SECNIDAZOLE

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 Search

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	( + / - )

Description
Sources: http://reference.medscape.com/drug/formulary/solosec-secnidazole-1000168#0

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

Primary Target	Pharmacology	Condition	Potency
Trichomonas vaginalis 11 Target ID: CHEMBL612884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18590939	Inhibitor 8504		810.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial vaginosis 10 Sources: http://reference.medscape.com/drug/solosec-secnidazole-1000168	Curative		Approved 8583	Solosec Approved Use Unknown
Giardiasis 13 Sources: https://clinicaltrials.gov/ct2/show/NCT00607074	Curative		Approved 8583	Solosec Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
45.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
17.6 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
95% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252 substrate 1946	inducer 440 inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 P-gp 1741 BCRP 910 OATP1B1 1079 OATP1B3 961 OAT3 747 OCT2 779 ALDH2 21	CYP1A2 1197 CYP2B6 776 CYP2C8 810 CYP3A5 446 P-gp 2052 BCRP 697 OATP1B1 503 OATP1B3 435 OAT1 395 OAT3 391 OCT2 434	CYP1A2 832 CYP2B6 669 CYP2C8 198 CYP2C19 329

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 9, 18, 54-56	no [IC50 3873 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 9, 18, 54-56	no [IC50 4306 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 10, 18, 54-56	no [IC50 >5000 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 10, 18, 54-56	no [IC50 >5000 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 10, 18, 54-56	no [IC50 >5000 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 10, 18, 54-56	no [IC50 >5000 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 10, 18, 54-56	no [IC50 >5000 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 10, 18, 54-56	no [IC50 >5000 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=56 Page: 10, 18, 54-56	no [IC50 >5000 uM]
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 10, 62, 64-65	unlikely [Inhibition 2300 uM]
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 10, 62, 64-65	unlikely [Inhibition 2300 uM]
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 10, 62, 64-65	unlikely [Inhibition 2300 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 10, 62, 64-65	unlikely [Inhibition 2400 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 10, 62, 64-65	unlikely [Inhibition 2400 uM]
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=64 Page: 10, 61, 63-64	unlikely [Inhibition 4300 uM]
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=64 Page: 10, 61, 63-64	unlikely [Inhibition 4300 uM]
ALDH2 21	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 17, 65-68	weak [IC50 503 uM]
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=10 Page: 9, 18, 50-52	yes
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=10 Page: 9, 18, 50-52	yes
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=10 Page: 9, 18, 50-52	yes
CYP2C8 1117	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=10 Page: 9, 18, 50-52	yes
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=10 Page: 9, 18, 50-52	yes
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=10 Page: 9, 18, 50-52	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=58 Page: 57-59	inconclusive
CYP2C8 810	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=58 Page: 57-59	inconclusive
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=58 Page: 57-59	minor
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=63 Page: 18, 61-63	no
OAT1 395	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 18, 62, 64-65	no
OAT3 391	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 18, 62, 64-65	no
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 18, 62, 64-65	no
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 18, 62, 64-65	no
OCT2 434	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=65 Page: 18, 62, 64-65	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=63 Page: 18, 61-63	no
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=58 Page: 57-59	yes
CYP3A5 446	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000ClinPharmR.pdf#page=58 Page: 57-59	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209363Orig1s000PharmR.pdf#page=13 Page: 24.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:140628	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:140628
ChemicalBook	CB7372041	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7372041
eMolecules	902453	https://www.emolecules.com/cgi-bin/more?vid=902453
MolPort	MolPort-000-811-111	https://www.molport.com/shop/molecule-link/MolPort-000-811-111
Selleck Chemicals	Secnidazole-Flagentyl	http://www.selleckchem.com/products/Secnidazole-Flagentyl.html

