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70458-96-7

Basic Information
CAS No.: 70458-96-7
Name: Norfloxacin
Article Data: 28
Molecular Structure:
Molecular Structure of 70458-96-7 (Norfloxacin)
Formula: C16H18FN3O3
Molecular Weight: 319.336
Synonyms: 1-Ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylicacid;AM 715;Amicrobin;Baccidal;Barazan;Barotham;Chibroxin;Chibroxine;Esclebin;Floxacin;Floxacin 400;Fulgram;Gonorcin;Lexinor;Mk 0366;N-Demethylpefloxacin;N-Desmethylpefloxacin;Neofloxacin;Neofloxin;Noflo;Nofocin;Nolicin;Noracin;Noraxin;Norbid;Norflox 400;
EINECS: 274-614-4
Density: 1.344 g/cm3
Melting Point: 220 °C
Boiling Point: 555.8 °C at 760 mmHg
Flash Point: 289.9 °C
Solubility: Soluble in acetic acid. Also soluble in acetone or cloroform. Slightly soluble in water
Appearance: Off-white to light yellow cryst powder
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 26-37/39
PSA: 74.57000
LogP: 1.66210
Synthetic route
94498-83-6

C16H17BF3N3O3

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide Heating;98%
110-85-0

piperazine

68077-26-9

7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
With aluminum tri-bromide In ethanol at 65℃; for 5h; Temperature; Solvent; Reagent/catalyst;91.7%
In N,N-dimethyl-formamide at 100 - 130℃; for 2h;82.9%
In ethanol at 120℃; for 0.583333h; Microwave irradiation;80%
at 130 - 140℃; for 5h;66%
In dimethyl sulfoxide at 140℃;

1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid sodium salt

110-85-0

piperazine

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
With aluminum (III) chloride In i-Amyl alcohol at 140℃; for 8h; Solvent; Temperature;90.9%
110-85-0

piperazine

68077-26-9

7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

A

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

B

75001-78-4

7-chloro-1-ethyl-1,4-dihydro-4-oxo-6-(1-piperazinyl)quinoline-3-carboxylic acid

Conditions
ConditionsYield
In water for 16h; Heating;A 85%
B n/a
In water at 150℃; for 5h;A 50%
B n/a
In dimethylsulfoxide-d6 at 100℃; Rate constant;
In dimethylsulfoxide-d6 at 120 - 130℃;A 80 % Spectr.
B 20 % Spectr.
74011-47-5

ethyl 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetic acid84%
With sodium hydroxide for 2h; Heating; Yield given;
110-85-0

piperazine

70032-25-6

6,7-difluoro-1-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
With triethylamine In water for 8h; Reflux;84%
With triethylamine In water for 5h; Substitution; Heating;79%
99726-81-5

1-Ethyl-6-fluoro-1,4-dihydro-7-<4-(cyanomethyl)-1-piperazinyl>-4-oxoquinoline-3-carboxylic acid

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 50℃; for 10h;83%
110-85-0

piperazine

106648-05-9

2-(2,4-Dichlor-5-fluorbenzoyl)-3-ethylaminoacrylsaeure-ethylester

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
Stage #1: 2-(2,4-Dichlor-5-fluorbenzoyl)-3-ethylaminoacrylsaeure-ethylester With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 125 - 130℃;
Stage #2: piperazine With aluminum (III) chloride In ethanol at 85℃; for 8h; Reagent/catalyst; Temperature; Solvent;
77.3%
118476-20-3

1-Ethyl-6-fluoro-1,4-dihydro-7-<4-<(ethoxycarbonyl)methyl>-1-piperazinyl>-4-oxoquinoline-3-carboxylic Acid

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 50℃; for 10h;77%
Multi-step reaction with 2 steps
1: 470 mg / m-chloroperbenzoic acid (MCPBA) / CHCl3 / 3 h / 0 °C
2: 239 mg / CHCl3 / 1) r.t., 5 min, 2) 50 deg C, 6 h
View Scheme
110-85-0

piperazine

68077-26-9

7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

7440-44-0

pyrographite

70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

Conditions
ConditionsYield
With pyridine; sodium hydroxide In phosphorus pentaoxide; ethanol; water; acetic acid; N,N-dimethyl-formamide70%
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    Name: Norfloxacin Synonyms: Norfloxacine; 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-quinoline-3-carboxylic acid; 2-hydroxypropanoic acid; 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid CAS: 70458-96-7 MF: C16H18FN3O3

