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Secnidazole, секнидазол , سيكنيدازول , 塞克硝唑 ,

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Secnidazole.svg ChemSpider 2D Image | Secnidazole | C7H11N3O3

Secnidazole

  • Molecular FormulaC7H11N3O3
  • Average mass185.180 Da
1-(2-Methyl-5-nitroimidazol-1-yl)-2-propanol
1H-Imidazole-1-ethanol, α,2-dimethyl-5-nitro- [ACD/Index Name]
222-134-0 [EINECS]
3366-95-8 [RN]
a,2-Dimethyl-5-nitro-1H-imidazole-1-ethanol
UNII:R3459K699K
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).

References

  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.
Secnidazole
Secnidazole.svg
Clinical data
Synonyms PM 185184, RP 14539
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
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

CC1=NC=C(N1CC(C)O)[N+](=O)[O-]

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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