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F124

Sigma-Aldrich

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:
80288-49-9
Molecular Weight:
260.25
MDL number:
MFCD00153799
UNSPSC Code:
41106305
PubChem Substance ID:
24278813
NACRES:
NA.77

product name

Furafylline, ≥98% (HPLC)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D Sesardic et al.
British journal of clinical pharmacology, 29(6), 651-663 (1990-06-01)
1. Furafylline (1,8-dimethyl-3-(2'-furfuryl)methylxanthine) is a methylxanthine derivative that was introduced as a long-acting replacement for theophylline in the treatment of asthma. Administration of furafylline was associated with an elevation in plasma levels of caffeine, due to inhibition of caffeine oxidation
Elisa Ollikainen et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 104, 124-132 (2017-04-04)
Engineered nanoparticles are increasingly used as drug carriers in pharmaceutical formulations. This study focuses on the hitherto unaddressed impact of porous silicon (PSi) nanoparticles on human cytochrome P450 (CYP) metabolism, which is the major detoxification route of most pharmaceuticals and
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
Accumulation of caffeine in healthy volunteers treated with furafylline.
Tarrus E, et al.
British Journal of Clinical Pharmacology, 23(1), 9-18 (1987)
R Hyland et al.
Drug metabolism and disposition: the biological fate of chemicals, 31(5), 540-547 (2003-04-16)
Voriconazole is a triazole antifungal agent with potent activity against a broad spectrum of clinically significant pathogens. In vivo and in vitro studies have demonstrated that voriconazole is extensively metabolized, with the major circulating metabolite resulting from N-oxidation. In the
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