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| CAS No.: | 70458-96-7 |
|---|---|
| Name: | Norfloxacin |
| Article Data: | 28 |
| Molecular Structure: | |
|
|
|
| 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 |
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- 94498-83-6
C16H17BF3N3O3
- 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid
| 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 | 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℃; |
- 110-85-0
piperazine
- 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid
| 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 | 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. |
- 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 | 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 | 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 | 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 | 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 | 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 | Yield |
|---|---|
| With pyridine; sodium hydroxide In phosphorus pentaoxide; ethanol; water; acetic acid; N,N-dimethyl-formamide | 70% |
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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: 
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.