Cefonicid sodium

Molecular Structure of Cefonicid Sodium (CAS NO.61270-78-8):

IUPAC Name: disodium (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[1-(sulfonatomethyl)tetrazol-5-yl]sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
Empirical Formula: C₁₈H₁₆N₆Na₂O₈S₃
Molecular Weight:586.53
ACD/LogP: -0.45
of Rule of 5 Violations: 2
ACD/LogD (pH 5.5): -5.19
ACD/LogD (pH 7.4): -5.2
ACD/BCF (pH 5.5): 1
ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 1
ACD/KOC (pH 7.4): 1
H bond acceptors: 14
H bond donors: 4
Freely Rotating Bonds: 10
Polar Surface Area: 244.1Ų
Melting point: > 160°C
Storage temp: Store at 0-5°C
Chemical Properties: White Powder
Classification Code: Antibacterial; Antibiotics
InChI
InChI=1/C18H18N6O8S3.2Na/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32;;/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32);;/q;2*+1/p-2/t11-,13-,16-;;/m1../s1
Smiles
N12[C@@H]([C@@H](NC([C@@H](c3ccccc3)O)=O)C2=O)SCC(=C1C(=O)[O-])CSc1n(nnn1)CS(=O)(=O)[O-].[Na+].[Na+]

The reaction of aminomethansulfonic acid (I) with phthalic anhydride (II) by means of potassium acetate in refluxing acetic acid gives phthalimidomethansulfonic acid (III), which by reaction with PCl₅ in refluxing benzene is converted into its acyl chloride (IV). The condensation of (IV) with tert-butylamine (A) in CHCl₃ affords N-tert-butylphthalimidomethansulfonamide (V), which by reaction with hydrazine hydrate in refluxing ethanol yields 2-aminomethan-N-tert-butylsulfonamide (VI). The reaction of (VI) with CS₂ and MeI by means of triethylamine in ethanol gives N-tert-butylsulfamoylmethyldithiocarbamic acid methyl ester (VII), which is cyclized with NaN₃ in hot water to afford 1-(N-tert-butylsulfamoylmethyl)tetrazol-5-thiol (VIII). The hydrolysis of (VIII) with trifluoroacetic acid yields compound 1-sulfamoylmethyltetrazol-5-thiol (IX).

  Cefonicid Sodium , with CAS number of 61270-78-8, can be called (6R,7R)-7-((R)-Mandelamido)-8-oxo-3-(((1-(sulfomethyl)-1-H-tetrazol-5-yl)thio)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, disodium salt ; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((hydroxyphenylacetyl)amino)-8-oxo-3-(((1-(sulfomethyl)-1H-tetrazol-5-yl)thio)methyl)disodium salt, (6R-(6alpha,7beta(R*)))- ; Monocid .