Moxifloxacin hydrochloride

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Moxifloxacin hydrochloride

Indications and Usage Mechanisms of Action Pharmacokinetics Adverse Effects Warnings and Precautions Adverse reactions Precautions

Product Name: Moxifloxacin hydrochloride
CAS No.: 186826-86-8
Chemical Name: Moxifloxacin hydrochloride
Synonyms: MOXIFLOXACIN HCL;Avelox;AVALOX;Moxifloxacin hydrochloride CRS;1-cyclopropyl-6-fluoro-8-methoxy-7-((4aS,7aS)-octahydropyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride;Actura;ACTIRA;MoxifL;PROFLOX;BAY-12-8039
CBNumber: CB3191433
Molecular Formula: C21H25ClFN3O4
Formula Weight: 437.8923032
MOL File: 186826-86-8.mol

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Moxifloxacin hydrochloride Property

Melting point:: Slightly yellow to yellow crystalline powder, mp 324-325°
alpha: 25D -256° (c = 0.5 in water)
Boiling point:: 636℃
RTECS: VB1983750
Flash point:: >110°(230°F)
storage temp.: 2-8°C
solubility: H2O: soluble5mg/mL, clear (warmed)
form: powder
color: white to beige
Water Solubility: Sparingly soluble in water. Soluble in DMSO
BRN: 8377447
InChIKey: IDIIJJHBXUESQI-DFIJPDEKSA-N
SMILES: N1(C2CC2)C2=C(C=C(F)C(N3C[C@]4([H])CCCN[C@]4([H])C3)=C2OC)C(=O)C(C(O)=O)=C1.[H]Cl |&1:12,18,r|
CAS DataBase Reference: 186826-86-8(CAS DataBase Reference)

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Safety

WGK Germany: 2
HazardClass: IRRITANT

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHR1542
Product name: Moxifloxacin hydrochloride
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1g
Price: $112
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1448606
Product name: Moxifloxacin hydrochloride
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 200mg
Price: $1160
Updated: 2024/03/01

Sigma-Aldrich

Product number: 32477
Product name: Moxifloxacin hydrochloride
Purity: VETRANAL?, analytical standard
Packaging: 50MG
Price: $335
Updated: 2022/05/15

Alfa Aesar

Product number: J66626
Product name: Moxifloxacin hydrochloride, 97%
Packaging: 100mg
Price: $180
Updated: 2024/03/01

Alfa Aesar

Product number: J66626
Product name: Moxifloxacin hydrochloride, 97%
Packaging: 500mg
Price: $776
Updated: 2024/03/01

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Moxifloxacin hydrochloride Chemical Properties,Usage,Production

Indications and Usage

Moxifloxacin Hydrochloride is a fluoroquinolone antibiotic developed by Bayer Pharmaceuticals (Germany.) It can be used to treat community-acquired pneumonia caused by Staphylococcus aureus, baccilus, pneumococcus, mucositis Moraxella, and Klebsiella pneumoniae, acute chronic bronchitis attacks, and acute sinusitis. For the treatment of adult bacterial lung infections, paranasal sinus, skin, and abdominal cavity. Also used to treat community-acquired pneumonia, chronic bronchitis, urogenital infection, and acute sinusitis.

Mechanisms of Action

Its active mechanisms and in vitro antibacterial spectrums are similar to those of other fluoroquinolones, but its profile towards gram-positive and anaerobic bacteria is similar to that of trovafloxacin, better than some older drugs. Compared with other fluoroquinolones, few gram-positive bacteria are resistant to Moxifloxacin Hydrochloride, or the spread of resistance is very slow. Gram-negative and enterococci strains with cross resistance to other fluoroquinolones have been found. It is effective at least against Staphylococcus aureus strains grlA, grlB, gyrA and gyrBcan, and 0.5-2 mg/L can inhibit Ciprofloxacin resistant Staphylococcus aureus, from large MIC to small Ciprofloxacin, Ofloxacin, Levofloxacin, Sparfloxacin, and Moxifloxacin.

