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Prestwick3_000473

Prestwick3_000473

Synopsis, Chemistry

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Also known as: 69712-56-7, Cefotetanum, Apacef, Cefotetanum [inn-latin], Ici 156834, Ici-156834

Molecular Formula

C₁₇H₁₇N₇O₈S₄

Molecular Weight

575.6 g/mol

InChI Key

SRZNHPXWXCNNDU-RHBCBLIFSA-N

FDA UNII

48SPP0PA9Q

A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.

Cefotetan is a Cephalosporin Antibacterial.

1 2D Structure

Prestwick3_000473

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7S)-7-[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/t13?,15-,17+/m1/s1

2.1.3 InChI Key

SRZNHPXWXCNNDU-RHBCBLIFSA-N

2.1.4 Canonical SMILES

CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)C4SC(=C(C(=O)N)C(=O)O)S4)OC)SC2)C(=O)O

2.1.5 Isomeric SMILES

CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)C4SC(=C(C(=O)N)C(=O)O)S4)OC)SC2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

48SPP0PA9Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Apacef

2. Apatef

3. Cefotan

4. Cefotetan Disodium

5. Cefotetan Disodium Salt

6. Ceftotan

7. Disodium Salt, Cefotetan

8. Disodium, Cefotetan

9. Ici 156834

10. Ici-156834

11. Ici156834

12. Salt, Cefotetan Disodium

13. Ym 09330

14. Ym-09330

15. Ym09330

2.3.2 Depositor-Supplied Synonyms

1. 69712-56-7

2. Cefotetanum

3. Apacef

4. Cefotetanum [inn-latin]

5. Ici 156834

6. Ici-156834

7. Ici 156,834

8. 48spp0pa9q

9. Mls002153829

10. Chebi:3499

11. Ici-156,834

12. Ym 09330

13. Nsc-760045

14. (6r,7s)-7-({[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

15. Smr001233197

16. (6r,7s)-7-(4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5- Yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2- Carboxylic Acid

17. 7beta-({[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}amino)-7alpha-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic Acid

18. Cefotetan Acid

19. (6r,7s)-7-[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

20. Unii-48spp0pa9q

21. Cefotetan [usan:usp:inn:ban]

22. Ncgc00016914-01

23. Einecs 274-093-3

24. Cas-69712-56-7

25. Ici156834

26. Brn 1208088

27. Cefotetan [inn]

28. Cefotetan [jan]

29. Cefotetan [mi]

30. Cefotetan [usan]

31. Prestwick0_000473

32. Prestwick1_000473

33. Prestwick2_000473

34. Prestwick3_000473

35. Cefotetan [vandf]

36. Dsstox_cid_2762

37. Cefotetan [mart.]

38. Cefotetan [who-dd]

39. Dsstox_rid_76720

40. Dsstox_gsid_22762

41. Schembl61376

42. Bspbio_000606

43. (6r,7s)-7-(4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

44. Cid_53025

45. Spbio_002545

46. Cefotetan (jp17/usp/inn)

47. Bpbio1_000668

48. Chembl474579

49. Cefotetan [usp Impurity]

50. Dtxsid1022762

51. Bdbm80643

52. Gtpl10936

53. Cefotetan [usp Monograph]

54. Hms1569o08

55. Hms2096o08

56. Hms2234c15

57. Hms3713o08

58. Amy28799

59. Bcp10745

60. Hy-n6670

61. Zinc3830441

62. Tox21_110681

63. Mfcd00864983

64. Akos015896100

65. Ac-2141

66. Ccg-220473

67. Db01330

68. Nsc 760045

69. Ncgc00016914-06

70. Ncgc00179507-01

71. (6r,7s)-4-((2-carboxy-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-7-yl)carbamoyl)-1,3-dithietane-delta(sup 2,alpha)-malonamic Acid

72. (6r,7s)-7-[[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-7-methoxy-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

73. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl)carbonyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7alpha))-

74. As-56133

75. Ab00513847

76. Cs-0092723

77. C06886

78. D00260

79. Cefotetan, Antibiotic For Culture Media Use Only

80. 712c567

81. A836615

82. Sr-01000842155

83. Q2602246

84. Sr-01000842155-3

85. W-104601

86. (6r,7s)-4-((2-carboxy-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-7-yl)carbamoyl)-1,3-dithietane-.delta.(sup 2,.alpha.)-malonamic Acid

87. (6r,7s)-7-(4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietane-2-carboxamido)-7-methoxy-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

88. (6r,7s)-7-[[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]-oxomethyl]amino]-7-methoxy-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

89. (6r,7s)-7-[[4-(1-amino-3-hydroxy-1,3-dioxopropan-2-ylidene)1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

90. (6r,7s)-7-[[4-(2-amino-1-carboxy-2-keto-ethylidene)-1,3-dithietane-2-carbonyl]amino]-8-keto-7-methoxy-3-[[(1-methyltetrazol-5-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

91. (6r,7s)-7-[[4-[1-azanyl-3-oxidanyl-1,3-bis(oxidanylidene)propan-2-ylidene]-1,3-dithietan-2-yl]carbonylamino]-7-methoxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanylmethyl]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

92. Disodium 7-[[4-(2-amino-1-carboxylato-2-oxo-ethylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₇N₇O₈S₄
Molecular Weight	575.6 g/mol
XLogP3	0.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	9
Exact Mass	575.00214522 g/mol
Monoisotopic Mass	575.00214522 g/mol
Topological Polar Surface Area	321 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	1090
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	Cefotetan
PubMed Health	Cefotetan (Injection)
Drug Classes	Antibiotic
Drug Label	CEFOTAN (cefotetan disodium for injection) and CEFOTAN (cefotetan injection) in Galaxy * plastic container (PL 2040) as cefotetan disodium are sterile, semisynthetic, broad-spectrum, beta-lactamase resistant, cephalosporin (cephamycin) antibiotics...
Active Ingredient	Cefotetan disodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Fresenius Kabi Usa; West-ward Pharm

2 of 2
Drug Name	Cefotetan
PubMed Health	Cefotetan (Injection)
Drug Classes	Antibiotic
Drug Label	CEFOTAN (cefotetan disodium for injection) and CEFOTAN (cefotetan injection) in Galaxy * plastic container (PL 2040) as cefotetan disodium are sterile, semisynthetic, broad-spectrum, beta-lactamase resistant, cephalosporin (cephamycin) antibiotics...
Active Ingredient	Cefotetan disodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Fresenius Kabi Usa; West-ward Pharm

4.2 Drug Indication

For prophylaxis and treatment of bacterial infections.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.

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

CEFOTETAN

5.3.2 FDA UNII

48SPP0PA9Q

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

J01DC05 - Cefotetan

5.5 Absorption, Distribution and Excretion

Route of Elimination

No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug. In normal patients, from 51% to 81% of an administered dose of Cefotetan is excreted unchanged by the kidneys over a 24 hour period, which results in high and prolonged urinary concentrations.

Volume of Distribution

10.4 L [elderly patients (greater than 65 years) with normal renal function]

10.3 L [healthy volunteers (aged 25 to 28 years)]

Clearance

1.8 +/- 0.1 L/h [elderly patients with normal renal function (.65 years)]

1.8 +/- 0.3 L/h [healthy volunteers (aged 25 to 28 years)]

5.6 Metabolism/Metabolites

5.7 Biological Half-Life

In volunteers with reduced renal function, the plasma half-life of cefotetan is prolonged

5.8 Mechanism of Action

The bactericidal action of cefotetan results from inhibition of cell wall synthesis by binding and inhibiting the bacterial penicillin binding proteins which help in the cell wall biosynthesis.