Details
Stereochemistry | RACEMIC |
Molecular Formula | C7H11N3O3 |
Molecular Weight | 185.1805 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)CN1C(C)=NC=C1[N+]([O-])=O
InChI
InChIKey=KPQZUUQMTUIKBP-UHFFFAOYSA-N
InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3
Molecular Formula | C7H11N3O3 |
Molecular Weight | 185.1805 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Secnidazole (trade names Flagentyl, Sindose, Solosec) is a nitroimidazole derivative used to in the treatment of amoebiasis and bacterial vaginosis. Secnidazole and other 5-nitroimidazole drugs enter micro-organisms by passive diffusion and undergo activation by reduction of the 5-nitro group. In anaerobic micro-organisms, such as Trichomonas, Giardia and Entamoeba spp., this intracellular reduction occurs via the pyruvate ferredoxin oxidoreductase complex and results in a concentration gradient across the cell membrane which, in tum, enhances transport of the parent drug into the cell. Because the electron affinity of the 5-nitroimidazoles is greater than that of reduced ferredoxin, the drug interrupts the normal electron flow. Aerobic micro-organisms have a more positive redox potential (i.e. are more efficient electron acceptors) than secnidazole and other 5-nitroimidazoles, which explains the selective toxicity of these drugs against anaerobic microorganisms. DNA is the intracellular target of the Secnidazole and other 5-nitroimidazoles. Secnidazole and other 5-nitroimidazoles possess selective activity against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. In general, secnidazole and metronidazole were approximately equipotent in activity against Bacteroides fragilis, Trichomonas vaginalis, and Entamoeba histolytica, in in vitro studies. Secnidazole is rapidly and completely absorbed after oral administration. Plasma drug concentrations are linear over the therapeutic dose range of 0.5 to 2g. The tolerability profile of secnidazole does not differ markedly from other 5-nitroimidazoles. The most commonly reported adverse events in clinical trials involved the gastrointestinal tract (nausea, vomiting, glossitis, anorexia, epigastric pain and a metallic taste) and occurred in 2 to 10% of patients. A headache and dizziness were experienced by about 2% of patients. The drug was equally well tolerated in adults and children, and no adverse event required therapeutic intervention or treatment withdrawal.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL612884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18590939 |
810.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Solosec Approved UseUnknown |
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Curative | Solosec Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45.4 μg/mL |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
SECNIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1410 μg × h/mL |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
SECNIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
17.6 h |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
SECNIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
95% |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
SECNIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
2 g single, oral Recommended Dose: 2 g Route: oral Route: single Dose: 2 g Sources: Page: Table 1 |
unhealthy, 15 - 54 years n = 197 Health Status: unhealthy Condition: bacterial vaginosis Age Group: 15 - 54 years Sex: F Population Size: 197 Sources: Page: Table 1 |
Other AEs: Vulvovaginal candidiasis, Headache... Other AEs: Vulvovaginal candidiasis (9.6%) Sources: Page: Table 1Headache (3.6%) Nausea (3.6%) Diarrhea (2.5%) Abdominal pain (2%) Vulvovaginal pruritus (2%) |
1 g single, oral Studied dose Dose: 1 g Route: oral Route: single Dose: 1 g Sources: Page: 6.1 |
unhealthy, 15 - 54 years n = 71 Health Status: unhealthy Condition: bacterial vaginosis Age Group: 15 - 54 years Sex: F Population Size: 71 Sources: Page: 6.1 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abdominal pain | 2% | 2 g single, oral Recommended Dose: 2 g Route: oral Route: single Dose: 2 g Sources: Page: Table 1 |
unhealthy, 15 - 54 years n = 197 Health Status: unhealthy Condition: bacterial vaginosis Age Group: 15 - 54 years Sex: F Population Size: 197 Sources: Page: Table 1 |
Vulvovaginal pruritus | 2% | 2 g single, oral Recommended Dose: 2 g Route: oral Route: single Dose: 2 g Sources: Page: Table 1 |
unhealthy, 15 - 54 years n = 197 Health Status: unhealthy Condition: bacterial vaginosis Age Group: 15 - 54 years Sex: F Population Size: 197 Sources: Page: Table 1 |
Diarrhea | 2.5% | 2 g single, oral Recommended Dose: 2 g Route: oral Route: single Dose: 2 g Sources: Page: Table 1 |
unhealthy, 15 - 54 years n = 197 Health Status: unhealthy Condition: bacterial vaginosis Age Group: 15 - 54 years Sex: F Population Size: 197 Sources: Page: Table 1 |
