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Moxifloxacin

HCID 152946
새 노트새 반응견적 요청하기인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
151096-09-2
표준 SMILES
COc1c(N2C[C@@H]3CCCN[C@@H]3C2)c(F)cc2c(=O)c(C(=O)O)cn(C3CC3)c12
InChIKey
FABPRXSRWADJSP-MEDUHNTESA-N
분자식
C21H24FN3O4
평균 분자량
401.4 g/mol
단동위원소 질량
401.17508447

개요

Moxifloxacin is a quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents. It has a role as an antibacterial drug. It is a quinolone, a quinolinemonocarboxylic acid, an aromatic ether, a member of cyclopropanes, a pyrrolidinopiperidine, a quinolone antibiotic and a fluoroquinolone antibiotic. It is a conjugate base of a moxifloxacinium(1+).

이름 및 식별자

우선 이름
Moxifloxacin
IUPAC
7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
영어명
Moxifloxacin
분자식
C21H24FN3O4
분자량
401.43

이름 및 동의어

moxifloxacin151096-09-2AveloxMoxifloxacineZimoxinAvelox IVMoxifloxacinoU188XYD42PIzilox1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-((4aS,7aS)-octahydro-6H-pyrrolo(3,4-b)pyridin-6-yl)-4-oxo-3-quinolinecarboxylic acid7-[(4aS,7aS)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acidCHEBI:63611
이름 더 보기
1-Cyclopropyl-6-fluoro-8-methoxy-7-(octahydro-pyrrolo[3,4-b]pyridin-6-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acidCS-83AvdoxAids070017Aids-070017MAXIOFFOXACINMoxifloxacin(Hclform)Moxifloxacin USP/EP/BP
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-DTXSID3048491ActiraAvaloxBAY128039BAY-1280397-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acidAvelox I.V.

물성

구조 계산 물성

XLogP
0.6
극성 표면적
82.1 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
8
회전 가능 결합 수
4
무거운 원자 수
29
형식 전하
0
복잡도
727

실험 및 물리화학적 성질

Drugs · 5건

Pharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic use

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics

LogP2.9
Solubility1.68e-01 g/L
Human Drugs · 3건

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Quinolones; Fluoroquinolones

Pharmaceuticals

Antituberculosis medicines

DecompositionWhen heated to decomposition material emits toxic fumes of /nitrogen oxides, hydrogen fluoride, hydrogen chloride/. /Moxifloxacin hydrochloride/
Melting Point · 3건

238-242 °C

208-209 °C (decomposes)

238 - 242 °C

Optical RotationSpecific optical rotation: -193 °C at 25 °C/D
Physical DescriptionSolid
Dissociation Constants · 4건

9.14

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 27 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Fire PotentialThis material is assumed to be combustible. /Moxifloxacin hydrochloride/
FDA Requirements · 1건

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including moxifloxacin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Moxifloxacin hydrochloride/

Toxic Combustion ProductsEmits toxic fumes under fire conditions. /Moxifloxacin hydrochloride/
Hazard Classes and CategoriesAcute Tox. 4 (100%)

안전 및 보호

Fire Fighting ProceduresWater spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials. /Moxifloxacin hydrochloride/
Storage Conditions · 2건

Store at 25 °C (77 °F); excursions permitted to 15-30 °C (59-86 °F)

Store in tight, light-resistant container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity. /Moxifloxacin hydrochloride/

화학 및 산업

약리 정보

ATC Code · 6건

J01MA14

S - Sensory organs

J - Antiinfectives for systemic use

QS - Sensory organs

QJ - Antiinfectives for systemic use

J01MA14

Protein Binding50% bound to serum proteins, independent of drug concentration.
Pharmacodynamics · 1건

Moxifloxacin is a quinolone/fluoroquinolone antibiotic. Moxifloxacin can be used to treat infections caused by the following bacteria: Aerobic Gram-positive microorganisms: _Corynebacterium_ species, _Micrococcus luteus_, _Staphylococcus aureus_, _Staphylococcus epidermidis_, _Staphylococcus haemolyticus_, _Staphylococcus hominis_, _Staphylococcus warneri_, _Streptococcus pneumoniae_, and _Streptococcus viridans_ group. Aerobic Gram-negative microorganisms: _Acinetobacter lwoffii_, _Haemophilus influenzae_, and _Haemophilus parainfluenzae_. Other microorganisms: _Chlamydia trachomatis_. Moxifloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Moxifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria.

