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Chemistry

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Also known as: 84305-41-9, Cefminox [inn], Cefminox sodium, Cmnx, Mt-141, 75481-73-1

Molecular Formula

C₁₆H₂₁N₇O₇S₃

Molecular Weight

519.6 g/mol

InChI Key

JSDXOWVAHXDYCU-VXSYNFHWSA-N

FDA UNII

PW08Y13465

Cefminox is a semisynthetic, second-generation, beta-lactamase-stable cephalosporin with antibacterial activity. Cefminox binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

1 2D Structure

cefminox sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7S)-7-[[2-[(2S)-2-amino-2-carboxyethyl]sulfanylacetyl]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/C16H21N7O7S3/c1-22-15(19-20-21-22)33-4-7-3-32-14-16(30-2,13(29)23(14)10(7)12(27)28)18-9(24)6-31-5-8(17)11(25)26/h8,14H,3-6,17H2,1-2H3,(H,18,24)(H,25,26)(H,27,28)/t8-,14-,16+/m1/s1

2.1.3 InChI Key

JSDXOWVAHXDYCU-VXSYNFHWSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

PW08Y13465

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alteporina

2. Cefminox Sodium

3. Mt 141

4. Mt-141

5. Tencef

2.3.2 Depositor-Supplied Synonyms

1. 84305-41-9

2. Cefminox [inn]

3. Cefminox Sodium

4. Cmnx

5. Mt-141

6. 75481-73-1

7. Cefminox (inn)

8. Pw08y13465

9. (6r,7s)-7-[[2-[(2s)-2-amino-2-carboxyethyl]sulfanylacetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

10. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((((2s)-2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r,7s)-

11. Cefminoxum

12. Mt 141

13. Cefminoxum [latin]

14. Ccris 5270

15. Ncgc00181749-01

16. Unii-pw08y13465

17. Cefminox [mi]

18. Cefminox [who-dd]

19. Mt-141 Free Acid

20. Schembl49565

21. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((((2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7alpha,7(s*)))-

22. Chembl1276342

23. Chebi:135817

24. Dtxsid301016174

25. Zinc3938624

26. Akos015895987

27. Db09062

28. D07642

29. 481c731

30. Q5057239

31. (6r,7s)-7-(2-(((s)-2-amino-2-carboxyethyl)thio)acetamido)-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

32. (6r,7s)-7-(2-{[(2s)-2-amino-2-carboxyethyl]sulfanyl}acetamido)-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

33. (7s)-7-(2-{[(2s)-2-amino-2-carboxyethyl]sulfanyl}acetamido)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic Acid

34. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((((2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6.alpha.,7.alpha.,7(s*)))-

35. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((2-(((2s)-2-amino-2-carboxyethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r,7s)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₁N₇O₇S₃
Molecular Weight	519.6 g/mol
XLogP3	-4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	11
Exact Mass	519.06645956 g/mol
Monoisotopic Mass	519.06645956 g/mol
Topological Polar Surface Area	279 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	862
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1