Alatrofloxacin Mesylate

Research Code：CP-116517-27; CP-116517,    Trade Name：Trovan I.V.^®          MOA：Quinolone antibiotic            Indication：Life- or limb-threatening infections caused by susceptible strains          Status：Withdrawn    Company：Pfizer (Originator)

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Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001

Alatrofloxacin mesylate was first approved by the U.S. Food and Drug Administration (FDA) on Dec 18, 1997. It was developed and marketed as Trovan I.V. ^® by Pfizer in the US.

Alatrofloxacin mesylate is a fluoronaphthyridone related to the fluoroquinolones with in vitro activity against a wide range of gram-negative and gram-positive aerobic and anaerobic microorganisms. The bactericidal action of alatrofloxacin results from inhibition of DNA gyrase and topoisomerase IV. Trovan I.V.^® is indicated for the treatment of patients initiating therapy in in-patient health care facilities (i.e., hospitals and long term nursing care facilities) with serious, life- or limb-threatening infections caused by susceptible strains of the designated microorganisms in the conditions listed below.

Trovan I.V.^® is available as injection solution for intravenous use, containing 7.86 mg/ml of Alatrofloxacin mesylate. The recommended starting dose is 200 mg or 300 mg administered intravenously.

Alatrofloxacin mesylate was withdrawn from the U.S. market in 2001.

Alatrofloxacin mesilate

Substances Referenced in Synthesis Path

CAS-RN	Formula	Chemical Name	CAS Index Name
27317-69-7	C11H20N2O5	N–tert-butoxycarbonyl-l-alanyl-l-alanine	L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-
186772-86-1	C33H37F3N6O7	N-[(1,1-dimethylethoxy)carbonyl]-l-alanyl-N-[(1α,5α,6α)-3-[8-(2,4-difluorophenyl)-6-(ethoxycarbonyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-l-alaninamide	L-Alaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-N-[(1α,5α,6α)-3-[8-(2,4-difluorophenyl)-6-(ethoxycarbonyl)-3-fluoro-5,8-dihydro-5-oxo-1,8-naphthyridin-2-yl]-3-azabicyclo[3.1.0]hex-6-yl]-
171176-56-0	C22H19F3N4O3	ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate	1,8-Naphthyridine-3-carboxylic acid, 7-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-, ethyl ester, (1α,5α,6α)-
134575-66-9	C27H27F3N4O5	ethyl (1α,5α,6α)-1-(2,4-difluorophenyl)-7-[6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate	1,8-Naphthyridine-3-carboxylic acid, 1-(2,4-difluorophenyl)-7-[6-[[(1,1-dimethylethoxy)carbonyl]amino]-3-azabicyclo[3.1.0]hex-3-yl]-6-fluoro-1,4-dihydro-4-oxo-, ethyl ester, (1α,5α,6α)-
75-75-2	CH4O3S	methanesulfonic acid	Methanesulfonic acid

Trade Names

Country	Trade Name	Vendor	Annotation
D	TROVAN	Pfizer	wfm
F	Turvel	Pfizer	wfm
GB	Turvel	Pfizer	wfm
I	Turvel	Pfizer	wfm
USA	Trovan	Pfizer	wfm

(wfm = withdrawn from market)

Formulations

• vial 200 mg/40 ml, 300 mg/60 ml (5 mg/ml) (as mesilate)

References

• • US 5 164 402 (Pfizer; 17.11.1992; appl. 4.2.1991; WO-prior. 16.8.1989).
  • US 5 229 396 (Pfizer; 20.7.1993; appl. 24.7.1992).
  • WO 9 700 268 (Pfizer; appl. 27.3.1996; USA-prior. 15.6.1995).
  • US 5 763 454 (Pfizer; 9.6.1998; appl. 21.5.1997; WO-prior. 6.6.1995).

• polymorphs:

  • US 6 080 756 (Pfizer; 27.6.2000; appl. 30.1.1998; WO-prior. 5.7.1996).

References
“Center for Drug Evaluation and Research – Application Number: 020759/020760 – Chemistry Review(s)” (PDF). Food and Drug Administration. Retrieved 29 August 2014.

Alatrofloxacin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a605016
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Intravenous
ATC code	none
Legal status
Legal status	Withdrawn
Pharmacokinetic data
Bioavailability	N/A
Protein binding	76% (trovafloxacin)
Metabolism	Quickly hydrolyzed to trovafloxacin
Elimination half-life	9 to 12 hours (trovafloxacin)
Excretion	Fecal and renal(trovafloxacin)
Identifiers
IUPAC name[show]
CAS Number	146961-76-4
ChemSpider	21243647
UNII	7QVV6I50DT
ChEMBL	CHEMBL1201197
Chemical and physical data
Formula	C26H25F3N6O5
Molar mass	558.509 g/mol
3D model (JSmol)	Interactive image

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