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Prestwick3_000832

Prestwick3_000832

Synopsis, Chemistry

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5 API Suppliers, 2 USDMF, 4 Listed Suppliers

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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

A semisynthetic cephamycin antibiotic resistant to beta-lactamase.

Cefoxitin is a Cephalosporin Antibacterial.

1 2D Structure

Prestwick3_000832

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 Formula	C₁₆H₁₇N₃O₇S₂
Molecular Weight	427.5 g/mol
XLogP3	0
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	8
Exact Mass	427.05079224 g/mol
Monoisotopic Mass	427.05079224 g/mol
Topological Polar Surface Area	202 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	744
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 Drug Information

1 of 2
Drug Name	Cefoxitin
PubMed Health	Cefoxitin (Injection)
Drug Classes	Antibiotic
Drug Label	Cefoxitin 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 Ingredient	Cefoxitin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Acs Dobfar; Hospira; Hikma Maple; Hikma Farmaceutica; Antibioticos Brasil

2 of 2
Drug Name	Cefoxitin
PubMed Health	Cefoxitin (Injection)
Drug Classes	Antibiotic
Drug Label	Cefoxitin 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 Ingredient	Cefoxitin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Acs 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.