API Export of Prestwick3_000832 obtained from Indian Customs Trade Statistics

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Chemistry

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Also known as: 35607-66-0, Mefoxin, Cefoxitinum, Rephoxitin, Cephoxitin, Cefoxitina
Molecular Formula
C16H17N3O7S2
Molecular Weight
427.5  g/mol
InChI Key
WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
FDA UNII
6OEV9DX57Y

Cefoxitin
A semisynthetic cephamycin antibiotic resistant to beta-lactamase.
Cefoxitin is a Cephalosporin Antibacterial.
1 2D Structure

Cefoxitin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-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/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
2.1.3 InChI Key
WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
2.1.4 Canonical SMILES
COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
2.1.5 Isomeric SMILES
CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
2.2 Other Identifiers
2.2.1 UNII
6OEV9DX57Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cefoxitin Sodium

2. Mfoxin

3. Mefoxin

4. Mefoxitin

5. Mk 306

6. Mk-306

7. Mk306

8. Sodium, Cefoxitin

2.3.2 Depositor-Supplied Synonyms

1. 35607-66-0

2. Mefoxin

3. Cefoxitinum

4. Rephoxitin

5. Cephoxitin

6. Cefoxitina

7. Cefoxitine

8. Mefoxitin

9. Ceftoxitin

10. Cfx

11. Cenomycin

12. Chebi:209807

13. Chembl996

14. 6oev9dx57y

15. J01dc01

16. Dsstox_cid_2764

17. Dsstox_rid_76721

18. Dsstox_gsid_22764

19. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

20. (6r,7s)-3-(hydroxymethyl)-7-methoxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid Carbamate (ester)

21. (6r,7s)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

22. (6r,7s)-3-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

23. Cas-35607-66-0

24. Ncgc00183034-01

25. Cefoxitine [inn-french]

26. Cefoxitinum [inn-latin]

27. Cefoxitina [inn-spanish]

28. Unii-6oev9dx57y

29. Cefoxotin

30. Cefoxitin [usan:inn:ban]

31. 4kow

32. Mk306

33. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, (6r,7s)-

34. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, (6r,7s)-

35. Einecs 252-641-2

36. Mfcd00072014

37. Spectrum_001399

38. Cefoxitin [inn]

39. Cefoxitin [mi]

40. Cefoxitin (usan/inn)

41. Cefoxitin [usan]

42. Prestwick0_000832

43. Prestwick1_000832

44. Prestwick2_000832

45. Prestwick3_000832

46. Spectrum2_000676

47. Spectrum3_001491

48. Spectrum4_000153

49. Spectrum5_001145

50. Cefoxitin [vandf]

51. Epitope Id:116201

52. C06887

53. Cefoxitin [usp-rs]

54. Cefoxitin [who-dd]

55. Schembl15971

56. Bspbio_000783

57. Bspbio_003101

58. Kbiogr_000626

59. Kbioss_001879

60. Divk1c_000576

61. Spbio_000771

62. Spbio_002704

63. Bpbio1_000863

64. Cefoxitin [orange Book]

65. Dtxsid1022764

66. Gtpl10937

67. Kbio1_000576

68. Kbio2_001879

69. Kbio2_004447

70. Kbio2_007015

71. Kbio3_002601

72. Ninds_000576

73. Bcp09061

74. Hy-b1825

75. Zinc3830449

76. Tox21_113009

77. Bdbm50335563

78. S5951

79. Akos022185232

80. Tox21_113009_1

81. Db01331

82. Ds-5384

83. Idi1_000576

84. Ncgc00093351-06

85. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, (6r-cis)-

86. 73356-24-8

87. Sbi-0051927.p002

88. C3598

89. Cs-0013876

90. (6r,7r)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

91. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

92. (6r,7s)-3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

93. (6r,7s)-4-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

94. (6s,7r)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

95. (6s,7r)-4-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

96. 3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

97. 3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Anion

98. 3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-3-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Anion

