{2-[({5-[(dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}[(E)-1-(methylamino)-2-nitroethenyl]amine hydrochloride

• ChemBase ID: 72805
• Molecular Formular: C13H23ClN4O3S
• Molecular Mass: 350.86472
• Monoisotopic Mass: 350.1179393
• SMILES: N(Cc1ccc(o1)CSCCN/C(=C/[N+](=O)[O-])/NC)(C)C.Cl
• Canonical SMILES: CN/C(=C\[N+](=O)[O-])/NCCSCc1ccc(o1)CN(C)C.Cl
• InChI: InChI=1S/C13H22N4O3S.ClH/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3;/h4-5,9,14-15H,6-8,10H2,1-3H3;1H/b13-9+
• InChIKey: GGWBHVILAJZWKJ-KJEVSKRMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[({5-[(dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}[(E)-1-(methylamino)-2-nitroethenyl]amine hydrochloride; [(E)-1-({2-[({5-[(dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}amino)-2-nitroethenyl](methyl)amine hydrochloride; dimethyl[(5-{[(2-{[1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}furan-2-yl)methyl]amine hydrochloride
• IUPAC Traditional name: {2-[({5-[(dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}[(E)-1-(methylamino)-2-nitroethenyl]amine hydrochloride; [(E)-1-({2-[({5-[(dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}amino)-2-nitroethenyl](methyl)amine hydrochloride; dimethyl[(5-{[(2-{[1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}furan-2-yl)methyl]amine hydrochloride
• Synonyms: N-[2-[[[-5-[(Dimethylamino)methyl)]-2-furanyl]methyl]thio]ethyl]-N’-methyl-2-nitro-1,1-ethenediamine Hydrochloride; Melfax; Raniben; Ranidil; Raniplex; Zintac; Ranaps; Rantec; Sostril; Taural; Terposen; Trigger; Ultidine; Zaedoc; Zantidon; Zantac; AH 19065; Azantac; Ranitidine Hydrochloride; Ranitidine hydrochloride

Database IDs

• CAS Number: 66357-59-3; 71130-06-8
• EC Number: 266-333-0
• MDL Number: MFCD00069339
• PubChem SID: 162037726; 24277803
• PubChem CID: 3033332

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.5527394
• LogD (pH = 7.4): 0.21904218
• Log P: 0.98147845
• Molar Refractivity: 95.153 cm^3
• Polarizability: 32.323387 Å^3
• Polar Surface Area: 86.26 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble7.0 mg/mL; Acetic Acid; H2O: soluble1.8 mg/mL; Methanol; Water
• Apperance: Off-White Solid; tan solid
• Melting Point: 133-134°C

Safety Information

• Storage Condition: -20°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: KM6557000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... HRH2(3274)
• Mechanism of Action: Histamine H 2-receptor antagonist

Product Information

• Salt Data: HCl; Hydrochloride
• Suitability: suitable for 1694 per US EPA
• Application(s): Antiulcer agent,; low toxicity
• Pharmacopeia Traceability: traceable to BP 471; traceable to PhEur R0150000; traceable to USP 1598405
• Empirical Formula (Hill Notation): C13H22N4O3S · HCl

DETAILS

Selleck Chemicals - S1801

Research Area: Metabolic Disease
Biological Activity:
Ranitidine (Zantac) is a histamine H2-receptor antagonist with IC50 of 3.3 ± 1.4 µM. It inhibits stomach acid production. It is also used alongside fexofenadine and other antihistamines for the treatment of skin conditions such as hives. It has 10% the affinity that cimetidine has to CYP450 so it causes fewer side effects, but other H2 blockers famotidine and nizatidine have no CYP450 significant interactions. [1][2]

Sigma Aldrich - R101

Biochem/physiol Actions
H2 histamine receptor antagonist; anti-ulcer agent.

Sigma Aldrich - 44404

Biochem/physiol Actions
H2 histamine receptor antagonist; anti-ulcer agent.

Toronto Research Chemicals - R120000

A histamine H2-receptor antagonist which inhibits gastric acid secretion. Antiulcerative.

REFERENCES

• Herling AW et al. Agents Actions. 1987 Feb;20(1-2)
• Bradshaw, J., et al.: Brit. J. Pharmacol., 66, 464 (1979)
• Berstad, A., et al.: Scand. J. Gastroenterol, 15, 637 (1979)
• Hohnjec, M., et al.: Anal. Profiles Drug Subs., 15, 533 (1979)
• Ger. Pat., 1978, Allen and Hanburys, 2 734 070; CA, 88, 190580b, (synth, pharmacol)
• Daly, M.J. et al., Br. J. Pharmacol., 1981, 72, 49; 55, (pharmacol)
• Kojic-Prodic, B. et al., Acta Cryst. B, 1982, 38, 1837, (cryst struct)
• Riley, A.J. et al., Curr. Clin. Pract. Ser., (Eds.), No. 1: Ranitidine, Excerpta Medica, Amsterdam, 1982, (book)
• Brogden, R.N. et al., Drugs, 1982, 24, 267, (rev, pharmacol)
• Gaginella, T.S. et al., Drug Intell. Clin. Pharm., 1983, 17, 873, (rev, pharmacol)
• Daly, M.J. et al., Prog. Med. Chem., 1983, 20, 337, (rev, pharmacol)
• Misiewicz, J.J. et al., Curr. Clin. Pract. Ser., 1984, 15, (book)
• Cholerton, T.J. et al., J.C.S. Perkin 2, 1984, 1761, (uv, ir, pmr, struct)
• Hohnjec, M. et al., Anal. Profiles Drug Subst., 1986, 15, 533, (rev, synth, anal, metab)
• Geraldes, C.F. et al., Magn. Reson. Chem., 1987, 25, 203, (pmr, cmr)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2946
• Kirch, W., Pharmacol. Ther., 1987, 33, 129, (rev)
• Grant, S.M. et al., Drugs, 1989, 37, 801, (pharmacol, rev)
• Spurling, N.W. et al., Hum. Toxicol., 1989, 8, 23, (chronic tox)
• The Landmark Papers: The H2-Receptor Antagonists, (Ed. Pounder, R.E.), Science Press, 1990, (pharmacol, book)
• Bradshaw, J., Chron. Drug Discovery, 1993, 3, 45, (rev)
• Wormsley, K.G., Drugs, 1993, 46, 976, (tox, rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1209; 1211
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, RBF400