Secnidazole

• CAT Number: A000802
• CAS Number: 3366-95-8
• Molecular Formula: C7H11N3O3
• Molecular Weight: 185.2
• Purity: ≥95%
• Synonyms: 3366-95-8; Flagentyl; Secnidazol; Secnidazolum; Secnidazolum [INN-Latin]
• Storage: -20°C
• InChI: 1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3
• InChIKey: KPQZUUQMTUIKBP-UHFFFAOYSA-N
• SMILES: CC1=NC=C(N1CC(C)O)[N+](=O)[O-]

Secnidazole (Cat No.:A000802), also known as SYM-1219, is a nitroimidazole antiprotozoal and anaerobic drug with a structure and pharmacological action similar to that of metronidazole.It was originally developed by the French pharmaceutical company Rhone-PoulencRorer and is used to kill protozoa and anaerobic bacteria by disrupting DNA strands or inhibiting DNA synthesis during the growth phase of the protozoa or anaerobic bacteria.

Reference

1: Pentikis HS, Adetoro N. Two Phase 1, Open-Label, Single-Dose, Randomized,
Crossover Studies to Assess the Pharmacokinetics, Safety, and Tolerability of
Orally Administered Granules of Secnidazole (2 g) in Healthy Female Volunteers
Under Different Administration Conditions. Clin Pharmacol Drug Dev. 2017 Nov 10.
doi: 10.1002/cpdd.406. [Epub ahead of print] PubMed PMID: 29125715.

2: Darpo B, Xue H, Adetoro N, Matthews BG, Pentikis HS. Thorough QT/QTc
Evaluation of the Cardiac Safety of Secnidazole at Therapeutic and
Supratherapeutic Doses in Healthy Individuals. J Clin Pharmacol. 2017 Oct 2. doi:
10.1002/jcph.1014. [Epub ahead of print] PubMed PMID: 28967984.

3: Schwebke JR, Morgan FG Jr, Koltun W, Nyirjesy P. A phase-3, double-blind,
placebo-controlled study of the effectiveness and safety of single oral doses of
secnidazole 2 g for the treatment of women with bacterial vaginosis. Am J Obstet
Gynecol. 2017 Sep 1. pii: S0002-9378(17)30964-X. doi: 10.1016/j.ajog.2017.08.017.
[Epub ahead of print] PubMed PMID: 28867602.

4: Hillier SL, Nyirjesy P, Waldbaum AS, Schwebke JR, Morgan FG, Adetoro NA, Braun
CJ. Secnidazole Treatment of Bacterial Vaginosis: A Randomized Controlled Trial.
Obstet Gynecol. 2017 Aug;130(2):379-386. doi: 10.1097/AOG.0000000000002135.
PubMed PMID: 28697102.

5: Petrina MAB, Cosentino LA, Rabe LK, Hillier SL. Susceptibility of bacterial
vaginosis (BV)-associated bacteria to secnidazole compared to metronidazole,
tinidazole and clindamycin. Anaerobe. 2017 Oct;47:115-119. doi:
10.1016/j.anaerobe.2017.05.005. Epub 2017 May 15. PubMed PMID: 28522362; PubMed
Central PMCID: PMC5623164.

6: Li M, Li R, Jin Q, Pang J, Xu Z. The efficacy of proanthocyanidins and
secnidazole in the treatment of chronic periodontitis after scaling and root
planing therapy. J Biol Regul Homeost Agents. 2017 Jan-Mar;31(1):93-97. PubMed
PMID: 28337876.

7: Pentikis HS, Adetoro N, Braun CJ. Lack of a Pharmacokinetic Interaction
Between SYM-1219 Granules Containing 2 Grams of Secnidazole and a Combined Oral
Contraceptive in a Phase 1, Randomized, Open-Label Study in Healthy Female
Volunteers. Adv Ther. 2017 Jan;33(12):2229-2241. Epub 2016 Oct 15. PubMed PMID:
27744624.

8: Khan S, Haseeb M, Baig MH, Bagga PS, Siddiqui HH, Kamal MA, Khan MS. Improved
efficiency and stability of secnidazole – An ideal delivery system. Saudi J Biol
Sci. 2015 Jan;22(1):42-9. doi: 10.1016/j.sjbs.2014.05.009. Epub 2014 Jun 12.
PubMed PMID: 25561882; PubMed Central PMCID: PMC4281584.

9: Du J, Zhang Y, Chen Y, Liu D, Chen X, Zhong D. Enantioselective HPLC
determination and pharmacokinetic study of secnidazole enantiomers in rats. J
Chromatogr B Analyt Technol Biomed Life Sci. 2014 Aug 15;965:224-30. doi:
10.1016/j.jchromb.2014.06.036. Epub 2014 Jul 5. PubMed PMID: 25049211.

10: Li Y, Zhao CP, Ma HP, Zhao MY, Xue YR, Wang XM, Zhu HL. Design, synthesis and
antimicrobial activities evaluation of Schiff base derived from secnidazole
derivatives as potential FabH inhibitors. Bioorg Med Chem. 2013 Jun
1;21(11):3120-6. doi: 10.1016/j.bmc.2013.03.023. Epub 2013 Mar 26. PubMed PMID:
23602519.