2-(carbamoylamino)-5-(4-fluorophenyl)thiophene-3-carboxamide

• ChemBase ID: 153914
• Molecular Formular: C12H10FN3O2S
• Molecular Mass: 279.2901032
• Monoisotopic Mass: 279.0477758
• SMILES: c1cc(ccc1c1cc(c(s1)NC(=O)N)C(=O)N)F
• Canonical SMILES: NC(=O)Nc1sc(cc1C(=O)N)c1ccc(cc1)F
• InChI: InChI=1S/C12H10FN3O2S/c13-7-3-1-6(2-4-7)9-5-8(10(14)17)11(19-9)16-12(15)18/h1-5H,(H2,14,17)(H3,15,16,18)
• InChIKey: SAYGKHKXGCPTLX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(carbamoylamino)-5-(4-fluorophenyl)thiophene-3-carboxamide
• IUPAC Traditional name: 2-(carbamoylamino)-5-(4-fluorophenyl)thiophene-3-carboxamide
• Synonyms: GW683965; GW683965A; [5-(p-Fluorophenyl)-2-ureido]thiophene-3-carboxamide; TPCA-1; TPCA-1

Database IDs

• CAS Number: 507475-17-4
• MDL Number: MFCD09037541
• PubChem SID: 162248053
• PubChem CID: 9903786

CALCULATED PROPERTIES

• Acid pKa: 10.184728
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 2.1111135
• LogD (pH = 7.4): 2.1104455
• Log P: 2.1111224
• Molar Refractivity: 70.0785 cm^3
• Polarizability: 26.686598 Å^3
• Polar Surface Area: 98.21 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL; H2O: insoluble
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: IKK

Product Information

• Purity: ≥95% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H10FN3O2S

DETAILS

Sigma Aldrich - T1452

Biochem/physiol Actions
TPCA-1 is a potent and selective inhibitor of human IκB kinase-2 (IKK-2) with IC50 = 17.9 nM for IKK-2 compared to 400nm for IKK-1. It has been used to study inhibition of IKK-2 to prevent inflammatory mediator release in animal models of arthritis and airway inflammation.