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Trovafloxacin Mesylate

Trovafloxacin Mesylate structure

CAS No.: 147059-75-4

Chemical Name:: Trovafloxacin Mesylate

Synonyms: Trovan;CP 99219-27;Unii-0p1lko80wn;Trovafloxacin MonoMeth;Trovafloxacin Methanesulfonate;Trovafloxacin monomethanesulfonate;147059-75-4 Trovafloxacin mesylate;Trovafloxacin mesylate - CP 99219 mesylate;7-[(1S,5R)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid;7-[(1α,5α,6α)-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-carboxylicacidmesylate

CBNumber:: CB31456463

Molecular Formula:: C21H19F3N4O6S

Molecular Weight:: 512.46

MDL Number:: MFCD00913361

MOL File:: 147059-75-4.mol

MSDS File:: SDS

Last updated:2023-09-04 15:50:00

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Trovafloxacin Mesylate Properties

Melting point	>250°C (dec.)
storage temp.	room temp
solubility	DMSO: >10mg/mL
form	powder
color	white to off-white
FDA UNII	0P1LKO80WN

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS05,GHS08

Signal word

Danger

Hazard statements

H314-H361

Precautionary statements

P201-P260-P280-P301+P330+P331-P303+P361+P353-P305+P351+P338

Hazard Codes

Risk Statements

63-34

Safety Statements

26-36-45

RIDADR

UN 1759 8 / PGIII

WGK Germany

RTECS

QN2791250

Toxicity

women,LDLo,oral,2mg/kg (2mg/kg),SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE",Archives of Internal Medicine. Vol. 159, Pg. 2225, 1999.

NFPA 704

	0
3		0

Trovafloxacin Mesylate price More Price(14)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	PZ0015	Trovafloxacin mesylate >98% (HPLC)	147059-75-4	5mg	$118	2024-03-01	Buy
Sigma-Aldrich	PZ0015	Trovafloxacin mesylate >98% (HPLC)	147059-75-4	25mg	$470	2024-03-01	Buy
Cayman Chemical	9000303	Trovafloxacin (mesylate) ≥98%	147059-75-4	5mg	$86	2024-03-01	Buy
Cayman Chemical	9000303	Trovafloxacin (mesylate) ≥98%	147059-75-4	10mg	$152	2024-03-01	Buy
Cayman Chemical	9000303	Trovafloxacin (mesylate) ≥98%	147059-75-4	50mg	$713	2024-03-01	Buy

Product number	Packaging	Price	Buy
PZ0015	5mg	$118	Buy
PZ0015	25mg	$470	Buy
9000303	5mg	$86	Buy
9000303	10mg	$152	Buy
9000303	50mg	$713	Buy

Trovafloxacin Mesylate Chemical Properties,Uses,Production

Description

Trovafloxacin is a broad spectrum antibiotic that inhibits the uncoiling of supercoiled DNA in bacteria by blocking the activity of topoisomerase IV (IC₅₀ = 3.02 μg/ml) and DNA gyrase (IC₅₀ = 7.13 μg/ml).

Chemical Properties

White Solid

Originator

Trovan,Pfizer,USA

Uses

Trovafloxacin mesylate has been used as a test compound in toxicity assay to assess its toxicity in 2D hepatocyte cultures. It has also been used to manipulate the mechanism of apoptotic cell disassembly during apoptosis.

Uses

Fluorinated quinolone antibacterial. Trovafloxacin mesylate blocks the activity of DNA gyrase and topoisomerase IV, enzymes essential in the repliction, transcription, and repair of bacterial DNA.

Definition

ChEBI: A methanesulfonate (mesylate) salt prepared from equimolar amounts of trovafloxacin and methanesulfonic acid. A broad-spectrum antibiotic that was withdrawn from the market due to risk of liver failure.

