1-[1-(1-benzothiophen-2-yl)(2H4)ethyl]-1-hydroxyurea

• ChemBase ID: 179577
• Molecular Formular: C11H12N2O2S
• Molecular Mass: 236.29018
• Monoisotopic Mass: 236.06194863
• SMILES: c1cccc2c1sc(c2)C(N(C(=O)N)O)C
• Canonical SMILES: ON(C(c1cc2c(s1)cccc2)C)C(=O)N
• InChI: InChI=1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)
• InChIKey: MWLSOWXNZPKENC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[1-(1-benzothiophen-2-yl)(^2H₄)ethyl]-1-hydroxyurea
• IUPAC Traditional name: 1-[1-(1-benzothiophen-2-yl)(^2H₄)ethyl]-1-hydroxyurea
• Synonyms: N-(1-Benzo[b]thien-2-yl-ethyl)-N-hydroxyurea-d4; A-64077-d4; Abbott 64077-d4; Leutrol-d4; Zyflo-d4; Zileuton-d4 (major)

Database IDs

• CAS Number: 1189878-76-9
• PubChem SID: 164235487
• PubChem CID: 45040698

CALCULATED PROPERTIES

• Acid pKa: 8.837783
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.0059743
• LogD (pH = 7.4): 1.9906728
• Log P: 2.006173
• Molar Refractivity: 61.9595 cm^3
• Polarizability: 24.979473 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 153-155°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Z420002

An inhibitor of 5-lipoxygenase, the initial enzyme in the biosynthesis of leukotrienes from Arachidonic Acid. Used as an antiasthmatic.

REFERENCES

• Carter, G.W., et al.: J. Pharmacol. Exp. Ther., 256, 929 (1991)
• Weinblatt, M.E., et al.: J. Rheumatol., 19, 1537 (1991)
• McGill, K and Busse, W.W.: Lancet, 348, 519 (1996)