Methapyrilene

Identification

Name
Methapyrilene
Accession Number
DB04819
Type
Small Molecule
Groups
Withdrawn
Description

Methapyrilene, formerly marketed in many drug products, was shown to be a potent carcinogen. Manufacturers voluntarily withdrew methapyriline drug products from the market in May and June 1979.

Structure
Thumb
Synonyms
  • 2-[[2-(Dimethylamino)ethyl]-2-thenylamino]pyridine
  • Methypyrilene
  • N-(α-pyridyl)-N-(α-thenyl)-N',N'-dimethylethylenediamine
  • N,N-dimethyl-N'-pyrid-2-yl-N'-2-thenylethylenediamine
  • N,N-dimethyl-N'-pyridin-2-yl-N'-(2-thienylmethyl)ethane-1,2-diamine
  • Thenylpyramine
External IDs
A 3322 / A-3322
Product Ingredients
IngredientUNIICASInChI Key
Methapyrilene fumarateKJ5I25TXYL33032-12-1GYIUBPDECOMZDC-WLHGVMLRSA-N
Methapyrilene hydrochloride00S42N58OM135-23-9BONORRGKLJBGRV-UHFFFAOYSA-N
International/Other Brands
Co-Pyronil / Histadyl / Lullamin
Categories
UNII
A01LX40298
CAS number
91-80-5
Weight
Average: 261.39
Monoisotopic: 261.129968798
Chemical Formula
C14H19N3S
InChI Key
HNJJXZKZRAWDPF-UHFFFAOYSA-N
InChI
InChI=1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3
IUPAC Name
N-[2-(dimethylamino)ethyl]-N-(thiophen-2-ylmethyl)pyridin-2-amine hydrochloride
SMILES
CN(C)CCN(CC1=CC=CS1)C1=NC=CC=C1

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
  • Humans and other mammals
Pathways
PathwayCategory
Methapyrilene H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Methapyrilene.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Methapyrilene.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Methapyrilene.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Methapyrilene.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Methapyrilene.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Methapyrilene is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Methapyrilene.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Methapyrilene is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Methapyrilene.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Methapyrilene.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C11114
PubChem Compound
8667
PubChem Substance
46505007
ChemSpider
3956
BindingDB
81469
ChEBI
6820
ChEMBL
CHEMBL1411979
Wikipedia
Methapyrilene
ATC Codes
R06AC05 — Methapyrilene

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
boiling point (°C)173-175 °C at 3.00E+00 mm HgNot Available
water solubility601 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.87SANGSTER (1994)
logS-2.64ADME Research, USCD
pKa8.85 (at 20 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
logP3.11ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.16 m3·mol-1ChemAxon
Polarizability29.5 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9873
Blood Brain Barrier+0.9492
Caco-2 permeable+0.6224
P-glycoprotein substrateSubstrate0.6832
P-glycoprotein inhibitor INon-inhibitor0.9755
P-glycoprotein inhibitor IINon-inhibitor0.9142
Renal organic cation transporterInhibitor0.5832
CYP450 2C9 substrateNon-substrate0.7548
CYP450 2D6 substrateNon-substrate0.7717
CYP450 3A4 substrateNon-substrate0.5307
CYP450 1A2 substrateInhibitor0.831
CYP450 2C9 inhibitorNon-inhibitor0.8932
CYP450 2D6 inhibitorInhibitor0.8168
CYP450 2C19 inhibitorNon-inhibitor0.7581
CYP450 3A4 inhibitorNon-inhibitor0.9942
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7722
Ames testNon AMES toxic0.888
CarcinogenicityNon-carcinogens0.9043
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5098 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.847
hERG inhibition (predictor II)Non-inhibitor0.6318
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-9321100000-38a0087cd9f89575fa1a

Taxonomy

Classification
Not classified

Drug created on September 11, 2007 14:19 / Updated on November 02, 2018 09:16