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354812-41-2 molecular structure
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7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

ChemBase ID: 103
Molecular Formular: C21H24FN3O4
Molecular Mass: 401.4313632
Monoisotopic Mass: 401.17508448
SMILES and InChIs

SMILES:
Fc1c(N2C[C@H]3[C@H](NCCC3)C2)c(OC)c2n(C3CC3)cc(c(=O)c2c1)C(=O)O
Canonical SMILES:
COc1c(N2C[C@@H]3[C@H](C2)CCCN3)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1
InChI:
InChI=1S/C21H24FN3O4/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)/t11-,16+/m0/s1
InChIKey:
FABPRXSRWADJSP-MEDUHNTESA-N

Cite this record

CBID:103 http://www.chembase.cn/molecule-103.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
7-[(4aS,7aS)-octahydro-1H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
IUPAC Traditional name
moxifloxacin
Brand Name
Avelox
Avelox I.V.
Vigamox
Synonyms
Moxifloxacin HCl
Moxifloxacin hydrochloride
BAY 12-8039
moxifloxacin
Moxifloxacin
CAS Number
354812-41-2
151096-09-2
PubChem SID
160963566
46508509
PubChem CID
152946

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 5.6861296  H Acceptors
H Donor LogD (pH = 5.5) -0.79074246 
LogD (pH = 7.4) -0.4932184  Log P -0.49897495 
Molar Refractivity 106.224 cm3 Polarizability 39.591274 Å3
Polar Surface Area 82.11 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.01  LOG S -3.38 
Solubility (Water) 1.68e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Product Information Bioassay(PubChem)
Hydrophobicity(logP)
2.9 expand Show data source
Purity
97% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00218 external link
Item Information
Drug Groups approved; investigational
Description Moxifloxacin is a synthetic fluoroquinolone antibiotic agent. Bayer AG developed the drug (initially called BAY 12-8039) and it is marketed worldwide (as the hydrochloride) under the brand name Avelox (in some countries also Avalox) for oral treatment.
Indication For the treatment of sinus and lung infections such as sinusitis, pneumonia, and secondary infections in chronic bronchitis. Also for the treatment of bacterial conjunctivitis (pinkeye).
Pharmacology 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.
Toxicity Symptoms of overdose include CNS and gastrointestinal effects such as decreased activity, somnolence, tremor, convulsions, vomiting, and diarrhea. The minimal lethal intravenous dose in mice and rats is 100 mg/kg.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation 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.
Absorption Well absorbed from the gastrointestinal tract. Absolute oral bioavailability is approximately 90%. Food has little effect on absorption.
Half Life 11.5-15.6 hours (single dose, oral)
Protein Binding 50% bound to serum proteins, independent of drug concentration.
Elimination Approximately 45% of an oral or intravenous dose of moxifloxacin is excreted as unchanged drug (~20% in urine and ~25% in feces).
Distribution * 1.7 to 2.7 L/kg
Clearance * 12 +/- 2 L/hr
References
Ginsburg AS, Hooper N, Parrish N, Dooley KE, Dorman SE, Booth J, Diener-West M, Merz WG, Bishai WR, Sterling TR: Fluoroquinolone resistance in patients with newly diagnosed tuberculosis. Clin Infect Dis. 2003 Dec 1;37(11):1448-52. Epub 2003 Nov 4. [Pubmed]
External Links
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PDRhealth
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REFERENCES

REFERENCES

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  • • Ginsburg AS, Hooper N, Parrish N, Dooley KE, Dorman SE, Booth J, Diener-West M, Merz WG, Bishai WR, Sterling TR: Fluoroquinolone resistance in patients with newly diagnosed tuberculosis. Clin Infect Dis. 2003 Dec 1;37(11):1448-52. Epub 2003 Nov 4. Pubmed
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PATENTS

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