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

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

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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

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

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 Formula	C₇H₁₁N₃O₃
Molecular Weight	185.18 g/mol
XLogP3	0.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	185.08004122 g/mol
Monoisotopic Mass	185.08004122 g/mol
Topological Polar Surface Area	83.9 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	194
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.