Mechanism of Action · 5건

The bactericidal action of moxifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV. DNA gyrase is an essential enzyme that is involved in the replication, transcription and repair of bacterial DNA. Topoisomerase IV is an enzyme known to play a key role in the partitioning of the chromosomal DNA during bacterial cell division.

The fluoroquinolone antibiotic moxifloxacin has been associated with the acquired long QT syndrome and is used as a positive control in the evaluation of the QT-interval prolonging potential of new drugs. In common with other QT-prolonging agents, moxifloxacin is known to inhibit the hERG potassium K+ channel, but at present there is little mechanistic information available on this action. This study was conducted in order to characterise the inhibition of hERG current (I(hERG)) by moxifloxacin, and to determine the role in drug binding of the S6 aromatic amino-acid residues Tyr652 and Phe656. hERG currents were studied using whole-cell patch clamp (at room temperature and at 35-37 degrees C) in an HEK293 cell line stably expressing hERG channels. Moxifloxacin reversibly inhibited currents in a dose-dependent manner. We investigated the effects of different voltage commands to elicit hERG currents on moxifloxacin potency. Using a 'step-ramp' protocol, the IC50 was 65 uM at room temperature and 29 microM at 35 degrees C. When a ventricular action potential waveform was used to elicit currents, the IC50 was 114 microM. Block of hERG by moxifloxacin was found to be voltage-dependent, occurred rapidly and was independent of stimulation frequency. Mutagenesis of the S6 helix residue Phe656 to Ala failed to eliminate or reduce the moxifloxacin-mediated block whereas mutation of Tyr652 to Ala reduced moxifloxacin block by approximately 66%. Our data demonstrate that moxifloxacin blocks the hERG channel with a preference for the activated channel state. The Tyr652 but not Phe656 S6 residue is involved in moxifloxacin block of hERG, concordant with an interaction in the channel inner cavity.

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관련 반응

6건
반응 기록 만들기
HRID 218344 반응식
HRID 218344반응물로uspto-grants-2012_06
HRID 218345 반응식
HRID 218345반응물로uspto-grants-2012_06
HRID 895307 반응식
HRID 895307반응물로uspto-grants-2005_07
HRID 1265944 반응식
HRID 1265944생성물로uspto-grants-2003_04
HRID 1265945 반응식
HRID 1265945생성물로uspto-grants-2003_04
HRID 1766108 반응식
HRID 1766108생성물로uspto-grants-2007_06

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

데이터베이스 식별자

CAS
151096-09-2、186826-86-8、354812-41-2
PubChem CID
152946
DTXSID
DTXSID3048491
ChEMBL
CHEMBL32
ChEBI
CHEBI:63611
UNII
U188XYD42P
EC Number
604-773-0
Nikkaji
J1.495.215B

6.2

6.3

9.3

Collision Cross Section · 3건

210.7 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]

193.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

208.98 Ų [M+Na]+

Other Experimental PropertiesSlightly yellow to yellow crystalline powder, mp 324-325 °C (decomposes), specific optical rotation: -256 °C at 25 °C/D (c = 0.5 in water) /Moxifloxacin hydrochloride/

