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100986-85-4

Basic Information
CAS No.: 100986-85-4
Name: Levofloxacin hydrochloride
Article Data: 41
Molecular Structure:
Molecular Structure of 100986-85-4 (Levofloxacin hydrochloride)
Formula: C18H20FN3O4
Molecular Weight: 361.373
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;
EINECS: 600-146-0
Density: 1.48 g/cm3
Melting Point: 218 °C
Boiling Point: 571.495 °C at 760 mmHg
Flash Point: 299.43 °C
Solubility: Slightly soluble in water or methanol. Soluble in glacial acetic acid or dichloromethane
Appearance: Slight yellow powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-42/43-68-20/21/22
Safety: 26-36/37/39-36
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In pyridine; diethyl ether74.3%
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
ConditionsYield
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
ConditionsYield
In dimethyl sulfoxide for 17h; Ambient temperature;52%
82419-36-1

ofloxacin

A

100986-85-4

levofloxacin

B

100986-86-5

(R)-ofloxacin

Conditions
ConditionsYield
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;
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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).

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: HarmfulXn
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:

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

Production of LevofloxacinProduction of Levofloxacin