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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
Structure of SECNIDAZOLE

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

HIDE SMILES / InChI

Molecular Formula C7H11N3O3
Molecular Weight 185.1805
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
810.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Solosec
Primary
Solosec
PubMed

PubMed

TitleDatePubMed
Amoebic dysentery.
2007 Jan 1
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
Prevalence and chemotherapy of Balantidium coli in cattle in the River Ravi region, Lahore (Pakistan).
2009 Jul 7
Validated method for determination of eight banned nitroimidazole residues in natural casings by LC/MS/MS with solid-phase extraction.
2009 Mar-Apr
A Stability-Indicating RP-HPLC Assay Method for 5-Fluorouracil.
2009 Nov
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
Preparation and characterization of a molecularly imprinted monolithic column for pressure-assisted CEC separation of nitroimidazole drugs.
2010 Aug
Could giardiasis be a risk factor for low zinc status in schoolchildren from northwestern Mexico? A cross-sectional study with longitudinal follow-up.
2010 Feb 20
Secnidazole-induced acute pancreatitis: a new side-effect for an old drug?
2010 Jan 8
A molecularly imprinted monolith for the fast chiral separation of antiparasitic drugs by pressurized CEC.
2010 Jul
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

Patents

Sample Use Guides

In Vivo Use Guide
2g as single-dose oral dose
Route of Administration: Oral
In Vitro Use Guide
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
on Tue Mar 06 10:56:20 UTC 2018
Edited
by admin
on Tue Mar 06 10:56:20 UTC 2018
Record UNII
R3459K699K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SECNIDAZOLE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
SECNIDAZOLE [MART.]
Common Name English
SECNIDAZOLE [WHO-DD]
Common Name English
PM-185184
Code English
SECNIDAZOLE [MI]
Common Name English
SECNIDAZOLE [INN]
Common Name English
RP 14539
Code English
SOLOSEC
Brand Name English
RP-14539
Code English
1H-IMIDAZOLE-1-ETHANOL, .ALPHA.,2-DIMETHYL-5-NITRO-
Systematic Name English
.ALPHA.,2-DIMETHYL-5-NITROIMIDAZOLE-1-ETHANOL
Systematic Name English
SECNIDAL
Brand Name English
SECNIDAZOLE ANHYDROUS
Common Name English
SECNIDAZOLE [USAN]
Common Name English
SYM-1219
Code English
Classification Tree Code System Code
WHO-ATC J01RA07
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
WHO-ATC P01AB07
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
Code System Code Type Description
PUBCHEM
71815
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY SWITZERF
ECHA (EC/EINECS)
222-134-0
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
RXCUI
36314
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY RxNorm
MESH
C016724
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
EVMPD
SUB126102
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
EPA CompTox
3366-95-8
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
INN
3506
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
EVMPD
SUB10467MIG
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
ChEMBL
CHEMBL498847
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
NCI_THESAURUS
C66529
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
WIKIPEDIA
SECNIDAZOLE
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
CAS
3366-95-8
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY
MERCK INDEX
M9826
Created by admin on Tue Mar 06 10:56:20 UTC 2018 , Edited by admin on Tue Mar 06 10:56:20 UTC 2018
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY