Carbenicillin disodium

Base Information

• Chemical Name: Carbenicillin disodium
• CAS No.: 4800-94-6
• Molecular Formula: C₁₇H₁₆N₂O₆S*2Na
• Molecular Weight: 422.369
• Hs Code.: 29411000
• European Community (EC) Number: 225-360-8
• UNII: 9TS4B3H261
• DSSTox Substance ID: DTXSID6045820
• Wikidata: Q27116177
• NCI Thesaurus Code: C65285
• ChEMBL ID: CHEMBL606260
• Mol file: 4800-94-6.mol

Synonyms:Anabactyl;Carbapen;Carbecin;Carbenicillin;Carbenicillin Disodium;Carboxybenzyl Penicillin;Disodium, Carbenicillin;Geopen;Microcillin;Penicillin, Carboxybenzyl;Pyopen

Chemical Property of Carbenicillin disodium

Chemical Property:

• Appearance/Colour: Almost white solid.
• Boiling Point: 737.8 °C at 760 mmHg
• Flash Point: 400 °C
• PSA: 154.97000
• LogP: -1.85410
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 422.05244597
• Heavy Atom Count: 28
• Complexity: 634

Purity/Quality:

99% ^*data from raw suppliers

Carbenicillin Disodium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-36/37-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)[O-])C(=O)[O-])C.[Na+].[Na+]
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)[O-])C(=O)[O-])C.[Na+].[Na+]
• Description: Carbenicillin is a broad-spectrum carboxypenicillin antibiotic. It is active against Gram-negative and certain Gram-positive bacteria, including S. pyogenes, S. epidermidis, P. mirabilis, P. vulgaris, E. coli, and P. aeruginosa (MICs = 0.19, 1.56, 1.56, 3.12, 3.12, and 50 μg/ml, respectively). It is also active against penicillinase-producing and non-producing strains of S. aureus (MICs = 1.56 and 12.5 μg/ml, respectively). Carbenicillin is protective against systemic S. pyogenes, P. vulgaris, E. coli, and S. aureus infection in a mouse model of systemic lethal infection with 50% protective dose (PD50) values of 7.8, 224, 19.3, and 34 mg/kg, respectively. It also decreases viable colony counts in the kidney in a rat model of P. vulgaris or E. coli urinary tract infection when administered at a dose of 100 mg/kg. Formulations containing carbenicillin have previously been used in the treatment of upper and lower urinary tract infections and prostatitis.
• Uses: Carbenicillin disodium salt is a water-soluble antibiotic which is effective against gram-negative bacteria.Carbenicillin disodium salt is widely utilized as an antibiotic which is used to control bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. It has been involved in the study of the role of penicillin-sensitive transpeptidases in cell wall biosynthesis.
• Therapeutic Function: Antibacterial
• Clinical Use: Carbenicillin disodium, disodium α-carboxybenzylpenicillin(Geopen, Pyopen), is a semisynthetic penicillin releasedin the United States in 1970, which was introduced inEngland and first reported by Ancred et al. in 1967.Examination of its structure shows that it differs from ampicillinin having an ionizable carboxyl group rather than anamino group substituted on the α-carbon atom of the benzylside chain. Carbenicillin has a broad range of antimicrobialactivity, broader than any other known penicillin, a propertyattributed to the unique carboxyl group. It has been proposedthat the carboxyl group improves penetration of themolecule through cell wall barriers of Gram-negativebacilli, compared with other penicillins.Carbenicillin is not stable in acids and is inactivated bypenicillinase. It is a malonic acid derivative and, as such, decarboxylatesreadily to penicillin G, which is acid labile.Solutions of the disodium salt should be freshly prepared but,when refrigerated, may be kept for 2 weeks. It must be administeredby injection and is usually given intravenously.Carbenicillin has been effective in the treatment of systemicand urinary tract infections caused by P. aeruginosa,indole-producing Proteus spp., and Providencia spp., all ofwhich are resistant to ampicillin. The low toxicity of carbenicillin,with the exception of allergic sensitivity, permits theuse of large dosages in serious infections. Most cliniciansprefer to use a combination of carbenicillin and gentamicinfor serious pseudomonal and mixed coliform infections. Thetwo antibiotics are chemically incompatible, however, andshould never be combined in an intravenous solution.

Technology Process of Carbenicillin disodium

There total 1 articles about Carbenicillin disodium 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:

6NHCl + 2.2-dimethyl-5-phenyl-1,3-dioxane-4,6-dione (15231-78-4) + 6-aminopenicillanic acid (551-16-6,1079-37-4,3115-55-7,21794-93-4,145920-51-0) + bis-(trimethylsilyl)acetamide (17879-45-7) → carbenicillin (95985-46-9,95985-47-0,4697-36-3) + carbenicillin disodium salt (4800-94-6,27025-51-0,32420-30-7,36912-57-9,83059-64-7,83113-57-9)

Guidance literature:

In tetrahydrofuran; methanol; water; Petroleum ether;

Reference yield: 94.0%

carbenicillin disodium salt (4800-94-6,27025-51-0,32420-30-7,36912-57-9,83059-64-7,83113-57-9) + amikacin sulfate (39831-55-5,56086-43-2,110660-84-9,149022-22-0) → C56H75N9O25S2(4-)*H2O4S*4Na(1+)

Guidance literature:

In water; at 25 ℃; for 72h;

DOI:10.1021/jm00155a004

Reference yield: 93.0%

chlorhexidine diacetate (56-95-1) + carbenicillin disodium salt (4800-94-6,27025-51-0,32420-30-7,36912-57-9,83059-64-7,83113-57-9) → chlorhexidine carbenicillin

Guidance literature:

In water; butan-1-ol; at 20 ℃; for 48h;

DOI:10.3390/molecules20046466

upstream raw materials:

2.2-dimethyl-5-phenyl-1,3-dioxane-4,6-dione

6-aminopenicillanic acid

bis-(trimethylsilyl)acetamide

Downstream raw materials:

C₃₅H₅₂N₆O₁₇S^(2-)*H₂O₄S*2Na⁽¹⁺⁾

C₃₅H₅₃N₇O₁₅S^(2-)*2H₂O₄S*2Na⁽¹⁺⁾

carbenicillin

Refernces