Headache | 3.6% | 2 g single, oral Recommended Dose: 2 g Route: oral Route: single Dose: 2 g Sources: Page: Table 1 |
unhealthy, 15 - 54 years n = 197 Health Status: unhealthy Condition: bacterial vaginosis Age Group: 15 - 54 years Sex: F Population Size: 197 Sources: Page: Table 1 |
Nausea | 3.6% | 2 g single, oral Recommended Dose: 2 g Route: oral Route: single Dose: 2 g Sources: Page: Table 1 |
unhealthy, 15 - 54 years n = 197 Health Status: unhealthy Condition: bacterial vaginosis Age Group: 15 - 54 years Sex: F Population Size: 197 Sources: Page: Table 1 |
Vulvovaginal candidiasis | 9.6% | 2 g single, oral Recommended Dose: 2 g Route: oral Route: single Dose: 2 g Sources: Page: Table 1 |
unhealthy, 15 - 54 years n = 197 Health Status: unhealthy Condition: bacterial vaginosis Age Group: 15 - 54 years Sex: F Population Size: 197 Sources: Page: Table 1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000PharmR.pdf#page=13 Page: 24.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Randomized trial of a quadruple-drug regimen and a triple-drug regimen for eradication of Helicobacter pylori: long-term follow-up study. | 2001 Sep-Oct |
|
Pre and post eradication gastric inflammation in Helicobacter pylori-associated duodenal ulcer. | 2002 Jan-Feb |
|
A randomized trial comparing mebendazole and secnidazole for the treatment of giardiasis. | 2003 Jul |
|
Spectrophotometric determination of metronidazole and secnidazole in pharmaceutical preparations. | 2004 Oct |
|
Prescription of fixed dose combination drugs for diarrhoea. | 2007 Oct-Dec |
|
Formulation and evaluation of PLA and PLGA in situ implants containing secnidazole and/or doxycycline for treatment of periodontitis. | 2008 |
|
Formulation and evaluation of secnidazole or doxycycline dento-oral gels. | 2008 Dec |
|
The concept of personal drugs in the undergraduate pharmacology practical curriculum. | 2008 Nov |
|
The old and new therapeutic approaches to the treatment of giardiasis: where are we? | 2009 |
|
[In vitro effect of secnidazole benzoate on Trichomonas vaginalis]. | 2009 Apr |
|
Formulation and in vitro evaluation of in situ gels containing secnidazole for vaginitis. | 2009 May |
|
Impact of anti-Giardia and anthelminthic treatment on infant growth and intestinal permeability in rural Bangladesh: a randomised double-blind controlled study. | 2009 May |
|
Comparison of azithromycin and metronidazole in a quadruple-therapy regimen for Helicobacter pylori eradication in dyspepsia. | 2009 Oct-Dec |
|
Infectious diseases and prematurity. | 2010 |
|
Treatment of bacterial vaginosis: a multicenter, double-blind, double-dummy, randomised phase III study comparing secnidazole and metronidazole. | 2010 |
|
Fixed drug eruption with ornidazole having cross-sensitivity to secnidazole but not to other nitro-imidazole compounds: a case report. | 2010 Jun |
|
In vitro activity of secnidazole against Atopobium vaginae, an anaerobic pathogen involved in bacterial vaginosis. | 2010 May |
|
A meta-analysis of the effectiveness of albendazole compared with metronidazole as treatments for infections with Giardia duodenalis. | 2010 May 11 |
|
[Using safocid for antibiotic prophylaxis in minimally-invasive endoscopic operations and manipulations]. | 2010 Nov-Dec |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02452866
Curator's Comment: http://reference.medscape.com/drug/formulary/solosec-secnidazole-1000168#0
2g as single-dose oral dose
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18590939
In vitro toxicity of nitroimidazoles was assessed on human monocytes (THP1 cells) maintained at 37 C in 6% CO2, in a medium of RPMI (Eurobio, Paris, France) supplemented with 10% foetal calf serum (Eurobio, Paris, France), 25 mM of HEPES, 25 mM of NaHCO3 (Gibco-BRL, Paisley, Scotland), and 1% of L-glutamine/penicillinestreptomycin mix. THP1 cell (105 cells/mL) were incubated with different concentrations of Secnidazole dissolved in DMSO. A viability control free of drug and a control containing DMSO (final concentration of 0.5%) were performed in parallel. After a 72 h-incubation at 37 C and 6% CO2 in complete RPMI medium, cell growth and viability were measured by flow cytometry after staining the monocytes by 5 mL of propidium iodide (1 mg/mL)
Substance Class |
Chemical
Created
by
admin
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Edited
Fri Dec 15 15:41:57 GMT 2023
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Record UNII |
R3459K699K
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Record Status |
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N0000175435
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2427
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C016724
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BINDER->LIGAND |
BINDING
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PARENT -> METABOLITE |
URINE
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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