Levofloxacin supplier | CasNO.100986-85-4

Name
Levofloxacin hydrochloride
EINECS 600-146-0
CAS No. 100986-85-4
Article Data41
CAS DataBase
Density 1.48 g/cm³
Solubility Slightly soluble in water or methanol. Soluble in glacial acetic acid or dichloromethane
Melting Point 218 °C
Formula C₁₈H₂₀FN₃O₄
Boiling Point 571.495 °C at 760 mmHg
Molecular Weight 361.373
Flash Point 299.43 °C
Transport Information
Appearance Slight yellow powder
Safety 26-36/37/39-36
Risk Codes 22-42/43-68-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms Elequine;(-)-Ofloxacin;7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6- carboxylic acid,9-fluoro-2,3-dihydro-3- methyl-10-(4-methyl-1-piperazinyl)-7-oxo-,(3S)-;Levaquin (TN);Levofloxacino [INN-Spanish];Levofloxacin (JAN/USAN);Levaquin;Levofloxacin [USAN:INN:JAN];Levofloxacine [INN-French];(S)-Ofloxacin;Ofloxacin S-(-)-form;Iquix;(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid;Levofloxacinum [INN-Latin];7H-Pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid, 2,3-dihydro-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-, (S)-;(S)-(-)-Ofloxacin;8-fluoro-3-methyl-9-(4-methyl-piperazin-1-yl)-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid;Levoflaoxacin;Levofloxacincas;
PSA 75.01000
LogP 1.54690

Synthetic route

: 109-01-3
1-methyl-piperazine

: 100986-89-8
levofloxacin Q-acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
With potassium hydroxide In water at 55℃; for 24h; Reagent/catalyst; Time; Temperature; Solvent;	97.1%
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.366667h; Reflux;	96%
at 150℃; Microwave irradiation;	89%

: 50398-09-9, 51545-09-6, 34352-59-5
N-methylpiperazine dihydrochloride

: 100986-89-8
levofloxacin Q-acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Stage #1: N-methylpiperazine dihydrochloride; levofloxacin Q-acid With boron trifluoride-tetrahydrofuran complex; triethylamine In acetonitrile at 20℃; for 24.5h; Stage #2: With methanol for 24h; Reflux; Stage #3: In ethanol at 20℃; for 16h;	92%

: 109-01-3
1-methyl-piperazine

: 106939-34-8
ethyl (S)-(-)-9,10-Difluoro-3-Methyl-7-Oxo-2,3-Dihydro-7H-Pyrido[1,2,3-de]-[1,4]Benzoxazine-6-Carboxylate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
With acetic acid In water; N,N-dimethyl-formamide at 70 - 105℃; for 10h; Temperature; Solvent; Reagent/catalyst;	85.7%

: 177472-29-6
(S)-ethyl 6,8-difluoro-1-(1-hydroxypropan-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Stage #1: (S)-ethyl 6,8-difluoro-1-(1-hydroxypropan-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate With potassium hydroxide; ethanol; water at 20℃; for 2.5h; Heating / reflux; Stage #2: With acetic acid In ethanol at 0 - 20℃; for 2h; pH=7; Product distribution / selectivity;	78%

: C20H24FN3O4

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water at 83℃; for 36h;	77.9%
With hydrogenchloride In ethanol; water at 83℃; for 36h;	75.3%

: 1036016-10-0
(S)-6,8-difluoro-1-(1-hydroxypropan-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Stage #1: (S)-6,8-difluoro-1-(1-hydroxypropan-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid With potassium hydroxide In ethanol; water for 3h; Heating / reflux; Stage #2: With acetic acid In ethanol; water at 0 - 20℃; Product distribution / selectivity;	76%

G of N-methylpiperazine: G of N-methylpiperazine

: 100986-89-8
levofloxacin Q-acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
In pyridine; diethyl ether	74.3%

: 50-00-0
formaldehyd

: 117707-40-1
S-(-)-9-fluoro-2,3-dihydro-3-methyl-10-(1-piperazinyl)-7-oxo-7H-pyrido-<1,2,3-de><1,4>benzoxazine-6-carboxylic acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
With formic acid In water at 90℃; for 10h; Temperature;	74.3%

