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F124

Sigma-Aldrich

Furafylline

≥98% (HPLC), powder, caffeine inhibitor

Sinónimos:

3-(2-Furanylmethyl)-3,7-dihydro-1,8-dimethyl-1H-purine-2,6-dione

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About This Item

Fórmula empírica (notación de Hill):
C12H12N4O3
Número de CAS:
80288-49-9
Peso molecular:
260.25
MDL number:
MFCD00153799
UNSPSC Code:
41106305
PubChem Substance ID:
24278813
NACRES:
NA.77

Nombre del producto

Furafylline, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

mp

274-275  °C

solubility

DMSO: 10 mg/mL, clear

storage temp.

room temp

SMILES string

CN1C(=O)N(Cc2ccco2)c3nc(C)[nH]c3C1=O

InChI

1S/C12H12N4O3/c1-7-13-9-10(14-7)16(6-8-4-3-5-19-8)12(18)15(2)11(9)17/h3-5H,6H2,1-2H3,(H,13,14)

InChI key

KGQZGCIVHYLPBH-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

Biochem/physiol Actions

Furafylline (1,8-dimethyl-3-(2′ -furfuryl)methylxanthine) is a xanthine derivative. It is preferred in treating asthma. It serves as a N3-demethylation inhibitor of caffeine. Furafylline does not show much effect on human monooxygenase activities. It is considered as an efficient bronchodilator and as an inhibitor of anaphylactic reactions, when compared to theophylline.
Furafylline is a methyl xanthine derivative with longer duration of action than theophylline and an inhibitor of cytochrome P4501A2.

Features and Benefits

This compound is a featured product for ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox and Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
025M4764V
103M4710V
022M4716V
041M4730V
108K4705

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Robert J Turesky et al.
Mutation research, 506-507, 187-195 (2002-09-28)
The metabolism of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) was investigated in primary human and rat hepatocytes. The genotoxic metabolites 2-(hydroxyamino)-3,8-dimethylimidazo[4,5-f]quinoxaline (HONH-MeIQx) and 2-(hydroxyamino)-1-methyl-6-phenylimidazo[4,5-b]pyridine (HONH-PhIP), which are formed by cytochrome P4501A2 (CYP1A2), were detected as stable N(2)-glucuronide and N(2)- and N(3)-glucuronide
Lars Brachtendorf et al.
Pharmacology & toxicology, 90(3), 144-149 (2002-06-20)
From case reports of patients treated with the tetracyclic antidepressant drug maprotiline, it appears that this drug is subject to polymorphic metabolism. Thus, we studied formation of the major maprotiline metabolite desmethylmaprotiline to identify the human cytochrome P-450 enzymes (CYP)
X Boulenc et al.
The Journal of pharmacology and experimental therapeutics, 263(3), 1471-1478 (1992-12-01)
The expression and inducibility of cytochrome P450IA1 isozyme was investigated in the human carcinoma cell line Caco-2 cultured between days 7 and 35 in the absence or the presence of various enzyme inducers such as 3-methylcholanthrene, beta-naphthoflavone (beta NF), dioxin
Furafylline is a potent and selective inhibitor of cytochrome P450IA2 in man.
Sesardicm D, et al.
British Journal of Clinical Pharmacology, 29(6), 651-663 (1990)
Michael Gillen et al.
Clinical pharmacology in drug development, 6(4), 363-376 (2017-01-10)
Lesinurad is a selective uric acid reabsorption inhibitor approved for the treatment of hyperuricemia associated with gout in combination with xanthine oxidase inhibitors. In vitro assays indicate that lesinurad is an inducer of CYPs in the order CYP3A > CYP2C8
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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

Discover Bioactive Small Molecules for ADME/Tox

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