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CAS No.: | 85721-33-1 |
---|---|
Name: | Ciprofloxacin |
Article Data: | 62 |
Molecular Structure: | |
Formula: | C17H18F N3 O3 |
Molecular Weight: | 331.347 |
Synonyms: | 1-Cyclopropyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid;1-Cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylicacid;BAY-q 3939;Catex;Ciflafin;Ciprine;Cipro IV;Ciprobay 100;Ciprofloxacillin;Ciprofloxacin;Ciprofloxacine;Ciprolet;Ciprolet DS;Cipromed;Cipropol;Ciprovet;Ciproxim;Ciproxina;Cunesin;Cyclofloxacin;Euciprin;Oftacifox;Procip;Quinox XR; |
EINECS: | 617-751-0 |
Density: | 1.461 g/cm3 |
Melting Point: | 255-257 °C |
Boiling Point: | 581.774 °C at 760 mmHg |
Flash Point: | 305.646 °C |
Solubility: | 86mg/L(25 oC) |
Appearance: | White powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36 |
PSA: | 74.57000 |
LogP: | 1.97710 |
7-[4-tert-butoxycarbonyl-piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid
ciprofloxacin
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h; | 98.7% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hydroxide at 70℃; for 5h; Reagent/catalyst; Temperature; | 96.2% |
ciprofloxacin hydrochloride
ciprofloxacin
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water | 96% |
With sodium hydrogencarbonate In water | 95% |
With ammonium hydroxide In water at 30 - 55℃; for 4.41667h; pH=6.8; Temperature; Reagent/catalyst; pH-value; | 82.52% |
piperazine
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid
ciprofloxacin
Conditions | Yield |
---|---|
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.366667h; Reflux; | 94% |
at 150℃; Microwave irradiation; | 90% |
With aluminum tri-bromide In ethanol at 75℃; for 4h; Reagent/catalyst; Solvent; Temperature; | 89.7% |
piperazine
ciprofloxacin
Conditions | Yield |
---|---|
With aluminum (III) chloride In i-Amyl alcohol at 140℃; for 8h; Reagent/catalyst; Temperature; | 91.2% |
piperazine
1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
ciprofloxacin
Conditions | Yield |
---|---|
In pyridine for 18h; Heating; | 89% |
In water | |
In dimethyl sulfoxide Heating; | 960 mg |
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid
ciprofloxacin
Conditions | Yield |
---|---|
88% |
piperazine
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid
A
ciprofloxacin
Conditions | Yield |
---|---|
In water for 15h; Heating; | A 86% B n/a |
In water at 150℃; for 5h; | A 65% B 10% |
In dimethylsulfoxide-d6 at 120 - 130℃; | A 87 % Spectr. B 13 % Spectr. |
ciprofloxacin
Conditions | Yield |
---|---|
With adsorption onto charcoal; trifluoroacetic acid 2.) dichloromethane; | 57% |
With adsorption onto charcoal; trifluoroacetic acid In dichloromethane Product distribution; solid/solution phase synthesis to eliminate impurities; | |
With water; pyrographite; trifluoroacetic acid In dichloromethane at 20℃; for 0.25h; Hydrolysis; |
piperazine
ethyl 2,4,5-trifluorobenzoylacetate
N,N-dimethyl-formamide dimethyl acetal
Cyclopropylamine
ciprofloxacin
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
IUPAC Name: 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate
Molecular Formula: C17H18FN3O3
Molecular Weight: 331.341523 g/mol
Appearance: White Powder
Melting Point: 255-257 °C
storage temp.: Store at 0-5 °C
Merck: 13,2337
Density: 1.461 g/cm3
Flash Point: 305.6 °C
Index of Refraction: 1.655
Surface Tension: 67.4 dyne/cm
Enthalpy of Vaporization: 91.5 kJ/mol
Boiling Point: 581.8 °C at 760 mmHg
Vapour Pressure: 2.24E-14 mmHg at 25 °C
Synonyms of Ciprofloxacin (CAS NO.85721-33-1): 1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarbox ; ciloxan; ciprobid ; ciproiv ; euciprin ; ciprobay ; ciprofloxacin ; 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
Categories: Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals
Ciprofloxacin (CAS NO.85721-33-1) was first introduced as the broad-spectrum oral fluoroquinolone in 1987 by Bayer. In 1991 the intravenous formulation was introduced. Ciprofloxacin (85721-33-1) was first patented Jan 21, 1986, in Germany, and was later approved by the U.S. Food and Drug Administration on October 22, 1987.
