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Ciprofloxacin
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Name

Ciprofloxacin

 EINECS 617-751-0
CAS No. 85721-33-1 Density 1.461 g/cm3
PSA 74.57000 LogP 1.97710
Solubility 86mg/L(25 oC) Melting Point 255-257 °C
Formula C17H18F N3 O3 Boiling Point 581.774 °C at 760 mmHg
Molecular Weight 331.347 Flash Point 305.646 °C
Transport Information N/A Appearance White powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 85721-33-1 (Ciprofloxacin) Hazard Symbols IrritantXi
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;

Article Data 62

Ciprofloxacin Synthetic route

93594-48-0

7-[4-tert-butoxycarbonyl-piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h;98.7%
110-85-0

piperazine

C15H16Cl2FNO3

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium hydroxide at 70℃; for 5h; Reagent/catalyst; Temperature;96.2%
93107-08-5

ciprofloxacin hydrochloride

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
With sodium hydrogencarbonate In water96%
With sodium hydrogencarbonate In water95%
With ammonium hydroxide In water at 30 - 55℃; for 4.41667h; pH=6.8; Temperature; Reagent/catalyst; pH-value;82.52%
110-85-0

piperazine

86393-33-1

7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
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%

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

110-85-0

piperazine

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
With aluminum (III) chloride In i-Amyl alcohol at 140℃; for 8h; Reagent/catalyst; Temperature;91.2%
110-85-0

piperazine

93107-30-3

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

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
In pyridine for 18h; Heating;89%
In water
In dimethyl sulfoxide Heating;960 mg

1-(t-butylmethylsilyl)piperazine

86393-33-1

7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
88%
110-85-0

piperazine

86393-33-1

7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

A

85721-33-1

ciprofloxacin

B

1-cyclopropyl-7-chloro-6-piperazinyl-4-oxo-1,2-dihydroquinoline-3-carboxylic acid

Conditions
ConditionsYield
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.

4-[10-(17'-Tetrabenzo[acgi]fluorenyl)decyloxy]benzyl 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylate

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
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;
110-85-0

piperazine

98349-24-7

ethyl 2,4,5-trifluorobenzoylacetate

4637-24-5

N,N-dimethyl-formamide dimethyl acetal

765-30-0

Cyclopropylamine

85721-33-1

ciprofloxacin

Conditions
ConditionsYield
Yield given. Multistep reaction;

Ciprofloxacin Chemical Properties


 

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 History

  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 Uses

 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.

Ciprofloxacin Toxicity Data With Reference

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.

Ciprofloxacin Safety Profile

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

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