Identification

Summary

Secnidazole is a nitroimidazole antibiotic used to treat bacterial vaginosis.

Brand Names
Solosec
Generic Name
Secnidazole
DrugBank Accession Number
DB12834
Background

Secnidazole is a second-generation 5-nitroimidazole antimicrobial agent. It is structurally related to other 5-nitroimidazoles, including Metronidazole and Tinidazole, but displays improved oral absorption and a longer terminal elimination half-life than other drugs in this class. Secnidazole is selective against many anaerobic Gram-positive and Gram-negative bacteria as well as protozoa.1 Once it enters bacteria and parasites, secnidazole is activated by bacterial or parasitic enzymes to form a radical anion, thereby damaging and killing the target pathogen.3

Secnidazole has been available in many other countries in Europe, Asia, South America, and Africa for decades.3,4 In September 2017, FDA approved secnidazole under the market name Solosec for the treatment of trichomoniasis and bacterial vaginosis.6

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 185.183
Monoisotopic: 185.080041226
Chemical Formula
C7H11N3O3
Synonyms
  • 1-(2­ hydroxypropyl)-2-methyl-5-nitroimidazole
  • 1-(2-methyl-5-nitro-1H-imidazol-1-yl) propan-2­ ol
  • Secnidazole
External IDs
  • PM-185184
  • RP 14539
  • RP-14539
  • SYM-1219

Pharmacology

Indication

Secnidazole is indicated for treating trichomoniasis and bacterial vaginosis in patients 12 years of age and older.6 In other countries, it is also available as a combination product with other antibacterial drugs, such as itraconazole.5

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Secnidazole is a broad-spectrum nitroimidazole antimicrobial drug.3 It is selective against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. According to in vitro studies, secnidazole mediates antibacterial effects against Bacteroides fragilis, Trichomonas vaginalis, Entamoeba histolytica, and Giardia lamblia.1 Secnidazole may prolong the QTc interval, but not to a clinically significant extent.6

Mechanism of action

Like other 5-nitroimidazole antimicrobials, the antimicrobial and antiprotozoal activity of secnidazole is accounted for by the nitro group in the imidazole ring.4 Upon entering the target pathogen, the nitro group of secnidazole is reduced by bacterial or parasitic nitroreductase enzymes, producing radical anions and reactive intermediates. Radical anions and reactive intermediates cause the depletion of thiols, DNA helix damage, disruption of bacterial or parasitic protein synthesis and replication, and ultimately, cell death of susceptible isolates of Gram positive bacteria, Gram negative bacteria and T. vaginalis.4,6

Absorption

Secnidazole is rapidly and completely absorbed after oral administration.1 Following administration of a single oral dose of 2 g in healthy adult female subjects, the mean (SD) Cmax was 45.4 (7.64) mcg/mL and mean (SD) systemic exposure (AUC0-inf) was 1331.6 (230.16) mcg x hr/mL. Tmax ranged from three to four hours. Food has negligible effects on drug absorption and systemic exposure.6

Volume of distribution

The apparent volume of distribution of secnidazole is approximately 42 L.6

Protein binding

The plasma protein binding of secnidazole is less than 5%.6

Metabolism

The metabolism of secnidazole has not been fully characterized. According to in vitro studies, secnidazole is metabolized by hepatic CYP450 enzymes, with less than or equal to 1% of the parent drug converted to metabolites.6 Secnidazole was found to be metabolized by CYP3A4 and CYP3A5 but to a limited extent.2 Secnidazole most likely undergoes oxidation. A hydroxymethyl metabolite and glucuronide conjugates of secnidazole have been detected in urine.1

Route of elimination

Following oral administration of a 2 g oral dose of secnidazole, approximately 15% of the drug was excreted as unchanged secnidazole in the urine.6

Half-life

The plasma elimination half-life for secnidazole is approximately 17 hours.6

Clearance

The total body clearance of secnidazole is approximately 25 mL/min. The renal clearance is approximately 3.9 mL/min.6

