Secnidazole is a second-generation 5-nitroimidazole antibiotic and analog of metronidazole. It has in vitro activity against anaerobic bacteria and can be used in research for trichomoniasis, amoebiasis, giardiasis, and bacterial vaginosis. The compound is structurally related to metronidazole and tinidazole. Secnidazole is a 'prodrug' thus bacterial enzymes reduce its nitro group to radical anions that interfere with bacterial DNA synthesis.
Secnidazole is freely soluble in methanol, ethanol, acetone and chloroform.
| Mechanism of Action |
Similar to other 5-nitroimidazoles, the antimicrobial properties are due to the nitro group in the imidazole ring. Once it enters the bacteria or parasite, it is activated by host nitroreductase enzymes to form radical anions and reactive intermediates. These cause damage to the DNA helix, disrupt protein synthesis/replication, adn ultimately cell death. It can inhibit quorum sensing (QS) thus it can attenuate the pathogenesis of Pseudomonas aeruginosa. |
| Spectrum | Secnidazole has broad spectrum vitro antimicrobial activity. Gram-positive and Gram-negative bacteria, along with protozoa are susceptible. |
| Eukaryotic Cell Culture Applications | Secnidazole was cultured with human hepatocytes to assess metabolic profiling, and was found the agent has minimal to no potential in vitro interactions with other compounds. |
| Molecular Formula | C7H11N3O3 |
| References |
Hernández-Mesa M, D'Orazio G, Rocco A, García-Campaña AM, Blanco CC, Fanali S. Capillary electrochromatography-mass spectrometry for the determination of 5-nitroimidazole antibiotics in urine samples. Electrophoresis. 2015 Oct;36(20):2606-15. doi: 10.1002/elps.201500126. Epub 2015 Sep 8. PMID: 26200811 Pentikis HS, Adetoro N, Kaufman G (2020) In vitro metabolic profile and drug-drug interaction assessment of Secnidazole, a high-dose 5-nitroimidazole antibiotic for the treatment of bacterial vaginosis. Pharmacol Res Perspect. 8(4):e00634. PMID: 32776491 |
| MIC | Aggregatibacter actinomycetemcomitans| 32|| Bacillus circulans| 0.125 － >32|| Bacillus subtilis (PCI219)| >200|| Bacteroides bivius| 2|| Bacteroides caccae| 0.5 － 16|| Bacteroides capillosus | ≤0.03 － 4|| Bacteroides disiens| 0.25 － 2|| Bacteroides distasonis| 0.25 － 4|| Bacteroides eggerthii (ATCC 27754)| ≥0.5|| Bacteroides forsythus| ≤6.2 － 12.5|| Bacteroides fragilis| ≤0.06 － >128|| Bacteroides melaninogenicus| 0.25 － 2|| Bacteroides merdae| 0.5 － 4|| Bacteroides oralis | 0.25 － 2|| Bacteroides ovatus| 0.25 － 4|| Bacteroides pneumosintes| ≥1|| Bacteroides ruminicola subsp. brevis| 0.25 － 2|| Bacteroides tectum | 0.125 － 2|| Bacteroides thetaiotaomicron| ≤0.062 － 4|| Bacteroides uniformis| 0.25 － 4|| Bacteroides ureolyticus| ≤0.03 － ≤6.2 || Bacteroides vulgatus| 0.12 － >128|| Bacteroides xylanisolvens | ≥0.25|| Bifidobacterium adolescentis| 16 - 32|| Bifidobacterium bifidum| 4 - 64|| Bifidobacterium breve| 0.125 － >32|| Bifidobacterium longum| 0.125 － >32|| Bifidobacterium longum| ≥8|| Bifidobacterium pseudolongum| 16 - >128|| Bifidobacterium spp.