3-cyano-1-methyl-2-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

• ChemBase ID: 103122
• Molecular Formular: C10H16N6S
• Molecular Mass: 252.33924
• Monoisotopic Mass: 252.11571554
• SMILES: CN/C(=N\CCSCc1c(C)[nH]cn1)/NC#N
• Canonical SMILES: N#CN/C(=N/CCSCc1nc[nH]c1C)/NC
• InChI: InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)
• InChIKey: AQIXAKUUQRKLND-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-cyano-1-methyl-2-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
• IUPAC Traditional name: 3-cyano-1-methyl-2-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
• Synonyms: Tagamet; N-Cyano-N'-Methyl-N''-(2-(((5-Methyl-1H-Imidazol-4-YL)Methyl)Thio)Ethyl) Guanidine; SKF-92334; CIMETIDINE; Cimetidine

Database IDs

• CAS Number: 51481-61-9
• EC Number: 257-232-2
• MDL Number: MFCD00133296
• PubChem SID: 162089818; 24277766
• PubChem CID: 2756

CALCULATED PROPERTIES

• Acid pKa: 13.382496
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.0659236
• LogD (pH = 7.4): -0.21997723
• Log P: -0.109356105
• Molar Refractivity: 70.3171 cm^3
• Polarizability: 25.88739 Å^3
• Polar Surface Area: 88.89 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 141-143°C

Safety Information

• Storage Condition: 2-8°C, Protect from light
• RTECS: MF0035500
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60
• Safety Statements: 26-36/37/39-45; 53-26-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ABCB1(5243), CYP1A2(1544), CYP3A4(1576), HRH2(3274), SLC9A2(6549), SLC9A5(6553)mouse ... Abcb1a(18671), Abcb1b(18669)rat ... Slc9a1(24782), Slc9a3(24784), Slc9a5(192215)

Product Information

• Suitability: suitable for 1694 per US EPA
• Pharmacopeia Traceability: traceable to BP 475; traceable to PhEur C2175000; traceable to USP 1134062
• Empirical Formula (Hill Notation): C10H16N6S

DETAILS

MP Biomedicals - 02150687

Crystalline
Histamine H₂ -receptor antagonist that inhibits gastric acid secretion and reduces pepsin production. Also a potent imidazoline I₁ receptor agonist.

Sigma Aldrich - C4522

Biochem/physiol Actions
H2 histamine receptor antagonist; I1 imidazoline receptor agonist; anti-ulcer agent. Blocks cancer metastasis by inhibiting the expression of E-selectin on the surface of endothelial cells, thus blocking tumor cell adhesion.

REFERENCES

• Brimblecombe, R.W., et al., J. Int. Med. Res. , 3 : 86 (1975).