: 109-01-3
1-methyl-piperazine

: 129306-33-8
(-)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid BF2-chelate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
In dimethyl sulfoxide for 17h; Ambient temperature;	52%

: 82419-36-1
ofloxacin

A: 100986-85-4
levofloxacin

B: 100986-86-5
(R)-ofloxacin

Conditions

Conditions	Yield
With Bis(2-ethylhexyl)phosphoric acid; sodium dodecyl-sulfate; O,O'-dibenzoyl-L-tartaric acid In octanol; water at 20℃; for 4h; pH=7; Reflux; Resolution of racemate; optical yield given as %ee; enantioselective reaction;	A 8.54% B 34.23%
With (2-hydroxypropyl)-α-cyclodextrin In phosphate buffer pH=2.3; capillary electrophoresis;
With Bis(2-ethylhexyl)phosphoric acid; Di-p-toluoyl-L-tartaric acid; O,O'-dibenzoyl-L-tartaric acid In octanol; water at 25℃; for 0.5h; pH=6.86; Resolution of racemate; aq. phosphate buffer; enantioselective reaction;

: 94695-50-8
ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic anhydride / 2 h / 110 °C 2: CH2Cl2 / 0.5 h / Ambient temperature 3: 59 percent / 50percent NaH / dimethylsulfoxide / 3 h / Ambient temperature 4: 70 percent / 10percent aq. KOH / tetrahydrofuran / 2 h / 65 - 70 °C 5: 83 percent / pyridine / 12 h / 120 °C View Scheme

: 103995-33-1
3-(2,3,4,5-tetrafluorophenyl)-3-oxo-2-(ethoxymethylene)-propanoic acid ethyl ester

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: CH2Cl2 / 0.5 h / Ambient temperature 2: 59 percent / 50percent NaH / dimethylsulfoxide / 3 h / Ambient temperature 3: 70 percent / 10percent aq. KOH / tetrahydrofuran / 2 h / 65 - 70 °C 4: 83 percent / pyridine / 12 h / 120 °C View Scheme

: 110548-02-2
(+)-ethyl 2-<<<(S)-1-hydroxyprop-2-yl>amino>methylene>-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 59 percent / 50percent NaH / dimethylsulfoxide / 3 h / Ambient temperature 2: 70 percent / 10percent aq. KOH / tetrahydrofuran / 2 h / 65 - 70 °C 3: 83 percent / pyridine / 12 h / 120 °C View Scheme

: 110548-03-3
(-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / 10percent aq. KOH / tetrahydrofuran / 2 h / 65 - 70 °C 2: 83 percent / pyridine / 12 h / 120 °C View Scheme

: 109-01-3
1-methyl-piperazine

: (3S)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid-boron difluoride chelate complex

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Stage #1: 1-methyl-piperazine; (3S)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid-boron difluoride chelate complex With triethylamine In dimethyl sulfoxide at 20℃; for 17h; Stage #2: With triethylamine In ethanol for 8h; Heating / reflux; Stage #3: With hydrogenchloride In water

: (-) potassium N-(1-hydroxy-propy-2(S)-yl)-6-fluoro-7-(N-methylpiperazinyl)-8-nitro-quinol-4-one-3-carboxylate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Stage #1: (-) potassium N-(1-hydroxy-propy-2(S)-yl)-6-fluoro-7-(N-methylpiperazinyl)-8-nitro-quinol-4-one-3-carboxylate With potassium hydroxide In methanol for 2.5h; Heating / reflux; Stage #2: With acetic acid In methanol

: 100986-89-8
levofloxacin Q-acid

: 50-81-7
ascorbic acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
In dimethyl sulfoxide	5.63 g (87.6%)

: sodium metabisulfite

: 100986-89-8
levofloxacin Q-acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
In dimethyl sulfoxide	11.8 g (92.4%)

: 109-01-3
1-methyl-piperazine

: 107-98-2
1-methoxy-2-propanol

: 142-82-5
n-heptane

: 100986-89-8
levofloxacin Q-acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
	2.98 g (77.3%)