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Chemistry

IUPAC Name: 1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
Synonyms of Norfloxacin (CAS NO.70458-96-7): 1,4-Dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid ;1-Ethyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsaeure ; Baccidal ; Barazan ; Norfloxacin ; Norfloxacinum ; 3-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-
CAS NO: 70458-96-7
Molecular Formula: C16H18FN3O3
Molecular Weight: 319.33
Molecular Structure:
EINECS: 274-614-4
H bond acceptors: 6
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 53.09 Å2
Index of Refraction: 1.595
Molar Refractivity: 80.7 cm3
Molar Volume: 237.4 cm3
Surface Tension: 53.1 dyne/cm
Density: 1.344 g/cm3
Flash Point: 289.9 °C
Enthalpy of Vaporization: 88.09 kJ/mol
Boiling Point: 555.8 °C at 760 mmHg
Vapour Pressure: 3.45E-13 mmHg at 25°C
Melting Point: 220°C
Storage temp: 2-8°C
Appearance: Off-white to light yellow cryst powder
SMILES: O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCNCC3)CC
InChI: InChI=1/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
InChIKey: OGJPXUAPXNRGGI-UHFFFAOYAC
Std. InChI: InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
Std. InChIKey: OGJPXUAPXNRGGI-UHFFFAOYSA-N
Product Categories of Norfloxacin (CAS NO.70458-96-7): Pharmaceutical;Active Pharmaceutical Ingredients;APIs;Intermediates & Fine Chemicals;Pharmaceuticals;API's

History

Uses of Norfloxacin has been licensed are quite limited as norfloxacin is to be considered a drug of last resort when all other antibiotics have failed. There are currently only three approved uses in the adult population  and the other ineffective due to bacterial resistance. And, Norfloxacin interacts with a number of other drugs, as well as a number of herbal and natural supplements. Such interactions increase the risk of anticoagulation and the formation of non-absorbable complexes, as well as increasing the risk of toxicity.

Uses

 Norfloxacin (CAS NO.70458-96-7) is limited to the treatment of proven bacterial infections as following: Complicated urinary tract infections (restricted use); Uncomplicated urethral and cervical gonorrhea (however this indication is no longer considered to be effective by some experts due to bacterial resistance) ; Prostatitis due to Escherichia coli ; Syphilis treatment: Norfloxacin has not been shown to be effective in the treatment of syphilis.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral > 4gm/kg (4000mg/kg)   Journal of Medicinal Chemistry. Vol. 32, Pg. 671, 1989.
man TDLo oral 94mg/kg/13D-I (94mg/kg) MUSCULOSKELETAL: OTHER CHANGES New Zealand Medical Journal. Vol. 96, Pg. 590, 1983.
mouse LD50 intramuscular 470mg/kg (470mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Chemotherapy Vol. 29(Suppl,
mouse LD50 intraperitoneal 1064mg/kg (1064mg/kg)   Ensho. Japanese Journal of Inflammation. Vol. 11, Pg. 343, 1991.
mouse LD50 intravenous 220mg/kg (220mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Chemotherapy Vol. 29(Suppl,
mouse LD50 oral 4gm/kg (4000mg/kg)   Journal of Medicinal Chemistry. Vol. 30, Pg. 2163, 1987.
mouse LD50 subcutaneous > 1500mg/kg (1500mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
rat LD50 intramuscular > 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 29(Suppl,
rat LD50 intravenous 245mg/kg (245mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Chemotherapy Vol. 29(Suppl,
rat LD50 oral > 4gm/kg (4000mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
rat LD50 subcutaneous > 1500mg/kg (1500mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 1625, 1984.
women TDLo oral 48mg/kg/2D-I (48mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: LIVER FUNCTION TESTS IMPAIRED
Medical Journal of Australia. Vol. 159, Pg. 423, 1993.
women TDLo oral 48mg/kg/2D-I (48mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

BEHAVIORAL: MUSCLE WEAKNESS

MUSCULOSKELETAL: JOINTS
Medical Journal of Australia. Vol. 159, Pg. 423, 1993.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 20/21/22-36/37/38
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: VB2005000

Specification

Overdose of Norfloxacin (CAS NO.70458-96-7):
Treatment of overdose include emptying of the stomach via induced vomiting or by gastric lavage. In addition Careful monitoring and supportive treatment, monitoring of renal and liver function, and maintaining adequate hydration is recommended by the manufacturer. Administration of magnesium, aluminum, or calcium containing antacids can reduce the absorption of norfloxacin.