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

Identification

Name
Bamifylline
Accession Number
DB13203
Type
Small Molecule
Groups
Experimental
Description

Bamifylline is a selective A1 adenosine receptor antagonist.

Structure
Thumb
Synonyms
  • Bamifilina
  • Bamifyllinum
Product Ingredients
IngredientUNIICASInChI Key
Bamifylline hydrochloride66466QLM3S20684-06-4PDBXHPORMXSXKO-UHFFFAOYSA-N
Categories
UNII
ZTY15D026H
CAS number
2016-63-9
Weight
Average: 385.468
Monoisotopic: 385.211389749
Chemical Formula
C20H27N5O3
InChI Key
VVUYEFBRTFASAH-UHFFFAOYSA-N
InChI
InChI=1S/C20H27N5O3/c1-4-24(12-13-26)10-11-25-16(14-15-8-6-5-7-9-15)21-18-17(25)19(27)23(3)20(28)22(18)2/h5-9,26H,4,10-14H2,1-3H3
IUPAC Name
8-benzyl-7-{2-[ethyl(2-hydroxyethyl)amino]ethyl}-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CCN(CCO)CCN1C(CC2=CC=CC=C2)=NC2=C1C(=O)N(C)C(=O)N2C

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

References

General References
Not Available
External Links
ChemSpider
15401
ChEBI
135605
ChEMBL
CHEMBL2110760
Wikipedia
Bamifylline
ATC Codes
R03DA08 — Bamifylline

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
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.79 mg/mLALOGPS
logP1.71ALOGPS
logP1.1ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)8.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.91 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity108.05 m3·mol-1ChemAxon
Polarizability42.46 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / Benzene and substituted derivatives / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Lactams / 1,2-aminoalcohols / Ureas
show 6 more
Substituents
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / Monocyclic benzene moiety / N-substituted imidazole / Pyrimidine / Benzenoid / Heteroaromatic compound
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Curator comments
This enzyme listing is based on pharmacokinetic data for methylxanthines as a drug class. Methylxanthines are metabolized by CYP1A2. Bamifylline is a methylxanthine and is therefore assumed to be metabolized by this enzyme.
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. Thorn CF, Aklillu E, McDonagh EM, Klein TE, Altman RB: PharmGKB summary: caffeine pathway. Pharmacogenet Genomics. 2012 May;22(5):389-95. doi: 10.1097/FPC.0b013e3283505d5e. [PubMed:22293536]
  2. Buters JT, Tang BK, Pineau T, Gelboin HV, Kimura S, Gonzalez FJ: Role of CYP1A2 in caffeine pharmacokinetics and metabolism: studies using mice deficient in CYP1A2. Pharmacogenetics. 1996 Aug;6(4):291-6. [PubMed:8873215]
  3. Hakooz NM: Caffeine metabolic ratios for the in vivo evaluation of CYP1A2, N-acetyltransferase 2, xanthine oxidase and CYP2A6 enzymatic activities. Curr Drug Metab. 2009 May;10(4):329-38. [PubMed:19519341]
  4. Rasmussen BB, Brosen K: Determination of urinary metabolites of caffeine for the assessment of cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activity in humans. Ther Drug Monit. 1996 Jun;18(3):254-62. [PubMed:8738764]
  5. Theophylline metabolic pathway [Link]
  6. CYP1A2 activity, gender and smoking, as variables influencing the toxicity of caffeine [File]

Drug created on June 23, 2017 14:37 / Updated on November 02, 2018 09:14