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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 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

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
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

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)
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:41:57 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:57 GMT 2023
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
ORNIDAZOLE METABOLITE M4
Common Name English
PM-185184
Code English
Secnidazole [WHO-DD]
Common Name 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 Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
WHO-ATC J01RA07
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
WHO-ATC P01AB07
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
Code System Code Type Description
DAILYMED
R3459K699K
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
PUBCHEM
71815
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PRIMARY
ECHA (EC/EINECS)
222-134-0
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
RXCUI
36314
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
2427
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PRIMARY
MESH
C016724
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
LACTMED
Secnidazole
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
USAN
CD-159
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PRIMARY
EVMPD
SUB126102
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PRIMARY
EPA CompTox
DTXSID3045934
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PRIMARY
INN
3506
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PRIMARY
FDA UNII
R3459K699K
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PRIMARY
SMS_ID
100000084084
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
NSC
759812
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PRIMARY
EVMPD
SUB10467MIG
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
DRUG BANK
DB12834
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PRIMARY
CHEBI
140628
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PRIMARY
ChEMBL
CHEMBL498847
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PRIMARY
NCI_THESAURUS
C66529
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
WIKIPEDIA
SECNIDAZOLE
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
CAS
3366-95-8
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY
MERCK INDEX
m9826
Created by admin on Fri Dec 15 15:41:57 GMT 2023 , Edited by admin on Fri Dec 15 15:41:57 GMT 2023
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
BINDER->LIGAND
BINDING
Related Record Type Details
PARENT -> METABOLITE
URINE
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC