Methapyrilene

Identification

Generic Name
Methapyrilene
DrugBank Accession Number
DB04819
Background

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.

Type
Small Molecule
Groups
Withdrawn
Structure
Thumb
Weight
Average: 261.39
Monoisotopic: 261.129968798
Chemical Formula
C14H19N3S
Synonyms
  • 2-[[2-(Dimethylamino)ethyl]-2-thenylamino]pyridine
  • Methapyrilene
  • 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

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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Toxicity

Not Available

Pathways
PathwayCategory
Methapyrilene H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Methapyrilene is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Methapyrilene.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Methapyrilene.
AclidiniumMethapyrilene may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Methapyrilene is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Methapyrilene.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Methapyrilene.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Methapyrilene.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Methapyrilene.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Methapyrilene.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Methapyrilene fumarateKJ5I25TXYL33032-12-1GYIUBPDECOMZDC-WLHGVMLRSA-N
Methapyrilene hydrochloride00S42N58OM135-23-9BONORRGKLJBGRV-UHFFFAOYSA-N
International/Other Brands
Co-Pyronil / Histadyl / Lullamin

Categories

ATC Codes
R06AC05 — Methapyrilene
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
A01LX40298
CAS number
91-80-5
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-yl)methyl]pyridin-2-amine
SMILES
CN(C)CCN(CC1=CC=CS1)C1=NC=CC=C1

References

General References
Not Available
KEGG Compound
C11114
PubChem Compound
8667
PubChem Substance
46505007
ChemSpider
3956
BindingDB
81469
RxNav
6822
ChEBI
6820
ChEMBL
CHEMBL1411979
ZINC
ZINC000002510048
Wikipedia
Methapyrilene

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Water Solubility0.287 mg/mLALOGPS
logP2.71ALOGPS
logP3.11ChemAxon
logS-3ALOGPS
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
Polarizability29.54 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

Drug created on September 11, 2007 20:19 / Updated on October 03, 2021 00:53