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MedKoo Cat#: 576843 | Name: Carfecillin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Carfecillin is the phenyl ester of Carbenicillin that, upon oral administration, is broken down in the intestinal mucosa to an active antibacterial. It is used for urinary tract infections.

Chemical Structure

Carfecillin
Carfecillin
CAS#27025-49-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 576843

Name: Carfecillin

CAS#: 27025-49-6 (free acid)

Chemical Formula: C23H22N2O6S

Exact Mass: 454.1199

Molecular Weight: 454.50

Elemental Analysis: C, 60.78; H, 4.88; N, 6.16; O, 21.12; S, 7.05

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
27025-49-6 (free acid) 21649-57-0 (sodium)
Synonym
Carfecillin; Carbenicillin phenyl; Carbenicillin phenyl ester; Carfecilline
IUPAC/Chemical Name
(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-carboxylic acid
InChi Key
NZDASSHFKWDBBU-KVMCETHSSA-N
InChi Code
InChI=1S/C23H22N2O6S/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)/t15?,16-,17+,20-/m1/s1
SMILES Code
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
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
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.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 454.50 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Humphrey MJ, Filer CW, Jeffery DJ, Langley PF, Wadds GA. The availability of carfecillin and its phenol moiety in rat and dog. Xenobiotica. 1980 Oct;10(10):771-8. PubMed PMID: 7456492. 2: Berezhinskaia VV, Solov'ev VN, Berezina EK, Dolgova GV, Egorenko GG. [Effect of carfecillin on the body of animals in single and multiple administrations]. Antibiotiki. 1980 Jul;25(7):513-8. Russian. PubMed PMID: 7406463. 3: Basker MJ, Comber KR, Sutherland R, Valler GH. Carfecillin: antibacterial activity in vitro and in vivo. Chemotherapy. 1977;23(6):424-35. PubMed PMID: 21771. 4: Filer CW, Humphrey MJ, Jeffery DJ, Jones KH, Langley PF. The metabolism of carfecillin in rat, dog and man. Xenobiotica. 1980 Oct;10(10):761-9. PubMed PMID: 6256982. 5: Berezovskaia LN, Gavrilova TA, Dedukh NG, Kiseleva TA, Grakovskaia LK. [Pharmaceutical aspects of creating an effective drug form of carfecillin]. Antibiot Med Biotekhnol. 1986 Sep;31(9):684-7. Russian. PubMed PMID: 3777896. 6: Lidovskiĭ MZ, Zel'tser IZ, Berezina EK. [Acute toxicity and the cumulative properties of carfecillin]. Antibiotiki. 1978 May;23(5):450-3. Russian. PubMed PMID: 655692. 7: Hayahara N, Nishijima T, Maeda T, Oyama T, Matsumura T, Nishio S, Funai K, Sasaki S, Nakanishi J, Tsujita M, Kishimoto T, Maekawa M. [Clinical study of carfecillin in chronic urinary tract infection (author's transl)]. Jpn J Antibiot. 1977 Dec;30(12):993-8. Japanese. PubMed PMID: 599660. 8: Graber H, Benesch L, Arr M, Magyar T. Pharmacokinetic and clinical studies with carfecillin. Int J Clin Pharmacol Biopharm. 1978 Feb;16(2):59-62. PubMed PMID: 631972. 9: Sachelariu N, Soranzo ML, Bosio G, Sattinger M, Bramato C, Salassa B. [Pharmacokinetic and clinical research of a new phenyl ester of carbecinillin: carfecillin]. Minerva Med. 1979 Jul 14;70(32):2255-64. Italian. PubMed PMID: 379704. 10: Tanigawara Y, Tamaoka K, Nakagawa T, Uno T. Absorption kinetics of carbenicillin phenyl sodium and carbenicillin indanyl sodium in man. Chem Pharm Bull (Tokyo). 1982 Jun;30(6):2174-80. PubMed PMID: 6897018. 11: Nouws JF, Ziv G, Van Ginneken CA, Vree TB. Clinical pharmacokinetics of carbenicillin, carfecillin, ticarcillin and BL-P 1654 in dairy cows. J Vet Pharmacol Ther. 1984 Mar;7(1):35-43. PubMed PMID: 6323731. 12: Khatib A. Comparative efficacy of single- and eight-day treatment of urinary tract infections with carfecillin (Uticillin). J Int Med Res. 1981;9(3):186-8. PubMed PMID: 7238994. 13: Tsuji A, Miyamoto E, Terasaki T, Yamana T. Carbenicillin prodrugs: stability kinetics of alpha-phenyl and alpha-indanyl esters in aqueous solution. J Pharm Sci. 1979 Oct;68(10):1259-63. PubMed PMID: 583161. 14: Wilkinson PJ, Reeves DS, Wise R, Allen JT. Volunteer and clinical studies with carfecillin: a new orally administered ester of carbenicillin. Br Med J. 1975 May 3;2(5965):250-2. PubMed PMID: 805625; PubMed Central PMCID: PMC1673274. 15: Jedlicková Z, Rýc M, Libánská A. Combination effect with some aminoglycoside antibiotics. J Hyg Epidemiol Microbiol Immunol. 1981;25(2):204-6. PubMed PMID: 6788839.

View History

NC-2100

NC-2100