Pharmacokinetics

After 45 healthy volunteers were orally administered single doses of 50-800 mg, their peak plasma concentration and area under the curve (AUC) increased linearly with dosage. Recommended oral dose is 400 mg, average Cmax is 2.5mg/L, peak time (tmax) is 1.5 hours, and AUC is 26.9 mg•h/L. For healthy volunteers who took 400 mg per day orally for 10 days, Cmax was 4.52 mg/L, 1.59 accumulated over 10 days. Oral bioavailability is 89%, apparent distribution volume 3.55 L/kg, plasma protein binding rate 48%. For 400 mg intravenously, Cmaxis 3.62 mg/L. AUC 34.6 mg•h/L. 24 hours after 13 healthy volunteers were given a single oral dose or intravenous injection of 400 mg, skin blister fluid concentration was twice that of serum, suggesting easier penetration of interstitial tissue. One hour after 18 patients ingested a single oral dose of 400 mg before undergoing bronchoscopy, bronchial epithelial cell fluid and bronchial biopsy tissue concentrations were 24.4 and 5.5 mg / L respectively, greater than the plasma concentration after 12 hours. An extremely high concentration (113.6 mg/L) was reached in macrophages. After 34 patients with chronic sinusitis received 5 oral doses of 400 mg, concentration in maxillary sinus mucosa exceeded blood plasma concentration. Three hours after the last dose, blood concentration peaked at 7.47 mg/kg; after 36 hours it was 1.25 mg/kg，suggesting a post-dosage effect.
After healthy volunteers received an oral dose of 400 mg, total clearance rate and renal clearance rates were 14.9 and 3.03 L per hour respectively. The drug apparently does not undergo P450 metabolism. Metabolized in vitro into N-sulfate and acyl glucuronide, metabolites inactive. After healthy volunteers took 400 mg/d orally, the average elimination half-life (t1/2β) during the first day was 9.3 hours, 11.95 hours over 10 days. Another study showed that the average t1/2β is about 10-16 hours. After a single oral dose or intravenous infusion of 400 mg, the urine reabsorption rates were 19%-20% and 22% respectively.

Adverse Effects

The adverse effects of this product are mostly mild and transient, and 3.8% of patients discontinued treatment as a result of adverse effects. The most common effects were nausea (7.2%) and diarrhea (5.7%). The incidence of dizziness was 2.8%. Healthy volunteers experienced no changes in vital signs, hematology, blood biochemistry, and ECG. Studies show that it is different from lomefloxacin and did not show any phototoxicity.

Warnings and Precautions

Similar to other fluoroquinones, bioavailability of 400 mg of Moxifloxacin Hydrochloride declined significantly after combination with antacids. AUC and cmax decreased 45% and 40% compared with when used alone, but Moxifloxacin Hydrochloride absorption was not significantly affected when taken 2 hours before or 4 hours after taking antacids. When taken with iron, absorption decreased significantly, with AUC and cmax was 39% and 59% lower, respectively. No interaction with theophylline, probenecid, ranitidine, or warfarine.

Adverse reactions

Side effects of this product are mostly mild and transient , 3.8% of the patient discontinued treatment due to adverse events . The most common adverse reactions are nausea (7.2%) and diarrhea (5.7%). Dizziness is 2.8%. In healthy volunteers, no changes in vital signs, hematology, blood biochemistry and electrocardiogram.
Studies have shown that the product is different from lomefloxacin , no drug-induced light toxicity.

Precautions

Similar to other fluoroquinolones , the product (400mg) in combination with antacids, bioavailability will fall significantly, AUC and cmax fall down 45% and 40% respectively when compared with alone, but using the moxifloxacin hydrochloride 2h before taking antacids or using antacids 4h after using this service, the absorption of the drug has no effect. If the product in combination with iron ,absorption rate decreases, AUC and cmax are reduced by 39% and 59%. The product has no interaction with theophylline, probenecid, ranitidine and warfarin .

Description

Moxifioxacin hydrochlodde is one of the two new fluoroquinolonecarboxylic acid antibiotics introduced in 1999 for the treatment of respiratory tract infections such as community-acquired pneumonia, acute exacerbations of bronchitis or acute sinusitis. Moxifloxacin can be synthesized through a 12 step sequence from the classical 4-quinolone-3-carboxylic acid template. Some advantages of Moxifloxacin over Ciprofloxacin, another of Bayer's launched quinolones, have been shown, i.e. an enhanced activity against Gram-positive bacteria (Streptococcus pneumoniae, Clostndium pneumoniae), a favorable pharmacokinetic profile (good tissue penetration and plasma concentrations above MICs) and a lack of phototoxicity (UVA irradiation).

