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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 26973-24-0, Ceftezol, Ceftezolum, Ceftezole [inn], 2z86syp11w, (6r,7r)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Molecular Formula

C₁₃H₁₂N₈O₄S₃

Molecular Weight

440.5 g/mol

InChI Key

DZMVCVMFETWNIU-LDYMZIIASA-N

FDA UNII

2Z86SYP11W

Ceftezole is a semisynthetic first-generation cephalosporin with antibacterial activity. Ceftezole 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

Ceftezole Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C13H12N8O4S3/c22-7(1-20-4-14-18-19-20)16-8-10(23)21-9(12(24)25)6(2-26-11(8)21)3-27-13-17-15-5-28-13/h4-5,8,11H,1-3H2,(H,16,22)(H,24,25)/t8-,11-/m1/s1

2.1.3 InChI Key

DZMVCVMFETWNIU-LDYMZIIASA-N

2.1.4 Canonical SMILES

C1C(=C(N2C(S1)C(C2=O)NC(=O)CN3C=NN=N3)C(=O)O)CSC4=NN=CS4

2.1.5 Isomeric SMILES

C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CN3C=NN=N3)C(=O)O)CSC4=NN=CS4

2.2 Other Identifiers

2.2.1 UNII

2Z86SYP11W

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ceftezol

2. Ceftezol, Sodium Salt

3. Ceftezole Sodium

4. Celoslin

5. Demethylcefazolin

6. Falomesin

2.3.2 Depositor-Supplied Synonyms

1. 26973-24-0

2. Ceftezol

3. Ceftezolum

4. Ceftezole [inn]

5. 2z86syp11w

6. (6r,7r)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

7. J01db12

8. Ceftezole (inn)

9. Demethylcefazolin

10. (6r,7r)-8-oxo-7-[(1h-tetrazol-1-ylacetyl)amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

11. Demethyl Cefazolin

12. (6r,7r)-8-oxo-7-(2-(1h-tetrazol-1-yl)acetamido)-3-((1,3,4-thiadiazol-2-ylthio)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

13. Cg-b 3 Q

14. Ncgc00182064-02

15. Ceftezol [inn-spanish]

16. Ceftezolum [inn-latin]

17. Unii-2z86syp11w

18. Ceftezole [mi]

19. Ceftezole [who-dd]

20. Mls006010107

21. Schembl147529

22. Chembl1697829

23. Dtxsid0022771

24. Chebi:135716

25. Bcp12070

26. Hy-n7095

27. Zinc3830473

28. Mfcd00274176

29. S5289

30. Akos037643294

31. Ccg-269124

32. Db13821

33. As-13011

34. Smr004701245

35. Cs-0077833

36. D07656

37. 973c240

38. A818761

39. J-016638

40. Q5057295

41. (6r,7r)-3-((1,3,4-thiadiazol-2-ylthio)methyl)-7-(2-(1h-tetrazol-1-yl)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

42. (6r,7r)-8-oxo-7-[[1-oxo-2-(1-tetrazolyl)ethyl]amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

43. (6r,7r)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;ceftezole

44. (6r,7r)-8-oxo-7-[2-(1h-tetrazol-1-yl)acetamido]-3-[(1,3,4-thiadiazol-2-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

45. 7-[2-(1h-tetrazol-1-yl)acetamido]-3-[(1,3,4-thiadiazol-2-ylsulfanyl)methyl]-3,4-didehydrocepham-4-carboxylic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₂N₈O₄S₃
Molecular Weight	440.5 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	7
Exact Mass	440.01436441 g/mol
Monoisotopic Mass	440.01436441 g/mol
Topological Polar Surface Area	235 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	709
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

4.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DB - First-generation cephalosporins

J01DB12 - Ceftezole

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ACTIVE PHARMA INGREDIENTS

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