secnidazole   Click here for help

GtoPdb Ligand ID: 12925

Synonyms: 14,539 RP | Solosec® | SYM-1219
Approved drug
secnidazole is an approved drug (FDA (2017))
Compound class: Synthetic organic
Comment: Secnidazole is a broad-spectrum nitroimidazole antimicrobial compound that exhibits antiprotozoal and antibacterial (Gram-positive and Gram-negative) activities.

secnidazole is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 78.97
Molecular weight 185.18
XLogP 0.32
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(CN1C(=NC=C1[N+](=O)[O-])C)O
Isomeric SMILES CC1=NC=C(N1CC(C)O)[N+](=O)[O-]
InChI InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3
InChI Key KPQZUUQMTUIKBP-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
In September 2017, the US FDA granted secnidazole oral granules approval for the treatment of bacterial vaginosis. In June 2021, the FDA expanded approval to include treatment of trichomoniasis caused by Trichomonas vaginalis. It is also available in other countries under various trade names, click here to link to Drugs.com's list of internationally marketed secnidazole drugs.
Pharmacokinetics Click here for help
Elimination
Secnidazole has a longer serum half-life (mean of 17.0 h) than other prescribed nitroimidazoles [3].
External links Click here for help
For extended ADME data see the following:

Drugs.com