Morinidazole
[R,S-1-(2-methyl-5-nitro-1H-imidazol-1-yl)-3-morpholinopropan-2-ol]
is a 5-nitroimidazole antimicrobial injection with potent activities against
anaerobic Gram-negative sporeless bacilli and Gram-positive cocci. Morinidazole is a novel third generation 5-nitroimidazole-class
antimicrobial agent indicated for the treatment of amoebiasis and anaerobic bacterial
infections including appendicitis and pelvic inflammatory disease [1].
Its
efficacy against Clostridium perfringens,
Bacteroides fragilis, Veillonella parvula, Bacteroides distasonis, Bacteroides
ovatus, Bacteroides vulgatus, and Bacteroides melaninogenicus is equal to
that of ornidazole and superior to those of metronidazole and tinidazole.
Morinidazole has
been approved for the treatment of amoebiasis, trichomoniasis, and anaerobic
bacterial infections in China.
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| Morinidazole: 2D and 3D Structure |
Mechanism of Action
Dosages
and Approvals
Morinidazole,
discovered and developed by Jiangsu Hansoh Pharmaceutical, was approved by the
CFDA in February 2014. The recommended dose is 500 mg (100 mL injection) twice
daily every 6-8 hours continuously for 5-7 days.
Summary
Common name: Morinidazole
Trademarks: -
Molecular Formula: C11H18N4O4
CAS Registry Number: 92478-27-8
CAS Name:R,S-1-(2-methyl-5-nitro-1H-imidazol-1-yl)-3-morpholinopropan-2-ol
Molecular Weight: 270.29
SMILES: OC(CN1CCOCC1)CN2C([N+]([O-])=O)=CN=C2
InChI Key: GAZGHCHCYRSPIV-UHFFFAOYSA-N
InChI: InChI=1S/C11H18N4O4/c1-9-12-6-11(15(17)18)14(9)8-10(16)7-13-2-4-19-5-3-13/h6,10,16H,2-5,7-8H2,1H3C
Mechanism of Action: Antimicrobial
Activity via Nitroreduction
Activity: Treatment of Amoebiasis; Treatment of
Trichomoniasis; Treatment of Anaerobic Bacterial Infections; Antimicrobial
Agents
Status: Launched 2014 (China)
Chemical Class: 5-Nitroimidazole; Small-molecules;
Imidazoles; Nitro containing; Hydroxyl containing; Morpholine containing
Originator: Jiangsu Hansoh
Pharmaceutical
Morinidazole
Synthesis
WO2006058457A1:
It appears to be the industrial process.
Identifications:
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| 1H NMR (Estimated) for Morinidazole |
Experimental: 1H NMR (CD3Cl)
δ 2.57 (3H, S) δ 4.25~4.35 (2H, m) δ 4.84~4.71 (3H, m) δ 7.92 (1H, S)
References:
1. Gao, R.; et. al. Metabolism and pharmacokinetics of morinidazole in humans: identification of diastereoisomeric morpholine N+-glucuronides catalyzed by UDP glucuronosyltransferase 1A9. Drug Metab Dispos 2012, 40(3), 556-67. (free copy)2. Kedderis, G. L.; et. al. Covalent interaction of 5-nitroimidazoles with DNA and protein in vitro: mechanism of reductive activation. Chem Res Toxicol 1989, 2(3), 146-9. (FMO only)
3. Cen, J.; et. al. Alpha-substituted 2-methyl-5-nitroimidazol-1-ethanol derivatives. WO2006058457
