Explore a selection of our essential drug information below, or:
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- Withdrawn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
Structure for Methapyrilene (DB04819)
- 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
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Methapyrilene H1-Antihistamine Action Drug 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Methapyrilene is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Methapyrilene. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Methapyrilene. Agomelatine The risk or severity of CNS depression can be increased when Methapyrilene is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Methapyrilene. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Methapyrilene fumarate KJ5I25TXYL 33032-12-1 GYIUBPDECOMZDC-WLHGVMLRSA-N Methapyrilene hydrochloride 00S42N58OM 135-23-9 BONORRGKLJBGRV-UHFFFAOYSA-N - International/Other Brands
- Co-Pyronil / Histadyl / Lullamin
Categories
- ATC Codes
- R06AC05 — Methapyrilene
- Drug Categories
- Amines
- Aminopyridines
- Anti-Allergic Agents
- Antihistamines for Systemic Use
- Central Nervous System Agents
- Central Nervous System Depressants
- Diamines
- Ethylenediamines
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Hypnotics and Sedatives
- Neurotransmitter Agents
- Polyamines
- Pyridines
- Substituted Ethylene Diamines
- 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
- External Links
- KEGG Compound
- C11114
- PubChem Compound
- 8667
- PubChem Substance
- 46505007
- ChemSpider
- 3956
- BindingDB
- 81469
- 6822
- ChEBI
- 6820
- ChEMBL
- CHEMBL1411979
- ZINC
- ZINC000002510048
- Wikipedia
- Methapyrilene
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source boiling point (°C) 173-175 °C at 3.00E+00 mm Hg Not Available water solubility 601 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 2.87 SANGSTER (1994) logS -2.64 ADME Research, USCD pKa 8.85 (at 20 °C) PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 0.287 mg/mL ALOGPS logP 2.71 ALOGPS logP 3.11 Chemaxon logS -3 ALOGPS pKa (Strongest Basic) 8.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 19.37 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 78.16 m3·mol-1 Chemaxon Polarizability 29.54 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9873 Blood Brain Barrier + 0.9492 Caco-2 permeable + 0.6224 P-glycoprotein substrate Substrate 0.6832 P-glycoprotein inhibitor I Non-inhibitor 0.9755 P-glycoprotein inhibitor II Non-inhibitor 0.9142 Renal organic cation transporter Inhibitor 0.5832 CYP450 2C9 substrate Non-substrate 0.7548 CYP450 2D6 substrate Non-substrate 0.7717 CYP450 3A4 substrate Non-substrate 0.5307 CYP450 1A2 substrate Inhibitor 0.831 CYP450 2C9 inhibitor Non-inhibitor 0.8932 CYP450 2D6 inhibitor Inhibitor 0.8168 CYP450 2C19 inhibitor Non-inhibitor 0.7581 CYP450 3A4 inhibitor Non-inhibitor 0.9942 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7722 Ames test Non AMES toxic 0.888 Carcinogenicity Non-carcinogens 0.9043 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5098 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.847 hERG inhibition (predictor II) Non-inhibitor 0.6318
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0090000000-55670f7da1fc95a8a81a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0190000000-31ef356746dee41ba354 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03xr-1090000000-8ed6f7922f1fd4ea72c9 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0ap0-1920000000-5ed8f6eeffa3e09de7d0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-06di-6920000000-9cd2a88700bb44f6e6a0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0900-1900000000-0ca3a3e483e90b7f8b48 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 150.39241 predictedDeepCCS 1.0 (2019) [M+H]+ 152.75044 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.77245 predictedDeepCCS 1.0 (2019)
Drug created at September 11, 2007 20:19 / Updated at August 02, 2024 07:34