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Compound Detail

CHEMBL1411979

METHAPYRILENE
💊 Approved Drug
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💊 Approved Drug
CN(C)CCN(Cc1cccs1)c1ccccn1

Basic Information

ChEMBL ID CHEMBL1411979
Name METHAPYRILENE
Phase Approved
Structure Type MOL
InChI Key HNJJXZKZRAWDPF-UHFFFAOYSA-N

Known Names

A 3322 A-3322 Metapirileno Metapyrilene Methapyrilene Pyrinistol Restryl Semikon Sleepwell Tenalin Thionylan
15
Targets
29
Activities
2
Assay Types
3
PK Parameters
20
Publications
11
Known Names
1
Indications

Molecular Properties

261.4
MW (Da)
2.71
ALogP
4
HBA
0
HBD
19.4
PSA (Ų)
0.80
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C14H19N3S
MW 261.39
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -2.08

Indications

Hypersensitivity

ATC Classification

R06AC05
methapyrilene
Level 1: RESPIRATORY SYSTEM
Level 2: ANTIHISTAMINES FOR SYSTEMIC USE

Drug Warnings

Withdrawn
carcinogenicity
suspected carcinogenicity
Country: Germany; United States; United Kingdom; Italy; India; Philippines; Egypt; Dominican Republic; Chile; Canada; Australia   Year: 1979
Withdrawn
General Warning
health risks associated with use
Country: Germany; United States; United Kingdom; Italy; India; Philippines; Egypt; Dominican Republic; Chile; Canada; Australia   Year: 1979

Activity Summary

IC50 15 meas. best 7.8
Ki 14 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H1 receptor
CHEMBL231
Ki 8.74 8.74 1.8 1
Histamine H1 receptor
CHEMBL231
IC50 7.8 7.8 16.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.97 6.97 106.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.75 6.75 180.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 6.7 6.7 200.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.41 6.41 390.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.36 6.36 437.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 6.27 6.27 537.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.23 6.23 592.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 6.2 6.2 628.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.13 6.13 744.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.07 6.07 843.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.94 5.94 1150.0 1
Unchecked
CHEMBL612545
Ki 5.94 5.94 1157.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.93 5.93 1165.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.86 5.86 1380.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.86 5.86 1391.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 5.84 5.84 1435.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.82 5.82 1515.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 5.78 5.78 1665.0 1
Unchecked
CHEMBL612545
IC50 5.76 5.76 1736.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.66 5.66 2190.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 5.63 5.63 2346.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.56 5.56 2757.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 5.56 5.56 2756.4 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 5.51 5.51 3091.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 5.49 5.49 3265.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.48 5.48 3318.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.32 5.32 4773.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 28.0 mL.min-1.kg-1 Homo sapiens
MRT 2.0 hr Homo sapiens
T1/2 1.6 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H1 receptor Ki = 1.802 nM 8.74 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Histamine H1 receptor IC50 = 16.0 nM 7.8 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Sodium-dependent serotonin transporter Ki = 106.0 nM 6.97 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
5-hydroxytryptamine receptor 2A Ki = 180.0 nM 6.75 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Sodium-dependent serotonin transporter IC50 = 200.0 nM 6.7 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
5-hydroxytryptamine receptor 2C Ki = 390.0 nM 6.41 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Alpha-2A adrenergic receptor Ki = 437.0 nM 6.36 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
5-hydroxytryptamine receptor 2B Ki = 537.0 nM 6.27 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M2 Ki = 592.0 nM 6.23 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2A IC50 = 628.0 nM 6.2 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C IC50 = 744.0 nM 6.13 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B IC50 = 843.0 nM 6.07 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Unchecked Ki = 1157.0 nM 5.94 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
Muscarinic acetylcholine receptor M1 Ki = 1150.0 nM 5.94 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Alpha-2A adrenergic receptor IC50 = 1165.0 nM 5.93 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Sodium-dependent noradrenaline transporter Ki = 1380.0 nM 5.86 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter IC50 = 1391.0 nM 5.86 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
5-hydroxytryptamine receptor 6 Ki = 1435.0 nM 5.84 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
Alpha-2B adrenergic receptor Ki = 1515.0 nM 5.82 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Muscarinic acetylcholine receptor M2 IC50 = 1665.0 nM 5.78 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1437
- 10.6019/CHEMBL3885881 Rattus norvegicus 669
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4808148 Histone deacetylase 6 3
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
21965623 10.1124/dmd.111.040758 Bile salt export pump 2
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
20843939 10.1124/dmd.110.035113 Hepatotoxicity 2
21965623 10.1124/dmd.111.040758 Plasma 1
22961681 10.1124/dmd.112.047068 Bile salt export pump 1
33226219 10.1021/acs.jnatprod.0c00946 No relevant target 1
33226219 10.1021/acs.jnatprod.0c00946 Salmon testes DNA 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1

Data from ChEMBL 36 via Core Engine