| >0.16 - >16|| Bilophila wadsworthia| 0.06 － >128|| Campylobacter coli| ≤0.12 － ≥64|| Campylobacter concisus| 0.25 － 4|| Campylobacter gracilis| 0.25 － 4|| Campylobacter helveticus| ≥16|| Campylobacter jejuni | 0.25 － >64|| Campylobacter mucosalis| 0.25 － 4|| Campylobacter rectus| 0.25 － 4|| Campylobacter showae| 0.25 － 4|| Campylobacter sputorum| 0.25 － 4|| Capnocytophaga ochracea | ≤0.03 － 4|| Capnocytophaga spp.| 16 － >32|| Citrobacter freundii (IFO 12681)| ≥128|| Clostridium baratii| 0.25 － 2|| Clostridium bifermentans| 0.02 － 2|| Clostridium butyricum| 0.02 － >128|| Clostridium cadaveris| 0.02 － 2|| Clostridium clostridioforme| 0.02 － >128|| Clostridium cochlearium| 0.02 － 2|| Clostridium difficile| 0.0039 －>8|| Clostridium fallax| 0.02 － 2|| Clostridium glycolicum| 0.02 － 2|| Clostridium hastiforme| ≤0.125 － 2|| Clostridium histolyticum | ≤0.125 － 1|| Clostridium innocuum| 0.12 － 2|| Clostridium malenominatum| 0.02 － 2|| Clostridium novyi| 0.02 － 2|| Clostridium oroticum| 0.02 － 2|| Clostridium paraputrificum| 0.02 － 2|| Clostridium perfringens| 0.06 － >128|| Clostridium ramosum| 0.12 － >128|| Clostridium septicum| 0.12 － >128|| Clostridium sordellii| 0.12 － 2|| Clostridium sp.| ≥0.5|| Clostridium species| 41276|| Clostridium spiroforme| 0.063 － 0.125|| Clostridium sporogenes| 0.12 － >128|| Clostridium spp.| 0.015 － >128|| Clostridium subterminale| ≥0.5|| Clostridium tertium| ≤0.125 － 2|| Collinsella aerofaciens| ≤0.03 － 2|| Desulfovibrio piger (DSM 749)| ≥0.25|| Dialister pneumosintes | ≤0.03 － 4|| Eggerthella lenta| 0.25 － 0.5|| Eikenella corrodens| 8 － >64|| Entamoeba histolytica| 2 － <2.5|| Enterobacter cloacae| ≥128|| Enterococcus avium| ≥1024|| Enterococcus faecalis| >128 － ≥1024|| Enterococcus faecium| ≥1024|| Escherichia coli| >8 － >200|| Eubacterium| 0.12 － >64|| Eubacterium aerofaciens | ≥16|| Eubacterium alactolyticum| ≥0.5|| Eubacterium brachy| 0.02 － 1|| Eubacterium combesii| 0.02 － 1|| Eubacterium contortum| 0.02 － 1|| Eubacterium lentum| 0.02 － >16|| Eubacterium limosum| 0.02 － >64|| Eubacterium nodatum| 0.12 － >64|| Eubacterium saburreum| 0.02 － 1|| Eubacterium spp.| ≤0.03 － >128|| Eubacterium tenue| 0.02 － 1|| Eubacterium timidum| 0.02 － 2|| Eubacterium yurii| 0.02 － 2|| Finegoldia magna| 0.094 － 2|| Fusobacteria| ≤0.125 － 1|| Fusobacterium glutinosum| ≥16|| Fusobacterium gonidiaformans | 0.125 － 4|| Fusobacterium mortiferum| 0.06 － >128|| Fusobacterium naviforme| ≤0.03 － 4|| Fusobacterium necrogenes | 0.125 － 1|| Fusobacterium necrophorum| 0.06 － >128|| Fusobacterium nucleatum| 0.016 － >128|| Fusobacterium russii | ≤0.015 － 0.25|| Fusobacterium spp.| 0.008 － >128|| Fusobacterium ulcerans | 0.125 － 1|| Fusobacterium varium| 0.06 － >128|| Gardnerella vaginalis| ≤0.25 － >32|| Gemella morbillorum| ≥16|| Giardia duodenalis| ≥8.5|| Helicobacter bilis| ≥2|| Helicobacter mustelae| ≥4|| Helicobacter pullorum| ≥16|| Helicobacter pylori| 0.125 － 256|| Klebsiella pneumonia| >128 － >200|| Lactobacillus acidophilus| 0.5 － >1000|| Lactobacillus brevis| 0.5 － >32|| Lactobacillus casei| 0.5 － >32|| Lactobacillus catenaforme| 0.125 － >32|| Lactobacillus delbrueckii| 0.125 － >32|| Lactobacillus fermentans| 0.5 － >32|| Lactobacillus fermentum| ≥16|| Lactobacillus gasseri | ≥1000|| Lactobacillus jensenii| 0.12 － >64|| Lactobacillus johnsonii| ≥1000|| Lactobacillus minutus| 0.5 － >32|| Lactobacillus oris| 0.125 － >32|| Lactobacillus paracasei| ≥1000|| Lactobacillus plantarum| 0.125 － >32|| Lactobacillus reuteri| ≥16|| Lactobacillus rhamnosus| 0.5 － >32|| Lactobacillus salivarius| >16 － >1000|| Lactobacillus sp.