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

There is no information available regarding the LD50 and overdose of secnidazole.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
  • Avoid alcohol. Avoid consumption of alcoholic beverages and preparations containing ethanol or propylene glycol during treatment with secnidazole and for at least two days after completing therapy.
  • Take with or without food. Sprinkle onto applesauce, yogurt, or pudding and ingest without crushing the granules.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SolosecGranule2 g/4.8gOralLupin Pharmaceuticals, Inc.2017-10-30Not applicableUS flag
SolosecGranule2 g/4.8gOralRopack Inc.2018-03-01Not applicableUS flag
SolosecGranule2 g/4.8gOralSymbiomix Therapeutics2017-09-292017-10-30US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ALBISEC®Secnidazole (166.66 mg) + Itraconazole (154.66 mg)Capsule, coatedOral2006-11-102013-06-13Colombia flag
BIOPROX® TABLETA RECUBIERTASecnidazole (666.667 mg) + Itraconazole (133.33 mg)Tablet, coatedOralBIOCHEM FARMACEUTICA DE COLOMBIAS.A.2018-03-22Not applicableColombia flag
CLOTRIMAX® 1000/75MG TABLETA CUBIERTA.Secnidazole (1000 mg) + Fluconazole (75 mg)Tablet, film coatedOralCOLOMPACK S.A.2011-05-20Not applicableColombia flag
FLUCIFEM ®Secnidazole (1000 mg) + Fluconazole (75 mg)Tablet, coatedOralLABORATORIOS SYNTHESIS S.A.S.2011-12-20Not applicableColombia flag
FLUCONAZOL+SECNIDAZOL 75MG/1000 MGSecnidazole (1000 mg) + Fluconazole (75 mg)Tablet, film coatedOralTECNOQUIMICAS S.A.2018-02-21Not applicableColombia flag
FLUNAZOL®Secnidazole (1000 mg) + Fluconazole (75 mg)Tablet, coatedOralPROCAPS S.A.2017-07-27Not applicableColombia flag
FUNEX® - S TABLETASecnidazole (500 mg) + Fluconazole (37.5 mg)TabletOralC.I. FARMACAPSULAS S.A.S - PLANTA NO. 22017-02-062017-09-25Colombia flag
GINDEX®TABLETASSecnidazole (1000 mg) + Fluconazole (75 mg)TabletOralSEVERIANO FERNÁNDEZS.A.S2017-08-25Not applicableColombia flag
GYNFLU® D TABLETASSecnidazole (1000 mg) + Fluconazole (75 mg)Tablet, coatedOralLABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S.2007-11-152022-03-25Colombia flag
RISPEROTS TABLETASSecnidazole (500 mg) + Fluconazole (37.5 mg)Tablet, coatedOralLABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S.2007-02-12Not applicableColombia flag

Categories

ATC Codes
P01AB07 — SecnidazoleJ01RA07 — Azithromycin, fluconazole and secnidazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
Nitroimidazoles
Alternative Parents
Nitroaromatic compounds / 1,2,5-trisubstituted imidazoles / N-substituted imidazoles / Heteroaromatic compounds / Secondary alcohols / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
1,2,5-trisubstituted-imidazole / Alcohol / Allyl-type 1,3-dipolar organic compound / Aromatic heteromonocyclic compound / Azacycle / C-nitro compound / Heteroaromatic compound / Hydrocarbon derivative / N-substituted imidazole / Nitroaromatic compound
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Trichomonas vaginalis, Giardia duodenalis, and Entamoeba histolytica
  • Bacteria and protozoa
  • Bacteroides fragilis

Chemical Identifiers

UNII
R3459K699K
CAS number
3366-95-8
InChI Key
KPQZUUQMTUIKBP-UHFFFAOYSA-N
InChI
InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3
IUPAC Name
1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
SMILES
CC(O)CN1C(C)=NC=C1N(=O)=O

References

General References
  1. Gillis JC, Wiseman LR: Secnidazole. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic use in the management of protozoal infections and bacterial vaginosis. Drugs. 1996 Apr;51(4):621-38. [Article]
  2. Pentikis HS, Adetoro N, Kaufman G: In vitro metabolic profile and drug-drug interaction assessment of secnidazole, a high-dose 5-nitroimidazole antibiotic for the treatment of bacterial vaginosis. Pharmacol Res Perspect. 2020 Aug;8(4):e00634. doi: 10.1002/prp2.634. [Article]
  3. Authors unspecified: Secnidazole . [Article]
  4. Nyirjesy P, Schwebke JR: Secnidazole: next-generation antimicrobial agent for bacterial vaginosis treatment. Future Microbiol. 2018 Apr;13:507-524. doi: 10.2217/fmb-2017-0270. Epub 2018 Jan 12. [Article]
  5. INVIMA Product Information: Bioprox (itraconazole/secnidazole) oral tablets [Link]
  6. FDA Approved Drug Products: Solosec (secnidazole) oral granules [Link]
PubChem Compound
71815
PubChem Substance
347829000
ChemSpider
64839
BindingDB
50349330
RxNav
36314
ChEBI
94433
ChEMBL
CHEMBL498847
Wikipedia
Secnidazole

