Name: Ciprofloxacin
SKU: 85721-33-1

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Basic Information

Molecular Structure:
CAS No.:	85721-33-1
Name:	Ciprofloxacin

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

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

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

: 110-85-0
piperazine

: C15H16Cl2FNO3

: 85721-33-1
ciprofloxacin

Conditions

Conditions	Yield
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

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%

: 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

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%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
	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

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.

...Expand

: 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

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;

: 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

Conditions	Yield
Yield given. Multistep reaction;

...Expand

Raw Materials

Downstream Products

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Chemistry

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

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.

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.

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.

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

85721-33-1

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Chemistry

History

Uses

Toxicity Data With Reference

Safety Profile