...Expand

: 100986-89-8
levofloxacin Q-acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
In 1-methyl-piperazine; n-heptane

: 109-01-3
1-methyl-piperazine

: 109-63-7
trifluoroborane diethyl ether

: 100986-89-8
levofloxacin Q-acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
With triethylamine In hydrogenchloride; methanol; diethyl ether; dimethyl sulfoxide

...Expand

: 109-01-3
1-methyl-piperazine

chloroform-methanol-water: chloroform-methanol-water

: 100986-89-8
levofloxacin Q-acid

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
In ethanol; dimethyl sulfoxide

...Expand

: 82419-36-1
ofloxacin

Cu(II)-coordinated G-rich oligonucleotides: Cu(II)-coordinated G-rich oligonucleotides

A: 100986-85-4
levofloxacin

B: 100986-86-5
(R)-ofloxacin

Conditions

Conditions	Yield
pH=7; Reagent/catalyst; Resolution of racemate;

...Expand

: 106939-34-8
ethyl (S)-(-)-9,10-Difluoro-3-Methyl-7-Oxo-2,3-Dihydro-7H-Pyrido[1,2,3-de]-[1,4]Benzoxazine-6-Carboxylate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid / water / 4 h / Reflux 2: triethylamine / dimethyl sulfoxide / 8 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; acetic acid / N,N-dimethyl-formamide / 1 h / Reflux; Green chemistry 2: water / 10.5 h / 110 °C / Green chemistry View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; acetic acid / water / 3 h / 20 °C / Reflux 2: water / 15.5 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; acetic acid / N,N-dimethyl-formamide / 1 h / Reflux 2: water / 10.5 h / 110 °C View Scheme

: (+)-ethyl 3-[(1-hydroxyprop-2(S)-yl)amino]acrylate

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: ammonia / toluene / 4 h / 50 °C 2: toluene / 50 - 100 °C / pH < 7 3: hydrogenchloride / toluene; water / pH < 7 4: potassium fluoride / N,N-dimethyl-formamide / Reflux 5: acetic acid; sulfuric acid / water / 4 h / Reflux 6: triethylamine / dimethyl sulfoxide / 8 h / 90 °C View Scheme

: C14H31NO3Si2

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: toluene / 50 - 100 °C / pH < 7 2: hydrogenchloride / toluene; water / pH < 7 3: potassium fluoride / N,N-dimethyl-formamide / Reflux 4: acetic acid; sulfuric acid / water / 4 h / Reflux 5: triethylamine / dimethyl sulfoxide / 8 h / 90 °C View Scheme

: C21H31F4NO4Si2

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / toluene; water / pH < 7 2: potassium fluoride / N,N-dimethyl-formamide / Reflux 3: acetic acid; sulfuric acid / water / 4 h / Reflux 4: triethylamine / dimethyl sulfoxide / 8 h / 90 °C View Scheme

: 3-(2-hydroxy-1-methylethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)acrylic acid ethyl ester

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / Reflux 2: acetic acid; sulfuric acid / water / 4 h / Reflux 3: triethylamine / dimethyl sulfoxide / 8 h / 90 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Green chemistry 2: sulfuric acid; acetic acid / N,N-dimethyl-formamide / 1 h / Reflux; Green chemistry 3: water / 10.5 h / 110 °C / Green chemistry View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 150 °C 2: sulfuric acid; acetic acid / water / 3 h / 20 °C / Reflux 3: water / 15.5 h / 120 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C 2: sulfuric acid; acetic acid / N,N-dimethyl-formamide / 1 h / Reflux 3: water / 10.5 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: 24 h / 120 °C 2: potassium carbonate / 16 h / 140 °C 3: hydrogenchloride / ethanol; water / 36 h / 83 °C View Scheme

: C20H24FN3O4S

: 100986-85-4
levofloxacin

Conditions

Conditions	Yield
With GLUTATHIONE In methanol at 23℃; pH=6.5; Kinetics;

