Levonadifloxacin arginine salt | CAS#306748-89-0 | levonadifloxacin prodrug

MedKoo Cat#: 598735 | Name: Levonadifloxacin arginine

Description:

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

Levonadifloxacin arginine salt is a novel l-alanine ester prodrug of levonadifloxacin that is being developed as an oral fluoroquinolone antibiotic.

Chemical Structure

Levonadifloxacin arginine

CAS#306748-89-0 (arginine)

Theoretical Analysis

MedKoo Cat#: 598735

Name: Levonadifloxacin arginine

CAS#: 306748-89-0 (arginine)

Chemical Formula: C25H35FN6O6

Exact Mass:

Molecular Weight: 534.59

Elemental Analysis: C, 56.17; H, 6.60; F, 3.55; N, 15.72; O, 17.96

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 #

154357-42-3 (free base) 627891-34-3 (arginine hydrate) 306748-89-0 (arginine)

Synonym

Levonadifloxacin arginine salt; WCK 771; WCK-771; WCK771;

IUPAC/Chemical Name

L-arginine compound with (S)-9-fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid (1:1)

InChi Key

WIFOPRFVQIVWTB-YBVIJTQESA-N

InChi Code

InChI=1S/C19H21FN2O4.C6H14N4O2/c1-10-2-3-12-16-13(18(24)14(19(25)26)9-22(10)16)8-15(20)17(12)21-6-4-11(23)5-7-21;7-4(5(11)12)2-1-3-10-6(8)9/h8-11,23H,2-7H2,1H3,(H,25,26);4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t10-;4-/m00/s1

SMILES Code

N[C@@H](CCCNC(N)=N)C(O)=O.O=C(C1=CN2[C@@H](C)CCC3=C2C(C1=O)=CC(F)=C3N4CCC(O)CC4)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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Levonadifloxacin arginine salt is a novel l-alanine ester prodrug of levonadifloxacin that is being developed as an oral fluoroquinolone antibiotic.

In vitro activity:

Levonadifloxacin demonstrated potent activity against MRSA, QRSA, and MR-CoNS strains with significantly lower minimum inhibitory concentration MIC 50/90 values of 0.5/1 mg/L as compared with levofloxacin (8/32 mg/L) and moxifloxacin (2/8 mg/L). Reference: J Lab Physicians. 2020 Dec;12(3):230-232. https://pubmed.ncbi.nlm.nih.gov/33268943/

In vivo activity:

Fluoroquinolones are reported to possess immunomodulatory activity; hence, a novel benzoquinolizine fluoroquinolone, levonadifloxacin, was evaluated in lipopolysaccharide-stimulated human whole-blood (HWB) and mouse acute lung injury (ALI) models. Levonadifloxacin significantly mitigated the inflammatory responses in an HWB assay through inhibition of proinflammatory cytokines and in the ALI model by lowering lung total white blood cell count, myeloperoxidase, and cytokine levels. Reference: Antimicrob Agents Chemother. 2020 Apr 21;64(5):e00084-20. https://pubmed.ncbi.nlm.nih.gov/32152077/

Preparing Stock Solutions

The following data is based on the product molecular weight 534.59 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. Mamtora D, Saseedharan S, Rampal R, Joshi P, Bhalekar P, Ahdal J, Jain R. In Vitro activity of a Novel Benzoquinolizine Antibiotic, Levonadifloxacin (WCK 771) against Blood Stream Gram-Positive Isolates from a Tertiary Care Hospital. J Lab Physicians. 2020 Dec;12(3):230-232. doi: 10.1055/s-0040-1720944. Epub 2020 Nov 23. PMID: 33268943; PMCID: PMC7684988. 2. Baliga S, Mamtora DK, Gupta V, Shanmugam P, Biswas S, Mukherjee DN, Shenoy S. Assessment of antibacterial activity of levonadifloxacin against contemporary gram-positive clinical isolates collected from various Indian hospitals using disk-diffusion assay. Indian J Med Microbiol. 2020 Jul-Dec;38(3 & 4):307-312. doi: 10.4103/ijmm.IJMM_20_307. PMID: 33154240. 3. Patel A, Sangle GV, Trivedi J, Shengule SA, Thorve D, Patil M, Deshmukh NJ, Choudhari B, Karade A, Gupta S, Bhagwat S, Patel M. Levonadifloxacin, a Novel Benzoquinolizine Fluoroquinolone, Modulates Lipopolysaccharide-Induced Inflammatory Responses in Human Whole-Blood Assay and Murine Acute Lung Injury Model. Antimicrob Agents Chemother. 2020 Apr 21;64(5):e00084-20. doi: 10.1128/AAC.00084-20. PMID: 32152077; PMCID: PMC7179645. 4. Bhagwat SS, Periasamy H, Takalkar SS, Chavan R, Tayde P, Kulkarni A, Satav J, Zope V, Patel M. In Vivo Pharmacokinetic/Pharmacodynamic Targets of Levonadifloxacin against Staphylococcus aureus in a Neutropenic Murine Lung Infection Model. Antimicrob Agents Chemother. 2019 Jul 25;63(8):e00909-19. doi: 10.1128/AAC.00909-19. PMID: 31208999; PMCID: PMC6658750.

In vitro protocol:

In vivo protocol:

1. Patel A, Sangle GV, Trivedi J, Shengule SA, Thorve D, Patil M, Deshmukh NJ, Choudhari B, Karade A, Gupta S, Bhagwat S, Patel M. Levonadifloxacin, a Novel Benzoquinolizine Fluoroquinolone, Modulates Lipopolysaccharide-Induced Inflammatory Responses in Human Whole-Blood Assay and Murine Acute Lung Injury Model. Antimicrob Agents Chemother. 2020 Apr 21;64(5):e00084-20. doi: 10.1128/AAC.00084-20. PMID: 32152077; PMCID: PMC7179645. 2. Bhagwat SS, Periasamy H, Takalkar SS, Chavan R, Tayde P, Kulkarni A, Satav J, Zope V, Patel M. In Vivo Pharmacokinetic/Pharmacodynamic Targets of Levonadifloxacin against Staphylococcus aureus in a Neutropenic Murine Lung Infection Model. Antimicrob Agents Chemother. 2019 Jul 25;63(8):e00909-19. doi: 10.1128/AAC.00909-19. PMID: 31208999; PMCID: PMC6658750.

1: Rodvold KA, Gotfried MH, Chugh R, Gupta M, Yeole R, Patel A, Bhatia A. Intrapulmonary Pharmacokinetics of Levonadifloxacin following Oral Administration of Alalevonadifloxacin to Healthy Adult Subjects. Antimicrob Agents Chemother. 2018 Feb 23;62(3). pii: e02297-17. doi: 10.1128/AAC.02297-17. Print 2018 Mar. PubMed PMID: 29263070; PubMed Central PMCID: PMC5826115.