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    Secnidazole

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    2D Structure
    Also known as: 3366-95-8, Secnidazol, Flagentyl, Secnidazolum, 1-(2-methyl-5-nitro-1h-imidazol-1-yl)propan-2-ol, Secnidazolum [inn-latin]
    Molecular Formula
    C7H11N3O3
    Molecular Weight
    185.18  g/mol
    InChI Key
    KPQZUUQMTUIKBP-UHFFFAOYSA-N
    FDA UNII
    R3459K699K
    Secnidazole is a second-generation 5-nitroimidazole antimicrobial that is structurally related to other 5-nitroimidazoles including [DB00916] and [DB00911], but displays improved oral absorption and longer terminal elimination half-life than antimicrobial agents in this class. 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.
    Secnidazole is a Nitroimidazole Antimicrobial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol
    2.1.2 InChI
    InChI=1S/C7H11N3O3/c1-5(11)4-9-6(2)8-3-7(9)10(12)13/h3,5,11H,4H2,1-2H3
    2.1.3 InChI Key
    KPQZUUQMTUIKBP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=NC=C(N1CC(C)O)[N+](=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    R3459K699K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(2'-hydroxypropyl)-2-methyl-5- Nitroimidazole

    2. 14,539 Rp

    3. Minovag

    4. Sabima

    5. Secnidal

    6. Secnol

    7. Solosec

    2.3.2 Depositor-Supplied Synonyms

    1. 3366-95-8

    2. Secnidazol

    3. Flagentyl

    4. Secnidazolum

    5. 1-(2-methyl-5-nitro-1h-imidazol-1-yl)propan-2-ol

    6. Secnidazolum [inn-latin]

    7. Solosec

    8. Rp 14539

    9. Secnidal

    10. 1-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol

    11. Pm 185184

    12. Pm-185184

    13. Sym-1219

    14. Secnidazole Anhydrous

    15. Rp-14539

    16. Secnidazole (flagentyl)

    17. Ornidazole Metabolite M4

    18. 1-(2-methyl-5-nitro-1-imidazolyl)-2-propanol

    19. Nsc-759812

    20. Mls000559043

    21. 1-(2-methyl-5-nitro-imidazol-1-yl)-propan-2-ol

    22. R3459k699k

    23. Ncgc00095158-01

    24. Smr000149359

    25. Rp-14539;pm-185184

    26. Dsstox_cid_25934

    27. Dsstox_rid_81233

    28. Dsstox_gsid_45934

    29. Secnidazol [inn-spanish]

    30. Cas-3366-95-8

    31. Sr-01000685111

    32. Einecs 222-134-0

    33. Alpha,2-dimethyl-5-nitro-1h-imidazole-1-ethanol

    34. Sindose

    35. Secnil

    36. Unii-r3459k699k

    37. 1-(2-hydroxypropyl)-2-methyl-5-nitroimidazol

    38. Secnidal (tn)

    39. Secnidazole-[d6]

    40. Secnidazole [usan:inn:ban:dcf]

    41. Sym 1219

    42. Solosec (tn)

    43. Secnidazole [mi]

    44. Opera_id_1811

    45. Spectrum2_000033

    46. Spectrum3_001956

    47. Secnidazole [inn]

    48. Alpha,2-dimethyl-5-nitroimidazole-1-ethanol

    49. Secnidazole (usan/inn)

    50. Secnidazole [usan]

    51. 1-(2-methyl-5-nitroimidazol-1-yl)-2-propanol

    52. Imidazole-1-ethanol, Alpha,2-dimethyl-5-nitro-

    53. Secnidazole [mart.]

    54. Bspbio_003556

    55. Secnidazole [who-dd]

    56. Mls000759496

    57. Mls001201813

    58. Mls001424126

    59. Mls006011434

    60. Schembl363924

    61. Spectrum1505304

    62. Spbio_000125

    63. 1h-imidazole-1-ethanol, .alpha.,2-dimethyl-5-nitro-

    64. Chembl498847

    65. Dtxsid3045934

    66. Chebi:94433

    67. Kbio3_002874

    68. Secnidazole [orange Book]

    69. Chebi:140628

    70. Hms1922b12

    71. Hms2051c20

    72. Hms2090n15

    73. Hms2231g11

    74. Hms3369n08

    75. Hms3393c20

    76. Hms3656g14

    77. Hms3714i05

    78. Pharmakon1600-01505304

    79. Bcp12459

    80. Hy-b1118

    81. Tox21_111457

    82. Bbl010784

    83. Bdbm50349330

    84. Ccg-39993

    85. Mfcd00864656

    86. Nsc759812

    87. Stk590474

    88. Akos005512552

    89. Akos025149490

    90. Tox21_111457_1

    91. Ccg-100896

    92. Cs-4641

    93. Db12834

    94. Ks-1191

    95. Nc00146

    96. Nsc 759812

    97. Sb19197

    98. Secnidazole 100 Microg/ml In Methanol

    99. Ncgc00095158-02

