F124
Furafylline
≥98% (HPLC), powder, caffeine inhibitor
Synonym(s):
3-(2-Furanylmethyl)-3,7-dihydro-1,8-dimethyl-1H-purine-2,6-dione
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About This Item
Empirical Formula (Hill Notation):
C12H12N4O3
CAS Number:
Molecular Weight:
260.25
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Product Name
Furafylline, ≥98% (HPLC)
Quality Level
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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