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Secnidazole, секнидазол , سيكنيدازول , 塞克硝唑 ,



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Secnidazole.svg ChemSpider 2D Image | Secnidazole | C7H11N3O3


  • Molecular FormulaC7H11N3O3
  • Average mass185.180 Da
1H-Imidazole-1-ethanol, α,2-dimethyl-5-nitro- [ACD/Index Name]
222-134-0 [EINECS]
3366-95-8 [RN]
секнидазол [Russian] [INN]
سيكنيدازول [Arabic] [INN]
塞克硝唑 [Chinese] [INN]
RP-14539, PM-185184, Flagentyl

Solosec (secnidazole) ; Symbiomix Therapeutics; For the treatment of bacterial vaginosis , Approved September 2017

Company: Symbiomix Therapeutics

Approval Status: Approved FDA September 2017

Specific Treatments: bacterial vaginosis

Therapeutic Areas Obstetrics/Gynecology (Women’s Health)

Infections and Infectious Diseases


Secnidazole is a second-generation 5-nitroimidazole antimicrobial that is structurally related to other 5-nitroimidazoles including Metronidazole and Tinidazole, but displays improved oral absorption and longer terminal elimination half-life than antimicrobial agents in this class [1]. Secnidazole is selective against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. In September 2017, FDA granted approval to secnidazole under the market name Solosec as a single-dose oral treatment for bacterial vaginosis, which is a common vaginal infection in women aged 15 to 44 years. The antimicrobial therapy is only intended to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria [FDA Label].

Title: Secnidazole
CAS Registry Number: 3366-95-8
CAS Name: a,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
Additional Names: 1-(2-hydroxypropyl)-2-methyl-5-nitroimidazole; 1-(2-methyl-5-nitroimidazol-1-yl)-2-propanol
Manufacturers’ Codes: PM-185184; RP-14539
Trademarks: Flagentyl (Rh>e-Poulenc)
Molecular Formula: C7H11N3O3
Molecular Weight: 185.18
Percent Composition: C 45.40%, H 5.99%, N 22.69%, O 25.92%
Literature References: Analog of metronidazole, q.v. Prepn: FR M3270 (1965 to Rhône-Poulenc), C.A. 63, 11571d (1965); C. Cosar et al., Arzneim.-Forsch. 16, 23 (1966). Anti-amebic and trichomonacidal activities: F. Benazet, L. Guillaume, Bull. Soc. Pathol. Exot. Ses Fil. 69, 309 (1976), C.A. 90, 145922v (1979). Serum half-life: J. Symonds, J. Antimicrob. Chemother. 5, 484 (1979). Therapeutic use: D. Videau et al., Br. J. Vener. Dis. 54, 77 (1978).
Properties: Cryst from toluene, mp 76° (Cosar).
Melting point: mp 76° (Cosar)
Therap-Cat: Antiamebic. Antiprotozoal (Trichomonas).
Keywords: Antiamebic; Antiprotozoal (Trichomonas).

Secnidazole (trade names FlagentylSindoseSecnil) is a nitroimidazole anti-infective. Effectiveness in the treatment of dientamoebiasis has been reported.[1] It has also been tested against Atopobium vaginae.[2]

Mechanism of Action

Solosec (secnidazole) is a 5-nitroimidazole antimicrobial. 5-nitroimidazoles enter the bacterial cell as an inactive prodrug where the nitro group is reduced by bacterial enzymes to radical anions. It is believed that these radical anions interfere with bacterial DNA synthesis of susceptible isolates.

DE 2107405; FR 2079880; GB 1278757; JP 49080066

The condensation of (I) with propylene oxide (A) in ethanol at 20 C gives 1-(2-hydroxypropyl)-2-methylimidazole (III), which is acetylated with acetyl chloride in refluxing acetonitrile yielding the corresponding acetate (IV). The nitration of (IV) by means of HNO3 and P2O5 affords 1-(2-acetoxypropyl)-2-methyl-4-nitroimidazole (V), which is finally hydrolyzed with 4N HCl at 90 C

CH 513177; DE 2107423; FR 2079879; GB 1278758; NL 7101641

The reaction of (I) with chloroacetone (C) by means of K2CO3 in refluxing acetone gives (2-methylimidazol-1-yl)acetone (VI), which is nitrated with HNO3 and P2O5 affording the corresponding nitro compound (VII). Finally, this product is reduced with NaBH4 in methanol at room temperature.

Drugs Fut 1979,4(4),280, Arzneim-Forsch Drug Res 1966,16(1),23-29

The nitration of (I) with HNO3 and H2SO4 gives 2-methyl-4(5)-nitroimidazole (II), which is then condensed with refluxing 1-chloroisopropanol (B) or with propylene oxide in 85% formic acid (A).


  1. Jump up^ Girginkardeşler, N.; Coşkun, S.; Cüneyt Balcioğlu, I.; Ertan, P.; Ok, U. Z. (2003). “Dientamoeba fragilis, a neglected cause of diarrhea, successfully treated with secnidazole”. Clinical Microbiology and Infection9 (2): 110–113. PMID 12588330doi:10.1046/j.1469-0691.2003.00504.x.
  2. Jump up^ De Backer, E.; Dubreuil, L.; Brauman, M.; Acar, J.; Vaneechoutte, M. (2009). “In vitro activity of secnidazole against Atopobium vaginae, an anaerobic pathogen involved in bacterial vaginosis”. Clinical Microbiology and Infection16 (5): 470–472. PMID 19548924doi:10.1111/j.1469-0691.2009.02852.x.

External links

  • Gillis, J. C.; Wiseman, L. R. (1996). “Secnidazole. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic use in the management of protozoal infections and bacterial vaginosis”. Drugs51 (4): 621–38. PMID 8706597doi:10.2165/00003495-199651040-00007.
Clinical data
Synonyms PM 185184, RP 14539
AHFS/ International Drug Names
Routes of
ATC code
CAS Number
PubChem CID
ECHA InfoCard 100.020.123
Chemical and physical data
Formula C7H11N3O3
Molar mass 185.180 g/mol
3D model (JSmol)

////////////Secnidazole, секнидазол سيكنيدازول 塞克硝唑 , FDA 2017, RP-14539, PM-185184, Flagentyl



“NEW DRUG APPROVALS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

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