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

• ChemBase ID: 467
• Molecular Formular: C12H21N5O2S2
• Molecular Mass: 331.45744
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 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
• Brand Name: 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
• Synonyms: 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; 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.5839727
• LogD (pH = 7.4): 0.65984267
• Log P: 0.76301336
• Molar Refractivity: 96.8422 cm^3
• Polarizability: 33.263428 Å^3
• Polar Surface Area: 86.01 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.7
• LOG S: -3.93
• Solubility (Water): 3.86e-02 g/l

PROPERTIES

Physical Property

• Solubility: 10-33mg/mL; Chloroform; DMSO; Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 130-132°C
• Hydrophobicity(logP): -0.162; 1.1

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: KM6565000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

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

DETAILS

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
Histamine H2 receptor antagonist. Used to treat gastroesophogeal reflux disease by preventing release of acid and pepsin into the stomach.

Toronto Research Chemicals - N598500

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

REFERENCES

• 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)