: 849585-22-4
LACTIC ACID

: 100986-85-4
levofloxacin

: levofloxacin lactate

Conditions

Conditions	Yield
In ethanol at 80℃; for 1h; Temperature;	94.3%

: cerium(IV) sulphate

: 7732-18-5
water

: 100986-85-4
levofloxacin

: [Ce(levofloxacin)2(H2O)2]SO4*5H2O

Conditions

Conditions	Yield
With sodium hydroxide In methanol; acetone at 20℃; for 24h;	94%

...Expand

: 100986-85-4
levofloxacin

: 2450-71-7
Propargylamine

: (S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-N-(prop-2-yn-1-yl)-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide

Conditions

Conditions	Yield
Stage #1: levofloxacin With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: Propargylamine With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	90.7%

: 100986-85-4
levofloxacin

: (-)-9-fluoro-3-methyl-10(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de]-1,4-benzoxazine-6-carboxylic acid hemihydrate

Conditions

Conditions	Yield
In water; ethyl acetate for 1h; Purification / work up; Heating / reflux;	90%
In 2,8-dimethylnonan-5-one; water for 1h; Purification / work up; Heating / reflux;	89.6%
In acetic acid methyl ester; water for 1h; Purification / work up; Heating / reflux;	85.6%

: 1202-34-2
di(pyridin-2-yl)amine

: copper(II) choride dihydrate

: 100986-85-4
levofloxacin

: C28H28ClCuFN6O4*ClH

Conditions

Conditions	Yield
Stage #1: copper(II) choride dihydrate; levofloxacin With potassium hydroxide In methanol at 20℃; for 0.5h; Stage #2: di(pyridin-2-yl)amine In methanol at 60℃; for 2h;	83%

...Expand

: 57-67-0
4-amino-N-(diaminomethylene) benzenesulfonamide

: 100986-85-4
levofloxacin

: (S)−7-((4-(N-carbamimidoylsulfamoyl)phenyl)imino)−9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)−2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

Conditions

Conditions	Yield
With acetic acid In methanol for 2h; Microwave irradiation; Reflux;	82.94%

: uranyl nirate hexahydrate

: 100986-85-4
levofloxacin

: [UO2(levofloxacin)2(H2O)2]*2H2O

Conditions

Conditions	Yield
With sodium hydroxide In methanol; acetone at 20℃; for 24h;	81.4%

: 77878-01-4
octadecanoic acid chloromethyl ester

: 100986-85-4
levofloxacin

A: 121819-05-4
C37H72O4

B: 1261134-66-0
(3S)-6-[(octadecanoyloxy)methyl] 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate

Conditions

Conditions	Yield
Stage #1: levofloxacin With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.333333h; Stage #2: octadecanoic acid chloromethyl ester In N,N-dimethyl-formamide at 90℃; for 1h;	A n/a B 81%
Stage #1: levofloxacin With potassium carbonate In acetonitrile for 8h; Reflux; Stage #2: octadecanoic acid chloromethyl ester With tetra-(n-butyl)ammonium iodide In acetonitrile for 168h; Reflux;

...Expand

: 54-85-3
isoniazid

: 100986-85-4
levofloxacin

: 2-[3(1-cyclopropyl-6-fluoro-8-methoxy)-7-(3-methylpiperazin-1-yl)-4-oxo-1H quinolinyl]-5-(pyridin-4-yl)-1,3,4-oxadiazole

Conditions

Conditions	Yield
With trichlorophosphate Reflux;	81%

: gold(III) tetrachloride trihydrate

: 100986-85-4
levofloxacin

: [AuCl2(levofloxacin)]Cl.2H2O

Conditions

Conditions	Yield
In methanol at 20℃; for 24h;	80%

: 63-74-1
sulfanilamide

: 100986-85-4
levofloxacin

: (S)−9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)−7-((4-sulfamoylphenyl)imino)−2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

Conditions

Conditions	Yield
With acetic acid In methanol for 2h; Microwave irradiation; Reflux;	80%

: 61413-67-0
chloromethyl n-dodecanoate

: 100986-85-4
levofloxacin

A: 1261134-88-6
C25H48O4

B: 1261134-60-4
(3S)-6-[(dodecanoyloxy)methyl] 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate

