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Merck

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

Key Documents

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Product Name

Furafylline, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

powder

color

white to beige

mp

274-275  °C

solubility

DMSO: 10 mg/mL, clear

storage temp.

room temp

Quality Level

100

Gene Information

human ... CYP1A2(1544)

Related Categories

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000479104
0000479104
0000509358
0000509358
0000477525

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Marilia N Siebert et al.
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology, 203, 115-121 (2016-10-23)
Cytochrome P450 family 1 (CYP1) is involved in polycyclic aromatic hydrocarbons (PAHs) biotransformation. PAHs can induce CYP1 protein expression and enzyme activity, the latter being usually quantified as 7-ethoxyresorufin O-deethylase activity (EROD). The aim of this study was to characterize
L Labbé et al.
Xenobiotica; the fate of foreign compounds in biological systems, 33(1), 13-25 (2003-01-10)
1. Mexiletine is extensively metabolized in man by C- and N-oxidation and the aim of the present study was to characterize major cytochrome P450 enzyme(s) involved in the formation of N-hydroxymexiletine. 2. Incubations with genetically engineered microsomes indicated that the
Nicholas Ekow Thomford et al.
Journal of ethnopharmacology, 211, 58-69 (2017-09-25)
Hyptis suaveolens (L) Poit and Boerhavia diffusa Linn are medicinal herbal plants commonly found in the tropics and sub-tropics. They are used to treat various conditions among them boils, dyslipidaemia, eczema, malaria, jaundice and gonorrhoea. Thus, the herbal medicinal extracts
Accumulation of caffeine in healthy volunteers treated with furafylline.
Tarrus E, et al.
British Journal of Clinical Pharmacology, 23(1), 9-18 (1987)
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
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