물리화학적 성질

녹는점
203 · 203-208 C
끓는 점
636.4 · 636.4±55.0 °C(Predicted)
밀도
1.408 · 1.408±0.06 g/cm3(Predicted)
저장 조건
2 · 2-8°C(protect from light)
용해도
아세토니트릴 (약간 용해됨), DMSO(약간 용해됨,가열, 초음파 처리), 메탄올 (약간 용해됨)
산도 계수 (pKa)
6.43 · 6.43±0.50(Predicted)
물리적 상태
고체
색상
황백색에서 밝은 노란색까지
안정성
흡습성
주요 응용
제약
InChIKey
FABPRXSRWADJSP-MEDUHNTESA-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
EPA
3 · 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- (151096-09-2)
Cleanup Methods · 1건

Wear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labelled container for disposal. Wash spill site. /Moxifloxacin hydrochloride/

Disposal Methods · 2건

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

Preventive Measures · 4건

Engineering controls such as exhaust ventilation are recommended. /Moxifloxacin hydrochloride/

As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity. /Moxifloxacin hydrochloride/

As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling. /Moxifloxacin hydrochloride/

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Personal Protective Equipment (PPE) · 1건

Respiratory Protection: Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used. Gloves: Chemically compatible. Eye Protection: Safety glasses or goggles. Protective Clothing: Protect exposed skin. /Moxifloxacin hydrochloride/

독성 정보

Interactions · 5건

Fifteen males and 5 females, mean age of 34 years, were given moxifloxacin under two conditions separated by a minimum 7-day washout period: alone as a single oral 400 mg dose, and immediately following 10 mg of IM morphine sulfate. Moxifloxacin serum concentrations were determined by a validated HPLC procedure. Pharmacokinetic parameters including Cmax, Tmax, AUC0-infinity, and t1/2 were estimated using noncompartmental methods and analyzed using ANOVA. Results: Moxifloxacin pharmacokinetics were similar between the two treatments. Geometric least square mean Cmax, values for moxifloxacin were 3.4 mg (alone) vs 2.8 mg/L (with morphine) (90% confidence interval (CI) of moxifloxacin alone vs with morphine sulfate was 71%-98%). Corresponding geometric mean AUC0-infinity values were 41.5 and 39.6 mgh/L (90% CI = 87%-104%). Tmax and t1/2 values for moxifloxacin were similar when coadministered with morphine. Conclusion: Moxifloxacin was well tolerated when taken with and without morphine sulfate. Administration of a single IM dose of morphine did not reduce the bioavailability or alter the elimination profile of oral moxifloxacin. Implications: Concurrent administration of morphine and moxifloxacin is unlikely to reduce the efficacy of this quinolone.

Pharmacokinetic interaction (decreased absorption of oral moxifloxacin). Moxifloxacin should be given at least 4 hours before or 8 hours after buffered didanosine (pediatric oral solution admixed with antacid).

Concomitant use of corticosteroids increases the risk of severe tendon disorders (e.g., tendinitis, tendon rupture), especially in geriatric patients older than 60 years of age.

Quinolones, including Avelox, have been reported to enhance the anticoagulant effects of warfarin or its derivatives in the patient population. In addition, infectious disease and its accompanying inflammatory process, age, and general status of the patient are risk factors for increased anticoagulant activity. Therefore the prothrombin time, International Normalized Ratio (INR), or other suitable anticoagulation tests should be closely monitored if a quinolone is administered concomitantly with warfarin or its derivatives.

For more Interactions (Complete) data for Moxifloxacin (17 total), please visit the HSDB record page.

Hepatotoxicity · 1건

Moxifloxacin, like other fluoroquinolones, is associated with a low rate (1% to 3%) of serum enzyme elevations during therapy. These abnormalities are generally mild, asymptomatic and transient, resolving even with continuation of therapy. Moxifloxacin has been linked to rare but occasionally severe and even fatal cases of acute liver injury. The time to onset is typically short (1 day to 3 weeks) and the presentation is often abrupt with nausea, fatigue, abdominal pain and jaundice. The pattern of serum enzyme elevations can be either hepatocellular or cholestatic, cases with the shorter times to onset usually being more hepatocellular. In addition, the onset of illness may occur a few days after the medication is stopped. Many (but not all) cases have prominent allergic manifestations with fever and rash, and the liver injury may occur in the context of a generalized hypersensitivity reaction (Case 1). Autoantibodies are usually not present. Cases with a cholestatic pattern of enzymes may run a prolonged course but are usually self-limiting, although at least one case of chronic cholestasis and vanishing bile duct syndrome leading to liver failure has been published. Most reported cases have been mild with recovery within 4 to 8 weeks of onset.

Adverse Effects · 1건

Moxifloxacin is associated with various adverse effects and can result in severe injuries in some cases. The common adverse drug reactions include gastrointestinal symptoms such as nausea, abdominal pain, vomiting, and diarrhea. Patients may experience headaches, dizziness, and, in rare cases, more severe central nervous system (CNS) effects such as confusion or hallucinations. A significant and potentially severe adverse effect of moxifloxacin is the increased risk of tendonitis and tendon rupture, especially in older adults and those concurrently using corticosteroids. Reports indicate that moxifloxacin can lead to changes in heart rhythm (QTc interval prolongation) and an elevated risk of arrhythmias, especially in patients with preexisting heart conditions. Some patients may experience skin rashes, itching, lips, face, and throat swelling due to an allergic reaction to moxifloxacin. Severe allergic reactions such as anaphylaxis are rare but possible. Moxifloxacin has been associated with increased photosensitivity, potentially resulting in heightened susceptibility to sunburn. According to the reports, there are indications of musculoskeletal pain and joint discomfort.

Milk Concentrations · 1건

Moxifloxacin is excreted in the breast milk of rats. Moxifloxacin may also be excreted in human milk. Because of the potential for serious adverse reactions in infants who are nursing from mothers taking Avelox, a decision should be made whether to discontinue nursing or to discontinue the drug, taking into account the importance of the drug to the mother.

Toxicity Summary · 1건

Currently, no specific antidote is available for moxifloxacin overdose. Therefore, treatment focuses primarily on symptom management and essential supportive care, including airway maintenance, oxygen supplementation, and hemodynamic support. Gastric lavage or activated charcoal may be considered to limit further drug absorption, depending on the patient's level of consciousness. If the patient is alert and capable of protecting their airway, gastric lavage or activated charcoal can be used to prevent systemic absorption.

Effluent Concentrations · 1건

The major factor in removal of fluoroquinolone antiobiotics such as moxifloxacin, is sorption to sludge. This along with long-term cycling and persistence of these drugs in the sewage treatment plant has made activated sludge a large reservoir of fluoroquinolone antibiotics(1).

Human Toxicity Excerpts · 5건

/HUMAN EXPOSURE STUDIES/ ... Nine men and 9 women participated in a double-blind, randomized, placebo-controlled, crossover study. Each participant received single oral doses (400 mg and 800 mg) of moxifloxacin or placebo. At the time of expected moxifloxacin maximum concentration, several electrocardiographic recordings were obtained at rest and during the course of a submaximal exercise test. QT interval and the corresponding RR interval value were measured within a wide range of RR intervals in each subject. ANOVA showed that both moxifloxacin doses increased mean QT intervals compared with placebo. The mean QT interval duration at RR = 1000 ms was 379 +/- 24 ms during placebo, 394 +/- 33 ms during moxifloxacin 400 mg (P < .05), and 396 +/- 28 ms during moxifloxacin 800 mg (P < .05). Moxifloxacin-induced QT interval prolongation remained significant at all tested heart rates. The increase in QT interval duration relative to placebo remained between 2.3% +/- 2.8% and 4.5% + 3.8% across the range of RR intervals tested. Moxifloxacin prolongs QT interval duration. The amplitude of this effect is small, and the risk of moxifloxacin-induced torsades de pointes is expected to be minimal when the drug is administered at the recommended dose of 400 mg/d. However, moxifloxacin should not be used in patients with predisposing factors of torsades de pointes such as electrolyte disturbances and bradycardia or during coadministration of proarrhythmic drugs.

/CASE REPORTS/ Torsade de pointes (TdP) is increasingly recognized as a complication of drug therapy. The most common cause of drug-induced QT prolongation is inhibition of the rapidly activating component of the delayed potassium current (I(Kr)). Moxifloxacin, a widely used fluoroquinolone, is a weak I(Kr) inhibitor and has been associated with QT prolongation. ... /The authors/ report a case of marked QT prolongation (618 ms) and TdP associated with moxifloxacin use. Although it is difficult to predict which patients are at risk from TdP, careful assessment of the risk/benefit ratio is important before prescribing drugs known to cause QT prolongation.

/CASE REPORTS/ An 87-year-old woman was admitted to the hospital for pneumonia, and antibiotic therapy with intravenous moxifloxacin 400 mg/day was initiated. The patient was noted to have significant QTc interval prolongation 2 hours after administration of moxifloxacin and developed torsade de pointes 8-10 hours after moxifloxacin administration. She was converted back to normal sinus rhythm after a precordial thump. Moxifloxacin was discontinued, and the woman's QTc interval subsequently returned to baseline.Torsade de pointes is a life-threatening arrhythmia that has previously been associated with the use of fluoroquinolones. ... According to the Naranjo probability scale, the episode in this case was probably related to administration of intravenous moxifloxacin.

/CASE REPORTS/ Torsade de pointes occuring due to a long QT interval is a rare but potentially fatal arrhythmia. Acquired long QT develops most commonly because of drugs that prolong ventricular repolarization. It has been reported that fluoroquinolone antimicrobials prolong the corrected QT interval but rarely cause torsade de pointes. A patient with torsade de pointes risk factors (female sex, advanced age, extreme bradycardia and renal failure) who developed the condition on the fourth day of 400 mg/day of oral moxifloxacin treatment is presented. After the moxifloxacin was stopped, the corrected QT interval normalized and a permanent cardiac pacemaker was implanted. During 11 months of follow-up, arrhythmia did not recur.

Drug Induced Liver Injury · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

moxifloxacin

DILI Positive

Oral

DOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity Excerpts · 5건

/LABORATORY ANIMALS: Acute Exposure/ The purpose of this study was to investigate the effects of moxifloxacin on the QT interval in conscious, healthy dogs. Four male mongrel dogs were chronically instrumented for the measurement of arterial blood pressure, left ventricular blood pressure, cardiac output, electrocardiograms (ECGs), and body temperature. Animals were administered a 1-hr iv infusion of moxifloxacin once per day via a catheter in the cephalic vein. Each dog received all doses (0, 1, 10, 25 and 50 mg/kg) in an escalating fashion. Moxifloxacin caused a statistically significant increase in arterial blood pressure at 50 mg/kg. A dose-response effect on QT and QTc prolongation was observed. A statistically significant prolongation in the QT interval was observed at 10, 25 and 50 mg/kg and a prolongation of QTc was observed at 25 and 50 mg/kg. These effects occurred at clinically relevant plasma concentrations.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Quinolones have been shown to cause arthropathy in immature animals. In studies in juvenile dogs oral doses of moxifloxacin = 30 mg/kg/day (approximately 1.5 times the maximum recommended human dose based upon systemic exposure) for 28 days resulted in arthropathy.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ In an oral pre- and postnatal development study conducted in rats, effects observed at 500 mg/kg/day included slight increases in duration of pregnancy and prenatal loss, reduced pup birth weight and decreased neonatal survival. Treatment-related maternal mortality occurred during gestation at 500 mg/kg/day in this study.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ There was no evidence of teratogenicity when pregnant cynomolgus monkeys were given oral doses as high as 100 mg/kg/day (2.5 times the maximum recommended human dose based upon systemic exposure). An increased incidence of smaller fetuses was observed at 100 mg/kg/day.

For more Non-Human Toxicity Excerpts (Complete) data for Moxifloxacin (7 total), please visit the HSDB record page.

