| Identification | Back Directory | [Name]
Sulbactam | [CAS]
68373-14-8 | [Synonyms]
Betamaze
CP-45899
sulbactum
SULBACTAM
Shu ba acid
Sulbactam CRS
Sulbactam >
2H5]-Sulbactam
SULBACTAM ACID
SALBACTAM ACID
Sulbactam free acid
SULBACTAM(BETAMAZE)
Sulbactam USP/EP/BP
SulbactaM - See S8244
SULBACTAM(ACIDSODIUM)
sulbactam acid (base)
Sulbactam/Sulbactam Acid
Sultamicillin Impurity A
Penicillanic acid dioxide
PENICILLANIC ACID SULFONE
Sultamicillin EP Impurity A
Penicillanic acid S,S-dioxide
Penicillanic acid 4,4-dioxide
penicillanic acid 1,1-dioxide
Sulbactam,Penicillanicacidsulfone
Sulbactam (CP 45899 and Betamaze)
Rimsulfuron Impurity 4(Sulfosulfuron)
Sulbactam for peak identification CRS
Sulbactam (250 mg)H0C3960.976mg/mg(ai)
Sulbactam (base and/or unspecified salts)
Sulbactam (250 mg) (COLD SHIPMENT REQUIRED)
Sultamicillin Tosilate Dihydrate Impurity A
Sulbactam (COLD SHIPMENT REQUIRED) (1623670)
Sultamicillin Tosilate Dihydrate EP Impurity A
Sulbactam, 98%, an irreversible β-lactamase inhibitor
Sultamicillin Impurity 1（Sultamicillin EP Impurity A）
Penicillanicacid 1,1-dioxide：CP-45899：CPL45899-2：Betamaze
N-[[(2RS)-1-éthylpyrrolidin-2-yl]méthyl]-2-hydroxy-5-sulfamoylbenzamide
(2S,5β)-2β-Carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4,4-dioxide
3,3-DIMETHYL-4,4,7-TRIOXO-4LAMBDA6-THIA-1-AZA-BICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-carboxylic acid 4,4-dioxid
(2S,5R)-3,3-dimethyl-7-oxo-4,4-dioxide-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
(2S-CIS)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3,2,0]HEPTANE-2-CARBOXYLIC ACID 4,4-DIOXIDE
(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5β)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid 4,4-dioxide
4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-
(2S,5R)-3,3-DIMETHYL-4,4,7-TRIOXO-4LAMBDA6-THIA-1-AZA-BICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
(2S-cis)-3,3-dimethyl-7-oxy-4-sulph-1-aza dicyclo[3,2,0]heptane-2-carboxylic acid 4,4-dioxide
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S-cis)-
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide[Sulbactam
(2S-cis)-3，3-Dimethyl-7-oxo-4，4-dioxide-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-4-oxide
SULBACTAM FREE ACID((2S-CIS)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3,2,0]HEPTANE-2-CARBOXYLIC ACID 4,4-DIOXIDE )
methylene (2S,5R,6R)-6-[[(2R)-[[[[(2R)-aminophenylacetyl]amino][(4S)-4-[[[[[(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]hept-2-yl]carbonyl]oxy]methoxy]carbonyl]-5,5-dimethylthiazolidin-2-yl]acetyl]amino]phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (sultamicillin dimer) | [EINECS(EC#)]
269-878-2 | [Molecular Formula]
C8H11NO5S | [MDL Number]
MFCD00867005 | [MOL File]
68373-14-8.mol | [Molecular Weight]
233.24 |
| Chemical Properties | Back Directory | [Melting point ]
154-157℃ | [alpha ]
D20 +251° (c = 0.01 in pH 5.0 buffer) | [Boiling point ]
567.7±50.0 °C(Predicted) | [density ]
1.62±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
H2O: ≥18mg/mL | [form ]
lyophilized powder
| [pka]
2.62±0.40(Predicted) | [color ]
white to tan | [optical activity]
[α]/D ≥+225°, c = 1 in H2O | [Water Solubility ]
Soluble in water at 18mg/ml | [Merck ]
14,8889 | [Stability:]
Hygroscopic | [InChIKey]
FKENQMMABCRJMK-RITPCOANSA-N | [CAS DataBase Reference]
68373-14-8 |
| Hazard Information | Back Directory | [Description]
Sulbactam is prepared by partial chemical synthesis from
penicillins. The oxidation of the sulfur atom to a sulfone greatly enhances the potency of sulbactam. The
combination of sulbactam and ampicillin (Unasyn) is now clinically popular. | [Originator]
Sulbactam-Sodium,Antibiotic Co.,Bulgaria | [Uses]
A β-lactamase inhibitor. | [Uses]
antidepressant, dopamine uptake inhibitor | [Uses]
Sulbactam sodium is a semi-synthetic penem antibiotic formed by the oxidation of penicillanic acid to its sulfone and was invented by Barth at Pfizer in 1978. Sulbactam sodium is a weak antibiotic but its action as an irreversible inhibitor of β-lactamase is exploited to block the degradation of other penicillin derivatives. Sulbactam acts as a synergist with cephalosporins and penicillins against Gram positive bacteria and is used commercially in combination with ampicillin. | [Definition]
ChEBI: Sulbactam is a member of penicillanic acids. | [Manufacturing Process]
Sulbactam sodium is semi-synthetic antibiotic of penicillinic group. Start
material for it's synthesis is 6-aminopenicillanic acid. First 6-aminopenicillanic
acid was isolated in 1957 year from benzylpenicilline as resalt of treating of it
by penicillinaze. Benzylpenicilline is produced by microorganism of genus
Streptomyces.
Further, 6-aminopenicillanic acid reacted with bromine, hydrochloric acid and
NaNO2. As a result the 6,6-dibromopenicillanic acid was obtained.
6,6-Dibromopenicillanic acid was oxidized by KMnO4, to give 6,6-dibromo-1,1-The 6,6-dibromo-1,1-dioxopenicillanic acid in presence of Fe was converted to
the 1,1-dioxopenicillanic acid (sulbactam acid). The sulbactam acid was
treated by sodium 2-ethylhexanoate and crude sulbactam sodium was
obtained. | [Therapeutic Function]
Beta-lactamase inhibitor | [Antimicrobial activity]
Sulbactam has very weak antimicrobial activity against most
bacteria. Its only notable activity is against N. gonorrhoeae,
N. meningitidis and Acinetobacter baumannii. | [Clinical Use]
Sulbactam is penicillanic acid sulfone or 1,1-dioxopenicillanicacid. This synthetic penicillin derivative is a potent inhibitorof S. aureus β-lactamase as well as many β-lactamaseselaborated by Gram-negative bacilli. Sulbactam has weak intrinsicantibacterial activity but potentiates the activity ofampicillin and carbenicillin against β-lactamase–producingS. aureus and members of the Enterobacteriaceae family. Itdoes not, however, synergize with either carbenicillin or ticarcillinagainst P. aeruginosa strains resistant to these agents.Failure of sulbactam to penetrate the cell envelope is a possibleexplanation for the lack of synergy.
Fixed-dose combinations of ampicillin sodium and sulbactamsodium, marketed under the trade name Unasyn assterile powders for injection, have been approved for use inthe United States. These combinations are recommended forthe treatment of skin, tissue, intra-abdominal, and gynecologicalinfections caused by β-lactamase–producing strainsof S. aureus, E. coli, Klebsiella spp., P. mirabilis, B. fragilis,and Enterobacter and Acinetobacter spp. | [storage]
Store at -20°C |
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