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentBacterial Vaginoses1
3CompletedTreatmentBacterial Vaginosis (BV)2
3CompletedTreatmentTrichomonas Vaginalis Infection1
3CompletedTreatmentVaginal Discharge1
3TerminatedTreatmentDiverticular Sigmoïditis1
2CompletedTreatmentBacterial Vaginosis (BV)1
2, 3RecruitingTreatmentRecurrent Bacterial Vaginosis (BV)1
1, 2CompletedBasic ScienceCholera (Disorder) / Disease caused by Salmonella typhi1
Not AvailableCompletedTreatmentGiardiasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, coatedOral
Powder, for suspensionOral2.7778 g
Powder, for solutionOral4.1667 g
GranuleOral750 mg
Powder, for suspensionOral5 g
Tablet, film coatedOral500 mg
SuspensionOral5 g
Tablet, film coatedOral
Tablet, coatedOral1 g
Powder, for suspensionOral4.99 g
TabletOral
Tablet, film coatedOral
Tablet, coatedOral250 mg
Powder, for suspensionOral3.333 g
Tablet, coatedOral1000 mg
Tablet, coatedOral
TabletOral500 mg
Powder, for suspensionOral3 g
TabletOral0.25 g
Powder, for suspensionOral0.75 g
GranuleOral3 g
GranuleOral500 mg
Powder, for suspensionOral900 mg
Tablet, film coatedOral1000 mg
Tablet, film coatedOral1 g
TabletOral1 g
TabletOral1000 mg
SuspensionOral500 mg
Tablet, coatedOral500 mg
Powder, for suspensionOral3.3 g
Powder, for suspensionOral750 mg
Powder, for suspensionOral3.49 g
Powder, for suspensionOral5.25 g
Powder, for solutionOral3.33 g
PowderOral15 g
Tablet, film coatedOral263.158 mg
TabletOral250 mg
Tablet, delayed releaseOral500 mg
Tablet, film coatedOral1 mg
Powder, for suspensionOral3.33 g
SuspensionOral4.99 g
GranuleOral2 g
Tablet, film coatedOral250 mg
GranuleOral2 g/4.8g
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US10335390No2019-07-022035-09-04US flag
US10682338No2020-06-162035-09-04US flag
US10849884No2020-12-012035-09-04US flag
US10857133No2020-12-082035-09-04US flag
US11000508No2021-05-112035-09-04US flag
US11000507No2021-05-112035-09-04US flag
US11020377No2021-06-012035-09-04US flag
US11324721No2015-09-042035-09-04US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.88 mg/mLALOGPS
logP0.25ALOGPS
logP-0.043ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)15.16ChemAxon
pKa (Strongest Basic)3.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.87 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.64 m3·mol-1ChemAxon
Polarizability17.57 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004r-0900000000-4607b9260ff959d777e0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-3900000000-b3c36444a446482a04bc

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Secnidazole had an IC50 of 3722 µmol/L.
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Pentikis HS, Adetoro N, Kaufman G: In vitro metabolic profile and drug-drug interaction assessment of secnidazole, a high-dose 5-nitroimidazole antibiotic for the treatment of bacterial vaginosis. Pharmacol Res Perspect. 2020 Aug;8(4):e00634. doi: 10.1002/prp2.634. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Pentikis HS, Adetoro N, Kaufman G: In vitro metabolic profile and drug-drug interaction assessment of secnidazole, a high-dose 5-nitroimidazole antibiotic for the treatment of bacterial vaginosis. Pharmacol Res Perspect. 2020 Aug;8(4):e00634. doi: 10.1002/prp2.634. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Secnidazole had an IC50 of 3873 µmol/L.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Pentikis HS, Adetoro N, Kaufman G: In vitro metabolic profile and drug-drug interaction assessment of secnidazole, a high-dose 5-nitroimidazole antibiotic for the treatment of bacterial vaginosis. Pharmacol Res Perspect. 2020 Aug;8(4):e00634. doi: 10.1002/prp2.634. [Article]

Drug created at October 21, 2016 00:36 / Updated at April 01, 2022 19:23