Sanfetrinem | CAS#156769-21-0 | antibiotic

MedKoo Cat#: 461767 | Name: Sanfetrinem

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

CAS#156769-21-0

Theoretical Analysis

MedKoo Cat#: 461767

Name: Sanfetrinem

CAS#: 156769-21-0

Chemical Formula: C14H19NO5

Exact Mass: 281.1263

Molecular Weight: 281.30

Elemental Analysis: C, 59.78; H, 6.81; N, 4.98; O, 28.44

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 #

No Data

Synonym

Sanfetrinem;

IUPAC/Chemical Name

(1S,5S,8aS,8bR)-1-(1-hydroxyethyl)-5-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydroazeto[2,1-a]isoindole-4-carboxylic acid

InChi Key

ICFDDEJRXZSWTA-RWVIBHTCSA-N

InChi Code

InChI=1S/C14H19NO5/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)/t6?,7-,8-,9+,11+/m0/s1

SMILES Code

O=C(C1=C2[C@@H](OC)CCC[C@]2([H])[C@@]3([H])N1C([C@@H]3C(O)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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 281.30 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: Babini GS, Yuan M, Livermore DM. Interactions of beta-lactamases with sanfetrinem (GV 104326) compared to those with imipenem and with oral beta-lactams. Antimicrob Agents Chemother. 1998 May;42(5):1168-75. PubMed PMID: 9593145; PubMed Central PMCID: PMC105767. 2: 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. PubMed PMID: 16852178. 3: Spangler SK, Jacobs MR, Appelbaum PC. MIC and time-kill studies of antipneumococcal activity of GV 118819X (sanfetrinem) compared with those of other agents. Antimicrob Agents Chemother. 1997 Jan;41(1):148-55. PubMed PMID: 8980771; PubMed Central PMCID: PMC163676. 4: 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. PubMed PMID: 9661015; PubMed Central PMCID: PMC105677. 5: Wieczorek P, Sacha PT, Leszczyńska K, Jakoniuk P, Zalewska M. [Sanfetrinem, the member of trinems--in vitro activity against Klebsiella pneumoniae producing ESBL]. Med Dosw Mikrobiol. 2006;58(1):27-32. Polish. PubMed PMID: 16871970. 6: Iavarone L, Bottacini M, Pugnaghi F, Morandini C, Grossi P. Sanfetrinem and sanfetrinem-cilexetil: disposition in rat and dog. Xenobiotica. 1997 Jul;27(7):693-709. PubMed PMID: 9253146. 7: 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. PubMed PMID: 10471590; PubMed Central PMCID: PMC89472. 8: Wise R, Andrews JM, Da Ros L, Child J, Mortiboy D. A study to determine the pharmacokinetics and inflammatory fluid penetration of two doses of a solid formulation of the hexetil prodrug of a trinem, sanfetrinem (GV 104326). Antimicrob Agents Chemother. 1997 Aug;41(8):1761-4. PubMed PMID: 9257756; PubMed Central PMCID: PMC164000. 9: 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. PubMed PMID: 9661036; PubMed Central PMCID: PMC105698. 10: 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. PubMed PMID: 9848449. 11: 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. PubMed PMID: 9738845. 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. PubMed PMID: 11254187. 13: Sifaoui F, Varon E, Kitzis MD, Gutmann L. In vitro activity of sanfetrinem and affinity for the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1998 Jan;42(1):173-5. PubMed PMID: 9449281; PubMed Central PMCID: PMC105476. 14: Spangler SK, Lin G, Jacobs MR, Appelbaum PC. Postantibiotic effect of sanfetrinem compared with those of six other agents against 12 penicillin-susceptible and -resistant pneumococci. Antimicrob Agents Chemother. 1997 Oct;41(10):2173-6. PubMed PMID: 9333043; PubMed Central PMCID: PMC164088. 15: 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. PubMed PMID: 11678379. 16: 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. PubMed PMID: 12113890. 17: Singh KV, Coque TM, Murray BE. In vitro activity of the trinem sanfetrinem (GV104326) against gram-positive organisms. Antimicrob Agents Chemother. 1996 Sep;40(9):2142-6. PubMed PMID: 8878596; PubMed Central PMCID: PMC163488. 18: 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. PubMed PMID: 19703371. 19: Doern GV, Pierce G, Brueggemann AB. In vitro activity of sanfetrinem (GV104326), a new trinem antimicrobial agent, versus Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. Diagn Microbiol Infect Dis. 1996 Sep;26(1):39-42. PubMed PMID: 8950528. 20: 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. PubMed PMID: 10640530.