Manufacturing Process

N-Benzylmaleimide (500 g, 2.67 mole), 90% bromonitromethane (831 g, 5.34 mole), powdered molecular sieves 200 mesh (2020 g) and toluene (12 dm3) were stirred under nitrogen at -10°C. 1,2-Dimethyl-1,4,5,6- tetrahydropyrimidine (616 g, 5.49 mole) was added slowly over about 3 h maintaining the reaction temperature at <-8°C throughout the addition. After completion of the addition, the reaction mixture was stirred for 1.5 h at 25°C, filtered under a nitrogen atmosphere in a sealed pressure filter to remove sieves and resulting tar, and the sieves were washed with toluene (2 L). The combined filtrates were washed with 2 N dilute hydrochloric acid (3 times 750 cm3), treated with carbon (50 g) at 70°C, 1 h filtered, concentrated, and triturated with 2-propanol (about 4 dm3) to obtain crystals of the (1α,5α,6α)- 3-N-benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane (223 g, 34%) melting point 116°-118°C.
Tetrahydrofuran (350 cm3), sodium borohydride (14.1 g) and (1α,5α,6α)-3-N_x0002_benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane (35.0 g, mmol) obtained above were stirred under nitrogen for 0.25 h and then treated dropwise with boron trifluoride-THF complex containing 21.5% BF3 (44.9 cm3) so that the exotherm was controlled to <40°C. After addition was completed, the reaction mixture was stirred for 3 h at 40°C, quenched slowly with water/THF 1:1 (70 cm3) to avoid excessive foaming, and stirred for 0.5 h at 50°C to ensure that the quench of unreacted diborane generated in situ was completed. The quench formed a salt slurry which was filtered and washed with THF (140 cm3); the combined filtrate was partially concentrated, diluted with water (350 cm3) and further concentrated to remove most of the THF, and extracted with ethyl acetate (140 cm3). The resulting ethyl acetate solution was concentrated to afford the (1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane as a clear oil (30.6 g, 97%).
(1α,5α,6α)-3-N-Benzyl-6-nitro-3-azabicyclo[3.1.0]hexane (30.9 g, 142 mmol) obtained above, 2-propanol (310 cm3), water (30 cm3), and 10% Pd on carbon, 50% water content (12.3 g) were hydrogenated at 50 psi and 50°C for 18-24 h in a Parr shaker. The Pd catalyst was filtered off, and the resulting pale yellow filtrate was azeotropically distilled at constant volume to remove water. The resulting solution was treated with triethylamine (46 g, 456 mmol) and heated to reflux. Benzaldehyde (15.0 g, 141 mmol) was added dropwise over 15 min. The reaction mixture was heated at reflux for 4 h to form (1α,5α,6α)-6-benzylidenylamino-3-azabicyclo[3.1.0]hexane in situ. The resulting orange solution was cooled to 40°-50°C, and ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (42.45 g, 111 mmol; see United Kingdom Patent Publication No. GB 2,191,776) and triethylamine (13.1 g, 130 mmol) were added. The resulting slurry was heated at reflux for 16-18 h, cooled to 20°C and stirred for 5 h. The slurry was filtered, and the compound was isolated as a white solid (75.5% yield based on (1α,5α,6α)-3-N-benzyl-6-nitro-2,4-dioxo-3- azabicyclo[3.1.0]hexane; 96.6% based on ethyl 7-chloro-1-(2,4- difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid). The ethyl (1α,5α,6α)-7-(6-benzylidenylamino-3-azabicyclo[3.1.0]hex- 3yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3- carboxylate was recrystallized from acetonitrile, melting point 148°-155°C decomp.
Tetrahydrofuran (250 cm3), ethyl (1α,5α,6α)-7-(6-benzylidenylamino-3- azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo- 1,8-naphthyridine-3-carboxylate (25.05 g, 47 mmol) obtained above, and water (250 cm3) were treated with 97% methanesulfonic acid (13.3 g, 138 mmol) and heated to reflux for 24 h. The resulting solution was cooled to 45°C, treated with activated carbon (2.5 g) for 1 h and filtered. The resulting filtrate was concentrated under vacuum to approximately 25% of its original volume to provide a white crystal slurry, cooled to 15°-25°C, granulated for 4 h and filtered to yield the trovafloxacin methanesulfonate salt (mesylate) (16.86 g, 70.0%). Melting point 253°-256°C decomp.

brand name

Trovan (Pfizer).

