthesis, probably by acylation of membrane-bound transpeptidase enzymes. This prevents cross-linkage of peptidoglycan chains, which is necessary for bacterial cell wall strength and rigidity. Also, cell division and growth are inhibited, and lysis and elongation of susceptible bacteria frequently occur. Rapidly dividing bacteria are those most susceptible to the action of cephalosporins. /Cephalosporins/

US Pharmacopeial Convention; US Pharmacopeia Dispensing Information (USP DI); Drug Information for the Health Care Professional 12th ed, VI p.846 (1992)