This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Furafylline
Accession Number
DB14029
Type
Small Molecule
Groups
Experimental
Description

Furafylline is a methylxanthine derivative that was introduced in hope of being a long-acting replacement for theophylline in the treatment of asthma.

Structure
Thumb
Synonyms
  • Furafilina
  • Furafyllinum
Categories
UNII
C2087G0XX3
CAS number
80288-49-9
Weight
Average: 293.345
Monoisotopic: 293.13282569
Chemical Formula
C18H16FN3
InChI Key
HMZQULPVMKITSP-UHFFFAOYSA-N
InChI
InChI=1S/C18H16FN3/c19-18-16(12-3-1-11(9-20)2-4-12)7-13(10-21-18)15-8-14-5-6-17(15)22-14/h1-4,7,10,14-15,17,22H,5-6,8H2
IUPAC Name
4-(5-{7-azabicyclo[2.2.1]heptan-2-yl}-2-fluoropyridin-3-yl)benzonitrile
SMILES
FC1=C(C=C(C=N1)C1CC2CCC1N2)C1=CC=C(C=C1)C#N

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Furafylline.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Furafylline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Furafylline.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Furafylline.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Furafylline.
3,5-diiodothyropropionic acidThe serum concentration of Furafylline can be increased when it is combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Furafylline.
6-Deoxyerythronolide BThe metabolism of Furafylline can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Furafylline.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Furafylline.
Food Interactions
Not Available

References

General References
  1. Sesardic D, Boobis AR, Murray BP, Murray S, Segura J, de la Torre R, Davies DS: Furafylline is a potent and selective inhibitor of cytochrome P450IA2 in man. Br J Clin Pharmacol. 1990 Jun;29(6):651-63. [PubMed:2378786]
External Links
ChemSpider
23262468
BindingDB
50171007
ChEMBL
CHEMBL372638
Wikipedia
Furafylline

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00961 mg/mLALOGPS
logP2.69ALOGPS
logP3.06ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area48.71 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity83.61 m3·mol-1ChemAxon
Polarizability31.36 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Racha JK, Rettie AE, Kunze KL: Mechanism-based inactivation of human cytochrome P450 1A2 by furafylline: detection of a 1:1 adduct to protein and evidence for the formation of a novel imidazomethide intermediate. Biochemistry. 1998 May 19;37(20):7407-19. doi: 10.1021/bi973011m. [PubMed:9585555]
  2. Fairman DA, Collins C, Chapple S: Progress curve analysis of CYP1A2 inhibition: a more informative approach to the assessment of mechanism-based inactivation? Drug Metab Dispos. 2007 Dec;35(12):2159-65. doi: 10.1124/dmd.107.017236. Epub 2007 Sep 6. [PubMed:17823234]
  3. Kunze KL, Trager WF: Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem Res Toxicol. 1993 Sep-Oct;6(5):649-56. [PubMed:8292742]
  4. Pilocarpine pharmacology review, FDA [File]

Drug created on May 15, 2018 16:28 / Updated on November 02, 2018 07:49