    100. Ncgc00095158-03

    101. Ncgc00095158-04

    102. Ncgc00095158-05

    103. Ncgc00095158-08

    104. Ac-12065

    105. Sbi-0207037.p001

    106. Secnidazole 100 Microg/ml In Acetonitrile

    107. Db-000688

    108. Ft-0601624

    109. S2537

    110. Sw197526-3

    111. D07353

    112. 1-(2- Hydroxypropyl)-2-methyl-5-nitroimidazole

    113. 1h-imidazole-1-ethanol, A,2-dimethyl-5-nitro-

    114. Ab00456738-13

    115. Ab00456738-15

    116. Ab00456738_16

    117. Ab00456738_17

    118. 366s958

    119. A821901

    120. J-019291

    121. Q4413249

    122. Sr-01000685111-4

    123. Sr-01000685111-6

    124. Sr-01000685111-7

    125. .alpha.,2-dimethyl-5-nitroimidazole-1-ethanol

    126. Brd-a70083328-001-02-9

    127. Brd-a70083328-001-12-8

    128. 1-(2-methyl-5-nitro-1h-imidazol-1-yl) Propan-2- Ol

    129. 1-(2-methyl-5-nitro-imidazol-1-yl)propan-2-ol;secnidazole

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 185.18 g/mol
    Molecular Formula C7H11N3O3
    XLogP30.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass185.08004122 g/mol
    Monoisotopic Mass185.08004122 g/mol
    Topological Polar Surface Area83.9 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity194
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Secnidazole is indicated for the treatment of trichomoniasis in adults and bacterial vaginosis in adult women.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Secnidazole is a nitroimidazole antimicrobial drug that displays selectivity against many anaerobic Gram-positive and Gram-negative bacteria and protozoa. In vitro studies demonstrates the effectiveness of the drug against *Bacteroides fragilis*, *Trichomonas vaginalis*, *Entamoeba histolytica* and *Giardia lamblia*. There is no significant bacterial or protozoal resistance reported from secnidazole treatment.

    5.2 MeSH Pharmacological Classification

    Antiprotozoal Agents

    Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    SECNIDAZOLE
    5.3.2 FDA UNII
    R3459K699K
    5.3.3 Pharmacological Classes
    Nitroimidazoles [CS]; Nitroimidazole Antimicrobial [EPC]
    5.4 ATC Code

    P01AB07

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    P - Antiparasitic products, insecticides and repellents

    P01 - Antiprotozoals

    P01A - Agents against amoebiasis and other protozoal diseases

    P01AB - Nitroimidazole derivatives

    P01AB07 - Secnidazole

    5.5 Absorption, Distribution and Excretion

    Absorption

    Secnidazole is rapidly and completely absorbed after oral administration. Following a single oral dose of 2 g in healthy adult female subjects, the mean (SD) secnidazole peak plasma concentration (Cmax) of 45.4 (7.64) mcg/mL and mean (SD) systemic exposure (AUC0-inf) of 1331.6 (230.16) mcg x hr/mL was reached. Median (range) time to peak concentration (Tmax) was 4.0 (3.0-4.0) hours.

    Route of Elimination

    The predominant route of elimination is renal elimination. Following a single oral dose of 2g secnidazole, approximately 15% of the drug is excreted as unchanged compoung in the urine.

    Volume of Distribution

    The apparent volume of distribution of secnidazole is approximately 42-49 L.

    Clearance

    The total body clearance of secnidazole is approximately 25 mL/min. The renal clearance of secnidazole is approximately 3.9 mL/min.

    5.6 Metabolism/Metabolites

    According to *in vitro* studies, secnidazole is metabolized via oxidation by human hepatic CYP450 enzyme system with 1% conversion to metabolites.

    5.7 Biological Half-Life

    The plasma elimination half-life for secnidazole is approximately 17 hours.

    5.8 Mechanism of Action

    Secnidazole enters the bacterial cell as a prodrug without an antimicrobial activity. The drug is converted to an active form via reduction of nitro groups to radical anions by bacterial enzymes. The radical anions are thought to interfere with bacterial DNA synthesis of susceptible isolates.