Conditions

Conditions	Yield
Stage #1: levofloxacin With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.333333h; Stage #2: chloromethyl n-dodecanoate In N,N-dimethyl-formamide at 90℃; for 1h;	A n/a B 79%
Stage #1: levofloxacin With potassium carbonate In acetonitrile for 8h; Reflux; Stage #2: chloromethyl n-dodecanoate With tetra-(n-butyl)ammonium iodide In acetonitrile for 168h; Reflux;

...Expand

: 100986-85-4
levofloxacin

: 61413-69-2
chloromethyl n-hexadecanoate

A: 91360-29-1
C33H64O4

B: 1261134-64-8
(3S)-6-[(hexadecanoyloxy)methyl] 9-fluoro-3,7-dihydro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2H-[1,4]oxazino-[2,3,4-ij]quinoline-6-carboxylate

Conditions

Conditions	Yield
Stage #1: levofloxacin With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.333333h; Stage #2: chloromethyl n-hexadecanoate In N,N-dimethyl-formamide at 90℃; for 1h;	A n/a B 79%
Stage #1: levofloxacin With potassium carbonate In acetonitrile for 8h; Reflux; Stage #2: chloromethyl n-hexadecanoate With tetra-(n-butyl)ammonium iodide In acetonitrile for 168h; Reflux;

...Expand

: 100986-85-4
levofloxacin

: 67317-62-8
decanoyloxymethyl chloride

A: 1261134-58-0
(3S)-6-[(decanoyloxy)methyl] 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate

B: 76068-80-9
Methylendidecanoat

Conditions

Conditions	Yield
Stage #1: levofloxacin With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.333333h; Stage #2: decanoyloxymethyl chloride In N,N-dimethyl-formamide at 90℃; for 1h;	A 79% B n/a

...Expand

: 95-14-7
1,2,3-Benzotriazole

: 100986-85-4
levofloxacin

: 1381763-83-2
(S)-6-(1H-benzo[d][1,2,3]triazole-1-carbonyl)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2H-[1,4]oxazino[2,3,4-ij]quinolin-7(3H)-one

Conditions

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃;	79%

: 753-73-1
dimethyltin dichloride

: 100986-85-4
levofloxacin

: C38H44F2N6O8Sn

Conditions

Conditions	Yield
Stage #1: levofloxacin With sodium hydrogencarbonate In water at 25℃; for 0.5h; Stage #2: dimethyltin dichloride In toluene Reflux;	79%

: copper(II) choride dihydrate

: 1662-01-7
bathophenanthroline

: 100986-85-4
levofloxacin

: C42H35ClCuFN5O4

Conditions

Conditions	Yield
Stage #1: copper(II) choride dihydrate; levofloxacin With potassium hydroxide In methanol at 20℃; for 0.5h; Stage #2: bathophenanthroline In methanol at 60℃; for 2h;	79%

...Expand

: 127-79-7
sulfamerazina

: 100986-85-4
levofloxacin

: (S)−9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)−7-((4-(N-(4-methylpyrimidin-2-yl)sulfamoyl)phenyl)imino)−2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

Conditions

Conditions	Yield
With acetic acid In methanol for 2h; Microwave irradiation; Reflux;	78.91%

: zirconyl chloride octahydrate

: 100986-85-4
levofloxacin

: [ZrO(levofloxacin)2(H2O)]*6H2O

Conditions

Conditions	Yield
With sodium hydroxide In methanol; acetone at 20℃; for 24h;	78.6%

Levofloxacin History

Levofloxacin is a fluoroquinolone antibiotic, marketed by sanofi aventis under the tradename "TAVANIC". Levaquin is also marketed worldwide for oral and IV use, as well as used in ophthalmic solutions. Daiichi Sankyo had granted an exclusive license to Sanofi-Aventis to make, use and sell pharmaceutical preparations containing levofloxacin in the UK and Mexico under the trade name TAVANIC. Other manufacturers include Novell Pharmaceutical Laboratories (Levores).

