192927-63-2

Basic information

• Product Name: MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE
• Synonyms: MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE;BAY-12-8039, Actira, Avalox, Proflox,1-Cyclopropyl-6-fluoro-1,4-dihydro- 8-methoxy-7- [(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo- 3-quinolinecarboxylic acid Hydrochloride;BAY-12-8039, Actira, Avalox, Proflox,1-Cyclopropyl-6-fluoro-1,4-dihydro- 8-methoxy-7- [(4aS,7aS)-octahydro-6H-pyrrolo[3,4-β]pyridin-6-yl]-4-oxo- 3-quinolinecarboxylic acid Hydrochloride;3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-Methoxy-7-(octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-, Monohydrochloride, Monohydrate, (4aS-cis)-
• CAS NO: 192927-63-2
• Molecular Formula: C₂₁H₂₄FN₃O₄*ClH*H₂O
• Molecular Weight: 455.9075832
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents;Heterocycles
• Mol File: 192927-63-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 243-246°C dec.
• Boiling Point: 636.4°Cat760mmHg
• Flash Point: 338.7°C
• Appearance: /
• Density: 1.408g/cm³
• Vapor Pressure: 4.56E-17mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• Merck: 14,6291
• CAS DataBase Reference: MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE(192927-63-2)
• EPA Substance Registry System: MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE(192927-63-2)

Safety Data

• RTECS: VB1983750
• Hazardous Substances Data: 192927-63-2(Hazardous Substances Data)

Usage

Description

MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE is a fluorinated quinolone antibacterial agent, which is a type of medication used to treat bacterial infections. It is a crystalline solid with potent antimicrobial properties, making it effective against a wide range of bacterial pathogens.

Uses

Used in Pharmaceutical Industry:
MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE is used as an antibacterial agent for treating various bacterial infections. It is particularly effective against gram-positive and gram-negative bacteria, including Streptococcus pneumoniae, Staphylococcus aureus, and Escherichia coli. The fluorinated quinolone structure of the compound allows it to penetrate bacterial cell walls and inhibit essential enzymes, leading to the disruption of bacterial DNA replication and ultimately causing cell death.
Used in Hospital Settings:
In hospital settings, MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE is used as a broad-spectrum antibiotic for the treatment of severe bacterial infections, such as pneumonia, skin and soft tissue infections, and urinary tract infections. Its effectiveness against a wide range of bacteria makes it a valuable tool in the management of complicated infections, especially in patients with compromised immune systems or those who are at risk for developing antibiotic-resistant infections.
Used in Outpatient Treatment:
MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE is also used in outpatient settings for the treatment of less severe bacterial infections, such as acute bacterial sinusitis, acute bacterial exacerbation of chronic bronchitis, and uncomplicated skin and skin structure infections. Its oral formulation allows for convenient administration and makes it suitable for patients who do not require hospitalization.
Used in Veterinary Medicine:
In veterinary medicine, MOXIFLOXACIN, HYDROCHLORIDE MONOHYDRATE is used as an antibacterial agent for the treatment of bacterial infections in animals, such as dogs, cats, and livestock. It is effective against various bacterial pathogens that cause infections in animals, including respiratory, urinary, and skin infections. Its use in veterinary medicine helps to ensure the health and well-being of animals and contributes to the prevention of the spread of zoonotic diseases to humans.

InChI:InChI=1/C21H24FN3O4.ClH.H2O/c1-29-20-17-13(19(26)14(21(27)28)9-25(17)12-4-5-12)7-15(22)18(20)24-8-11-3-2-6-23-16(11)10-24;;/h7,9,11-12,16,23H,2-6,8,10H2,1H3,(H,27,28);1H;1H2/t11-,16+;;/m0../s1

Synthetic route

L(+)-moxifloxacin tartrate (1082245-30-4) → 1-cyclopropyl-7-([S,S]-2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid monohydrochloride monohydrate (192927-63-2)

Conditions	Yield
With hydrogenchloride; water In ethanol at 25 - 30℃; for 1h; Product distribution / selectivity;	85%

1-cyclopropyl-7-[(S,S)-2,8-diazabicyclo[4.3.0]non-8-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid fumarate (1082245-33-7) → 1-cyclopropyl-7-([S,S]-2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid monohydrochloride monohydrate (192927-63-2)

Conditions	Yield
With hydrogenchloride; water In ethanol at 25 - 30℃; for 1h; Product distribution / selectivity;	81.82%

1-cyclopropyl-7-[(S,S)-2,8-diazabicyclo[4.3.0]non-8-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid di-p-toluoyl-L-tartarate (1082245-36-0) → 1-cyclopropyl-7-([S,S]-2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid monohydrochloride monohydrate (192927-63-2)

Conditions	Yield
With hydrogenchloride; water In ethanol at 25 - 30℃; for 1h; Product distribution / selectivity;	69.2%

1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (112811-72-0) + (1S,6S)-2,8-diazabicyclo[4.3.0]nonane (151213-40-0) → 1-cyclopropyl-7-([S,S]-2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid monohydrochloride monohydrate (192927-63-2)

Conditions	Yield
Stage #1: 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid With boric acid; acetic anhydride; zinc(II) chloride at 25 - 120℃; for 1.5h; Stage #2: (1S,6S)-2,8-diazabicyclo[4.3.0]nonane With triethylamine In acetonitrile for 1.5h; Heating / reflux; Stage #3: With hydrogenchloride; sodium hydroxide; water; acetic acid more than 3 stages;

1-cyclopropyl-7-([S,S]-2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid monohydrochloride monohydrate (192927-63-2) → moxifloxacin hydrochloride (186826-86-8)

Conditions	Yield
In toluene Heating / reflux;

Upstream product

• 1082245-33-7 1-cyclopropyl-7-[(S,S)-2,8-diazabicyclo[4.3.0]non-8-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid fumarate 
• 1082245-30-4 moxifloxacin tartaric acid 
• 1082245-36-0 1-cyclopropyl-7-[(S,S)-2,8-diazabicyclo[4.3.0]non-8-yl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid di-p-toluoyl-L-tartarate 
• 112811-72-0 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid 
• 151213-40-0 (1S,6S)-2,8-diazabicyclo[4.3.0]nonane 

Downstream Products

• 186826-86-8 moxifloxacin hydrochloride 

Relevant articles and documents

Process for the preparation of moxifloxacin hydrochloride

The present invention relates to a process for the preparation of Moxifloxacin hydrochloride monohydrate, of the formula