CAS No.70458-96-7,Norfloxacin Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	70458-96-7
Name:	Norfloxacin
Article Data:	28

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:	Xn
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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.

...Expand

: 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

Conditions	Yield
With hydrogenchloride In water; acetic acid	84%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With pyridine; sodium hydroxide In phosphorus pentaoxide; ethanol; water; acetic acid; N,N-dimethyl-formamide	70%

...Expand

Raw Materials

68-12-2

110-85-0

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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: Harmful Xn
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.