Populations at Special Risk · 5건

No dosage adjustment is recommended for mild, moderate, or severe hepatic insufficiency (Child-Pugh Classes A, B, or C). However, due to metabolic disturbances associated with hepatic insufficiency, which may lead to QT prolongation, Avelox should be used with caution in these patients.

Use of moxifloxacin should be avoided in patients with known prolongation of the QT interval, in those with uncorrected hypokalemia, ... .

Avoid Avelox in patients with known history of myasthenia gravis.

Concomitant use of corticosteroids increases the risk of severe tendon disorders (e.g., tendinitis, tendon rupture), especially in geriatric patients older than 60 years of age.

For more Populations at Special Risk (Complete) data for Moxifloxacin (7 total), please visit the HSDB record page.

Environmental Water Concentrations · 1건

While data specific to moxifloxacin were not located(SRC, 2012), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2). Studies have indicated that several polar pharmaceutically active compounds can leach through soils(1).

Antidote and Emergency Treatment · 5건

In the event of acute overdose ... adequate hydration /should be/ maintained. ECG monitoring is recommended due to the possibility of QT interval prolongation. The patient should be carefully observed and given supportive treatment. The administration of activated charcoal as soon as possible after oral overdose may prevent excessive increase of systemic moxifloxacin exposure. About 3% and 9% of the dose of moxifloxacin, as well as about 2% and 4.5% of its glucuronide metabolite are removed by continuous ambulatory peritoneal dialysis and hemodialysis, respectively.

Emergency and supportive measures: Maintain an open airway and assist ventilation if necessary. Treat coma, seizures, hypotension, anaphylaxis, and hemolysis if they occur. replace fluid losses resulting from gastroenteritis with IV crystalloids. ... /Antibacterial agents/

Decontamination: Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. /Antibacterial agents/

Enhanced elimination: Most antibiotics are excreted unchanged in the urine, so maintenance of adequate urine flow is important. The role of forced diuresis is unclear. Hemodialysis is not usually indicated, except perhaps in patients with renal dysfunction and a high level of a toxic agent. ... /Antibacterial agents/

For more Antidote and Emergency Treatment (Complete) data for Moxifloxacin (7 total), please visit the HSDB record page.

규제 정보

FDA Requirements · 1건

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including moxifloxacin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Moxifloxacin hydrochloride/

안전 데이터

wgk
WGK 2
risk_code
22-40
hazard_code
Xn
safety_code
36/37
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
151096-09-2(Hazardous Substances Data)

The bactericidal action of moxifloxacin results from inhibition of the topoisomerase II (DNA gyrase) and topoisomerase IV required for bacterial DNA replication, transcription, repair, and recombination. It appears that the C8-methoxy moiety contributes to enhanced activity and lower selection of resistant mutants of Gram-positive bacteria compared to the C8-H moiety. The presence of the bulky bicycloamine substituent at the C-7 position prevents active efflux, associated with the NorA or pmrA genes seen in certain Gram-positive bacteria.

Torsade de pointes (TdP) is increasingly recognized as a complication of drug therapy. The most common cause of drug-induced QT prolongation is inhibition of the rapidly activating component of the delayed potassium current (I(Kr)). Moxifloxacin, a widely used fluoroquinolone, is a weak I(Kr) inhibitor and has been associated with QT prolongation.

Fluoroquinolones prolong the QT interval by blocking voltage-gated potassium channels, especially the rapid component of the delayed rectifier potassium current I(Kr), expressed by HERG (the human ether-a-go-go-related gene). According to the available case reports and clinical studies, moxifloxacin carries the greatest risk of QT prolongation from all available quinolones in clinical practice and it should be used with caution in patients with predisposing factors for Torsades de pointes (TdP).

Biological Half-Life · 2건

11.5-15.6 hours (single dose, oral)

The mean (+ or - SD) elimination half-life from plasma is 12 + or - 1.3 hours

Metabolism/Metabolites · 2건

Approximately 52% or oral or intravenous dose is metabolized via glucuronide and sulphate conjugation. The cytochrome P450 system is not involved in metabolism. The sulphate conjugate accounts for 38% of the dose, and the glucuronide conjugate accounts for 14% of the dose.

