FURAFYLLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H12N4O3
Molecular Weight	260.2487
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(=O)N(CC2=CC=CO2)C3=C(NC(C)=N3)C1=O

InChI

InChIKey=KGQZGCIVHYLPBH-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C12H12N4O3
Molecular Weight	260.2487
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2378786 | https://www.ncbi.nlm.nih.gov/pubmed/3814465

Furafylline is a methylxanthine derivative that was introduced as a long-acting replacement for theophylline in the treatment of asthma, it was a bronchodilator with extended duration compared to theophylline, but then subsequently reported the adverse side effects the inhibition of the oxidation of caffeine, a reaction catalyzed by CYP1A2. Furafylline is now widely used in biochemical studies as a selective mechanism-based inhibitor of cytochrome p450 1A2.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 1A2 73 Target ID: P05177 Gene ID: 1544.0 Gene Symbol: CYP1A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2378786	Inhibitor 8504		0.07 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
DNA adducts of the tobacco carcinogens 2-amino-9H-pyrido[2,3-b]indole and 4-aminobiphenyl are formed at environmental exposure levels and persist in human hepatocytes.	2013-09-16	23898916
Interactions of sesquiterpenes zederone and germacrone with the human cytochrome P450 system.	2013-09	23850985
Non-dioxin-like AhR ligands in a mouse peanut allergy model.	2012-07	22491429
Role of P450 1A1 and P450 1A2 in bioactivation versus detoxication of the renal carcinogen aristolochic acid I: studies in Cyp1a1-/-, Cyp1a2-/-, and Cyp1a1/1a2-/- mice.	2011-10-17	21932800
Characterization of glutathione conjugates of duloxetine by mass spectrometry and evaluation of in silico approaches to rationalize the site of conjugation for thiophene containing drugs.	2010-08-16	20669986
Comparative study of the oxidation of propranolol enantiomers in hepatic and small intestinal microsomes from cynomolgus and marmoset monkeys.	2010-01-05	19853591
Identification of the human cytochrome P450 enzymes involved in the two oxidative steps in the bioactivation of clopidogrel to its pharmacologically active metabolite.	2010-01	19812348
Functional expression, inhibition and induction of CYP enzymes in HepaRG cells.	2009-06	19328226
In vitro nimesulide studies toward understanding idiosyncratic hepatotoxicity: diiminoquinone formation and conjugation.	2009-01	19053182
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.	2008-12	18493746
Automated assessment of time-dependent inhibition of human cytochrome P450 enzymes using liquid chromatography-tandem mass spectrometry analysis.	2005-11	16049126
Characterization of microsomal cytochrome P450-dependent monooxygenases in the rat olfactory mucosa.	2005-08	15879494
Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.	2005-08	15860655
Rate-limiting biotransformation of triamterene is mediated by CYP1A2.	2005-07	16035375
Molecular cloning and functional analysis of cytochrome P450 1A2 from Japanese monkey liver: comparison with marmoset cytochrome P450 1A2.	2005-02-28	15766918
Metabolism of territrem B and C in liver microsomes from 14-wk-old Wistar rats is catalyzed by cytochrome P-450 3A.	2005-02-27	15799453
Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast.	2005-01	15507517
Effects of avasimibe on cytochrome P450 2C9 expression in vitro and in vivo.	2004-12	15333513
Drug-drug interactions of Z-338, a novel gastroprokinetic agent, with terfenadine, comparison with cisapride, and involvement of UGT1A9 and 1A8 in the human metabolism of Z-338.	2004-08-23	15306208
Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes.	2004-08-15	15276085
Identification of cytochrome P-450s involved in the formation of APNH from norharman with aniline.	2004-08-08	15279827
Validated assays for human cytochrome P450 activities.	2004-06	15155557
Selectivities of human cytochrome P450 inhibitors toward rat P450 isoforms: study with cDNA-expressed systems of the rat.	2003-07	12814958
High-throughput inhibition screening of major human cytochrome P450 enzymes using an in vitro cocktail and liquid chromatography-tandem mass spectrometry.	2003-01-01	12467917
Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate.	2003	12569440
Azole-antifungal binding to a novel cytochrome P450 from Mycobacterium tuberculosis: implications for treatment of tuberculosis.	2001-06-15	11377375
Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism.	1999-03	10215755
Identification of enzymes involved in the metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in human liver microsomes.	1997-09	9305587
Assessing human risk to heterocyclic amines.	1997-05-12	9202738
Human cytochrome P450 isoform specificity in the regioselective metabolism of toluene and o-, m- and p-xylene.	1996-01	8558417
Metabolism of the food derived mutagen and carcinogen 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine (PhIP) by human liver microsomes.	1994-06	8020169

Patents

Sample Use Guides

In Vivo Use Guide

in normal volunteers: steady state was achieved on the first day following the administration of 90 mg and maintained by subsequent daily doses of 30 mg.

Route of Administration: Oral

In Vitro Use Guide

Furafylline was a potent, non-competitive inhibitor of high affinity phenacetin O-deethylase activity of microsomal fractions of human liver, a reaction catalysed by P450IA2, with an IC50 value of 0.07 microM. Furafylline was added to the samples at a concentration of 0-200 um. Furafylline had either very little or no effect on human monooxygenase activities catalysed by other isoenzymes of P450, including P450IID1, P450IIC, P450IIA.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:21:12 GMT 2025` Edited by `admin` on `Wed Apr 02 09:21:12 GMT 2025`
Record UNII	C2087G0XX3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FURAFYLLINE

Official Name

English

Furafylline [WHO-DD]

Preferred Name

English

furafylline [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744