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(Top) 1 Synthesis 2 See also 3 References

Rosoxacin

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Rosoxacin
Clinical data

Trade names	Eradacil
AHFS/Drugs.com	International Drug Names
ATC code	J01MB01 (WHO)
Identifiers
IUPAC name 1-Ethyl-4-oxo-7-pyridin-4-ylquinoline-3-carboxylic acid
CAS Number	40034-42-2^Y
PubChem CID	287180
DrugBank	DB00817^N
ChemSpider	253208^N
UNII	3Y1OT3J4NW
KEGG	D02305^N
ChEBI	CHEBI:131715^N
ChEMBL	ChEMBL291157^N
CompTox Dashboard (EPA)	DTXSID90193091
ECHA InfoCard	100.049.763
Chemical and physical data
Formula	C₁₇H₁₄N₂O₃
Molar mass	294.310 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	290 °C (554 °F)
SMILES CCn1cc(C(=O)O)c(=O)c2ccc(-c3ccncc3)cc21
InChI InChI=1S/C17H14N2O3/c1-2-19-10-14(17(21)22)16(20)13-4-3-12(9-15(13)19)11-5-7-18-8-6-11/h3-10H,2H2,1H3,(H,21,22)^Y Key:XBPZXDSZHPDXQU-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Rosoxacin (also known as acrosoxacin, tradename Eradacil) is a quinolone antibiotic indicated for the treatment of urinary tract infections and certain sexually transmitted diseases. Rosoxacin is not available in the United States.

It was developed in 1978 by George Lesher and his colleagues at Winthrop-Stearns (now part of sanofi-aventis), as an extension of the work that originally led to nalidixic acid.^[1]^[2]

It is classified as a first generation quinolone.^[3]

Synthesis[edit]

Rosoxacin synthesis:^[4]

The synthesis of rosoxacin begins with a modified Hantzsch pyridine synthesis employing as component parts ammonium acetate, two equivalents of methyl propiolate, and one of 3-nitrobenzaldehyde. Oxidation of the resulting dihydropyridine (2) with nitric acid followed by saponification, decarboxylation, and reduction of the nitro group with iron and HCl acid gives aniline 3. This undergoes the classic sequence of Gould-Jacobs reaction with methoxymethylenemalonate ester to form the 4-hydroxyquinoline ring, and then alkylation with ethyl iodide and saponification of the ester to complete the synthesis of the antibacterial agent rosoxacin (4).

References[edit]

^ Carabateas PM, Brundage RP, Gelotte KO, Gruett MD, Lorenz RR, Opalka Jr CJ, et al. (1984). "1-Ethyl-1,4-dihydro-4-oxo-7-(pyridinyl)-3-quinolinecarboxylic acids. I. Synthesis of 3- and 4-(3-aminophenyl)pyridine intermediates". Journal of Heterocyclic Chemistry. 21 (6): 1849–1856. doi:10.1002/jhet.5570210654.

^ Carabateas PM, Brundage RP, Gelotte KO, Gruett MD, Lorenz RR, Opalka Jr CJ, et al. (1984). "1-Ethyl-1,4-dihydro-4-oxo-7-(pyridinyl)-3-quinolinecarboxylic acids. II. Synthesis". Journal of Heterocyclic Chemistry. 21 (6): 1857–1863. doi:10.1002/jhet.5570210655.

^ Przybilla B, Georgii A, Bergner T, Ring J (1990). "Demonstration of quinolone phototoxicity in vitro". Dermatologica. 181 (2): 98–103. doi:10.1159/000247894. PMID 2173670.

^ US 3907808, Lescher Y, Carabateas PM, "1,4-Dihydro-4-oxo-7-pyridyl-3-quinolinecarboxylic acid derivatives", issued 23 September 1975, assigned to STWB Inc.; Chem. Abstr., 84, 43880p (1975).

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

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^‡