NAV

Fenethylline

Identification

Generic Name
Fenethylline
DrugBank Accession Number
DB01482
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 341.415
Monoisotopic: 341.185175001
Chemical Formula
C18H23N5O2
Synonyms
  • Amfetyline
  • Fenethylline
  • Fenetilina
  • Fenetillina
  • Fenetylline
  • Fenetyllinum
External IDs
  • D323
  • HOMBURG-814
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Fenethylline.
AbametapirThe serum concentration of Fenethylline can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Fenethylline can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Fenethylline can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Fenethylline.
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Fenethylline hydrochlorideYA7K8ADZ2V1892-80-4MVXGSLGVWBVZCA-UHFFFAOYSA-N
International/Other Brands
Captagon (Meda)

Categories

ATC Codes
N06BA10 — Fenetylline
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
YZ0N7VL5R3
CAS number
3736-08-1
InChI Key
NMCHYWGKBADVMK-UHFFFAOYSA-N
InChI
InChI=1S/C18H23N5O2/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
IUPAC Name
1,3-dimethyl-7-{2-[(1-phenylpropan-2-yl)amino]ethyl}-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CC(CC1=CC=CC=C1)NCCN1C=NC2=C1C(=O)N(C)C(=O)N2C

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
PubChem Compound
102710
PubChem Substance
46505193
ChemSpider
18398
RxNav
24840
ChEBI
135451
ChEMBL
CHEMBL2111152
Wikipedia
Fenethylline

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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)10.03Chemaxon
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/MSsplash10-0006-0009000000-49a242a0d13f2c1e0ffa
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0019000000-9f48bcabdf91f3cd2aca
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-2339000000-f747e4c1916db1774c6e
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0091000000-d9c01736a62ff5a23e0f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-2941000000-6d7a5970f6b15baa3cab
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-4983000000-ed24dc298457b64fb7bb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-170.20203
predicted
DeepCCS 1.0 (2019)
[M+H]+172.56001
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.41505
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Theophylline metabolic pathway [Link]
  6. CYP1A2 activity, gender and smoking, as variables influencing the toxicity of caffeine [File]

Drug created at July 31, 2007 13:09 / Updated at June 12, 2020 16:51