Sanfetrinem sodium | CAS# 141611-76-9 | Biochemical

MedKoo Cat#: 575216 | Name: Sanfetrinem sodium

Description:

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

Sanfetrinem is the first member of tricyclic beta-lactams (trinems) which can be administered orally as a hexatil ester and acts as an antibiotic.

Chemical Structure

Sanfetrinem sodium

CAS#141611-76-9 (sodium)

Theoretical Analysis

MedKoo Cat#: 575216

Name: Sanfetrinem sodium

CAS#: 141611-76-9 (sodium)

Chemical Formula: C14H18NNaO5

Exact Mass: 303.1083

Molecular Weight: 303.29

Elemental Analysis: C, 55.44; H, 5.98; N, 4.62; Na, 7.58; O, 26.38

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.

Bulk Inquiry

Related CAS #

156769-21-0 (free acid) 141611-76-9 (sodium)

Synonym

GV 104326; GV-104326; GV104326; GV 104326B; GV104326B; GV-104326B; GV 326; GV326;GV-326; LK 176; LK-176; LK176; Sanfetrinem sodium

IUPAC/Chemical Name

Azeto(2,1-a)isoindole-4-carboxylic acid, 1,2,5,6,7,8,8a,8b-octahydro-1-(1-hydroxyethyl)-5-methoxy-2-oxo-, sodium salt, (1S-(1alpha(S(sup *)),5alpha,8aalpha,8balpha))-

InChi Key

YXEMRWDSRDEZLB-KOKFPPFCSA-M

InChi Code

InChI=1S/C14H19NO5.Na/c1-6(16)9-11-7-4-3-5-8(20-2)10(7)12(14(18)19)15(11)13(9)17;/h6-9,11,16H,3-5H2,1-2H3,(H,18,19);/q;+1/p-1/t6-,7+,8+,9-,11-;/m1./s1

SMILES Code

[Na+].CO[C@H]1CCC[C@@H]2[C@@H]3[C@@H]([C@@H](C)O)C(=O)N3C(=C12)C(=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

Soluble in DMSO

Shelf Life

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 303.29 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

