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
Structure for Secnidazole (DB12834)
- 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
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bacterial vaginosis •••••••••••• ••••••••••• ••••• ••••••• Used in combination to treat Candidiasis Combination Product in combination with: Fluconazole (DB00196) •••••••••••• •••••• Used in combination to treat Trichomonas vaginitis Combination Product in combination with: Itraconazole (DB01167) •••••••••••• •••••••• ••••••• ••••••• •••••• Treatment of Trichomoniasis •••••••••••• ••••••••••• ••••• ••••••• Used in combination to treat Trichomoniasis Combination Product in combination with: Fluconazole (DB00196) •••••••••••• •••••• - Contraindications & Blackbox Warnings
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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
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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 regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Solosec Granule 2 g/4.8g Oral Ropack Inc. 2018-03-01 Not applicable US 
Solosec Granule 2 g/4.8g Oral Symbiomix Therapeutics 2017-09-29 2017-10-30 US Solosec Granule 2 g/4.8g Oral Lupin Pharmaceuticals, Inc. 2017-10-30 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ALBISEC® Secnidazole (166.66 mg) + Itraconazole (154.66 mg) Capsule, coated Oral 2006-11-10 2013-06-13 Colombia 
BIOPROX® TABLETA RECUBIERTA Secnidazole (666.667 mg) + Itraconazole (133.33 mg) Tablet, coated Oral BIOCHEM FARMACEUTICA DE COLOMBIAS.A. 2018-03-22 Not applicable Colombia FLUCIFEM ® Secnidazole (1000 mg) + Fluconazole (75 mg) Tablet, coated Oral LABORATORIOS SYNTHESIS S.A.S. 2011-12-20 Not applicable Colombia FLUCONAZOL+SECNIDAZOL 75MG/1000 MG Secnidazole (1000 mg) + Fluconazole (75 mg) Tablet, film coated Oral TECNOQUIMICAS S.A. (PLANTA JAMUNDI) 2018-02-21 Not applicable Colombia FLUNAZOL® Secnidazole (1000 mg) + Fluconazole (75 mg) Tablet, coated Oral EUROFARMA COLOMBIA S.A.S 2017-07-27 Not applicable Colombia
Categories
- ATC Codes
- P01AB07 — Secnidazole
- P01AB — Nitroimidazole derivatives
- P01A — AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Imidazoles
- Nitro Compounds
- Nitroimidazole Antimicrobial
- Nitroimidazole Derivatives
- Nitroimidazoles
- 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
- 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]
- 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]
- Authors unspecified: Secnidazole . [Article]
- 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]
- INVIMA Product Information: Bioprox (itraconazole/secnidazole) oral tablets [Link]
- FDA Approved Drug Products: Solosec (secnidazole) oral granules [Link]
- External Links
- PubChem Compound
- 71815
- PubChem Substance
- 347829000
- ChemSpider
- 64839
- BindingDB
- 50349330
- 36314
- ChEBI
- 94433
- ChEMBL
- CHEMBL498847
- Wikipedia
- Secnidazole
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Bacterial Vaginoses 1 4 Not Yet Recruiting Treatment Trichomonas Vaginitis 1 3 Completed Treatment Bacterial Vaginosis (BV) 2 3 Completed Treatment Trichomonas Vaginalis Infection 1 3 Completed Treatment Vaginal Discharge 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule, coated Oral Powder, for suspension Oral 2.7778 g Powder, for solution Oral 4.1667 g Tablet Oral 100000000 mg Granule Oral 500 mg Granule Oral 750 mg Powder, for suspension Oral 5 g Suspension Oral 5 g Tablet, film coated Oral Tablet Oral Tablet, coated Oral 50000000 mg Powder, for suspension Oral 4.99 g Tablet, coated Oral 250 mg Tablet Oral 500.00 mg Tablet, coated Oral 1000 mg Powder, for suspension Oral 3.333 g Tablet, coated Oral Tablet Oral 500 mg Powder, for suspension Oral 3 g Tablet Oral 0.25 g Powder, for suspension Oral 0.75 g Tablet, film coated Oral 1 g Granule Oral 3 g Powder, for suspension Oral 900 mg Tablet, film coated Oral 1000 mg Tablet Oral 1 g Tablet, coated Oral 1 g Tablet Oral 1000 mg Tablet, film coated Oral 500 mg Suspension Oral 500 mg Powder, for suspension Oral 3.3 g Powder, for suspension Oral 750 mg Powder, for suspension Oral 3.49 g Powder, for suspension Oral 5.25 g Powder, for solution Oral 3.33 g Powder Oral 15 g Tablet, coated Oral 500 mg Tablet Oral 1 mg Tablet, film coated Oral 263.158 mg Tablet Oral 250 mg Tablet, film coated Oral Tablet, delayed release Oral 500 mg Tablet, film coated Oral 1 mg Powder, for suspension Oral 3.33 g Suspension Oral 4.99 g Granule Oral 2 g Capsule Oral Tablet, film coated Oral 250 mg Granule Oral 2 g/4.8g - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US10335390 No 2019-07-02 2035-09-04 US US10682338 No 2020-06-16 2035-09-04 US US10849884 No 2020-12-01 2035-09-04 US US10857133 No 2020-12-08 2035-09-04 US US11000508 No 2021-05-11 2035-09-04 US US11000507 No 2021-05-11 2035-09-04 US US11020377 No 2021-06-01 2035-09-04 US US11324721 No 2015-09-04 2035-09-04 US US11602522 No 2015-09-04 2035-09-04 US US11684607 No 2015-09-16 2035-09-16 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 4.88 mg/mL ALOGPS logP 0.25 ALOGPS logP -0.043 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 15.16 Chemaxon pKa (Strongest Basic) 3.08 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 83.87 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 45.64 m3·mol-1 Chemaxon Polarizability 17.57 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 129.84093 predictedDeepCCS 1.0 (2019) [M+H]+ 133.66882 predictedDeepCCS 1.0 (2019) [M+Na]+ 142.79594 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- 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
- 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
- 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