186826-86-8 Usage
Description
Moxifloxacin hydrochloride is an anti-infectious compound belonging to the class of fluoroquinolone antibiotics. It is a broad-spectrum antibiotic prescription medicine effective against a variety of Gram-positive and Gram-negative bacteria, including anaerobic types. Moxifloxacin hydrochloride works by inhibiting the activities of crucial enzymes involved in the replication, transcription, recombination, and repair of bacterial deoxyribonucleic acid, such as DNA gyrase (topoisomerase II) and topoisomerase IV.
Uses
1. Used in Pharmaceutical Industry:
Moxifloxacin hydrochloride is used as an antibacterial agent for inhibiting the activities of Topo II (DNA gyrase) and topoisomerase IV, which are essential for bacterial DNA replication and repair.
2. Used in Respiratory Tract Infections Treatment:
Moxifloxacin hydrochloride is used as a treatment for respiratory tract infections such as community-acquired pneumonia, acute exacerbations of bronchitis, or acute sinusitis due to its broad-spectrum antibacterial activity and favorable pharmacokinetic profile.
3. Used in Ocular Infections Treatment:
Moxifloxacin hydrochloride is used as an ocular antibacterial agent for treating various eye infections, benefiting from its broad-spectrum activity and good tissue penetration.
4. Used in Cognitive Enhancement:
Moxifloxacin hydrochloride is used as an acetylcholinesterase inhibitor (reversible) and cognitive enhancer, potentially improving cognitive function by modulating the activity of acetylcholinesterase, an enzyme involved in the breakdown of the neurotransmitter acetylcholine.
5. Used in Antimicrobial Research:
Moxifloxacin hydrochloride serves as a subject of study for understanding the mechanisms of bacterial resistance and the development of new antimicrobial agents, given its broad-spectrum activity and the need for new treatments to combat antibiotic-resistant bacteria.
Brand names:
Avelox (Bayer)
Vigamox (Alcon)
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 .
Originator
Bayer (Germany)
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)
Therapeutic Function
Antibacterial
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.
Check Digit Verification of cas no
The CAS Registry Mumber 186826-86-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,6,8,2 and 6 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 186826-86:
(8*1)+(7*8)+(6*6)+(5*8)+(4*2)+(3*6)+(2*8)+(1*6)=188
188 % 10 = 8
So 186826-86-8 is a valid CAS Registry Number.
InChI:InChI=1/C21H24FN3O4.ClH/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
186826-86-8Relevant articles and documents
Preparation method of quinolone carboxylic acid derivative or phthalazinone carboxylic acid derivative
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, (2021/10/27)
The invention belongs to the field of pharmaceutical chemicals, relates to a preparation method of a quinolone carboxylic acid derivative or a phthalazinone carboxylic acid derivative, and particularly relates to a preparation method of a 7-substituted-3-quinolone carboxylic acid derivative or a 7-substituted-1,5-phthalazinone carboxylic acid derivative. The preparation method comprises the following steps: (1) in an organic solvent, carrying out coupling reaction on a boron chelate II and organic amine III in the presence of an organosilicon compound to obtain a compound IV; and (2) mixing the compound IV with hydrochloric acid, and then filtering and separating the precipitated compound I. Compared with conventional methods, the preparation method provided by the invention has the advantages that the conditions are milder, the hydrolysis of the substrate quinoline carboxylic acid boric acid ester can be reduced, and meanwhile, the influence of a byproduct HF on the product purity is avoided. The method is high in yield and high in purity; compared with the traditional alkali, the organic silicon is more suitable for industrial preparation of the 7-substituted-3-quinolone carboxylic acid derivative or the 7-substituted-1,5-phthalazinone carboxylic acid derivative.
Preparation method of moxifloxacin hydrochloride (by machine translation)
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Paragraph 0048-0055; 0066-0080, (2020/05/01)
The reaction: the reaction, is added into the reaction kettle, to heat, and then the,dihydro - 8 8-oxo- 3 3-dihydro-8-methoxy - 4 4-dioxanone introduced into the reaction kettle, is added to the reaction still 1 - for heating and reacting the, by the reaction; first and then, refluxing under, heating. 1st. The method comprises, condensation reaction; adding a protecting gas, to a reaction kettle.] and reacting, to obtain moxifloxacin hydrochloride; second by heating and reacting with a heating reaction of, by a heating reaction of a heating reaction unit of a reaction scheme of, second in a reaction still further, heating a reaction, solution in, a reaction still further to react with a, reaction gas, second and refluxing, the reaction. (S,S) - 2,8 - The method comprises the following steps of heating and separating [4.3 .0] out of a reaction; and refluxing the reaction gas . The reaction mixture; is introduced, into the reaction kettle. (by machine translation)
Synthetic method of moxifloxacin hydrochloride
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Paragraph 0037-0057, (2020/07/13)
The invention discloses a synthetic method of moxifloxacin hydrochloride. The synthetic method comprises the following steps: under the protection of argon, taking gatifloxacin carboxylate and (S,S)-2,8-diazabicyclo[4.3.0]nonane as raw materials; taking an organic alkali or an inorganic alkali as an acid-binding agent and a Lewis acid as a catalyst; reacting in a certain solvent at a proper temperature; concentrating, processing by alkali liquor, separating out moxifloxacin monomers at an isoelectric point, reacting moxifloxacin monomers with an acid to form salt, concentrating to obtain a moxifloxacin hydrochloride crude product, re-crystallizing, filtering, washing and drying to obtain a refined moxifloxacin hydrochloride finished product. The preparation method is mild in reaction conditions, simple to operate, less in pollution, and high in yield and industrial production can be realized easily.