Temocillin

Base Information

• Chemical Name: Temocillin
• CAS No.: 66148-78-5
• Molecular Formula: C16H18N2O7S2
• Molecular Weight: 414.46
• European Community (EC) Number: 266-184-1
• UNII: 03QB156W6I
• DSSTox Substance ID: DTXSID201009398
• Nikkaji Number: J21.367E
• Wikipedia: Temocillin
• Wikidata: Q3983108
• NCI Thesaurus Code: C76858
• Metabolomics Workbench ID: 57904
• ChEMBL ID: CHEMBL1276310
• Mol file: 66148-78-5.mol

Synonyms:BRL 17421;disodium 6beta-(2-carboxy-2-thien-3-ylacetamido)-6alpha-methoxypenicillanate;temocillin;temocillin, (2S-(2alpha,5alpha,6alpha))-isomer

Chemical Property of Temocillin

Chemical Property:

• Vapor Pressure: 2.09E-24mmHg at 25°C
• Refractive Index: 1.675
• Boiling Point: 761.9 °C at 760 mmHg
• PKA: 2.46±0.50(Predicted)
• Flash Point: 414.6 °C
• PSA: 186.78000
• Density: 1.6 g/cm³
• LogP: 0.85090
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 414.05554326
• Heavy Atom Count: 27
• Complexity: 700

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@](C2=O)(NC(=O)C(C3=CSC=C3)C(=O)O)OC)C(=O)O)C
• Recent ClinicalTrials: Temocillin vs Meropenem for the Targeted Treatment of Bacteraemia Resistant to Third Gen Cephalosporins
• Recent EU Clinical Trials: Piperacillin-tazobactam and temocillin as carbapenem-alternatives for the treatment of severe infections due to extended-spectrum beta-lactamase–producing Gram-negative Enterobacteriaceae in the intensive care unit
• Uses: Antibacterial.
• Clinical Use: Severe infection with susceptible bacteria, including urinary and respiratory tract infections, peritonitis and septicemia.
• Drug interactions: Potentially hazardous interactions with other drugs Temocillin can reduce the excretion of methotrexate (increased risk of toxicity).

Technology Process of Temocillin

There total 5 articles about Temocillin 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:

→ temocillin (66148-78-5,94493-48-8,94536-98-8)

Guidance literature:

Reference yield:

→ temocillin (66148-78-5)

Guidance literature:

/BRN= 61679/, Na2B4O7*10H2O;

Reference yield:

rac-6β-((Ξ)-2-benzyloxycarbonyl-2-thiophen-3-yl-acetylamino)-6α-methoxy-penicillanic acid benzyl ester (61545-07-1) → rac-6β-((Ξ)-2-carboxy-2-thiophen-3-yl-acetylamino)-6α-methoxy-penicillanic acid (66148-78-5,94493-48-8,94536-98-8)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In methanol; water;

upstream raw materials:

rac-6β-((Ξ)-2-benzyloxycarbonyl-2-thiophen-3-yl-acetylamino)-6α-methoxy-penicillanic acid benzyl ester

6β-amino-6α-methoxy-penicillanic acid benzyl ester

monobenzyl 3-thienylmalonic acid chloride

Refernces