Carfecillin Sodium | Carbenicillin Phenyl Sodium | BRL-3475 | CAS#21649-57-0 | Antibacterial

MedKoo Cat#: 329204 | Name: Carfecillin Sodium

Description:

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

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.

Chemical Structure

Carfecillin Sodium

CAS#21649-57-0 (sodium)

Theoretical Analysis

MedKoo Cat#: 329204

Name: Carfecillin Sodium

CAS#: 21649-57-0 (sodium)

Chemical Formula: C23H21N2NaO6S

Exact Mass: 0.0000

Molecular Weight: 476.48

Elemental Analysis: C, 57.98; H, 4.44; N, 5.88; Na, 4.82; O, 20.15; S, 6.73

Price and Availability

Size	Price	Availability
1mg	USD 190.00	Ready to ship
5mg	USD 550.00	Ready to ship
10mg	USD 950.00	Ready to ship
25mg	USD 1,650.00	Ready to ship
50mg	USD 2,950.00	Ready to ship
100mg	USD 4,250.00	Ready to ship

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Related CAS #

27025-49-6 (free acid) 21649-57-0 (sodium)

Synonym

Carfecillin Sodium; BRL-3475; BRL 3475; BRL3475; Carbenicillin Phenyl Sodium; Uticillin

IUPAC/Chemical 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

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

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-].[Na+]

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

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Note: This compound is not stable in solution. It is not recommended to store the stock solution for more than 4 hours.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A22N01B10

QC Data

View QC data: current batch, Lot#A22N01B10

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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.

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 476.48 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.

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

Formulation protocol:

1. Basker MJ, Comber KR, Sutherland R, Valler GH. Carfecillin: antibacterial activity in vitro and in vivo. Chemotherapy. 1977;23(6):424-35. doi: 10.1159/000222012. PMID: 21771. 2. Barthélémy M, Péduzzi J, Rowlands D, Paul G, Moreau G, Labia R. Val-237 for Ala substitution in the TEM-2 beta-lactamase dramatically alters the catalytic efficiencies towards carbenicillin and ticarcillin. FEMS Microbiol Lett. 1994 Apr 15;117(3):333-9. doi: 10.1111/j.1574-6968.1994.tb06788.x. PMID: 8200509. 3. 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. doi: 10.3109/00498258009033805. PMID: 7456492.

In vitro protocol:

In vivo protocol:

1. Basker MJ, Comber KR, Sutherland R, Valler GH. Carfecillin: antibacterial activity in vitro and in vivo. Chemotherapy. 1977;23(6):424-35. doi: 10.1159/000222012. PMID: 21771. 2. 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. doi: 10.3109/00498258009033805. PMID: 7456492.

1: Carfecillin. Drug Ther Bull. 1975 Apr 25;13(9):35-6. PMID: 1220948. 2: 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. doi: 10.3109/00498258009033805. PMID: 7456492. 3: Basker MJ, Comber KR, Sutherland R, Valler GH. Carfecillin: antibacterial activity in vitro and in vivo. Chemotherapy. 1977;23(6):424-35. doi: 10.1159/000222012. PMID: 21771. 4: Modr Z, Dvovácek K, Janků I, Krebs V. Pharmacokinetics of carfecillin and carindacillin. Int J Clin Pharmacol Biopharm. 1977 Feb;15(2):81-3. doi: 10.103/00006450-11000-00004. PMID: 577917. 5: 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. doi: 10.3109/00498258009033804. PMID: 6256982. 6: 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. PMID: 631972. 7: Berezhinskaia VV, Solov'ev VN, Berezina EK, Dolgova GV, Egorenko GG. Izuchenie vliianiia karfetsillina na organizm zhivotnykh pri odno- i mnogokdratnom vvedenii [Effect of carfecillin on the body of animals in single and multiple administrations]. Antibiotiki. 1980 Jul;25(7):513-8. Russian. PMID: 7406463. 8: Borowski J, Musierowicz A, Czerniawski J, Dzierzanowska D, Zarebski M, Ginel Z. Laboratory and clinical studies on carfecillin. J Antimicrob Chemother. 1976 Jun;2(2):175-80. doi: 10.1093/jac/2.2.175. PMID: 956080. 9: Wise R. For and against carfecillin--a matter of resistance? J Antimicrob Chemother. 1975 Mar;1(1):4-5. doi: 10.1093/jac/1.1.4. PMID: 809405. 10: Berezovskaia LN, Gavrilova TA, Dedukh NG, Kiseleva TA, Grakovskaia LK. Farmatsevticheskie aspekty sozdaniia éffektivnoĭ lekarstvennoĭ formy karfetsillina [Pharmaceutical aspects of creating an effective drug form of carfecillin]. Antibiot Med Biotekhnol. 1986 Sep;31(9):684-7. Russian. PMID: 3777896. 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. doi: 10.1111/j.1365-2885.1984.tb00876.x. PMID: 6323731. 12: 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. PMID: 599660. 13: Williams PS, Sewell RD, Smith HJ, Gonzalez JP. Novel inhibitors of enkephalin-degrading enzymes. I: Inhibitors of enkephalinase by penicillins. J Enzyme Inhib. 1989;3(2):91-101. doi: 10.3109/14756368909030368. PMID: 2489237. 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. doi: 10.1136/bmj.2.5965.250. PMID: 805625; PMCID: PMC1673274. 15: Lidovskiĭ MZ, Zel'tser IZ, Berezina EK. Ostraia toksichnost' i kumuliativnye svoĭstva karfetsillina [Acute toxicity and the cumulative properties of carfecillin]. Antibiotiki. 1978 May;23(5):450-3. Russian. PMID: 655692. 16: 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. doi: 10.1177/030006058100900306. PMID: 7238994. 17: Sachelariu N, Soranzo ML, Bosio G, Sattinger M, Bramato C, Salassa B. Ricerca farmacocinetica e clinica su un nuovo estere fenilico di carbenicillina: carfecillina [Pharmacokinetic and clinical research of a new phenyl ester of carbecinillin: carfecillin]. Minerva Med. 1979 Jul 14;70(32):2255-64. Italian. PMID: 379704. 18: Leigh DA, Simmons K. The treatment of simple and complicated urinary tract infections with carfecillin; a new oral ester of carbenicillin. J Antimicrob Chemother. 1976 Sep;2(3):293-8. doi: 10.1093/jac/2.3.293. PMID: 789326. 19: Lees LJ, Harding JW. Urinary tract infections in general practice a preliminary trial of carfecillin. Br J Clin Pract. 1974 Oct;28(10):349-52. PMID: 4613369. 20: Shah PJ, Williams G, Chaudary M. Short-term antibiotic prophylaxis and prostatectomy. Br J Urol. 1981 Aug;53(4):339-43. doi: 10.1111/j.1464-410x.1981.tb03193.x. PMID: 7020820.