Alatrofloxacin

Alatrofloxacin
Systematic (IUPAC) name

7-[(1R,5S)-6-{[(2S)-1-{[(2S)-2-Aminopropanoyl]amino}-1-oxopropan-2-yl]amino}-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a605016
Pregnancy category	US: C (Risk not ruled out)
Legal status	Withdrawn
Routes of administration	Intravenous
Pharmacokinetic data
Bioavailability	N/A
Protein binding	76% (trovafloxacin)
Metabolism	Quickly hydrolyzed to trovafloxacin
Half-life	9 to 12 hours (trovafloxacin)
Excretion	Fecal and renal (trovafloxacin)
Identifiers
CAS Registry Number	146961-76-4^N
ATC code	None
ChemSpider	21243647^N
UNII	7QVV6I50DT^Y
ChEMBL	CHEMBL1201197^N
Chemical data
Formula	C₂₆H₂₅F₃N₆O₅
Molecular mass	558.509 g/mol
SMILES C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@H]1[C@H]2[C@@H]1CN(C2)C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F)N
InChI InChI=1S/C26H25F3N6O5/c1-10(30)24(37)31-11(2)25(38)32-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)33-23)19-4-3-12(27)5-17(19)28/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40)/t10-,11-,14-,15+,20+/m0/s1 ^N Key:UUZPPAMZDFLUHD-VUJLHGSVSA-N ^N
N (what is this?) (verify)

Alatrofloxacin (Trovan IV) is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt.^[1]

Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001.

References

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

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Enoxacin^‡ Fleroxacin^‡ Lomefloxacin Nadifloxacin Ofloxacin Norfloxacin Pefloxacin Rufloxacin

3rd g.	Balofloxacin Grepafloxacin^‡ Levofloxacin Pazufloxacin Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin

4th g.	Besifloxacin Clinafloxacin^† Garenoxacin Gemifloxacin Moxifloxacin Gatifloxacin^‡ Sitafloxacin Trovafloxacin^‡/Alatrofloxacin^‡ Prulifloxacin

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Related (DG)	Aminocoumarins: Novobiocin

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin

Index of bacterial disease

Description	Bacteria classification Growth media

Disease	Gram-positive firmicutes Gram-positive actinobacteria Gram-negative proteobacteria Gram-negative non-proteobacteria Cholera Tuberculosis

Treatment	Antibiotics cell wall nucleic acid mycobacteria protein synthesis other Antibodies Vaccines