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Also known as: 118443-89-3, Cefquinome sulphate, Hr111v-sulfate, Cefquinome sulfate [usan], Hr111v-sulphate, (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;sulfuric acid

Molecular Formula

C₂₃H₂₆N₆O₉S₃

Molecular Weight

626.7 g/mol

InChI Key

KYOHRXSGUROPGY-OFNLCGNNSA-N

FDA UNII

3858K104DQ

Cefquinome Sulfate is the sulfate form of cefquinome, 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

Cefquinome Sulfate

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;sulfuric acid

2.1.2 InChI

InChI=1S/C23H24N6O5S2.H2O4S/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;1-5(2,3)4/h4,6,8,11,17,21H,2-3,5,7,9-10H2,1H3,(H3-,24,25,26,30,32,33);(H2,1,2,3,4)/b27-16-;/t17-,21-;/m1./s1

2.1.3 InChI Key

KYOHRXSGUROPGY-OFNLCGNNSA-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-].OS(=O)(=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-].OS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

3858K104DQ

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 118443-89-3

2. Cefquinome Sulphate

3. Hr111v-sulfate

4. Cefquinome Sulfate [usan]

5. Hr111v-sulphate

6. (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;sulfuric Acid

7. 3858k104dq

8. Unii-3858k104dq

9. 118443-88-2

10. 1-(((6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydroquinolin-1-ium Hydrogensulfate

11. Hr-111v-sulfate

12. Schembl988522

13. Cefquinome Sulfate [mi]

14. Chembl2103931

15. Cefquinome Sulfate [mart.]

16. Mfcd11864966

17. Akos025310170

18. Gs-3615

19. 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), Sulfate (1:1)

20. 1-{[(6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-5,6,7,8-tetrahydroquinolin-1-ium; Sulfuric Acid

21. 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)))-, Sulfate (1:1)

22. 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)))-, Sulphate (1:1)

23. 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-(6alpha,7beta(z)))-, Sulfate (1:1)

2.4 Create Date

2006-10-24

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₆N₆O₉S₃
Molecular Weight	626.7 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	6
Exact Mass	626.09233995 g/mol
Monoisotopic Mass	626.09233995 g/mol
Topological Polar Surface Area	290 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	1050
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	2