Description

Moxifloxacin is a fluoroquinolone antibiotic. It is active against 390 clinical isolates of aerobic and anaerobic Gram-positive and Gram-negative bacteria (MIC₉₀s = ≤0.25 μg/ml), as well as clinical isolates of methicillin-susceptible and -resistant S. aureus (MIC₉₀s = 0.12 and 2 μg/ml, respectively). Moxifloxacin is an inhibitor of E. coli DNA gyrase that is selective for DNA gyrase over E. coli topoisomerase IV (IC₅₀s = 0.51 and 38.8 mg/L, respectively, in cell-free assays). It prevents S. aureus- or P. aeruginosa-induced increases in bronchoalveolar lavage fluid (BALF) neutrophil infiltration and reduces S. aureus- or P. aeruginosa-induced increases in lung chemokine (C-X-C motif) ligand 1 (CXCL1) and IL-1β levels in mouse models of bacterial pneumonia when administered at a dose of 100 mg/kg twice per day for two days. Moxifloxacin (100 mg/kg) decreases the number of lung and spleen colony forming units (CFUs) in a mouse model of systemic M. tuberculosis infection. Formulations containing moxifloxacin have been used in the treatment of various bacterial infections.

Chemical Properties

Light yellow to yellow crystalline powder

Originator

Bayer (Germany)

Uses

Moxifloxacin Hydrochloride is an antibacterial agent that inhibits the activities of Topo II (DNA gyrase) and topoisomerase IV.

Uses

acetylcholinesterase inhibitor (reversible), cognitive enhancer

Definition

ChEBI: A hydrochloride comprising equimolar amounts of moxifloxacin and hydrogen chloride.

Manufacturing Process

Manufacturing process for Moxifloxacin hydrochloride includes 3 steps: Synthesis of intermidate octahydropyrrolo[3,4-b]pyridine (2,8- diazabicyclo[4.3.0]nonane);Synthesis of intermidate 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4- oxo-3-quinolinecarboxylic acid;Syntesis of 1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-1,4- dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid hydrochloride (moxifloxacin hydrochloride)

brand name

Avelox (Bayer); Vigamox (Alcon.

Therapeutic Function

Antibacterial

General Description

Moxifloxacin Hydrochloride is an anti-infectious compound that belongs to the class of fluoroquinolone antibiotics. It is a well-known broad-spectrum antibiotic prescription medicine effective against a variety of Gram-positive and Gram-negative bacteria including the anaerobic type. It is an S,S-isomer with two chiral centers. It works by preventing the activity of various crucial enzymes involved in the replication, transcription, recombination, and repair of deoxyribonucleic acid in the bacteria such as DNA gyrase (topoisomerase II), topoisomerase IV. It finds its application in the treatment of various ocular and respiratory tract infections.

Biochem/physiol Actions

Moxifloxacin has proved to be effective in treating sinusitis, community-acquired respiratory tract infection, pneumonia and acute exacerbations of chronic bronchitis. It has improved anti-gram positive activity compared to other fluoroquinolone such as ciprofloxacin and ofloxacin. Moxifloxacin is useful in treating skin infections that is of bacterial origin. It is known to have proper penetration into peripheral tissues and inflammatory fluids. Fluoroquinolones stabilize DNA strand breaks created by DNA gyrase and topoisomerase IV by binding to the enzyme-DNA complex. Compared to mammalian DNA gyrase, moxifloxacin has 100 times higher affinity for bacterial DNA gyrase. Moxifloxacin is an antibiotic and works against both Gram-positive and Gram-negative bacteria. Moxifloxacin is being investigated for the treatment of multidrug-resistant tuberculosis.

References

[1]. cruz la, hall r: enantiomeric purity assay of moxifloxacin hydrochloride by capillary electrophoresis. j pharm biomed anal 2005, 38(1):8-13.
[2]. kamruzzaman m, alam am, lee sh, ragupathy d, kim yh, park sr, kim sh: spectrofluorimetric study of the interaction between europium(iii) and moxifloxacin in micellar solution and its analytical application. spectrochim acta a mol biomol spectrosc 2012, 86:375-380.
[3]. culley cm, lacy mk, klutman n, edwards b: moxifloxacin: clinical efficacy and safety. am j health syst pharm 2001, 58(5):379-388.
[4]. turkes c, soyut h, beydemir s: human serum paraoxonase-1 (hpon1): in vitro inhibition effects of moxifloxacin hydrochloride, levofloxacin hemihidrate, cefepime hydrochloride, cefotaxime sodium and ceftizoxime sodium. j enzyme inhib med chem 2014:1-7.

