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Details

Stereochemistry RACEMIC
Molecular Formula C7H11N3O3
Molecular Weight 185.1808
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SECNIDAZOLE

SMILES

CC(Cn1c(C)ncc1N(=O)=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
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

Targets

Primary TargetPharmacologyConditionPotency
810.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Solosec

Approved Use

Unknown
Curative
Solosec

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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%)
Headache (3.6%)
Nausea (3.6%)
Diarrhea (2.5%)
Abdominal pain (2%)
Vulvovaginal pruritus (2%)
Sources: Page: Table 1
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

AEs

AESignificanceDosePopulation
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
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 3873 uM]
no [IC50 4306 uM]
no [IC50 >5000 uM]
no [IC50 >5000 uM]
no [IC50 >5000 uM]
no [IC50 >5000 uM]
no [IC50 >5000 uM]
no [IC50 >5000 uM]
no [IC50 >5000 uM]
unlikely [Inhibition 2300 uM]
unlikely [Inhibition 2300 uM]
unlikely [Inhibition 2300 uM]
unlikely [Inhibition 2400 uM]
unlikely [Inhibition 2400 uM]
unlikely [Inhibition 4300 uM]
unlikely [Inhibition 4300 uM]
weak [IC50 503 uM]
yes
yes
yes
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
inconclusive
inconclusive
minor
no
no
no
no
no
no
no
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Low efficacy of an ultra-short term, once-daily dose triple therapy with omeprazole, azithromycin, and secnidazole for Helicobacter pylori eradication in peptic ulcer.
2002 Jan-Feb
Dientamoeba fragilis, a neglected cause of diarrhea, successfully treated with secnidazole.
2003 Feb
Spectrophotometric determination of metronidazole and secnidazole in pharmaceutical preparations.
2004 Oct
Low-dose secnidazole in the treatment of bacterial vaginosis.
2005 Mar
Short-term therapy for mixed vaginal infections.
2006 Feb
Comparative efficacy of two regimens in syndromic management of lower genital infections.
2006 Jan
Evaluation of the bioequivalence and pharmacokinetics of two formulations of secnidazole after single oral administration in healthy volunteers.
2007
Short-term triple therapy with azithromycin for Helicobacter pylori eradication: low cost, high compliance, but low efficacy.
2008 May 29
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
A Stability-Indicating RP-HPLC Assay Method for 5-Fluorouracil.
2009 Nov
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
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
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
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 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
SECNIDAZOLE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
SECNIDAZOLE [MART.]
Common Name English
ORNIDAZOLE METABOLITE M4
Common Name English
SECNIDAZOLE [WHO-DD]
Common Name English
PM-185184
Code English
SECNIDAZOLE [MI]
Common Name English
SECNIDAZOLE [INN]
Common Name English
SECNIDAZOLE [ORANGE BOOK]
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
NSC-759812
Code English
SECNIDAL
Brand Name English
SECNIDAZOLE ANHYDROUS
Common Name English
SECNIDAZOLE [USAN]
Common Name English
SYM-1219
Code English
Classification Tree Code System Code
NDF-RT N0000175435
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
WHO-ATC J01RA07
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
WHO-ATC P01AB07
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
Code System Code Type Description
PUBCHEM
71815
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
ECHA (EC/EINECS)
222-134-0
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
RXCUI
36314
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
2427
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
MESH
C016724
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
LACTMED
Secnidazole
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
EVMPD
SUB126102
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
EPA CompTox
3366-95-8
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
INN
3506
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
FDA UNII
R3459K699K
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
EVMPD
SUB10467MIG
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
DRUG BANK
DB12834
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL498847
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
NCI_THESAURUS
C66529
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
WIKIPEDIA
SECNIDAZOLE
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
CAS
3366-95-8
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY
MERCK INDEX
M9826
Created by admin on Fri Jun 25 21:49:49 UTC 2021 , Edited by admin on Fri Jun 25 21:49:49 UTC 2021
PRIMARY Merck Index