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Chemistry

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Also known as: Cefalotin, 153-61-7, Cephalotin, Cefalothin, Cephalothinum, Cefalotina
Molecular Formula
C16H16N2O6S2
Molecular Weight
396.4  g/mol
InChI Key
XIURVHNZVLADCM-IUODEOHRSA-N
FDA UNII
R72LW146E6

Cephalothin
A cephalosporin antibiotic.
1 2D Structure

Cephalothin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
2.1.2 InChI
InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
2.1.3 InChI Key
XIURVHNZVLADCM-IUODEOHRSA-N
2.1.4 Canonical SMILES
CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O
2.1.5 Isomeric SMILES
CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
R72LW146E6
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cefalotin

2. Cefalotina Normon

3. Cefalotina Sodica Spaly

4. Ceftina

5. Cephalothin Monosodium Salt

6. Cephalothin, Sodium

7. Keflin

8. Monosodium Salt, Cephalothin

9. Salt, Cephalothin Monosodium

10. Seffin

11. Sodium Cephalothin

2.3.2 Depositor-Supplied Synonyms

1. Cefalotin

2. 153-61-7

3. Cephalotin

4. Cefalothin

5. Cephalothinum

6. Cefalotina

7. Cefalotine

8. Cefalotinum

9. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

10. Cemastin

11. 7-(2-thienylacetamido)cephalosporanic Acid

12. Coaxin

13. Keflin

14. Cefalotine [inn-french]

15. Cefalotinum [inn-latin]

16. Cefalotina [inn-spanish]

17. Averon-1

18. Cephalotin Acid

19. 7-(thiophene-2-acetamido)cephalosporin

20. (6r,7r)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

21. 3-acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic Acid

22. Cefalotin [inn]

23. (6r,7r)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

24. Chebi:124991

25. Mls001048966

26. 7-(2'-thienylacetamido)cephalosporanic Acid

27. R72lw146e6

28. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-((acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-, (6r-trans)-

29. Ncgc00159332-02

30. Smr000386987

31. Dsstox_cid_2783

32. Dsstox_rid_76728

33. Dsstox_gsid_22783

34. Cefalotin (ban)

35. 7-(thiophene-2-acetamido)cephalosporanic Acid

36. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

37. Cas-153-61-7

38. 7-(2-(2-thienyl)acetylamido)cephalosporanic Acid

39. Hsdb 3024

40. Cefalotina Fabra (tn)

41. 58-71-9

42. Einecs 205-815-7

43. Brn 0945586

44. Unii-r72lw146e6

45. 6r-trans-3-((acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-carboxylic Acid

46. 4kox

47. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-((acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-, (6r,7r)-

48. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6r,7r)-

49. (+-)-cephalothin

50. 3-(acetoxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

51. 3-(hydroxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid Acetate

52. Spectrum_000110

53. Cephalothin [mi]

54. Prestwick0_000719

55. Prestwick1_000719

56. Prestwick2_000719

57. Prestwick3_000719

58. Spectrum2_000121

59. Spectrum3_000332

60. Spectrum4_000269

61. Spectrum5_000669

62. Cephalothin [hsdb]

63. Chembl617

64. Epitope Id:116207

65. Cephalothin [vandf]

66. Cefalotin [who-dd]

67. Cid_6024

68. Schembl2990

69. Lopac0_000283

70. Bspbio_000937

71. Bspbio_001963

72. Kbiogr_000738

73. Kbioss_000550

74. 3-acetoxymethyl-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

75. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(hydroxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-, Acetate (ester)

76. Divk1c_000097

77. Spbio_000162

78. Spbio_002858

79. Bpbio1_001031

80. Gtpl8798

81. Cephalothin [green Book]

82. Dtxsid4022783

83. Schembl20477170

84. Bdbm82898

85. Hy-b1275a

86. Kbio1_000097

87. Kbio2_000550

88. Kbio2_003118

89. Kbio2_005686

90. Kbio3_001183

91. Ninds_000097

92. Hms2267p23

93. Zinc3830507

94. Tox21_111579

95. Mfcd00242614

96. S5294

97. Akos015920120

98. Tox21_111579_1

99. Ccg-268605

100. Cs-w008776

101. Db00456

102. Gs-3577

103. Sdccgsbi-0050271.p005

104. 7beta-(thiophen-2-ylacetamido)-3-acetoxymethyl-3,4-didehydrocepham-4-carboxylic Acid

105. Idi1_000097

106. Ncgc00023699-09

107. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid

108. (6r,7r)-3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

109. Sbi-0050271.p004

110. 7-(2-thienylacetamido) Cephalosporanic Acid

111. 7-(2-thienylacetamido)-cephalosporanic Acid

112. C-2484

113. C07761

114. D07635

115. 153c617

116. A809447

117. Cephalothin, Antibiotic For Culture Media Use Only

118. Sr-01000003118

119. Q2736126

120. Sr-01000003118-3

121. Brd-k28210218-236-05-7

122. Z1741977144

123. Cephalothin 7-(2-thienylacetamido)cephalosporanic Acid

124. 3-acetoxymethyl-7beta-(2-thienylacetamido) Ceph-3-em-4-carboxylic Acid

125. 3-acetoxymethyl-7beta-(2-thienylacetamido)-3-cephem-4-carboxylic Acid

126. 3-acetoxymethyl-7beta-(2-thienylacetamido)ceph-3-em-4-carboxylic Acid

127. (6r,7r)-3-(acetoxymethyl)-8-keto-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

128. (6r,7r)-3-(acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

129. (6r,7r)-3-(acetyloxymethyl)-8-oxidanylidene-7-(2-thiophen-2-ylethanoylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

130. (6r,7r)-3-(acetyloxymethyl)-8-oxo-7-[(1-oxo-2-thiophen-2-ylethyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

131. (6r,7r)-3-[(acetyloxy)methyl]-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

132. 51098-29-4

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 396.4 g/mol
Molecular Formula C16H16N2O6S2
XLogP3-0.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass396.04497858 g/mol
Monoisotopic Mass396.04497858 g/mol
Topological Polar Surface Area167 Ų
Heavy Atom Count26
Formal Charge0
Complexity680
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

Since, among the cephalosporins, cephalothin is the most impervious to attack by Staphylococcal beta-lactamase, it is very effective in severe Staphylococcal infections, such as endocarditis.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1210


Mesh Heading: anti-bacterial agents

National Library of Medicine, SIS; ChemIDplus Record for Cephalothin (153-61-7). Available from, as of April 13, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp


Use should be restricted to treatment of serious infections caused by susceptible organisms, most commonly when patient is hypersensitive to penicillins. /Sodium/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 715


... Cephalosporin is ... drug of first choice ... for Klebsiella infections ... They are useful as alternative choices to penicillin. /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. 1096


For more Therapeutic Uses (Complete) data for CEPHALOTHIN (28 total), please visit the HSDB record page.


4.2 Drug Warning

Excretion is delayed in presence of decr renal function, and intervals between doses must be lengthened when renal failure is severe.

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


Cephalothin should not be used to treat bacterial meningitis.

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. 1093


Infections due to Enterococci are usually unaffected by these cmpd ... Enterococcal endocarditis cannot be cured with cephalosporin even when it is given concurrently with gentamicin or streptomycin. /Cephalosporins/

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


Patients with a history of a mild or a temporally distant reaction to penicillin appear to be at low risk of rash or other allergic reaction following the admin of a cephalosporin ... Patients who have had a recent severe, immediate reaction to a penicillin should be given a cephalosporin with great caution, if at all. /Cephalosporin/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1212


For more Drug Warnings (Complete) data for CEPHALOTHIN (21 total), please visit the HSDB record page.


4.3 Drug Indication

Used to prevent infection during surgery and to treat many kinds of infections of the blood, bone or joints, respiratory tract, skin, and urinary tract.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefalotin (INN) or cephalothin (USAN) is a semisynthetic first generation cephalosporin having a broad spectrum of antibiotic activity that is administered parenterally.


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

J01DB03 - Cefalotin


5.4 Absorption, Distribution and Excretion

CEPHALOTHIN ENTERS AQUEOUS HUMOR AFTER SUBCONJUNCTIVAL INJECTIONS YIELDING PEAK LEVELS CA 1-2 HR AFTER DOSING. RATIO OF AQ HUMOR:SERUM ANTIBIOTIC LEVELS RANGES FROM 4.0 TO 67.0 DURING 5 HR AFTER DOSING, & LOSS OF ANTIBIOTIC FROM AQ HUMOR OCCURS BY BIPHASIC PROCESS.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 177


...CEPHALOTHIN...WERE SHOWN...TO PENETRATE INTO BONE TO VERY LIMITED EXTENT AFTER SC OR ORAL DOSES TO RATS. RATIOS OF BONE TO SERUM CONCN AVG 1:4 FOR CEPHALOTHIN... DESPITE DIFFERENCES IN CONCN, T/2 IN BONE & SERUM WERE SIMILAR.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 452


DRUGS RECENTLY SHOWN TO ACTIVELY CROSS HUMAN PLACENTA INCL...CEPHALOTHIN...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 433


Concn of cephalothin present in urine after admin of 1 g range from 0.7 to 5 mg/mL. Excretion is delayed in presence of decr renal function ...

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


For more Absorption, Distribution and Excretion (Complete) data for CEPHALOTHIN (11 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Metabolized to a less active desacetyl metabolite, although 50-75% of the drug is eliminated unchanged in the urine.


Approx 25% of cephalothin dose admin was eliminated in urine as deacetylcephalothin.

PMID:411623 ROLEWICZ TF ET AL; CLIN PHARMACOL THER 22 (DEC): 928-35 (1977)


Cephalothin ... /is/ deacetylated in vivo, and these metabolites have less antimicrobial activity than the parent cmpd ... The deacetylated metabolites also are excreted by the kidneys.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1210


5.6 Biological Half-Life

30 minutes


Half-life = 0.6 hr /by/ injection /From table/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1206


5.7 Mechanism of Action

The bactericidal activity of cefalotin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). The PBPs are transpeptidases which are vital in peptidoglycan biosynthesis. Therefore, their inhibition prevents this vital cell wall compenent from being properly synthesized.


Bactericidal; action depends on ability to reach and bind penicillin-binding proteins located in bacterial cytoplasmic membranes. Cephalosporins inhibit bacterial septum and cell wall synthesis, probably by action 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 elongation of susceptible bacteria and lysis frequently occur. Rapidly dividing bacteria are those most susceptible to the actin of cephalosporins. /Cephalosporins/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 822


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06-Jan-2021
23-Aug-2024
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