Moxifloxacin hydrochloride Preparation Products And Raw materials

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Shanghai Affida new material science and technology center

Product: Moxifloxacin hydrochloride 186826-86-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99
Supply Ability: 10 tons
Release date: 2024-04-25

Sinoway Industrial co., ltd.

Product: Moxifloxacin hydrochloride 186826-86-8
Price: US $450.00-320.00/KG
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Purity: 99% up, DMF
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Release date: 2024-01-04

Hangzhou Hyper Chemicals Limited

Product: Moxifloxacin Hydrochloride 186826-86-8
Price: US $0.00-0.00/KG
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Purity: USP, BP, EP
Supply Ability: 5,000KG
Release date: 2024-05-17

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Moxifloxacin Hydrochloride Tablets

Moxifloxacin hydrochlorideUSP, 98.0-102.0% (HPLC)

Actura

AVELOX; AVALOX

ACTIRA

PROFLOX

MOXIFLOXACIN HCL

MOXIFLOXACIN HYDROCHLORIDE

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

1-CYCLOPROPYL-7-[(S,S)-2,8-DIAZA-BICYCLO[4.3.0]NON-8-YL]-6-FLUORO-8-METHOXY-1,4-DIHYDRO-4-OXO-3-QUINOLINE CARBOXYLIC ACID HYDROCHLORIDE

MoxifloxacineHCl

Moxifloxacinehydrochloride

3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7- [(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-,monohydrochloride

Moxiflaxacin HCL

Moxifloxacin Hydrochloride (200 mg)

1-Cyclopropyl-6-fluoro-7-((4aS,7aS)-hexahydro-1H-pyrrolo[3,4-b]pyridin-6(2H)-yl)-8-Methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

Avelox

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, (4aS-cis)-

1-Cyclopropyl-6-fluoro-8-Methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

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 (1:1)

Moxifloxacin Hydrochlorideand

MoxifL

oxacin hydrochL

Moxifloxacin：Moxifloxacin HCl

Moxifloxacin hydrochloride CRS

Moxifloxacin hydrochloride solution in Methanol, 1000μg/mL

Moxifloxacin Hydrochloride ABCDEFGHJKL

Moxifloxacin hydrochloride USP/EP/BP

Moxifloxacin Hyderochlodire

Moxifioxacin hydrochloride

Moxifloxacin HCl (BAY12-8039)

7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6- yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-di hydroquinoline-3-carboxylic acid hydrochloride

Moxifloxacin D4 HydrochlorideQ: What is Moxifloxacin D4 Hydrochloride Q: What is the CAS Number of Moxifloxacin D4 Hydrochloride Q: What is the storage condition of Moxifloxacin D4 Hydrochloride

moxifloxacin for peak identification(Y0000717)Q: What is moxifloxacin for peak identification(Y0000717) Q: What is the CAS Number of moxifloxacin for peak identification(Y0000717)

Moxifloxacin HydrochlorideQ: What is Moxifloxacin Hydrochloride Q: What is the CAS Number of Moxifloxacin Hydrochloride Q: What is the storage condition of Moxifloxacin Hydrochloride

Nepafenac (CAS 78281-72-8) and Moxifloxacin hydrochloride (CAS 186826-86-8)

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 AcidMonohydrochloride

Moxifloxacin hydrochlorid

2,4-Imidazolidinedione,5-(3-bromophenyl)-11-methyl-

Moxifloxacin hydrochloride hcl

Moxifloxacin HCl 1-Cyclopropyl-6-fluoro-8-methoxy-7-[(4aS,7aS)-octahydro-6H- pyrrolo[3,4-b]pyridin-6-yl]-4-oxo-1,4-dihydroquinoline-3- carboxylic acid hydrochloride

Moxifloxacin (BAY12-8039) HCl

186826-86-8

196826-86-8

86826-86-8

C21H25FN3O4Cl