| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
|
||
| 250mg |
|
||
| 500mg |
|
||
| 1g |
|
||
| Other Sizes |
| Targets |
Carfecillin Sodium targets bacterial cell wall synthesis, a common mechanism for beta-lactam antibiotics. As a prodrug, it is hydrolyzed to carbenicillin, which then inhibits the transpeptidase enzymes (penicillin-binding proteins) involved in the final stages of peptidoglycan synthesis. After absorption, carfecillin sodium rapidly hydrolyzes to active carbenicillin, which binds to and inactivates penicillin-binding protein (PBP) on the inner membrane of bacterial cell walls, thereby preventing the cross-linking of peptidoglycan, a key component of the bacterial cell wall. This leads to a weakened bacterial cell wall, ultimately resulting in bacterial cell lysis.
|
|---|---|
| ln Vitro |
In vitro, carfecillin sodium exhibits antibacterial activity against a range of gram-positive and gram-negative bacteria. Its activity is due to its conversion to carbenicillin, which is the active antibacterial agent. The compound's spectrum of activity is similar to that of carbenicillin, making it effective against many urinary tract pathogens. In vitro susceptibility testing, such as disk diffusion or broth microdilution, is used to determine the minimum inhibitory concentration (MIC) for various bacterial isolates.
|
| ln Vivo |
In vivo, carfecillin sodium is effective in treating urinary tract infections. After oral administration, it is absorbed and hydrolyzed in the intestinal mucosa to release carbenicillin, which is then distributed to the urine, where it exerts its antibacterial activity. Its use is primarily for the treatment of urinary tract infections caused by susceptible organisms. The compound is not effective against infections outside the urinary tract due to its limited distribution.
|
| Enzyme Assay |
In vitro enzyme or receptor binding (non-cell) assays for carfecillin sodium are not applicable, as it is a prodrug that is converted to an antibiotic that targets bacterial cell wall synthesis. However, its hydrolysis to carbenicillin can be studied using in vitro enzymatic assays with esterases. The antibacterial activity of the active metabolite, carbenicillin, can be assessed by measuring its inhibition of penicillin-binding proteins (PBPs) or by using a bacterial cell wall synthesis assay.
|
| Cell Assay |
In vitro cell-based assays for carfecillin sodium are performed using standard antimicrobial susceptibility testing methods. Bacterial cultures are grown in the presence of the compound, and the minimum inhibitory concentration (MIC) is determined. Time-kill studies can also be performed to assess the bactericidal activity. These assays confirm the compound's antibacterial activity and its spectrum of activity against various bacterial species.
|
| Animal Protocol |
In vivo animal experiments for carfecillin sodium are conducted using animal models of urinary tract infection. The compound is administered orally, and its efficacy is evaluated by measuring the reduction in bacterial load in the urine and kidneys. These studies confirm the compound's effectiveness in treating urinary tract infections and its oral bioavailability.
|
| ADME/Pharmacokinetics |
Pharmacokinetic (PK) properties of carfecillin sodium are characterized by its oral absorption and hydrolysis to carbenicillin. The compound has a molecular weight of 476.4788 and a molecular formula of C23H21N2NaO6S. It is a solid powder with a boiling point of 770.9°C and a flash point of 420°C. The LogP is 1.001. It is a prodrug that is designed to be absorbed after oral administration. It is hydrolyzed in the intestinal mucosa to release carbenicillin, which is then absorbed into the systemic circulation. Carbenicillin is excreted renally, achieving high concentrations in the urine, which is important for the treatment of urinary tract infections.
|
| Toxicity/Toxicokinetics |
Toxicology (toxicology) data for carfecillin sodium are similar to those of other penicillins. It is generally well-tolerated, but allergic reactions can occur, including rash, urticaria, and anaphylaxis. As a penicillin, it is contraindicated in patients with a history of hypersensitivity to penicillins. Other side effects may include gastrointestinal disturbances, such as diarrhea and nausea. The compound's safety profile is well-established based on its use as an antibiotic.
|
| Additional Infomation |
Carfricillin sodium is an organosodium salt containing carfricillin (1-) molecules. Cabennicillin benzyl sodium is the sodium salt of cabennicillin phenyl ester, a broad-spectrum semi-synthetic penicillin derivative with antibacterial activity. After absorption, cabennicillin benzyl sodium rapidly hydrolyzes to active cabennicillin, which binds to and inactivates penicillin-binding protein (PBP) on the inner membrane of bacterial cell walls, thereby preventing the cross-linking of peptidoglycan, a key component of the bacterial cell wall. This leads to a weakened bacterial cell wall, ultimately resulting in bacterial cell lysis. After oral administration, cabennicillin phenyl ester is broken down in the intestinal mucosa into an active antibacterial agent used to treat urinary tract infections.
Other information: Carfecillin Sodium is a semisynthetic penicillin antibiotic used for the treatment of urinary tract infections. It is a prodrug of carbenicillin. The compound is also known as BRL-3475 and Uticillin. Its CAS number is 21649-57-0. The free acid has CAS number 27025-49-6. |
| Molecular Formula |
C23H21N2NAO6S
|
|---|---|
| Molecular Weight |
476.4788
|
| Exact Mass |
476.102
|
| Elemental Analysis |
C, 57.98; H, 4.44; N, 5.88; Na, 4.82; O, 20.15; S, 6.73
|
| CAS # |
21649-57-0
|
| Related CAS # |
27025-49-6 (free acid);21649-57-0 (sodium);
|
| PubChem CID |
23674995
|
| Appearance |
Solid powder
|
| Boiling Point |
770.9ºC at 760mmHg
|
| Flash Point |
420ºC
|
| LogP |
1.001
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
33
|
| Complexity |
781
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(C(C3=CC=CC=C3)C(OC4=CC=CC=C4)=O)=O)N1C2=O)[O-].[Na+]
|
| InChi Key |
JXSBZDNBNJTHBJ-JPZUGYNPSA-M
|
| InChi Code |
InChI=1S/C23H22N2O6S.Na/c1-23(2)17(21(28)29)25-19(27)16(20(25)32-23)24-18(26)15(13-9-5-3-6-10-13)22(30)31-14-11-7-4-8-12-14;/h3-12,15-17,20H,1-2H3,(H,24,26)(H,28,29);/q;+1/p-1/t15?,16-,17+,20-;/m1./s1
|
| Chemical Name |
sodium;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(3-oxo-3-phenoxy-2-phenylpropanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
|
| Synonyms |
Carfecillin Sodium; BRL-3475; BRL 3475; BRL3475; Carbenicillin Phenyl Sodium; Uticillin
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0987 mL | 10.4936 mL | 20.9872 mL | |
| 5 mM | 0.4197 mL | 2.0987 mL | 4.1974 mL | |
| 10 mM | 0.2099 mL | 1.0494 mL | 2.0987 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
