Alalevonadifloxacin

Chemical compound

Rx in India

Identifiers

IUPAC name

(12S)-8-[4-[(2S)-2-Aminopropanoyl]oxypiperidin-1-yl]-7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0^5,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid

CAS Number

706809-20-3

PubChem CID

16734914

IUPHAR/BPS

10756

ChemSpider

19538972

UNII

57B7E1D1TG

ChEMBL

ChEMBL5095635

Chemical and physical dataFormulaC₂₂H₂₆FN₃O₅Molar mass431.464 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C[C@H]1CCC2=C3N1C=C(C(=O)C3=CC(=C2N4CCC(CC4)OC(=O)[C@H](C)N)F)C(=O)O

InChI

InChI=InChI=1S/C22H26FN3O5/c1-11-3-4-14-18-15(20(27)16(21(28)29)10-26(11)18)9-17(23)19(14)25-7-5-13(6-8-25)31-22(30)12(2)24/h9-13H,3-8,24H2,1-2H3,(H,28,29)/t11-,12-/m0/s1
Key:OUXXDXXQNWKOIF-RYUDHWBXSA-N

Alalevonadifloxacin (trade name Emrok O) is an antibiotic of the fluoroquinolone class.^[1] It is a prodrug of levonadifloxacin with increased oral bioavailability.^[2] In India, it is approved for the treatment of infections with Gram-positive bacteria.^[3]

References

^ Saseedharan S, Dubey D, Singh RK, Zirpe K, Choudhuri AH, Mukherjee DN, et al. (2024). "Treatment challenges in the management of difficult-to-treat gram-positive infections: A consensus view apropos therapeutic role of novel anti-MRSA antibiotics, levonadifloxacin (IV) and alalevonadifloxacin (oral)". Indian Journal of Medical Microbiology. 47: 100528. doi:10.1016/j.ijmmb.2024.100528. PMID 38228227.
^ Bhawsar S, Kale R, Deshpande P, Yeole R, Bhagwat S, Patel M (December 2021). "Design and synthesis of an oral prodrug alalevonadifloxacin for the treatment of MRSA infection". Bioorganic & Medicinal Chemistry Letters. 54: 128432. doi:10.1016/j.bmcl.2021.128432. PMID 34757217.
^ "Alalevonadifloxacin". AdisInsight. Springer Nature Switzerland AG.

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Brodimoprim
- Iclaprim^†
- Ormetoprim
- Pyrimethamine^#
- Tetroxoprim
- Trimethoprim^#

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Trimethoprim/sulfamethoxazole^#
Ormetoprim/sulfadimethoxine
Pyrimethamine/dapsone
Pyrimethamine/sulfadoxine

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Fluoroquinolones

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡/Levonadifloxacin/Alalevonadifloxacin Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡
3rd generation	Levofloxacin^# Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin^# Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin^‡

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Metronidazole^# Ornidazole Secnidazole Tinidazole
Nitrofuran derivatives	Furazolidone^‡ Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin^# Nitrofurazone