99. D02345

100. 607c660

101. A822898

102. Q2353907

103. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

104. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

105. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;cefoxitin

106. (6r,7s)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

107. (6r,7s)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

108. (6r,7s)-3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- Carboxylic Acid

109. (6r,7s)-3-{[(aminocarbonyl)oxy]methyl}-7-(methyloxy)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

110. (6r,7s)-4-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-enyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

111. 3-[(carbamoyloxy)methyl]-7alpha-methoxy-7beta-[(thiophen-2-yl)acetamido]-3,4-didehydrocepham-4-carboxylic Acid

112. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, (6r-cis)-

113. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,(6r,7s)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 427.5 g/mol
Molecular Formula C16H17N3O7S2
XLogP30
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Exact Mass427.05079224 g/mol
Monoisotopic Mass427.05079224 g/mol
Topological Polar Surface Area202 Ų
Heavy Atom Count28
Formal Charge0
Complexity744
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 Drug Information
1 of 2  
Drug NameCefoxitin
PubMed HealthCefoxitin (Injection)
Drug ClassesAntibiotic
Drug LabelCefoxitin for Injection, USP contains cefoxitin sodium a semi-synthetic, broad-spectrum cephalosporin antibiotic for parenteral administration. It is derived from cephalosporin C, which is produced by Cephalosporium Acremonium. Its chemical name is s...
Active IngredientCefoxitin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAcs Dobfar; Hospira; Hikma Maple; Hikma Farmaceutica; Antibioticos Brasil

2 of 2  
Drug NameCefoxitin
PubMed HealthCefoxitin (Injection)
Drug ClassesAntibiotic
Drug LabelCefoxitin for Injection, USP contains cefoxitin sodium a semi-synthetic, broad-spectrum cephalosporin antibiotic for parenteral administration. It is derived from cephalosporin C, which is produced by Cephalosporium Acremonium. Its chemical name is s...
Active IngredientCefoxitin sodium
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyAcs Dobfar; Hospira; Hikma Maple; Hikma Farmaceutica; Antibioticos Brasil

4.2 Drug Indication

For the treatment of serious infections caused by susceptible strains microorganisms.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefoxitin is a cephamycin antibiotic often grouped with the second-generation cephalosporins. It is active against a broad range of gram-negative bacteria including anaerobes. The methoxy group in the 7a position provides cefoxitin with a high degree of stability in the presence of beta-lactamases, both penicillinases and cephalosporinases, of gram-negative bacteria.


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 FDA Pharmacological Classification
5.3.1 Active Moiety
CEFOXITIN
5.3.2 FDA UNII
6OEV9DX57Y
5.3.3 Pharmacological Classes
Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DC - Second-generation cephalosporins

J01DC01 - Cefoxitin


5.5 Absorption, Distribution and Excretion

Route of Elimination

Approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period, resulting in high urinary concentrations. Cefoxitin passes into pleural and joint fluids and is detectable in antibacterial concentrations in bile.


5.6 Metabolism/Metabolites

Minimal (approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period).


5.7 Biological Half-Life

The half-life after an intravenous dose is 41 to 59 minutes.


5.8 Mechanism of Action

The bactericidal action of cefoxitin results from inhibition of cell wall synthesis.


API Reference Price

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25-Feb-2021
01-Aug-2024
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Cefoxitin

Brand Name : Mefoxin

Dosage Form : Cefoxitina 1.000Mg 2Ml 1 Units Parenteral Use

Dosage Strength : 1 vial IM 1 g + 1 ampoule solv 2 ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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02

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Cefoxitin

Brand Name : Mefoxin

Dosage Form : Cefoxitina 1.000Mg 10Ml 1 Units Parenteral Use Ev

Dosage Strength : 1 ampoule EV 1 g + 1 ampoule solv 10 ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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03

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Cefoxitin

Brand Name : Mefoxin

Dosage Form : Cefoxitina 2.000Mg 20Ml 1 Units Parenteral Use Ev

Dosage Strength : 1 ampoule EV 2 g + 1 ampoule solv 20 ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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