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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

Cephapirin
Cephalosporin antibiotic, partly plasma-bound, that is effective against gram-negative and gram-positive organisms.
1 2D Structure

Cephapirin

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 Weight 423.5 g/mol
Molecular Formula C17H17N3O6S2
XLogP3-1.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Exact Mass423.05587762 g/mol
Monoisotopic Mass423.05587762 g/mol
Topological Polar Surface Area177 Ų
Heavy Atom Count28
Formal Charge0
Complexity707
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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)


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ABOUT THIS PAGE

Cephapirin, Sodium Manufacturers

A Cephapirin, Sodium manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Cephapirin, Sodium, including repackagers and relabelers. The FDA regulates Cephapirin, Sodium manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Cephapirin, Sodium API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Cephapirin, Sodium manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Cephapirin, Sodium Suppliers

A Cephapirin, Sodium supplier is an individual or a company that provides Cephapirin, Sodium active pharmaceutical ingredient (API) or Cephapirin, Sodium finished formulations upon request. The Cephapirin, Sodium suppliers may include Cephapirin, Sodium API manufacturers, exporters, distributors and traders.

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Cephapirin, Sodium USDMF

A Cephapirin, Sodium DMF (Drug Master File) is a document detailing the whole manufacturing process of Cephapirin, Sodium active pharmaceutical ingredient (API) in detail. Different forms of Cephapirin, Sodium DMFs exist exist since differing nations have different regulations, such as Cephapirin, Sodium USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Cephapirin, Sodium DMF submitted to regulatory agencies in the US is known as a USDMF. Cephapirin, Sodium USDMF includes data on Cephapirin, Sodium's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Cephapirin, Sodium USDMF is kept confidential to protect the manufacturer’s intellectual property.

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Cephapirin, Sodium GMP

Cephapirin, Sodium Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Cephapirin, Sodium GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Cephapirin, Sodium GMP manufacturer or Cephapirin, Sodium GMP API supplier for your needs.

Cephapirin, Sodium CoA

A Cephapirin, Sodium CoA (Certificate of Analysis) is a formal document that attests to Cephapirin, Sodium's compliance with Cephapirin, Sodium specifications and serves as a tool for batch-level quality control.

Cephapirin, Sodium CoA mostly includes findings from lab analyses of a specific batch. For each Cephapirin, Sodium CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Cephapirin, Sodium may be tested according to a variety of international standards, such as European Pharmacopoeia (Cephapirin, Sodium EP), Cephapirin, Sodium JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Cephapirin, Sodium USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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