Carfecillin Sodium

• CAS: 21649-57-0
• Catalog Number: ACM21649570-1
• Category: Others
• Molecular Weight: 476.48
• Molecular Formula: C23H21N2NaO6S
• Description: Carfecillin Sodium, also known as Carbenicillin Phenyl Sodium and BRL-3475, is the phenyl ester of Carbenicillin that, upon oral administration, is broken down in the intestinal mucosa to the active antibacterial. It is used for urinary tract infections.
• Synonyms: Carfecillin Sodium; BRL-3475; BRL 3475; BRL3475; Carbenicillin Phenyl Sodium; Uticillin
• IUPAC Name: sodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(3-oxo-3-phenoxy-2-phenylpropanamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Canonical 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: 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
• InChI Key: JXSBZDNBNJTHBJ-JPZUGYNPSA-M
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Shelf Life: >2 years if stored properly
• Storage: Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
• Alternative CAS: 27025-49-6 (free acid); 21649-57-0 (sodium)
• Biological Target: Carfecillin, the alpha-phenyl ester of carbenicillin, hydrolyses rapidly in the presence of serum or body tissues to liberate carbenicillin but hydrolysis is less rapid in aqueous solution.
• Drug Formulation: This drug may be formulated in DMSO
• Elemental Analysis: C, 57.98; H, 4.44; N, 5.88; Na, 4.82; O, 20.15; S, 6.73
• HS Tariff Code: 2934.99.9001
• In Vitro Activity: The activity of carfecillin in antibacterial tests in vitro depends upon the extent of hydrolysis to carbenicillin, and in conventional serial dilution tests carfecillin shows an antibacterial spectrum generally similar to that of carbenicillin due to extensive hydrolysis. However, in tests in which the extent of hydrolysis is reduced, carfecillin displays lesser activity than carbenicillin against gram-negative bacilli and greater activity against gram-positive cocci. In the presence of serum carfecillin is hydrolysed rapidly to carbenicillin and the activity shown is solely that of carbenicillin.; Reference: Chemotherapy. 1977;23(6):424-35. https://pubmed.ncbi.nlm.nih.gov/21771/
• In Vivo Activity: Absorption studies in intestinally-perfused rats showed that following administration of either [14C]phenol or [phenol-14C]carfecillin, the half-life values of radioactivity in the intestinal lumen were 6 min and 47 min respectively. Following oral administration of phenol to rats and dogs at 300 mg/kg and 40 mg/kg respectively, maximum plasma concn. of phenol were 26 microgram/ml. However, following oral administration of carfecillin to rats and dogs at dose levels of 3000 and 800 mg/kg respectively, no significant amounts of free phenol or intact carfecillin were detected (< 1 microgram/ml). The very low concentrations of phenol found after carfecillin administration and the concomitant absence of acute phenol toxicity is explained by the slow absorption of carfecillin and its slow hydrolysis to phenol in the gut lumen. In the dog, phenol which enters the portal circulation as carfecillin appears to undergo significant 'first pass' metabolism by the liver.; Reference: Xenobiotica. 1980 Oct;10(10):771-8. https://pubmed.ncbi.nlm.nih.gov/7456492/
• Shipping: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
• Stock Solution Storage: 0-4 °C for short term (days to weeks), or -20 °C for long term (months).