Sulbactam

Base Information

• Chemical Name: Sulbactam
• CAS No.: 68373-14-8
• Molecular Formula: C8H11NO5S
• Molecular Weight: 233.245
• Hs Code.: 29349990
• European Community (EC) Number: 269-878-2
• UNII: S4TF6I2330
• DSSTox Substance ID: DTXSID1023605
• Nikkaji Number: J19.104C,J689.013J
• Wikipedia: Sulbactam
• Wikidata: Q423393
• NCI Thesaurus Code: C61957
• RXCUI: 10167
• Metabolomics Workbench ID: 53453
• ChEMBL ID: CHEMBL403
• Mol file: 68373-14-8.mol

Synonyms:Bétamaze;Combactam;CP 45899;CP-45899;CP45899;Penicillanic Acid Sulfone;Sodium, Sulbactam;Sulbactam;Sulbactam Sodium;Sulfone, Penicillanic Acid

Chemical Property of Sulbactam

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 2.26E-14mmHg at 25°C
• Melting Point: 146-151oC
• Refractive Index: 1.605
• Boiling Point: 567.7 °C at 760 mmHg
• PKA: 2.62±0.40(Predicted)
• Flash Point: 297.1 °C
• PSA: 100.13000
• Density: 1.62 g/cm³
• LogP: 0.22370
• Storage Temp.: −20°C
• Solubility.: H2O: ≥18mg/mL
• Water Solubility.: Soluble in water at 18mg/ml
• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 233.03579362
• Heavy Atom Count: 15
• Complexity: 446

Purity/Quality:

99% ^*data from raw suppliers

Sulbactam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)C
• Recent ClinicalTrials: Study to Evaluate the Efficacy and Safety of Intravenous Sulbactam-ETX2514 in the Treatment of Patients With Infections Caused by Acinetobacter Baumannii-calcoaceticus Complex
• Recent EU Clinical Trials: A Randomized, Active-Controlled Study to Evaluate the Efficacy and Safety of Intravenous Sulbactam-ETX2514 in the Treatment of Patients With Infections Caused by Acinetobacter baumannii-calcoaceticus Complex
• Recent NIPH Clinical Trials: Prophylaxis of post-bronchoscopy pneumonia with antibiotics based on a risk prediction score
• 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.
• Uses: antidepressant, dopamine uptake inhibitor 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. A β-lactamase inhibitor.
• 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.

Technology Process of Sulbactam

There total 37 articles about Sulbactam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester → sulbactum (68373-14-8,1217600-46-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium 4-methylbenzenesulfinate; In tetrahydrofuran; methanol; for 1h; Ambient temperature;

DOI:10.1021/jo971194c

Reference yield: 96.0%

6,6-dibromopenicillanic acid-1,1-dioxide (76646-91-8) → sulbactum (68373-14-8,1217600-46-8)

Guidance literature:

With sulfuric acid; zinc; In water; at 12 ℃; for 2h; Temperature; Large scale;

Reference yield: 96.0%

(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4,4-Dioxide (69388-78-9) → sulbactum (68373-14-8,1217600-46-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 1h; Ambient temperature;

DOI:10.1021/jo00304a024

upstream raw materials:

6,6-dibromopenicillanic acid-1,1-dioxide

(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4,4-Dioxide

(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl penicillanate 1,1-dioxide

6,6-dibromopenicillanic acid

Downstream raw materials:

chloromethyl penicillanate 1,1-dioxide

1,1-dioxopenicillanic acid (5-phenyl-2-oxo-1,3-dioxolen-4-yl)-methyl ester

(pivaloyloxy)methyl 6,6-dihydropenicillanate S,S-dioxide

iodomethyl penicillanate 1,1-dioxide

Refernces

• 1、 -. "Synthesis method of sulbactam". Paragraph 0027; 0030-0031; 0034-0035; 0038. . Retrieved 2020/11/02.
• 2、 -. "Sulbactam acid synthesis method". Paragraph 0026-0034. . Retrieved 2020/09/16.