Methapyrilene

Summary

Methapyrilene (CHEMBL1411979) is an approved small-molecule H1-receptor antagonist (ATC R06AC05); indicated across 1 condition including allergic disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: R06AC05
• Indications: 1 condition
• Clinical trials: 1
• Chemistry: 261.39 Da · C14H19N3S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1411979
Name	Methapyrilene
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	4098
ChEBI	CHEBI:6820
ATC	R06AC05
Molecular formula	C14H19N3S
Molecular weight	261.39
InChIKey	HNJJXZKZRAWDPF-UHFFFAOYSA-N

SMILES: CN(C)CCN(CC1=CC=CS1)C2=CC=CC=N2

IUPAC name: N,N-dimethyl-N’-pyridin-2-yl-N’-(thiophen-2-ylmethyl)ethane-1,2-diamine

ChEBI definition: A member of the class of ethylenediamine derivatives that is ethylenediamine in which one of the nitrogens is substituted by two methyl groups, and the other nitrogen is substituted by a 2-pyridyl group and a (2-thienyl)methyl group.

Pharmacological roles (ChEBI): H1-receptor antagonist, anti-allergic agent, sedative, carcinogenic agent.

Also known as: A 3322, A-3322, Metapirileno, Metapyrilene, Methapyrilene, Pyrinistol, Restryl, Semikon, Sleepwell, Tenalin, Thionylan, SID11111497

Parent form; salt/anhydrous children: CHEMBL1255739, CHEMBL3187246

Patent coverage: 1,938 distinct patent families (6,036 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 22 (assay-derived). Sample: 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Alpha-2B adrenergic receptor, Muscarinic acetylcholine receptor M5, D(1A) dopamine receptor, Muscarinic acetylcholine receptor M2, Muscarinic acetylcholine receptor M1, Sodium-dependent noradrenaline transporter, 5-hydroxytryptamine receptor 2A, 5-hydroxytryptamine receptor 2C.

Bioactivity

ChEMBL activities: 40 potent at pChembl ≥ 5 of 46 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
HRH1	8.74	Ki	1.8	nM	CHEMBL_ACT_7764470
HRH1	7.8	IC50	16	nM	CHEMBL_ACT_7764469
SLC6A4	6.97	Ki	106	nM	CHEMBL_ACT_7766584
HTR2A	6.75	Ki	180	nM	CHEMBL_ACT_7766572
SLC6A4	6.7	IC50	200	nM	CHEMBL_ACT_7766583
HTR2C	6.41	Ki	390	nM	CHEMBL_ACT_7766576
ADRA2A	6.36	Ki	437	nM	CHEMBL_ACT_7764368
CYP2D6	6.3	Potency	501.2	nM	CHEMBL_ACT_4998403
CYP2D6	6.3	AC50	501.2	nM	CHEMBL_ACT_5988696
HTR2B	6.27	Ki	537	nM	CHEMBL_ACT_7766574
CHRM2	6.23	Ki	592	nM	CHEMBL_ACT_7764500
HTR2A	6.2	IC50	628	nM	CHEMBL_ACT_7766571
HTR2C	6.13	IC50	744	nM	CHEMBL_ACT_7766575
HTR2B	6.07	IC50	843	nM	CHEMBL_ACT_7766573
CHRM1	5.94	Ki	1150	nM	CHEMBL_ACT_7764498
ADRA2A	5.93	IC50	1165	nM	CHEMBL_ACT_7764367
SLC6A2	5.86	IC50	1391	nM	CHEMBL_ACT_7764379
SLC6A2	5.86	Ki	1380	nM	CHEMBL_ACT_7764380
HTR6	5.84	Ki	1435	nM	CHEMBL_ACT_7766582
ADRA2B	5.82	Ki	1515	nM	CHEMBL_ACT_7764370
CYP2D6	5.8	Potency	1585	nM	CHEMBL_ACT_4998335
CYP2D6	5.8	AC50	1585	nM	CHEMBL_ACT_6019795
CHRM2	5.78	IC50	1665	nM	CHEMBL_ACT_7764499
NFKB1	5.75	Potency	1778	nM	CHEMBL_ACT_3672649
NFKB1	5.75	Potency	1778	nM	CHEMBL_ACT_4585385
SLC6A3	5.66	Ki	2190	nM	CHEMBL_ACT_7764444
CHRM5	5.63	Ki	2346	nM	CHEMBL_ACT_7766498
KCNH2	5.57	AC50	2700	nM	CHEMBL_ACT_25117167
CYP2D6	5.56	IC50	2756	nM	CHEMBL_ACT_7764429
SLC6A3	5.56	IC50	2757	nM	CHEMBL_ACT_7764443

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 indication (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
allergic disease	4	MONDO:0005271	MONDO:0005271

Clinical trials

Total trials: 1.

Phase distribution

Phase	Trials
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT04406103	Not specified	COMPLETED	Protocol - Your Answers When Needing Sleep in New Brunswick

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).