86393-32-0

Basic information

• Product Name: Ciprofloxacin hydrochloride hydrate
• Synonyms: CIPROFLOXACIN HCL;3-QUINOLINECARBOXYLIC ACID HYDROCHLORIDE;CIPROFLOXACIN HCL/ CIPROFLOXACIN MONOHYDROCHLORIDE;CIPROFLOXACIN HCL USP;CIPROFLOXACINHYDROCHLORIDE,USP;1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride hydrate;Ciprofloxacin hydrochloride hydrate;1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride monohydrate
• CAS NO: 86393-32-0
• Molecular Formula: C₁₇H₁₈FN₃O₃*ClH*H₂O
• Molecular Weight: 385.82
• EINECS: 1308068-626-2
• Product Categories: Active Pharmaceutical Ingredients;Quinolones (Antibiotics for Research and Experimental Use);Antibiotics for Research and Experimental Use;Biochemistry;Antibiotic Explorer;Peptide Synthesis/Antibiotics;Pharmaceutical raw materials
• Mol File: 86393-32-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 318-320 °C
• Boiling Point: 581.8 °C at 760 mmHg
• Flash Point: 305.6 °C
• Appearance: White or yellowish crystalline powder
• Vapor Pressure: 2.24E-14mmHg at 25°C
• Storage Temp.: 0-6°C
• Solubility: Soluble in water, slightly soluble in methanol, very slightly soluble in anhydrous ethanol, practically insoluble in acetone, in ethyl acetate and in methylene chloride.
• Water Solubility: Soluble in water (35mg/ml).
• Merck: 14,2314
• CAS DataBase Reference: Ciprofloxacin hydrochloride hydrate(CAS DataBase Reference)
• NIST Chemistry Reference: Ciprofloxacin hydrochloride hydrate(86393-32-0)
• EPA Substance Registry System: Ciprofloxacin hydrochloride hydrate(86393-32-0)

Safety Data

• WGK Germany: 3
• RTECS: VB1993800
• HazardClass: IRRITANT
• Hazardous Substances Data: 86393-32-0(Hazardous Substances Data)

Usage

Description

Ciprofloxacin hydrochloride hydrate is a fluoroquinolone antibacterial agent that is used to treat a wide range of infections caused by susceptible organisms. It is a Nalidixic acid analogue and is effective against infections of the urinary, respiratory, and gastrointestinal tracts, gonorrhoea, and septicaemia.

Uses

Used in Pharmaceutical Industry:
Ciprofloxacin hydrochloride hydrate is used as an antibacterial agent for treating infections caused by susceptible organisms. Its broad-spectrum activity makes it a versatile treatment option for various types of infections.
Used in Urinary Tract Infections:
Ciprofloxacin hydrochloride hydrate is used as a treatment for urinary tract infections, including those caused by Escherichia coli and other susceptible bacteria. Its effectiveness in combating these infections makes it a popular choice for UTI treatment.
Used in Respiratory Tract Infections:
Ciprofloxacin hydrochloride hydrate is used as a treatment for respiratory tract infections, such as pneumonia and bronchitis, caused by susceptible organisms. Its ability to target a wide range of bacteria makes it a valuable option for respiratory infections.
Used in Gastrointestinal Tract Infections:
Ciprofloxacin hydrochloride hydrate is used as a treatment for gastrointestinal tract infections, including those caused by Salmonella and other susceptible bacteria. Its effectiveness in treating these infections makes it a useful option for gastrointestinal health.
Used in Gonorrhoea Treatment:
Ciprofloxacin hydrochloride hydrate is used as a treatment for gonorrhoea, a sexually transmitted infection caused by the bacterium Neisseria gonorrhoeae. Its ability to target and eliminate this bacterium makes it a key component in gonorrhoea treatment.
Used in Septicaemia Treatment:
Ciprofloxacin hydrochloride hydrate is used as a treatment for septicaemia, a serious blood infection caused by susceptible bacteria. Its broad-spectrum activity and ability to target a wide range of bacteria make it a crucial option in the treatment of septicaemia.

in vitro

Ciprofloxacin (hydrochloride monohydrate) is a fluoroquinolone antibiotic, exhibiting potent antibacterial activity. Ciprofloxacin (hydrochloride monohydrate) (CIP) shows potent activity against Y. pestis with MIC 90 of 0.03 μg/mL.

in vivo

Ciprofloxacin (hydrochloride monohydrate) (1 mg/L) induces glutathione-S-transferase (GST) activity, in contrast with inhibited GST and Catalase (CAT) of larvae exposed to enrofloxacin. Ciprofloxacin (hydrochloride monohydrate) (≥10 μg/L) is ecotoxic for development, growth, detoxifying, and oxidative stress enzymes in anuran amphibian larvae. In a murine model of pneumonic plague, Ciprofloxacin (hydrochloride monohydrate) (30 mg/kg, i.p.) results in a drug exposure which is similar to the drug exposure observed in human following a 500 mg dose of oral Ciprofloxacin (hydrochloride monohydrate). Intraperitoneal Ciprofloxacin (hydrochloride monohydrate) reduces the lung bacterial load compare to controls treated with intraperitoneal PBS.

InChI:InChI=1/C17H18FN3O3.ClH.H2O/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24;;/h7-10,19H,1-6H2,(H,23,24);1H;1H2

Synthetic route

1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid HCl monohydrate (86393-32-0) → ciprofloxacin hydrochloride (93107-08-5)

Conditions	Yield
In ethanol for 24 - 72h; Product distribution / selectivity;	88%
In iso-butanol for 2h; Product distribution / selectivity;	88%

1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid HCl monohydrate (86393-32-0) + europium(III) chloride hexahydrate + water (7732-18-5) → [Eu(ciprofloxacin)(ciprofloxacin(-1H))(H2O)4]Cl2*8H2O

Conditions	Yield
With 1,3-bis(dimethylamino)-2-propanol In ethanol; water High Pressure; Eu salt, ligand and 1,3-bis(dimethylamino)-2-propanol added to a mixt. of H2O and EtOH, stirred, placed in an autoclave, heated at 150°C for 48 h; crystd. for 1 wk; elem. anal.;	47.2%

1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid HCl monohydrate (86393-32-0) + water (7732-18-5) + mercury dichloride → (H-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid)2HgCl4*2H2O

Conditions	Yield
In water satd. aq. solns. ligand and HgCl2 were mixed in 2:1 ratio; ppt. was filtered off, dried in air; elem. anal.;

1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid HCl monohydrate (86393-32-0) + aqueous cadmium chloride → (H-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carbohylic acid)2(CdCl4)*2H2O

Conditions	Yield
In water satd. aq. solns. ligand and CdCl2*2.5H2O were mixed in 2:1 ratio; ppt. was filtered off, dried in air; elem. anal.;

1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid HCl monohydrate (86393-32-0) + aqueous cadmium chloride → (H2-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid)CdCl4*H2O

Conditions	Yield
With HCl In hydrogenchloride solns. ligand and CdCl2*2.5H2O in concd. HCl were mixed in 1:1 ratio, mixt. was stand for several days; ppt. was filtered off, washed with acetone, dried in air; elem. anal.;

1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid HCl monohydrate (86393-32-0) + mercury dichloride → (H2-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid)HgCl4

Conditions	Yield
With HCl In hydrogenchloride solns. ligand and HgCl2 in concd. HCl were mixed in 1:1 ratio, mixt. wasstand for several days; ppt. was filtered off, washed with acetone, dried in air; elem. anal.;

Downstream Products

• 93107-08-5 ciprofloxacin hydrochloride