Identification

Name
Fenethylline
Accession Number
DB01482
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Fenethylline
  • Fenethylline hcl
  • Fenetylline
International/Other Brands
Captagon (Meda)
Categories
UNII
YZ0N7VL5R3
CAS number
3736-08-1
Weight
Average: 377.868
Monoisotopic: 377.161852744
Chemical Formula
C18H24ClN5O2
InChI Key
MVXGSLGVWBVZCA-UHFFFAOYSA-N
InChI
InChI=1S/C18H23N5O2.ClH/c1-13(11-14-7-5-4-6-8-14)19-9-10-23-12-20-16-15(23)17(24)22(3)18(25)21(16)2;/h4-8,12-13,19H,9-11H2,1-3H3;1H
IUPAC Name
1,3-dimethyl-7-{2-[(1-phenylpropan-2-yl)amino]ethyl}-2,3,6,7-tetrahydro-1H-purine-2,6-dione hydrochloride
SMILES
Cl.CC(CC1=CC=CC=C1)NCCN1C=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 Fenethylline 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 Fenethylline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Fenethylline.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Fenethylline.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Fenethylline.
3,5-diiodothyropropionic acidThe serum concentration of Fenethylline 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 Fenethylline.
6-Deoxyerythronolide BThe metabolism of Fenethylline 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 Fenethylline.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Fenethylline.
Food Interactions
Not Available

References

Synthesis Reference

Kohlstaedt, E. and Klingler, K.H.; U.S. Patent 3,029,239; April 10, 1962; assigned to Chemiewerke Homburg.

General References
Not Available
External Links
PubChem Compound
102710
PubChem Substance
46505193
ChemSpider
92775
ChEMBL
CHEMBL2107591
Wikipedia
Fenethylline
ATC Codes
N06BA10 — Fenetylline

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
PropertyValueSource
melting point (°C)227-229Kohlstaedt, E. and Klingler, K.H.; U.S. Patent 3,029,239; April 10, 1962; assigned to Chemiewerke Homburg.
Predicted Properties
PropertyValueSource
logP1.52ChemAxon
pKa (Strongest Basic)10.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area70.47 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.34 m3·mol-1ChemAxon
Polarizability36.03 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9145
Caco-2 permeable-0.6141
P-glycoprotein substrateSubstrate0.7324
P-glycoprotein inhibitor INon-inhibitor0.706
P-glycoprotein inhibitor IIInhibitor0.7238
Renal organic cation transporterNon-inhibitor0.6446
CYP450 2C9 substrateNon-substrate0.722
CYP450 2D6 substrateNon-substrate0.8058
CYP450 3A4 substrateSubstrate0.6524
CYP450 1A2 substrateNon-inhibitor0.7432
CYP450 2C9 inhibitorNon-inhibitor0.7196
CYP450 2D6 inhibitorNon-inhibitor0.7984
CYP450 2C19 inhibitorNon-inhibitor0.6107
CYP450 3A4 inhibitorInhibitor0.6417
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.624
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.788
BiodegradationNot ready biodegradable0.9918
Rat acute toxicity3.1898 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Inhibitor0.6707
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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 / Amphetamines and derivatives / Phenylpropanes / Alkaloids and derivatives / Pyrimidones / Aralkylamines / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Ureas
show 8 more
Substituents
Xanthine / 6-oxopurine / Amphetamine or derivatives / Purinone / Phenylpropane / Alkaloid or derivatives / Pyrimidone / Aralkylamine / Monocyclic benzene moiety / N-substituted imidazole
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. This drug 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. 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]
  2. 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]
  3. 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]
  4. 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]
  5. Theophylline metabolic pathway [Link]
  6. CYP1A2 activity, gender and smoking, as variables influencing the toxicity of caffeine [File]

Drug created on July 31, 2007 07:09 / Updated on November 02, 2018 05:01