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ACTIVE PHARMA INGREDIENTS

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Also known as: Cefozopran, Cefozopran [inn], 113359-04-9, Czop, Sce 2787, Cefozopranum

Molecular Formula

C₁₉H₁₇N₉O₅S₂

Molecular Weight

515.5 g/mol

InChI Key

QDUIJCOKQCCXQY-WHJQOFBOSA-N

FDA UNII

1LG87K28LW

Cefozopran is a semisynthetic, broad-spectrum, fourth-generation cephalosporin with antibacterial activity. Cefozopran 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

Cefozopran

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-3-(imidazo[1,2-b]pyridazin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C19H17N9O5S2/c1-33-24-11(14-23-19(20)35-25-14)15(29)22-12-16(30)28-13(18(31)32)9(8-34-17(12)28)7-26-5-6-27-10(26)3-2-4-21-27/h2-6,12,17H,7-8H2,1H3,(H3-,20,22,23,25,29,31,32)/b24-11-/t12-,17-/m1/s1

2.1.3 InChI Key

QDUIJCOKQCCXQY-WHJQOFBOSA-N

2.1.4 Canonical SMILES

CON=C(C1=NSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=C5C=CC=NN5C=C4)C(=O)[O-]

2.1.5 Isomeric SMILES

CO/N=C(/C1=NSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=C5C=CC=NN5C=C4)C(=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

1LG87K28LW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cefozopran

2. Czop

3. Sce 2787

4. Sce-2787

2.3.2 Depositor-Supplied Synonyms

1. Cefozopran

2. Cefozopran [inn]

3. 113359-04-9

4. Czop

5. Sce 2787

6. Cefozopranum

7. Cefozopran (inn)

8. 1lg87k28lw

9. Chebi:3502

10. Imidazo[1,2-b]pyridazinium,1-[[(6r,7r)-7-[[(2z)-(5-amino-1,2,4-thiadiazol-3-yl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-, Inner Salt

11. Ccris 6737

12. Unii-1lg87k28lw

13. Cefozopran [mi]

14. Cefozopran [who-dd]

15. Schembl49106

16. (-)-1-(((6r,7r)-7-(2-(5-amino-1,2,4-thiadiazol-3-yl)glyoxylamido)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-1h-imidazo(1,2-b)pyridazin-4-ium Hydroxide Inner Salt, 7(sup 2)-(z)-(o-methyloxime)

17. Imidazo(1,2-b)pyridazinium, 1-((6r,7r)-7-(((2z)-(5-amino-1,2,4-thiadiazol-3-yl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-, Inner Salt

18. Chembl1276663

19. Dtxsid701025943

20. (6r,7r)-7-[[(2z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-3-(imidazo[1,2-b]pyridazin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

21. Hy-b0771

22. Cefozopran Hydrochloride [jan]

23. Akos015896118

24. Db13667

25. Imidazo(1,2-b)pyridazinium, 1-((7-(((5-amino-1,2,4-thiadiazol-3-yl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-, Inner Salt, (6r-(6alpha,7beta(z)))-

26. D01052

27. J-504081

28. (-)-1-(((6r,7r)-7-(2-(5-amino-1,2,4-thiadiazol-3-yl)glyoxylamido)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-1h-imidazo(1,2-b)pyridazin-4-ium Hydroxide Inner Salt, 7^2-(z)-(o-methyloxime)

29. (6r,7r)-7-{[(2z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl]amino}-3-(imidazo[1,2-b]pyridazin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

30. 1-[[(6r,7r)-7-[[(2z)-(5-amino-1,2,4-thiadiazol-3-yl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3 -yl]methyl]-imidazo[1,2-b]pyridazinium Hydroxide Inner Salt

31. 7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(imidazo[1,2-b]pyridazin-1-ium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylate

2.4 Create Date

2006-10-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₇N₉O₅S₂
Molecular Weight	515.5 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	6
Exact Mass	515.07940702 g/mol
Monoisotopic Mass	515.07940702 g/mol
Topological Polar Surface Area	238 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	960
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1