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Chemistry

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Also known as: Cefovecin sodium, Uk-287074-02, Cefovecin sodium salt, Chembl2104475, Ex-a3268, A936300
Molecular Formula
C17H18N5NaO6S2
Molecular Weight
475.5  g/mol
InChI Key
QRIBXVGHDLFNNE-BMCBYEKFSA-M

Cefovecin
Cefovecin Sodium is the sodium salt form of cefovecin, a semisynthetic, broad-spectrum, third-generation cephalosporin with antibacterial activity. Cefovecin 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

Cefovecin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-[(2S)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
2.1.2 InChI
InChI=1S/C17H19N5O6S2.Na/c1-27-21-10(8-6-30-17(18)19-8)13(23)20-11-14(24)22-12(16(25)26)7(5-29-15(11)22)9-3-2-4-28-9;/h6,9,11,15H,2-5H2,1H3,(H2,18,19)(H,20,23)(H,25,26);/q;+1/p-1/b21-10+;/t9-,11+,15+;/m0./s1
2.1.3 InChI Key
QRIBXVGHDLFNNE-BMCBYEKFSA-M
2.1.4 Canonical SMILES
CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C4CCCO4)C(=O)[O-].[Na+]
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@@H]4CCCO4)C(=O)[O-].[Na+]
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. Cefovecin Sodium

2. Uk-287074-02

3. Cefovecin Sodium Salt

4. Chembl2104475

5. Ex-a3268

6. A936300

7. Q27114290

8. Sodium (6r,7r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-acetyl] Amino]-8-oxo-3-[(2s)-oxolan-2-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene- 2-carboxylate

9. Sodium (6r,7r)-7-[2-(2-aminothiazol-4-yl)-2-(z)-methoxyiminoacetamido]-3-[(s) -tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate

10. Sodium (6r,7r)-7-[2-(2-aminothiazol-4-yl)-2-(z)-methoxyiminoacetamido]-3-[(s)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate

2.3 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 475.5 g/mol
Molecular Formula C17H18N5NaO6S2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count6
Exact Mass475.05961994 g/mol
Monoisotopic Mass475.05961994 g/mol
Topological Polar Surface Area213 Ų
Heavy Atom Count31
Formal Charge0
Complexity827
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2

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