CAS 3366-95-8|1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol|Secnidazole|secnidazole|PM 185184; RP 14539; Sindose; Secnil|1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol|PM 185184, RP 14539|Secni...

General Information

Structure

Molecular Formula

C₇H₁₁N₃O₃

Molecular Mass

185.18054

Exact Mass

185.08004123

Charge

InChI

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

Canonic Smiles

CC(Cn1c(C)ncc1[N+](=O)[O-])O

Isomeric Smiles

n1(CC(C)O)c(cnc1C)[N+](=O)[O-]

Calculated Properties

JChem

LogD (pH = 7.4)

-0.04

LogD (pH = 5.5)

-0.04

Log P

-0.04

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.02

Polar Surface Area

81.19

Polarizability

17.69

Molar Refractivity

44.64

LOG S

-0.83

Data Source

Names and Identifiers

IUPAC name

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

Synonyms

SecnidazolePM 185184; RP 14539; Sindose; Secnil1-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-olPM 185184, RP 14539SecnidazoleApexFlowSecnidalFlagentylDaksolFamidePM 1851841-(2-Methyl-5-nitroimidazol-1-yl)-2-propanolRP 14539α,2-Dimethyl-5-nitro-1H-imidazole-1-ethanolsecnidazole

IUPAC Traditional name

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

International Nonproprietary Name (INN)

secnidazolesecnidazolumsecnidazol

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

CHEMBL

Wikipedia Title

ATC CODE

Chemspider ID

Unique Ingredient Identifier

R3459K699K

KEGG ID

D07353

PubChem SID

16203799185340306

MetaboLights Database

MTBLS2224MTBLS2291

PubMed Citation Links

2837219728337876293279472932362728967984296352642968466428697102

LINCS Database

LSM-5131

BRENDA Ligand Database

67138

SureChEMBL Database

SCHEMBL363924

ACToR Database

3366-95-8

Drug Central Database

2,427

Patent number

US5549911US4920141US4925952US4957918US4925951

BKMS React Database

CompTox Database

Reaxys Registry

KEGG DRUG Database

CHEBI ID

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

Refrigerator

MSDS Link

Download link

Pharmacology Properties

Admin Routes

Oral

Mechanism of Action

Interacts with DNA to cause a loss of helical DNA structure and strand breakage resulting in inhibition of protein synthesis and cell death in susceptible organisms

Physical Property

Solubility

Methanol

Chloroform

Melting Point

70-72°C

Apperance

Pale Yellow Solid

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2537

Research Area: Infection
Biological Activity:
Secnidazole (Flagentyl) is a nitroimidazole anti-infective. Secnidazole (Flagentyl) is effective in the treatment of dientamoebiasis. Secnidazole (Flagentyl) has also been tested against Atopobium vaginae. An MIC range for secnidazole (Flagentyl) is 4-128 mg/L. The MIC50 for secnidazole (Flagentyl) is 16 mg/L. The MIC90 for secnidazole (Flagentyl) is 64 mg/L. Secnidazole (Flagentyl) is highly effective in achieving parasitologic. [1][2][3]

Wikipedia

Secnidazole

TRC

S225000

Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas).

ChEBI

CHEBI:140628

A C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by 2-hydroxypropyl and methyl groups, respectively.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Secnidazole

• Cosar, C., et al.: Arzneim.-Forsch., 16, 23 (1966)

• Symonds, J., et al.: J. Antimicrob. Chemother., 5, 484 (1966)

• Videau, D., et al.: Br. J. Vener. Dis., 54, 77 (1966)

• Nagarajan, K. et al., Indian J. Chem., Sect. B, 1982, 21, 1006, (uv, pmr, ms)

• Bhatia, S.C. et al., J. Chromatogr., 1984, 305, 325, (gc)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 875, (synonyms)

• Cosar, C. et al., Arzneim.-Forsch., 1966, 16, 23, (synth, pharmacol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 526

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

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

Synonyms

IUPAC Traditional name

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

International Nonproprietary Name (INN)

secnidazolesecnidazolumsecnidazol

Registration numbers

CAS Number

PubChem CID

CHEMBL

Wikipedia Title

ATC CODE

Chemspider ID

Unique Ingredient Identifier

R3459K699K

KEGG ID

D07353

PubChem SID

16203799185340306

MetaboLights Database

MTBLS2224MTBLS2291

PubMed Citation Links

2837219728337876293279472932362728967984296352642968466428697102

LINCS Database

LSM-5131

BRENDA Ligand Database

67138

SureChEMBL Database

SCHEMBL363924

ACToR Database

3366-95-8

Drug Central Database

2,427

Patent number

US5549911US4920141US4925952US4957918US4925951

BKMS React Database

CompTox Database

Reaxys Registry

KEGG DRUG Database

CHEBI ID

Properties

Safety Information

Storage Condition

-20°C

Refrigerator

MSDS Link

Download link

Pharmacology Properties

Admin Routes

Oral

Mechanism of Action

Interacts with DNA to cause a loss of helical DNA structure and strand breakage resulting in inhibition of protein synthesis and cell death in susceptible organisms

Physical Property

Solubility

Methanol

Chloroform

Melting Point

70-72°C

Apperance

Pale Yellow Solid

Molecule Details

S2537

S225000

Analog of Metronidazole. Antiamebic. Antiprotozoal (Trichomonas).

ChEBI

CHEBI:140628

A C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by 2-hydroxypropyl and methyl groups, respectively.

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Secnidazole

• Cosar, C., et al.: Arzneim.-Forsch., 16, 23 (1966)

• Symonds, J., et al.: J. Antimicrob. Chemother., 5, 484 (1966)

• Videau, D., et al.: Br. J. Vener. Dis., 54, 77 (1966)

• Nagarajan, K. et al., Indian J. Chem., Sect. B, 1982, 21, 1006, (uv, pmr, ms)

• Bhatia, S.C. et al., J. Chromatogr., 1984, 305, 325, (gc)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 875, (synonyms)

• Cosar, C. et al., Arzneim.-Forsch., 1966, 16, 23, (synth, pharmacol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 526

Bioactivity

PubChem BioAssay

Molecule

ID:73071