PubMed

Title	Date	PubMed
[Using safocid for antibiotic prophylaxis in minimally-invasive endoscopic operations and manipulations].	2011-03-25	21427992
Preparation and characterization of a molecularly imprinted monolithic column for pressure-assisted CEC separation of nitroimidazole drugs.	2010-08	20661943
A molecularly imprinted monolith for the fast chiral separation of antiparasitic drugs by pressurized CEC.	2010-07	20535749
Fixed drug eruption with ornidazole having cross-sensitivity to secnidazole but not to other nitro-imidazole compounds: a case report.	2010-06	20565463
A meta-analysis of the effectiveness of albendazole compared with metronidazole as treatments for infections with Giardia duodenalis.	2010-05-11	20485492
In vitro activity of secnidazole against Atopobium vaginae, an anaerobic pathogen involved in bacterial vaginosis.	2010-05	19548924
Could giardiasis be a risk factor for low zinc status in schoolchildren from northwestern Mexico? A cross-sectional study with longitudinal follow-up.	2010-02-20	20170531
Secnidazole-induced acute pancreatitis: a new side-effect for an old drug?	2010-01-08	20065562
Infectious diseases and prematurity.	2010	21512590
Treatment of bacterial vaginosis: a multicenter, double-blind, double-dummy, randomised phase III study comparing secnidazole and metronidazole.	2010	20885970
A Stability-Indicating RP-HPLC Assay Method for 5-Fluorouracil.	2009-11	20376215
Comparison of azithromycin and metronidazole in a quadruple-therapy regimen for Helicobacter pylori eradication in dyspepsia.	2009-10-02	19794266
Prevalence and chemotherapy of Balantidium coli in cattle in the River Ravi region, Lahore (Pakistan).	2009-07-07	19428186
Validated method for determination of eight banned nitroimidazole residues in natural casings by LC/MS/MS with solid-phase extraction.	2009-06-03	19485222
Formulation and in vitro evaluation of in situ gels containing secnidazole for vaginitis.	2009-05	19420887
Impact of anti-Giardia and anthelminthic treatment on infant growth and intestinal permeability in rural Bangladesh: a randomised double-blind controlled study.	2009-05	18789466
[In vitro effect of secnidazole benzoate on Trichomonas vaginalis].	2009-04	19856497
Molecular structure and vibrational spectroscopic investigation of secnidazole using density functional theory.	2009-01-08	19072620
Antibody response in children infected with Giardia intestinalis before and after treatment with Secnidazole.	2009-01	19141831
The old and new therapeutic approaches to the treatment of giardiasis: where are we?	2009	19707415
Formulation and evaluation of secnidazole or doxycycline dento-oral gels.	2008-12	18785044
The concept of personal drugs in the undergraduate pharmacology practical curriculum.	2008-11	21279187
Oh my aching gut: irritable bowel syndrome, Blastocystis, and asymptomatic infection.	2008-10-21	18937874
Role of cytochrome P450 in drug interactions.	2008-10-18	18928560
[Efficacy of 5-nitroimidazole derivatives in treatment of bacterial vaginosis].	2008-08-12	19080672
Prescription of fixed dose combination drugs for diarrhoea.	2008-07-17	18630234
Short-term triple therapy with azithromycin for Helicobacter pylori eradication: low cost, high compliance, but low efficacy.	2008-05-29	18510773
Formulation and evaluation of PLA and PLGA in situ implants containing secnidazole and/or doxycycline for treatment of periodontitis.	2008	18654864
Simultaneous determination of seven nitroimidazole residues in meat by using HPLC-UV detection with solid-phase extraction.	2007-10-01	17719280
Determination of secnidazole in human plasma by high-performance liquid chromatography with UV detection and its application to the bioequivalence studies.	2007-03	17221933
Amoebic dysentery.	2007-01-01	19454043
Evaluation of the bioequivalence and pharmacokinetics of two formulations of secnidazole after single oral administration in healthy volunteers.	2007	18193695
Short-term therapy for mixed vaginal infections.	2006-02	16364325
Comparative efficacy of two regimens in syndromic management of lower genital infections.	2006-01	16247610
Impact of treatment for bacterial vaginosis on prematurity among Brazilian pregnant women: a retrospective cohort study.	2005-05-02	16021272
Low-dose secnidazole in the treatment of bacterial vaginosis.	2005-03	15733882
Probing NMR parameters, structure and dynamics of 5-nitroimidazole derivatives. Density functional study of prototypical radiosensitizers.	2005-02	15558660
ICH guidance in practice: establishment of inherent stability of secnidazole and development of a validated stability-indicating high-performance liquid chromatographic assay method.	2004-11-19	15533669
Spectrophotometric determination of metronidazole and secnidazole in pharmaceutical preparations.	2004-10	15474063
[New drugs for the treatment of human parasitic protozoa].	2004-06	15305692
Ciprofloxacin-tinidazole combination, fluconazole- azithromicin-secnidazole-kit and doxycycline- metronidazole combination therapy in syndromic management of pelvic inflammatory disease: a prospective randomized controlled trial.	2003-12	14701947
A randomized trial comparing mebendazole and secnidazole for the treatment of giardiasis.	2003-07	12930613
Nitroheterocyclic drugs with broad spectrum activity.	2003-06	12811546
Dientamoeba fragilis, a neglected cause of diarrhea, successfully treated with secnidazole.	2003-02	12588330
Low efficacy of an ultra-short term, once-daily dose triple therapy with omeprazole, azithromycin, and secnidazole for Helicobacter pylori eradication in peptic ulcer.	2002-08-10	12170343
Pre and post eradication gastric inflammation in Helicobacter pylori-associated duodenal ulcer.	2002-03-02	11871846
Randomized trial of a quadruple-drug regimen and a triple-drug regimen for eradication of Helicobacter pylori: long-term follow-up study.	2001-10-26	11676331

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 `Mon Mar 31 18:05:55 GMT 2025` Edited by `admin` on `Mon Mar 31 18:05:55 GMT 2025`
Record UNII	R3459K699K
Record Status	`Validated (UNII)`
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Name

Type

Language

SECNIDAZOLE

Official Name

English

SECNIDAL

Preferred 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

SECNIDAZOLE ANHYDROUS

Common Name

English

SECNIDAZOLE [USAN]

Common Name

English

SYM-1219

Code

English

Classification Tree Code System Code

NDF-RT

N0000175435