dimethyl[(4-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}-1,3-thiazol-2-yl)methyl]amine

• ChemBase编号: 467
• 分子式: C12H21N5O2S2
• 平均质量: 331.45744
• 单一同位素质量: 331.11366694
• SMILES: S(CCN/C(=C/[N+](=O)[O-])/NC)Cc1nc(sc1)CN(C)C
• Canonical SMILES: CN/C(=C\[N+](=O)[O-])/NCCSCc1csc(n1)CN(C)C
• InChI: InChI=1S/C12H21N5O2S2/c1-13-11(6-17(18)19)14-4-5-20-8-10-9-21-12(15-10)7-16(2)3/h6,9,13-14H,4-5,7-8H2,1-3H3/b11-6+
• InChIKey: SGXXNSQHWDMGGP-IZZDOVSWSA-N

名称和登记号

名称

• IUPAC标准名: dimethyl[(4-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}-1,3-thiazol-2-yl)methyl]amine; [1-({2-[({2-[(dimethylamino)methyl]-1,3-thiazol-4-yl}methyl)sulfanyl]ethyl}amino)-2-nitroethenyl](methyl)amine; dimethyl[(4-{[(2-{[1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}-1,3-thiazol-2-yl)methyl]amine
• IUPAC传统名: nizatidine; [1-({2-[({2-[(dimethylamino)methyl]-1,3-thiazol-4-yl}methyl)sulfanyl]ethyl}amino)-2-nitroethenyl](methyl)amine; dimethyl[(4-{[(2-{[1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}-1,3-thiazol-2-yl)methyl]amine
• 商标名: Acinon; Antizid; Axid; Axid Ar; Calmaxid; Cronizat; Distaxid; Galitidin; Gastrax; Naxidine; Niatidine; Nizatidina [Spanish]; Nizatidine [Usan:Ban:Inn:Jan]; Nizatidinum [Latin]; Nizax; Nizaxid; Panaxid; Splendil Er; Tazac; Ulcosol; Ulxid; Zanizal; Zinga
• 别名: N-[2-[[[2-[(二甲氨基)甲基]-4-噻唑基]甲基]硫基]乙基]-N′-甲基-2-硝基-1,1-亚乙烯基二胺; 尼扎替丁; Nizatidine; [1-({2-[({2-[(dimethylamino)methyl]-1,3-thiazol-4-yl}methyl)sulfanyl]ethyl}amino)-2-nitroethenyl](methyl)amine; N-[2-[[[2-[(Dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-N’-methyl-2-nitro-1,1-ethenediamine; LY-139037; ZE-101; ZL-101; Axid; Calmaxid; Cronizat; Distaxid; Gastrax; Nizax; Nizaxid; N-[2-[[[2-[(Dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-N′-methyl-2-nitro-1,1-ethenediamine; Nizatidine

登记号

• CAS号: 76963-41-2
• MDL号: MFCD00865660
• PubChem SID: 46507554; 160963930
• PubChem CID: 3033637

理论计算性质

JChem

• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -0.5839727
• LogD (pH = 7.4): 0.65984267
• Log P: 0.76301336
• 摩尔折射率: 96.8422 cm^3
• 极化性: 33.263428 Å^3
• 极化表面积: 86.01 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.7
• LOG S: -3.93
• 溶解度: 3.86e-02 g/l

分子性质

理化性质

• 溶解度: 10-33mg/mL; Chloroform; DMSO; Methanol; Water
• 外观: Pale Yellow Solid
• 熔点: 130-132°C
• 疏水性(logP): -0.162; 1.1

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: KM6565000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: 95%
• Empirical Formula (Hill Notation): C12H21N5O2S2

详细说明

DrugBank - DB00585

• Drug Groups: approved
• Description: A histamine H2 receptor antagonist with low toxicity that inhibits gastric acid secretion. The drug is used for the treatment of duodenal ulcers. [PubChem]
• Indication: For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, active benign gastric ulcer, and active duodenal ulcer.
• Pharmacology: Nizatidine is a competitive, reversible inhibitor of histamine at the histamine H2-receptors, particularly those in the gastric parietal cells. By inhibiting the action of histamine on stomach cells, nizatidine reduces stomach acid production. Nizatidine had no demonstrable antiandrogenic action. Full-dose therapy for the problems treated by nizatidine lasts no longer than 8 weeks. It has been demonstrated that treatment with a reduced dose of nizatidine is effective as maintenance therapy following healing of active duodenal ulcers.
• Toxicity: Oral, rat LD₅₀: 301 mg/kg. Symptoms of overdose include cholinergic-type effects including lacrimation, salivation, emesis, miosis, and diarrhea.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Less than 7% of an oral dose is metabolized as N2-monodes-methylnizatidine, an H2-receptor antagonist, which is the principal metabolite excreted in the urine. Other likely metabolites are the N2-oxide (less than 5% of the dose) and the S-oxide (less than 6% of the dose).
• Absorption: Rapid (bioavailability of nizatidine exceeds 70%)
• Half Life: 1-2 hours
• Protein Binding: 35%
• Distribution: * 0.8 to 1.5 L/kg
• Clearance: * 40-60 L/h; * 7 – 14 L/h [functionally anephric patients]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - N7035

Application
组胺 H2 受体拮抗剂。防止向胃里释放酸和胃蛋白酶，从而治疗胃食管反流病。

Toronto Research Chemicals - N598500

Histamine H2-receptor antagonist related to Ranitidine (R120000). Antiulcerative.

参考文献

• Callaghan, J.T., et al.: Clin. Pharmacol. Ther., 37, 162 (1985)
• Secor, J.W., et al.: Br. J. Clin. Pharmacol., 20, 710 (1985)
• Knadler, M.P., et al.: Drug Metab. Dispos., 14, 175 (1985)
• Wozniak, T.J., et al.: Anal. Profiles Drug Subs., 19, 397(1990)