Ciprofloxacin (CAS NO.85721-33-1) is a third-generation quinolone antibiotics used for the treatment of respiratory tract infections, urinary tract, ENT, skin and soft tissue, gastrointestinal tract infections. It is also used as fluorinated quinolone antibacterial.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | LDLo | oral | 5714ug/kg/2D- (5.714mg/kg) | BEHAVIORAL: COMA LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" LIVER: LIVER FUNCTION TESTS IMPAIRED | Lancet. Vol. 343, Pg. 738, 1994. |
man | TDLo | oral | 21mg/kg/3D-I (21mg/kg) | KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED KIDNEY, URETER, AND BLADDER: PROTEINURIS KIDNEY, URETER, AND BLADDER: HEMATURIA | Annals of Pharmacotherpy. Vol. 29, Pg. 84, 1995. |
man | TDLo | oral | 21429ug/kg/3D (21.429mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TOXIC PSYCHOSIS | Annals of Pharmacotherpy. Vol. 26, Pg. 930, 1992. |
man | TDLo | oral | 129mg/kg/6D-I (129mg/kg) | BEHAVIORAL: REGIDITY | Journal of Clinical Psychiatry. Vol. 54, Pg. 115, 1993. |
man | TDLo | oral | 200mg/kg (200mg/kg) | BEHAVIORAL: TREMOR GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: OTHER CHANGES | Annals of Pharmacotherpy. Vol. 28, Pg. 805, 1994. |
mouse | LD50 | intraperitoneal | 1165mg/kg (1165mg/kg) | Ensho. Japanese Journal of Inflammation. Vol. 11, Pg. 343, 1991. | |
mouse | LD50 | intravenous | 122mg/kg (122mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Korean Journal of Toxicology. Vol. 8, Pg. 161, 1993. |
mouse | LD50 | oral | 5gm/kg (5000mg/kg) | Journal of Medicinal Chemistry. Vol. 33, Pg. 1344, 1990. | |
mouse | LD50 | subcutaneous | > 1gm/kg (1000mg/kg) | Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992. | |
rat | LD50 | intravenous | 207mg/kg (207mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Korean Journal of Toxicology. Vol. 8, Pg. 161, 1993. |
rat | LD50 | oral | > 2gm/kg (2000mg/kg) | Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992. | |
rat | LD50 | subcutaneous | > 1gm/kg (1000mg/kg) | Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992. | |
women | TDLo | multiple routes | 40mg/kg/6D-I (40mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Acta Clinica Belgica. Vol. 49, Pg. 173, 1994. |
women | TDLo | oral | 10mg/kg (10mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" GASTROINTESTINAL: NAUSEA OR VOMITING | Allergy. Vol. 50(Suppl, |
women | TDLo | oral | 40mg/kg/2D-I (40mg/kg) | BEHAVIORAL: HEADACHE BLOOD: EOSINOPHILIA | American Journal of Medicine. Vol. 87, Pg. 589, 1989. |
women | TDLo | oral | 135mg/kg/3D-I (135mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Archives of Internal Medicine. Vol. 153, Pg. 1258, 1993. |
women | TDLo | oral | 280mg/kg/2W-I (280mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" | American Journal of Kidney Diseases. Vol. 22, Pg. 598, 1993. |
Safety Information of Ciprofloxacin (CAS NO.85721-33-1):
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
WGK Germany: 2
RTECS: VB1993800