Secnidazole

Secnidazole

Clinical data
Synonyms	PM 185184, RP 14539
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	P01AB07 (WHO)
Identifiers
IUPAC name 1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
CAS Number	3366-95-8 N
PubChem CID	71815
ChemSpider	64839 Y
UNII	R3459K699K
KEGG	D07353 Y
ChEMBL	ChEMBL498847 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C7H11N3O3
Molar mass	185.180 g/mol
3D model (JSmol)	Interactive image
SMILES [O-][N+](=O)c1cnc(n1CC(O)C)C
InChI InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3 Y Key:KPQZUUQMTUIKBP-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Secnidazole (trade names Flagentyl, Sindose, Secnil) is a nitroimidazole anti-infective. Effectiveness in the treatment of dientamoebiasis has been reported. It has also been tested against Atopobium vaginae.

Secnidazole is structurally related to the commonly used 5-nitroimidazoles metronidazole and tinidazole. These drugs share a common spectrum of activity against anaerobic micro-organisms and they appear particularly effective in the treatment of amoebiasis, giardiasis, trichomoniasis and bacterial vaginosis. Secnidazole is rapidly and completely absorbed after oral administration and has a longer terminal elimination half-life (approximately 17 to 29 hours) than commonly used drugs in this class. In patients with intestinal amoebiasis or giardiasis, clinical or parasistological cure rates of 80 to 100% are achieved after treatment with a single dose of secnidazole 2 g (30 mg/kg in children), similar to the response rates achieved with multiple dosage regimens of metronidazole or tinidazole. Patients with hepatic amoebiasis appears to respond well to 5- to 7-day therapy with secnidazole, but the efficacy of this drug regimen requires further evaluation in larger numbers of patients. After administration of a single dose of secnidazole, parasitological eradication was achieved in approximately 92 to 100% of patients with urogenital trichomoniasis. Patients with bacteria vaginosis respond at least as well to a single dose of secnidazole as to single-dose tinidazole, or single- or 7-day treatment with metronidazole; clinical improvement and/or microbiological evidence of cure was attained in approximately 59 to 96% of patients. In the clinical trials reviewed, secnidazole was well tolerated; most adverse events were gastrointestinal in nature and did not require treatment intervention or withdrawal from therapy.

In summary, available evidence suggests that secnidazole is as efficacious as other 5-nitroimidazole drugs in the treatment of protozoal infections and bacterial vaginosis. The convenience and ease of administration associated with single-dose therapy, combined with a good tolerability profile, make secnidazole a suitable option to other single-dose treatments and an attractive alternative to multiple dosage regimens with other drugs in this class.

References

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