Therapeutic Function

Antibacterial

Biological Activity

Fluoroquinolone antibiotic. Inhibits bacterial DNA topoisomerase IV and DNA gyrase and forms a stable quinolone-DNA complex with these enzymes which reversibly inhibits DNA synthesis. Displays potent activity against gram-positive and gram-negative bacteria.

Biochem/physiol Actions

Trovafloxacin mesylate acts as a pannexin1 (Panx1) inhibitor.

storage

Desiccate at RT

Trovafloxacin Mesylate Preparation Products And Raw materials

Raw materials

NAPHTHYRIDINE-3-CARBOXYLIC ACID Bromonitromethane 1,2-Dimethyl-1,4,5,6-tetrahydropyrimidine (4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate N-Benzylmaleimide

Preparation Products

Trovafloxacin Mesylate Suppliers

Global( 65)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
career henan chemical co	+86-0371-86658258 15093356674;	factory@coreychem.com	China	29826	58
TargetMol Chemicals Inc.	+1-781-999-5354 +1-00000000000	marketing@targetmol.com	United States	19892	58
Finetech Industry Limited	+86-27-87465837 +8618971612321	info@finetechnology-ind.com	China	9626	58
InvivoChem	+1-708-310-1919 +1-13798911105	sales@invivochem.cn	United States	6393	58
Nantong HI-FUTURE Biology Co., Ltd.	+undefined18051384581	sales@chemhifuture.com	China	3136	58
GIHI CHEMICALS CO.,LIMITED	+8618058761490	info@gihichemicals.com	China	50000	58
LEAPCHEM CO., LTD.	+86-852-30606658	market18@leapchem.com	China	43348	58
Shanghai Acmec Biochemical Technology Co., Ltd.	+undefined18621343501	product@acmec-e.com	China	33350	58
Nanjing Bicbiotechnology Co., Ltd	+86-2552131256 +86-18251840740	sales@bicbiotech.com	China	6000	58
Aladdin Scientific	+1-+1(833)-552-7181	sales@aladdinsci.com	United States	52927	58

Supplier	Advantage
career henan chemical co	58
TargetMol Chemicals Inc.	58
Finetech Industry Limited	58
InvivoChem	58
Nantong HI-FUTURE Biology Co., Ltd.	58
GIHI CHEMICALS CO.,LIMITED	58
LEAPCHEM CO., LTD.	58
Shanghai Acmec Biochemical Technology Co., Ltd.	58
Nanjing Bicbiotechnology Co., Ltd	58
Aladdin Scientific	58

View Lastest Price from Trovafloxacin Mesylate manufacturers

Image	Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
	2019-12-26	7-[(1S,5R)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid 147059-75-4	US $1.00 / g	1g	≥98%	g/kg/Ton	Career Henan Chemical Co

7-[(1S,5R)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
147059-75-4
US $1.00 / g
≥98%
Career Henan Chemical Co

Trovafloxacin Mesylate Spectrum

Trovafloxacin Mesylate(147059-75-4)¹HNMR

7-[(1α,5α,6α)-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-carboxylic Acid Methanesulfonate CP 99219-27 7-[(1S,5R)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Trovafloxacin monomethanesulfonate Trovan Unii-0p1lko80wn 7-[(1α,5α,6α)-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-carboxylicacidmesylate Trovafloxacin Methanesulfonate Trovafloxacin MonoMeth (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-carboxylic acid methanesulfonate Trovafloxacin mesylate - CP 99219 mesylate 147059-75-4 Trovafloxacin mesylate topoisomerase-IV,TNF,gyrase,Bacterial,hepatotoxicity,LPS,Trovafloxacin,broad-spectrum,Trovafloxacin mesylate,Antibiotic,DNA,Inhibitor,PANX1,Topoisomerase,pneumococci,inhibit,pro-inflammatory,NF-κB 1,8-Naphthyridine-3-carboxylic acid, 7-[(1α,5α,6α)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-, methanesulfonate (1:1) 147059-75-4 C21H19F3N4O6S C20H15F3N4O3CH3SO3H Amines Chiral Reagents Heterocycles Intermediates & Fine Chemicals Pfizer compounds Pharmaceuticals