MedKoo Cat#: 585354 | Name: Premafloxacin

Description:

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

Premafloxacin is an 8-methoxy fluoroquinolone with enhanced activity against Staphylococcus aureus.

Chemical Structure

Premafloxacin
CAS#143383-65-7

Theoretical Analysis

MedKoo Cat#: 585354

Name: Premafloxacin

CAS#: 143383-65-7

Chemical Formula: C21H26FN3O4

Exact Mass: 403.1907

Molecular Weight: 403.45

Elemental Analysis: C, 62.52; H, 6.50; F, 4.71; N, 10.42; O, 15.86

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 #
No Data
Synonym
Premafloxacin; U-95376; U95376; U 95376
IUPAC/Chemical Name
1-cyclopropyl-6-fluoro-8-methoxy-7-[(3R)-3-[(1S)-1-(methylamino)ethyl]pyrrolidin-1-yl]-4-oxoquinoline-3-carboxylic acid
InChi Key
SUQUWONDIBHQOZ-NWDGAFQWSA-N
InChi Code
InChI=1S/C21H26FN3O4/c1-11(23-2)12-6-7-24(9-12)18-16(22)8-14-17(20(18)29-3)25(13-4-5-13)10-15(19(14)26)21(27)28/h8,10-13,23H,4-7,9H2,1-3H3,(H,27,28)/t11-,12+/m0/s1
SMILES Code
O=C(C1=CN(C2CC2)C3=C(C=C(F)C(N4C[C@H]([C@@H](NC)C)CC4)=C3OC)C1=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

Preparing Stock Solutions

The following data is based on the product molecular weight 403.45 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: Bao DH, Gu XS, Xie JH, Zhou QL. Iridium-Catalyzed Asymmetric Hydrogenation of Racemic β-Keto Lactams via Dynamic Kinetic Resolution. Org Lett. 2017 Jan 6;19(1):118-121. doi: 10.1021/acs.orglett.6b03397. Epub 2016 Dec 12. PubMed PMID: 27936808. 2: Fioritto AF, Bhattachar SN, Wesley JA. Solubility measurement of polymorphic compounds via the pH-metric titration technique. Int J Pharm. 2007 Feb 7;330(1-2):105-13. Epub 2006 Sep 10. PubMed PMID: 17049191. 3: Sakai T, Kawamoto Y, Tomioka K. Asymmetric synthesis of intermediates for otamixaban and premafloxacin by the chiral ligand-controlled asymmetric conjugate addition of a lithium amide. J Org Chem. 2006 Jun 9;71(12):4706-9. PubMed PMID: 16749814. 4: Wang M, Sahm DF, Jacoby GA, Zhang Y, Hooper DC. Activities of newer quinolones against Escherichia coli and Klebsiella pneumoniae containing the plasmid-mediated quinolone resistance determinant qnr. Antimicrob Agents Chemother. 2004 Apr;48(4):1400-1. PubMed PMID: 15047552; PubMed Central PMCID: PMC375334. 5: Fleck TJ, McWhorter WW Jr, DeKam RN, Pearlman BA. Synthesis of N-methyl-N-[(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl]amine. J Org Chem. 2003 Dec 12;68(25):9612-7. PubMed PMID: 14656085. 6: Ince D, Hooper DC. Quinolone resistance due to reduced target enzyme expression. J Bacteriol. 2003 Dec;185(23):6883-92. PubMed PMID: 14617652; PubMed Central PMCID: PMC262703. 7: Chang CF, Chang LC, Chang YF, Chen M, Chiang TS. Antimicrobial susceptibility of Actinobacillus pleuropneumoniae, Escherichia coli, and Salmonella choleraesuis recovered from Taiwanese swine. J Vet Diagn Invest. 2002 Mar;14(2):153-7. PubMed PMID: 11939337. 8: Gu CH, Grant DJ. Estimating the relative stability of polymorphs and hydrates from heats of solution and solubility data. J Pharm Sci. 2001 Sep;90(9):1277-87. PubMed PMID: 11745780. 9: Ince D, Hooper DC. Mechanisms and frequency of resistance to premafloxacin in Staphylococcus aureus: novel mutations suggest novel drug-target interactions. Antimicrob Agents Chemother. 2000 Dec;44(12):3344-50. PubMed PMID: 11083638; PubMed Central PMCID: PMC90203. 10: De Oliveira AP, Watts JL, Salmon SA, Aarestrup FM. Antimicrobial susceptibility of Staphylococcus aureus isolated from bovine mastitis in Europe and the United States. J Dairy Sci. 2000 Apr;83(4):855-62. PubMed PMID: 10791803. 11: Bowersock TL, Salmon SA, Portis ES, Prescott JF, Robison DA, Ford CW, Watts JL. MICs of oxazolidinones for Rhodococcus equi strains isolated from humans and animals. Antimicrob Agents Chemother. 2000 May;44(5):1367-9. PubMed PMID: 10770781; PubMed Central PMCID: PMC89874. 12: Odland BA, Erwin ME, Jones RN. Quality control guidelines for disk diffusion and broth microdilution antimicrobial susceptibility tests with seven drugs for veterinary applications. J Clin Microbiol. 2000 Jan;38(1):453-5. PubMed PMID: 10618141; PubMed Central PMCID: PMC88749. 13: Schinzer WC, Bergren MS, Aldrich DS, Chao RS, Dunn MJ, Jeganathan A, Madden LM. Characterization and interconversion of polymorphs of premafloxacin, a new quinolone antibiotic. J Pharm Sci. 1997 Dec;86(12):1426-31. PubMed PMID: 9423158. 14: Watts JL, Salmon SA, Sanchez MS, Yancey RJ Jr. In vitro activity of premafloxacin, a new extended-spectrum fluoroquinolone, against pathogens of veterinary importance. Antimicrob Agents Chemother. 1997 May;41(5):1190-2. PubMed PMID: 9145899; PubMed Central PMCID: PMC163880. 15: Zerva L, Marshall SA, Jones RN. Premafloxacin: a projected veterinary use fluoro-quinolone with significant activity against multi-resistant gram-positive human pathogens. J Antimicrob Chemother. 1996 Oct;38(4):742-4. PubMed PMID: 8937972. 16: Marshall SA, Jones RN, Wanger A, Washington JA, Doern GV, Leber AL, Haugen TH. Proposed MIC quality control guidelines for National Committee for Clinical Laboratory Standards susceptibility tests using seven veterinary antimicrobial agents: ceftiofur, enrofloxacin, florfenicol, penicillin G-novobiocin, pirlimycin, premafloxacin, and spectinomycin. J Clin Microbiol. 1996 Aug;34(8):2027-9. PubMed PMID: 8818906; PubMed Central PMCID: PMC229178.