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 |
|||
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 |
---|---|---|
Ciprofloxacin-tinidazole combination, fluconazole- azithromicin-secnidazole-kit and doxycycline- metronidazole combination therapy in syndromic management of pelvic inflammatory disease: a prospective randomized controlled trial. | 2003 Dec |
|
Dientamoeba fragilis, a neglected cause of diarrhea, successfully treated with secnidazole. | 2003 Feb |
|
Nitroheterocyclic drugs with broad spectrum activity. | 2003 Jun |
|
[New drugs for the treatment of human parasitic protozoa]. | 2004 Jun |
|
Comparative efficacy of two regimens in syndromic management of lower genital infections. | 2006 Jan |
|
Simultaneous determination of seven nitroimidazole residues in meat by using HPLC-UV detection with solid-phase extraction. | 2007 Oct 1 |
|
Prescription of fixed dose combination drugs for diarrhoea. | 2007 Oct-Dec |
|
Oh my aching gut: irritable bowel syndrome, Blastocystis, and asymptomatic infection. | 2008 Oct 21 |
|
Validated method for determination of eight banned nitroimidazole residues in natural casings by LC/MS/MS with solid-phase extraction. | 2009 Mar-Apr |
|
Formulation and in vitro evaluation of in situ gels containing secnidazole for vaginitis. | 2009 May |
|
Infectious diseases and prematurity. | 2010 |
|
A meta-analysis of the effectiveness of albendazole compared with metronidazole as treatments for infections with Giardia duodenalis. | 2010 May 11 |
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
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admin
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Edited
Fri Dec 15 15:41:57 UTC 2023
by
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on
Fri Dec 15 15:41:57 UTC 2023
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Record UNII |
R3459K699K
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Record Status |
Validated (UNII)
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Record Version |
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N0000175435
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J01RA07
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P01AB07
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R3459K699K
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71815
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222-134-0
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36314
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2427
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C016724
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Secnidazole
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CD-159
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R3459K699K
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SUB10467MIG
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DB12834
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CHEMBL498847
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C66529
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SECNIDAZOLE
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3366-95-8
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m9826
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PRIMARY | Merck Index |
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
URINE
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Related Record | Type | Details | ||
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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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