1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole

• ChemBase ID: 787
• Molecular Formular: C8H13N3O4S
• Molecular Mass: 247.27152
• Monoisotopic Mass: 247.06267691
• SMILES: S(=O)(=O)(CCn1c(ncc1[N+](=O)[O-])C)CC
• Canonical SMILES: CCS(=O)(=O)CCn1c(C)ncc1[N+](=O)[O-]
• InChI: InChI=1S/C8H13N3O4S/c1-3-16(14,15)5-4-10-7(2)9-6-8(10)11(12)13/h6H,3-5H2,1-2H3
• InChIKey: HJLSLZFTEKNLFI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole
• IUPAC Traditional name: tinidazole; 1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole
• Brand Name: Fasigyn; Tindamax
• Synonyms: 1-[2-(Ethylsulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole; Bioshik; CP 12574; Ethyl [2-(2-methyl-5-nitroimidazol-1-yl)ethyl] sulfone; Fasigin; Fasigyn; Glongyn; Pletil; Simplotan; Sorquetan; Tindamax; Tini 300; Tinidazol; Tiprogyn; Tricolam; Trimonase; 1-(2-(ethylsulfonyl)ethyl)-2-methyl-5-nitro-1H-imidazole; tinidazole; Tinidazole; 1-[2-(Ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole; Tinidazole; Fasigyne; 1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole; 1-[2-(乙磺酰基)乙基]-2-甲基-5-硝基咪唑; 替硝唑

Database IDs

• CAS Number: 19387-91-8
• EC Number: 243-014-4
• MDL Number: MFCD00057217
• Beilstein Number: 618182
• PubChem SID: 160964250; 46506396
• PubChem CID: 5479

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.5809963
• LogD (pH = 7.4): -0.5805245
• Log P: -0.5805185
• Molar Refractivity: 56.657 cm^3
• Polarizability: 22.506113 Å^3
• Polar Surface Area: 95.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.41
• LOG S: -1.91
• Solubility (Water): 3.03e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.99E+004 mg/L; Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 118-120°C
• Hydrophobicity(logP): -0.319; 0.7

Safety Information

• Storage Condition: Refrigerator
• RTECS: NI6255000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-40
• Safety Statements: 26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H312-H332-H341-H351
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Target: S4068
• Mechanism of Action: The free nitro radical generated as a result of this reduction may be responsible for the antiprotozoal activity; The nitro group of tinidazole is reduced by cell extracts of Trichomonas.

Product Information

• Purity: 95%; 97%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Antitrichomonal, antimicrobial agent; Protozoacide
• Empirical Formula (Hill Notation): C8H13N3O4S

DETAILS

DrugBank - DB00911

• Drug Groups: approved; investigational
• Description: A nitroimidazole antitrichomonal agent effective against Trichomonas vaginalis, Entamoeba histolytica, and Giardia lamblia infections. [PubChem]
• Indication: For the treatment of trichomoniasis caused by T. vaginalis in both female and male patients. Also for the treatment of giardiasis caused by G. duodenalis in both adults and pediatric patients older than three years of age and for the treatment of intestinal amebiasis and amebic liver abscess caused by E. histolytica in both adults and pediatric patients older than three years of age.
• Pharmacology: Tinidazole is a synthetic antiprotozoal agent. Tinidazole demonstrates activity both in vitro and in clinical infections against the following protozoa: Trichomonas vaginalis, Giardia duodenalis (also termed G. lamblia), and Entamoeba histolytica. Tinidazole does not appear to have activity against most strains of vaginal lactobacilli.
• Toxicity: There are no reported overdoses with tinidazole in humans. In acute studies with mice and rats, the LD 50 for mice was generally > 3,600 mg/kg for oral administration and was > 2,300 mg/kg for intraperitoneal administration. In rats, the LD 50 was > 2,000 mg/kg for both oral and intraperitoneal administration.
• Affected Organisms: Trichomonas vaginalis, Giardia duodenalis, and Entamoeba histolytica
• Biotransformation: Hepatic, mainly via CYP3A4. Tinidazole, like metronidazole, is significantly metabolized in humans prior to excretion. Tinidazole is partly metabolized by oxidation, hydroxylation and conjugation. Tinidazole is the major drug-related constituent in plasma after human treatment, along with a small amount of the 2-hydroxymethyl metabolite.
• Absorption: Rapidly and completely absorbed under fasting conditions. Administration with food results in a delay in T_max of approximately 2 hours and a decline in C_max of approximately 10% and an AUC of 901.6 ± 126.5 mcg hr/mL.
• Half Life: Elimination half-life is 13.2 ± 1.4 hours. Plasma half-life is 12 to 14 hours.
• Protein Binding: Plasma protein binding of tinidazole is 12%.
• Elimination: Tinidazole crosses the placental barrier and is secreted in breast milk. Tinidazole is excreted by the liver and the kidneys.; Tinidazole is excreted in the urine mainly as unchanged drug (approximately 20-25% of the administered dose).; Approximately 12% of the drug is excreted in the feces.
• Distribution: * 50 L
• References: [Link] ; Lopez Nigro MM, Carballo MA: Genotoxicity and cell death induced by tinidazole (TNZ). Toxicol Lett. 2008 Jul 30;180(1):46-52. Epub 2008 Jun 5. [Pubmed] ; Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. [Pubmed]
• External Links: Wikipedia; PDRhealth; Drugs.com

Sigma Aldrich - 32553

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - T443900

Antiprotozoal (Trichomonas, Giardia); antiamebic; antibacterial.

REFERENCES

• Link
• Lopez Nigro MM, Carballo MA: Genotoxicity and cell death induced by tinidazole (TNZ). Toxicol Lett. 2008 Jul 30;180(1):46-52. Epub 2008 Jun 5. Pubmed
• Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. Pubmed
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