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
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 |
|
Nitroheterocyclic drugs with broad spectrum activity. | 2003 Jun |
|
Probing NMR parameters, structure and dynamics of 5-nitroimidazole derivatives. Density functional study of prototypical radiosensitizers. | 2005 Feb |
|
Impact of treatment for bacterial vaginosis on prematurity among Brazilian pregnant women: a retrospective cohort study. | 2005 May 2 |
|
Comparative efficacy of two regimens in syndromic management of lower genital infections. | 2006 Jan |
|
Amoebic dysentery. | 2007 Jan 1 |
|
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 |
|
[Efficacy of 5-nitroimidazole derivatives in treatment of bacterial vaginosis]. | 2008 Aug 12 |
|
The old and new therapeutic approaches to the treatment of giardiasis: where are we? | 2009 |
|
Molecular structure and vibrational spectroscopic investigation of secnidazole using density functional theory. | 2009 Jan 8 |
|
Prevalence and chemotherapy of Balantidium coli in cattle in the River Ravi region, Lahore (Pakistan). | 2009 Jul 7 |
|
Formulation and in vitro evaluation of in situ gels containing secnidazole for vaginitis. | 2009 May |
|
Comparison of azithromycin and metronidazole in a quadruple-therapy regimen for Helicobacter pylori eradication in dyspepsia. | 2009 Oct-Dec |
|
Preparation and characterization of a molecularly imprinted monolithic column for pressure-assisted CEC separation of nitroimidazole drugs. | 2010 Aug |
|
[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)
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NDF-RT |
N0000175435
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
||
|
WHO-ATC |
J01RA07
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
||
|
WHO-ATC |
P01AB07
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
R3459K699K
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
71815
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
222-134-0
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
36314
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | RxNorm | ||
|
2427
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
C016724
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
Secnidazole
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
CD-159
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
SUB126102
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
DTXSID3045934
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
3506
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
R3459K699K
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
100000084084
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
759812
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
SUB10467MIG
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
DB12834
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
140628
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
CHEMBL498847
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
C66529
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
SECNIDAZOLE
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
3366-95-8
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | |||
|
m9826
Created by
admin on Fri Dec 15 15:41:57 UTC 2023 , Edited by admin on Fri Dec 15 15:41:57 UTC 2023
|
PRIMARY | Merck Index |
ACTIVE MOIETY
PARENT (METABOLITE)