1: El-Gamal MI, Brahim I, Hisham N, Aladdin R, Mohammed H, Bahaaeldin A. Recent updates of carbapenem antibiotics. Eur J Med Chem. 2017 May 5;131:185-195. doi: 10.1016/j.ejmech.2017.03.022. Epub 2017 Mar 16. PMID: 28324783. 2: Iglicar P, Legen I, Vilfan G, Selic L, Prezelj A. Permeability of a novel beta-lactamase inhibitor LK-157 and its ester prodrugs across rat jejunum in vitro. J Pharm Pharmacol. 2009 Sep;61(9):1211-8. doi: 10.1211/jpp/61.09.0011. PMID: 19703371. 3: Wieczorek P, Sacha PT, Leszczyńska K, Jakoniuk P, Zalewska M. Sanfetrinem, przedstawiciel trinemów--aktywność in vitro wobec szczepów Klebsiella pneumoniae wytwarzajacych ESBL [Sanfetrinem, the member of trinems--in vitro activity against Klebsiella pneumoniae producing ESBL]. Med Dosw Mikrobiol. 2006;58(1):27-32. Polish. PMID: 16871970. 4: Fasoli HJ, Frau J, Fenollar-Ferrer C, Muñoz F, Donoso J. Molecular modeling and chemical reactivity of sanfetrinem and derivatives. J Phys Chem B. 2005 May 19;109(19):9780-6. doi: 10.1021/jp044192m. PMID: 16852178. 5: Reato G, Cuffini AM, Tullio V, Mandras N, Roana J, Banche G, Foa R, Carlone NA. Immunomodulating effect of antimicrobial agents on cytokine production by human polymorphonuclear neutrophils. Int J Antimicrob Agents. 2004 Feb;23(2):150-4. doi: 10.1016/j.ijantimicag.2003.07.006. PMID: 15013040. 6: Braggio S, Ferrara A, Sartori M, Bottacini M, Zanelli U, Zonzini L, Petrone M. Evaluation of the role of intestinal and liver metabolism in the conversion of two different ester prodrugs of sanfetrinem to the parent drug in vitro and in vivo using different rat tissues and a surgically prepared rat model. Eur J Pharm Sci. 2002 Jul;16(1-2):45-51. doi: 10.1016/s0928-0987(02)00056-8. PMID: 12113890. 7: Jacobsen MF, Turks M, Hazell R, Skrydstrup T. SmI(2)-mediated cyclizations of derivatized beta-lactams for the highly diastereoselective construction of functionalized prolines. J Org Chem. 2002 Apr 19;67(8):2411-7. doi: 10.1021/jo0104983. PMID: 11950281. 8: Bonfiglio G, Russo G, Nicoletti G. Recent developments in carbapenems. Expert Opin Investig Drugs. 2002 Apr;11(4):529-44. doi: 10.1517/13543784.11.4.529. PMID: 11922861. 9: De Nardi C, Braggio S, Ferrari L, Fontana S. Development and validation of a high-performance liquid chromatography-tandem mass spectrometry assay for the determination of sanfetrinem in human plasma. J Chromatogr B Biomed Sci Appl. 2001 Oct 25;762(2):193-201. doi: 10.1016/s0378-4347(01)00362-0. PMID: 11678379. 10: Nicolaides E, Symillides M, Dressman JB, Reppas C. Biorelevant dissolution testing to predict the plasma profile of lipophilic drugs after oral administration. Pharm Res. 2001 Mar;18(3):380-8. doi: 10.1023/a:1011071401306. PMID: 11442280. 11: Sader HS, Gales AC. Emerging strategies in infectious diseases: new carbapenem and trinem antibacterial agents. Drugs. 2001;61(5):553-64. doi: 10.2165/00003495-200161050-00001. PMID: 11368281. 12: De Nardi C, Ferrari L, Nardin E, Ruffo A, Braggio S. Development and validation of a column-switching high-performance liquid chromatographic method for the determination of sanfetrinem in rat and dog plasma by direct injection. J Chromatogr B Biomed Sci Appl. 2001 Mar 5;752(1):133-9. doi: 10.1016/s0378-4347(00)00533-8. PMID: 11254187. 13: Marini A, Berbenni V, Bruni G, Sinistri C, Maggioni A, Orlandi A, Villa M. Physico-chemical characterization of a novel tricyclic beta-lactam antibiotic. J Pharm Sci. 2000 Feb;89(2):232-40. doi: 10.1002/(SICI)1520-6017(200002)89:2<232::AID-JPS10>3.0.CO;2-5. PMID: 10688752. 14: Nicolaides E, Galia E, Efthymiopoulos C, Dressman JB, Reppas C. Forecasting the in vivo performance of four low solubility drugs from their in vitro dissolution data. Pharm Res. 1999 Dec;16(12):1876-82. doi: 10.1023/a:1018959511323. PMID: 10644077. 15: Oliver J, Naidoo A, Vandin L, Pugnaghi F, Gatehouse D, Comelli R. Carboxylesterases, a key factor in evaluating potential genotoxicity of Trinem antibiotics. Mutagenesis. 2000 Jan;15(1):45-55. doi: 10.1093/mutage/15.1.45. PMID: 10640530. 16: Betriu C, Gómez M, Palau ML, Sánchez A, Picazo JJ. Activities of new antimicrobial agents (trovafloxacin, moxifloxacin, sanfetrinem, and quinupristin-dalfopristin) against Bacteroides fragilis group: comparison with the activities of 14 other agents. Antimicrob Agents Chemother. 1999 Sep;43(9):2320-2. doi: 10.1128/AAC.43.9.2320. PMID: 10471590; PMCID: PMC89472. 17: Johnson AP, Warner M, Speller DC. In-vitro activity of sanfetrinem against isolates of Streptococcus pneumoniae and Staphylococcus aureus. J Antimicrob Chemother. 1998 Nov;42(5):643-6. doi: 10.1093/jac/42.5.643. PMID: 9848449. 18: Cuffini AM, Tullio V, Palarchio AI, Bonino A, Carlone NA. Sub-MICs of sanfetrinem promote the interaction of human polymorphonuclear granulocytes with a multiply resistant strain of Klebsiella pneumoniae. J Antimicrob Chemother. 1998 Aug;42(2):249-52. doi: 10.1093/jac/42.2.249. PMID: 9738845. 19: Tamura S, Miyazaki S, Tateda K, Ohno A, Ishii Y, Matsumoto T, Furuya N, Yamaguchi K. In vivo antibacterial activities of sanfetrinem cilexetil, a new oral tricyclic antibiotic. Antimicrob Agents Chemother. 1998 Jul;42(7):1858-61. doi: 10.1128/AAC.42.7.1858. PMID: 9661036; PMCID: PMC105698. 20: Cuffini AM, Tullio V, Bonino A, Allocco A, Palarchio AI, Carlone NA. Entry of sanfetrinem into human polymorphonuclear granulocytes and its cell-associated activity against intracellular, penicillin-resistant Streptococcus pneumoniae. Antimicrob Agents Chemother. 1998 Jul;42(7):1745-50. doi: 10.1128/AAC.42.7.1745. PMID: 9661015; PMCID: PMC105677.