| Identification | More | [Name]
Sulbenicillin sodium | [CAS]
28002-18-8 | [Synonyms]
disodium (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(r)-2-phenyl-2-sulfonatoacetamido]-4-thia-azabicyclo[3.2.0]heptane-2-carboxylate
SULBENICILLIN DISODIUM SALT
SULBENICILLIN SODIUM
alpha-sulfobenzylpenicillindisodium
disodiumalpha-sulfobenzylpenicillin
disodiumsulbenicillin
disodiumsulfobenzylpenicillin
kedacillin
lilacillin
sulbenicillindisodium
sulfobenzylpenicillin
sulfocillin
sulpelin
disodium [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylsulphonatoacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenyl-2-sulfoacetamido)-, disodium salt (8CI)
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylsulfoacetyl)amino]-, disodium salt, (2S,5R,6R)-(9CI)
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylsulfoacetyl)amino]-, disodium salt, [2S-(2a,5a,6b)]-
a-Sulfobenzylpenicillin disodium salt
a-Sulfobenzylpenicillin sodium salt
a-Sulfocillin | [EINECS(EC#)]
248-769-3 | [Molecular Formula]
C16H16N2Na2O7S2 | [MDL Number]
MFCD01682086 | [Molecular Weight]
458.42 | [MOL File]
28002-18-8.mol |
| Chemical Properties | Back Directory | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Solid | [color ]
White to off-white | [Water Solubility ]
Water: 250 mg/mL (545.35 mM) | [InChIKey]
FWRNIJIOFYDBES-OVLVVYMKNA-L | [SMILES]
N12C([C@@H](NC(=O)C(S(=O)(=O)[O-])C3C=CC=CC=3)[C@H]1SC(C)(C)[C@@H]2C(=O)[O-])=O.[Na+].[Na+] |&1:2,17,22,r| | [CAS DataBase Reference]
28002-18-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Originator]
Lillacillin,Takeda,Japan,1973 | [Uses]
Sulbenicillin Sodium is an antibiotic which belongs to a group of compounds known as penicillin antibiotics. Sulbenicillin Sodium is a combination of sulbactam and ampicillin. Sulbactam is a beta-lactamase inhibitor that works by binding to bacterial beta-lactamase enzymes, which are produced by some Gram-negative and Gram-positive bacteria to inactivate beta-lactam antibiotics including penicillins. By inhibiting the activity of beta-lactamase enzymes, sulbactam restores the activity of ampicillin against susceptible bacteria, thereby enhancing the spectrum and potency of the antibiotic. | [Definition]
ChEBI: Sulbenicillin disodium is an organic sodium salt. It contains a sulbenicillin(2-). | [Manufacturing Process]
To a suspension of 1.08 parts by weight of 6-aminopenicillanic acid in 8 parts
by volume of water is added 1.48 parts by weight of sodium bicarbonate.
After the mixture is dissolved, a solution of 1.18 parts by weight of α-sulfophenylacetyl chloride in 10 parts by volume of diethylether is gradually
added thereto. The mixture is stirred at a temperature in the neighborhood of
0°C for 1 hour. The aqueous layer is washed twice with 10 parts by volume of
portions of ether and adjusted to pH 1.2 with cation exchange resin of
polystyrene sulfonic acid type under constant cooling. Then the solution is
washed twice with 15 parts by volume of portions of ethyl acetate, followed
by extraction twice with 15 parts by volume of portions of n-butanol. The
extracts are combined and washed twice with 15 parts by volume of portions
of water and, then, extracted with an aqueous solution of sodium bicarbonate.
The extract is adjusted to pH 6.5, washed with ether and lyophilized to give
the sodium salt of α-sulfobenzylpenicillin. Yield is 1.2 parts by weight. | [Therapeutic Function]
Antibacterial | [Biological Activity]
Sulbenicillin Sodium inhibits bacterial cell wall synthesis and the inhibition of beta-lactamase enzymes th at would otherwise inactivate the penicillin antibiotic. | [References]
[1] Patent: CN108373475, 2018, A. Location in patent: Paragraph 0058; 0065; 0073
[2] Patent: CN107641130, 2018, A. Location in patent: Paragraph 0059; 0060; 0065; 0072; 0077 |
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