| 0.12 － >128|| Leptotrichia buccalis| ≤0.03 － 2|| Micromonas micros| 0.12 － 2|| Moraxella catarrhalis| ≥4|| Morganella morganii| >128 － >200|| Olsenella uli| 0.125 － >32|| Parvimonas micra| 0.032 － >256|| Peptococcus asaccharolyticus| 0.5 － 1|| Peptococcus magnus | 0.125 － 2|| Peptococcus niger| ≤6.2|| Peptococcus sp.| 0.25 － 2|| Peptoniphilus asaccharolyticus| ≤0.125 － 2|| Peptoniphilus gorbachii | 0.023 － 0.5|| Peptoniphilus harei | 0.032 － 2|| Peptoniphilus indolicus (GAI 0915)| ≥0.5|| Peptoniphilus ivorii | 0.094 － 0.25|| Peptoniphilus lacrimalis | 0.023 － 0.38|| Peptoniphilus octavius | ≥0.38|| Peptostreptococcus| 0.12 － 2|| Peptostreptococcus anaerobius| 0.12 － >128|| Peptostreptococcus asaccharolyticus| 0.12 － >16|| Peptostreptococcus magnus| 0.06 － >128|| Peptostreptococcus micros| 0.06 － >128|| Peptostreptococcus prevotii| ≤0.062 － >16|| Peptostreptococcus spp.| ≤0.03 － >128|| Peptostreptococcus tetradius| ≤0.125 － >16|| Porphyromonas| 0.125 － 8|| Porphyromonas asaccharolytica| ≤0.015 － 12.5|| Porphyromonas cangingivalis | ≤0.015 － 0.25|| Porphyromonas canoris | ≤0.015 － 0.5|| Porphyromonas cansulci | ≤0.015 － 0.25|| Porphyromonas circumdentaria | ≤0.015 － 0.25|| Porphyromonas endodontalis | ≤0.03 － 4|| Porphyromonas gingivalis| ≤0.03 － 4|| Porphyromonas levii | ≤0.015 － 0.25|| Porphyromonas macacae | ≤0.015 － 0.125|| Porphyromonas spp.| ≤0.125 － >128|| Prevotella bivia| 0.12 － >16|| Prevotella buccae| 0.06 － >128|| Prevotella buccalis| 0.06 － ≤6.2|| Prevotella corporis | ≤0.03 － 2|| Prevotella dentalis | 0.06 － 2|| Prevotella denticola| ≤0.03 － 4|| Prevotella disiens| 0.06 － 4|| Prevotella heparinolytica | 0.06 － 1|| Prevotella intermedia| 0.03 － >128|| Prevotella loescheii| ≤0.03 － ≤6.2|| Prevotella melaninogenica| ≤0.03 － 4|| Prevotella melaninogenicus | 0.12 － >128|| Prevotella nigrescens| 0.06 － 2|| Prevotella oralis| 0.06 － >128|| Prevotella oris| 0.06 － 4|| Prevotella pallens | 0.06 － 2|| Prevotella spp.| 0.06 － >128|| Prevotella tannerae | ≤0.03 － 2|| Prevotella zooglioformans | 0.06 － 2|| Prevotella/Porphyromonas spp.| ≤0.125 － 2|| Propionibacteria| >16|| Propionibacterium| 0.12 － >64|| Propionibacterium acnes| ≥16|| Propionibacterium avidum| 0.125 － >32|| Propionibacterium granulosum| 8 － >200|| Propionibacterium propionicus| 8 － >32|| Propionibacterium spp.| ≥16|| Proteus mirabilis| ≥200|| Proteus vulgaris| 64 － >200|| Providencia rettgeri| ≥200|| Pseudomonas aeruginosa | >128 － >200|| Ruminococcus gnavus| ≥0.094|| Selenomonas flueggei | ≤0.03 － 4|| Selenomonas infelix | ≤0.03 － 4|| Selenomonas spp.| ≤0.03 － 4|| Serratia marcescens| >128 － >200|| Staphylococcus aureus| 2 － >1024|| Staphylococcus epidermidis| 4 － >1024|| Staphylococcus saccharolyticus| ≥16|| Streptococcus constellatus| ≥16|| Streptococcus intermedius| ≥16|| Streptococcus pneumonia| ≥128|| Sutterella wadsworthensis| 0.25 － >128|| Treponema hyodysenteriae | ≤0.1 － 0.39|| Veillonella dispar | 2|| Veillonella parvula| 0.12 － >128|| Veillonella spp.| 0.12 － >128|| Xanthomonas campestris| 512|| |