Approximately 52% of an oral or intravenous dose of moxifloxacin is metabolized via glucuronide and sulfate conjugation. The cytochrome P450 system is not involved in moxifloxacin metabolism, and is not affected by moxifloxacin. The sulfate conjugate (M1) accounts for approximately 38% of the dose, and is eliminated primarily in the feces. Approximately 14% of an oral or intravenous dose is converted to a glucuronide conjugate (M2), which is excreted exclusively in the urine. Peak plasma concentrations of M2 are approximately 40% those of the parent drug, while plasma concentrations of M1 are generally less than 10% those of moxifloxacin.

FDA Pharmacological Classification · 6건

U188XYD42P

MOXIFLOXACIN

Established Pharmacologic Class [EPC] - Fluoroquinolone Antibacterial

Chemical Structure [CS] - Fluoroquinolones

Moxifloxacin is a Fluoroquinolone Antibacterial.

MOXIFLOXACIN

MeSH Pharmacological Classification · 2건

Substances that inhibit the growth or reproduction of BACTERIA.

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.

Absorption, Distribution and Excretion · 6건

Well absorbed from the gastrointestinal tract. Absolute oral bioavailability is approximately 90%. Food has little effect on absorption.

Approximately 45% of an oral or intravenous dose of moxifloxacin is excreted as unchanged drug (~20% in urine and ~25% in feces).

1.7 to 2.7 L/kg

12 +/- 2 L/hr

Moxifloxacin is approximately 30-50% bound to serum proteins, independent of drug concentration. The volume of distribution of moxifloxacin ranges from 1.7 to 2.7 L/kg. Moxifloxacin is widely distributed throughout the body, with tissue concentrations often exceeding plasma concentrations. Moxifloxacin has been detected in the saliva, nasal and bronchial secretions, mucosa of the sinuses, skin blister fluid, subcutaneous tissue, skeletal muscle, and abdominal tissues and fluids following oral or intravenous administration of 400 mg.

Approximately 45% of an oral or intravenous dose of moxifloxacin is excreted as unchanged drug (~20% in urine and ~25% in feces). A total of 96% + or - 4% of an oral dose is excreted as either unchanged drug or known metabolites. The mean (+ or - SD) apparent total body clearance and renal clearance are 12 + or - 2 L/hr and 2.6 + or - 0.5 L/hr, respectively.

Cellular LocationsCytoplasm

용도 및 제조

Uses · 2건

MEDICATION

Use (kg; approx.) in Germany (2009): >2500

Methods of ManufacturingPreparation: U. Petersen et al., EP 550903 (1993 to Bayer)
Formulations/Preparations · 4건

Table: Moxifloxacin Hydrochloride Preparations [Table#7970]

Ophthalmic: Solution: 0.5% (of moxifloxacin) Vigamox (Alcon). /Moxifloxacin hydrochloride/

Moxeza

Vigamox

Use ClassificationPharmaceuticals

응용 분야

용도Moxifloxacin is an antibiotic for the treatment of bacterial infections like bacterial sinusitis, acute bacterial exacerbations of chronic bronchitis, and community-acquired pneumonia.

상·하류 제품 정보

상류 원료

노르말옥탄Quinoline-3-carboxylic acidClotrimazole무수초산DiethylstilbestrolmonomethyletherPyridine-2-3-DicarboxylicAcid-N-Benzylimide황산피리딘2Ethylene glycol시안화 제I구리마그네슘에틸레이트염화제2철6수화물Palladium hydroxide염화 티오닐시클로프로필아민오소포름산에틸불화소다P-톨루엔설폰 산말론산 디에틸수산화칼륨중탄산나트륨(중조)아세트산(빙초산)
추가 설명 · 1건

정의ChEBI: A quinolone that consits of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b /ital>]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.

For more Human Toxicity Excerpts (Complete) data for Moxifloxacin (11 total), please visit the HSDB record page.