Secnidazole
JFDA label: Secnezole 500mg tablet
Mechanism of Action
Inhibitor of DNA — DNA inhibitor
| Target | Action | Gene / class |
|---|---|---|
| DNA efficacy | INHIBITOR |
Indications
Approved
- Bacterial vaginosis
Antimicrobial Spectrum
Expected / intrinsic spectrum (EUCAST breakpoints & labels) — not local resistance. Source: openfda-label.
Protozoa
| Organism | Activity | MIC |
|---|---|---|
| Trichomonas cells | Active | — |
| Trichomonas vaginalis | Active | — |
Contraindications
Source: Lexicomp
- Hypersensitivity to secnidazole, other nitroimidazole derivatives, or any component of the formulation Absolute
Adverse Reactions
Nervous system disorders (1)
Common Headache
Renal and urinary disorders (1)
Common Vulvovaginal candidiasis
Gastrointestinal disorders (2)
Common diarrhea · Nausea
Other (1)
Not Known Nonapproved dosing regimens are included in the reported incidences
Dosing
Source: Lexicomp
Warnings & Precautions
Source: Lexicomp
Carcinogenic
Carcinogenicity has been observed in mice and rats with nitroimidazole agents that are structurally similar to secnidazole in animal studies; it is unknown whether secnidazole is associated with carcinogenicity in humans. Avoid chronic use. Disease-related concerns:
Candidiasis
Vulvovaginal candidiasis may occur; antifungal treatment may be necessary if patient is symptomatic.
Pregnancy & Lactation
Pregnancy
Adverse events were not observed in animal reproduction studies. Information related to the use of secnidazole in pregnancy is limited (Camargo 2015).
Lactation
It is not known if secnidazole is present in breast milk. Due to the potential for adverse events, the manufacturer recommends breastfeeding be avoided during therapy and for 96 hours after the last dose.
Chemistry & Properties
| Formula | C7H11N3O3 |
|---|---|
| Molecular weight | 185.18 g/mol |
| IUPAC name | 1-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol |
| CAS | 3366-95-8 |
| PubChem CID | 71815 |
| InChIKey | KPQZUUQMTUIKBP-UHFFFAOYSA-N |
| logP | 0.48 (XLogP 0.2) |
| Polar surface area | 81.19 Ų |
| H-bond acceptors / donors | 5 / 1 |
| Drug-likeness (QED) | 0.55 |
| Lipinski violations | 0 |
SMILES
Cc1ncc([N+](=O)[O-])n1CC(C)OBiology & Pharmacokinetics
Pharmacokinetics predicted
| Bioavailability | 10.0% |
|---|---|
| Half-life | 2.182 h |
| Volume of distribution | 0.916 L/kg |
| Protein binding | 8.3% |
| BBB penetrant | Yes |
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP2C19 | Substrate | — |
| CYP2C9 | Substrate | — |
| CYP3A4 | Substrate | — |
Transporters
BCRP (Inhibitor)BCRP (Inhibitor)BSEP (Inhibitor)MDR1 (Inhibitor)MRP1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)BCRP (Substrate)MDR1 (Substrate)OAT1 (Substrate)OAT3 (Substrate)OATP1B1 (Substrate)OATP1B3 (Substrate)OCT2 (Substrate)P-gp (Substrate)
Drug–drug interactions (92, DDInter)
| Interacting drug | Severity | Management |
|---|---|---|
| Typhoid vaccine (live) | major | |
| Vibrio cholerae CVD 103-HgR strain live antigen (live) | major | |
| Adalimumab | moderate | |
| Amiodarone | moderate | |
| Atorvastatin | moderate | |
| Auranofin | moderate | |
| Aurothioglucose | moderate | |
| Benznidazole | moderate | |
| Bifidobacterium longum infantis | moderate | |
| Bortezomib | moderate | |
| Brentuximab vedotin | moderate | |
| Cabazitaxel | moderate | |
| Carboplatin | moderate | |
| Carfilzomib | moderate | |
| Cerivastatin | moderate | |
| Certolizumab pegol | moderate | |
| Chloramphenicol | moderate | |
| Chloroquine | moderate | |
| Cisplatin | moderate | |
| Colchicine | moderate | |
| Crizotinib | moderate | |
| Dapsone | moderate | |
| Didanosine | moderate | |
| Diiodohydroxyquinoline | moderate | |
| Dinutuximab | moderate | |
| Disulfiram | moderate | |
| Docetaxel | moderate | |
| Elotuzumab | moderate | |
| Enfortumab vedotin | moderate | |
| Eribulin | moderate | |
| Etanercept | moderate | |
| Ethambutol | moderate | |
| Ethionamide | moderate | |
| Etoposide | moderate | |
| Etravirine | moderate | |
| Fludarabine | moderate | |
| Fluvastatin | moderate | |
| Golimumab | moderate | |
| Hydralazine | moderate | |
| Hydroxychloroquine | moderate |
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Registered Products (2)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| Secnezole | Tablet 500 mg | 4 tab pack varies | THE JORDANIAN PHARMACEUTICAL MANUFACTURING COMPANY/JORDAN | 3.610 |
| Secnezole | Tablet 500 mg | 12 tab pack varies | THE JORDANIAN PHARMACEUTICAL MANUFACTURING COMPANY/JORDAN | 8.820 |