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Technical details about Cefquinome, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. Also known as: 84957-30-2, Cobactan, Cefquinoma, Hr111v, Z74s078cwp, 1-[[(6r,7r)-7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-5,6,7,8-tetrahydro-quinolinium inner salt
Molecular Formula
C23H24N6O5S2
Molecular Weight
528.6  g/mol
InChI Key
YWKJNRNSJKEFMK-PQFQYKRASA-N
FDA UNII
Z74S078CWP

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

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
2.1.2 InChI
InChI=1S/C23H24N6O5S2/c1-34-27-16(14-11-36-23(24)25-14)19(30)26-17-20(31)29-18(22(32)33)13(10-35-21(17)29)9-28-8-4-6-12-5-2-3-7-15(12)28/h4,6,8,11,17,21H,2-3,5,7,9-10H2,1H3,(H3-,24,25,26,30,32,33)/b27-16-/t17-,21-/m1/s1
2.1.3 InChI Key
YWKJNRNSJKEFMK-PQFQYKRASA-N
2.1.4 Canonical SMILES
CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCCC5)C(=O)[O-]
2.1.5 Isomeric SMILES
CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCCC5)C(=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
Z74S078CWP
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hoe 111

2. Hoe-111

3. Hr 111v

4. Hr-111v

2.3.2 Depositor-Supplied Synonyms

1. 84957-30-2

2. Cobactan

3. Cefquinoma

4. Hr111v

5. Z74s078cwp

6. 1-[[(6r,7r)-7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-5,6,7,8-tetrahydro-quinolinium Inner Salt

7. Cefquinome (inn)

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

9. Cefquinome [inn]

10. Cefquinomum

11. Cefquinome [inn:ban]

12. Cefquinomum [inn-latin]

13. Cefquinoma [inn-spanish]

14. Unii-z74s078cwp

15. Cefquinome [mi]

16. Cobactan [veterinary] (tn)

17. Schembl149896

18. Chembl1631107

19. Dtxsid00894103

20. Akos025402360

21. D07652

22. 1-(((6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydroquinolinium Hydroxide, Inner Salt, 7(sup 2)-(z)-(o-methyloxime)

23. 1-(((6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydroquinolinium Hydroxide, Inner Salt, 72-(z)-(o-methyloxime)

24. Quinolinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, Hydroxide, Inner Salt, (6r-(6.alpha.,7.beta.(z)))-

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 528.6 g/mol
Molecular Formula C23H24N6O5S2
XLogP31.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Exact Mass528.12496023 g/mol
Monoisotopic Mass528.12496023 g/mol
Topological Polar Surface Area208 Ų
Heavy Atom Count36
Formal Charge0
Complexity971
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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