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

• ChemBase编号: 787
• 分子式: C8H13N3O4S
• 平均质量: 247.27152
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole
• IUPAC传统名: tinidazole; 1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole
• 商标名: Fasigyn; Tindamax
• 别名: 1-[2-(乙磺酰基)乙基]-2-甲基-5-硝基咪唑; 替硝唑; 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

登记号

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

理论计算性质

JChem

• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): -0.5809963
• LogD (pH = 7.4): -0.5805245
• Log P: -0.5805185
• 摩尔折射率: 56.657 cm^3
• 极化性: 22.506113 Å^3
• 极化表面积: 95.1 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.41
• LOG S: -1.91
• 溶解度: 3.03e+00 g/l

分子性质

理化性质

• 溶解度: 1.99E+004 mg/L; Chloroform; Methanol
• 外观: Pale Yellow Solid
• 熔点: 118-120°C
• 疏水性(logP): -0.319; 0.7

安全信息

• 保存条件: Refrigerator
• RTECS编号: NI6255000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22-40
• 安全公开号: 26-36
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H312-H332-H341-H351
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

药理学性质

• 作用靶点: S4068
• 生物活性机理: 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.

产品相关信息

• 纯度: 95%; 97%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 应用领域: Antitrichomonal, antimicrobial agent; Protozoacide
• Empirical Formula (Hill Notation): C8H13N3O4S

详细说明

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - T443900

Antiprotozoal (Trichomonas, Giardia); antiamebic; antibacterial.

参考文献

• 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
• Miller, M.W., et al.: J. Med. Chem., 13, 849 (1970)
• Oderdea, G., et al.: Gut, 33, 1328 (1970)
• Caplar, V. et al., J. Het. Chem., 1974, 11, 1055, (synth, bibl)
• Carmine, A.A. et al., Drugs, 1982, 24, 85, (rev, pharmacol)
• Nagarajan, K. et al., Indian J. Chem., Sect. B, 1982, 21, 1006, (pmr, uv, ms)
• Reddy, K.C. et al., Indian J. Pharm. Sci., 1982, 44, 6, (synth)
• Nord, C.E. et al., J. Antimicrob. Chemother., (Eds.), Suppl. 8, 1982, 10, 1, (numerous papers)
• Chasseaud, L.F. et al., Chem. Comm., 1984, 491, (cryst struct, props)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 987
• Rao, A.K.S.B. et al., J.C.S. Perkin 1, 1989, 1352
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 528
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TGD250