Levofloxacin Specification

1. Introduction of Levofloxacin
Levofloxacin is slight yellow powder. The IUPAC Name of this chemical is (S)-7-fluoro-6-(4-methylpiperazin-1-yl)-10-oxo-4-thia-1-azatricyclo[7.3.1.05,13] trideca-5(13),6,8,11-tetraene-11-carboxylic acid. Besides, Levofloxacin belongs to Pharmaceutical material and intermeidates;Active Pharmaceutical Ingredients;Anti-Infective;Antibiotics for Research and Experimental Use;Biochemistry;Quinolones (Antibiotics for Research and Experimental Use);Peptide Synthesis/Antibiotics;Pharmaceutical intermediate.

The Classification Code of it is Anti-Bacterial Agents; Anti-Infective Agents; Anti-infective agents, urinary; Drug / Therapeutic Agent; Enzyme Inhibitors; Nucleic Acid Synthesis Inhibitors; Renal Agents; Reproductive Effect. Levofloxacin is considered soluble to freely soluble in this pH range, as defined by USP nomenclature.

2. Properties of Levofloxacin
Physical properties about Levofloxacin are:
(1)Melting Point: 218 °C ; (2)storage temp.: Store at 0-5 °C ; (3)Index of Refraction: 1.669; (4)Molar Refractivity: 91.09 cm³; (5)Molar Volume: 243.9 cm³; (6)Surface Tension: 70.3 dyne/cm ; (7)Density: 1.48 g/cm³; (8)Flash Point: 299.4 °C; (9)Enthalpy of Vaporization: 90.15 kJ/mol; (10)Boiling Point: 571.5 °C at 760 mmHg; (11)Vapour Pressure of Levofloxacin: 6.7E-14 mmHg at 25 °C.

3. Structure Descriptors of Levofloxacin
(1)SMILES: Fc4cc1c2N(/C=C(\C1=O)C(=O)O)C(COc2c4N3CCN(C)CC3)C
(2)InChI: InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)/t10-/m0/s1
(3)InChIKey: GSDSWSVVBLHKDQ-JTQLQIEISA-N
(4)Canonical SMILES: CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
(5)Isomeric SMILES: C[C@H]1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O

4. Toxicity of Levofloxacin

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
monkey	LD50	oral	> 250mg/kg (250mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Arzneimittel-Forschung. Drug Research. Vol. 42, Pg. 365, 1992.
mouse	LD50	oral	1803mg/kg (1803mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Arzneimittel-Forschung. Drug Research. Vol. 42, Pg. 365, 1992.
rat	LD50	oral	1478mg/kg (1478mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Arzneimittel-Forschung. Drug Research. Vol. 42, Pg. 365, 1992.
women	TDLo	oral	122mg/kg/10D- (122mg/kg)	MUSCULOSKELETAL: OTHER CHANGES	Annals of Pharmacotherpy. Vol. 33, Pg. 792, 1999.

5. Safety information of Levofloxacin
Hazard Codes: Harmful

Xn
Risk Statements: 22-42/43-68-20/21/22
R22:Harmful if swallowed.
R42/43:May cause sensitization by inhalation and skin contact.
R68:Possible risk of irreversible effects.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS of Levofloxacin (CAS NO.100986-85-4): UU8815550

6. Uses of Levofloxacin
Levofloxacin is a broad spectrum antibiotic of the fluoroquinolone drug class. Levofloxacin is a chiral fluorinated carboxyquinolone. Investigation of ofloxacin, an older drug that is the racemic mixture, found that the l form [the (–)-(S) enantiomer] is more active. This specific component is levofloxacin.

7. Production of Levofloxacin
(1)2,3,4,5-Tetrafluorobenzoic acid can used to manufacture the Levofloxacin. And the condition is (S)-(+)-1-Amino-2-propanol and SOCl₂ and so on. The detailed reaction is as follows:

(2)2,3-DIFLUORO-6-NITROPHENOL can used to produce the Levofloxacin as follows:

Production of Levofloxacin

Product Name

Levofloxacin hydrochloride

Synthetic route

Levofloxacin History

Levofloxacin Specification

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