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.
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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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 CDK toolkit. 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
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.

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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
References
1. Jokipii L, Jokipii AM. (1985)
Comparative evaluation of the 2-methyl-5-nitroimidazole compounds dimetridazole, metronidazole, secnidazole, ornidazole, tinidazole, carnidazole, and panidazole against Bacteroides fragilis and other bacteria of the Bacteroides fragilis group.
Antimicrob Agents Chemother, 28 (4): 561-4. [PMID:4073879]
2. Petrina MAB, Cosentino LA, Rabe LK, Hillier SL. (2017)
Susceptibility of bacterial vaginosis (BV)-associated bacteria to secnidazole compared to metronidazole, tinidazole and clindamycin.
Anaerobe, 47: 115-119. [PMID:28522362]
3. Videau D, Niel G, Siboulet A, Catalan F. (1978)
Secnidazole. A 5-nitroimidazole derivative with a long half-life.
Br J Vener Dis, 54 (2): 77-80. [PMID:305808]