Pyrilamine
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Also known as MepiraminaMepyramineNSC-13136SID11111639SID11111640SID11113355SID17389532SID26751558SID90341279SID104171213SID50100317SID50104164SID144203781SID144208176SID170464656
Summary
Pyrilamine (CHEMBL511) is an approved small-molecule H1-receptor antagonist (ATC R06AC01) targeting HRH1; indicated across 2 conditions including allergic disease.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: R06AC01 (+1 more)
- Targets: 1 (HRH1)
- Indications: 2 conditions
- Clinical trials: 1
- Chemistry: 285.4 Da · C17H23N3O
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL511 |
| Name | Pyrilamine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 4992 |
| ChEBI | CHEBI:6762 |
| ATC | R06AC01, D04AA02 |
| Molecular formula | C17H23N3O |
| Molecular weight | 285.4 |
| InChIKey | YECBIJXISLIIDS-UHFFFAOYSA-N |
SMILES: CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2
IUPAC name: N’-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N’-pyridin-2-ylethane-1,2-diamine
ChEBI definition: An ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group.
Pharmacological roles (ChEBI): H1-receptor antagonist.
Also known as: Mepiramina, Mepyramine, NSC-13136, mepyramine, pyrilamine, Pyrilamine, SID11111639, SID11111640, SID11113355, SID17389532, SID26751558, SID90341279
Parent form; salt/anhydrous children: CHEMBL1201006
Patent coverage: 21,133 distinct patent families (42,415 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 42,346 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| HRH1 | H1 receptor | Inverse agonist | 9 | 0% | P35367 |
Broader ChEMBL bioactivity targets: 24 (assay-derived). Sample: Prelamin-A/C, 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Thyrotropin receptor, D(1A) dopamine receptor, Menin/Histone-lysine N-methyltransferase MLL, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, 5-hydroxytryptamine receptor 2A, 5-hydroxytryptamine receptor 2C.
Bioactivity
ChEMBL activities: 79 potent at pChembl ≥ 5 of 94 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| HRH1 | 10.85 | IC50 | 0.01 | nM | CHEMBL_ACT_16501820 |
| P31389 | 9.5 | Kd | 0.32 | nM | CHEMBL_ACT_12530445 |
| P31389 | 9.42 | Kd | 0.38 | nM | CHEMBL_ACT_885378 |
| HRH1 | 9.37 | Ki | 0.43 | nM | CHEMBL_ACT_7733126 |
| P31389 | 9.18 | Kd | 0.66 | nM | CHEMBL_ACT_19481222 |
| HRH1 | 9.15 | Ki | 0.71 | nM | CHEMBL_ACT_17995187 |
| P31389 | 9.1 | Kd | 0.79 | nM | CHEMBL_ACT_649584 |
| P31389 | 9.1 | Kd | 0.79 | nM | CHEMBL_ACT_979805 |
| HRH1 | 9.09 | IC50 | 0.82 | nM | CHEMBL_ACT_13336196 |
| P31389 | 9.07 | Kd | 0.85 | nM | CHEMBL_ACT_34628 |
| P31389 | 9.07 | Kd | 0.85 | nM | CHEMBL_ACT_7846169 |
| HRH1 | 9.02 | Ki | 0.95 | nM | CHEMBL_ACT_13342028 |
| P31389 | 9 | Kd | 1 | nM | CHEMBL_ACT_395711 |
| P31389 | 8.96 | Kd | 1.1 | nM | CHEMBL_ACT_2290439 |
| LMNA | 8.96 | Potency | 1.1 | nM | CHEMBL_ACT_3624951 |
| HRH1 | 8.9 | Ki | 1.26 | nM | CHEMBL_ACT_16792501 |
| HRH1 | 8.89 | IC50 | 1.3 | nM | CHEMBL_ACT_1611125 |
| HRH1 | 8.85 | IC50 | 1.4 | nM | CHEMBL_ACT_16838424 |
| P31389 | 8.84 | Kd | 1.45 | nM | CHEMBL_ACT_15176662 |
| HRH1 | 8.82 | IC50 | 1.5 | nM | CHEMBL_ACT_13342100 |
| P31389 | 8.82 | IC50 | 1.5 | nM | CHEMBL_ACT_5166007 |
| HRH1 | 8.8 | Ki | 1.6 | nM | CHEMBL_ACT_13340311 |
| HRH1 | 8.77 | Ki | 1.7 | nM | CHEMBL_ACT_14738661 |
| HRH1 | 8.77 | Ki | 1.7 | nM | CHEMBL_ACT_15187869 |
| HRH1 | 8.74 | IC50 | 1.8 | nM | CHEMBL_ACT_2573328 |
| HRH1 | 8.72 | IC50 | 1.9 | nM | CHEMBL_ACT_17995172 |
| HRH1 | 8.68 | Ki | 2.09 | nM | CHEMBL_ACT_7945363 |
| HRH1 | 8.66 | Ki | 2.2 | nM | CHEMBL_ACT_2381323 |
| HRH1 | 8.59 | EC50 | 2.6 | nM | CHEMBL_ACT_2555657 |
| HRH1 | 8.52 | IC50 | 3 | nM | CHEMBL_ACT_14738680 |
Target pathways
Aggregated over 1 target gene(s): HRH1.
Top Reactome pathways
2 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Histamine receptors | 1 | HRH1 |
| G alpha (q) signalling events | 1 | HRH1 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| inflammatory response | 1 |
| G protein-coupled receptor signaling pathway | 1 |
| G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger | 1 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| chemical synaptic transmission | 1 |
| memory | 1 |
| visual learning | 1 |
| regulation of vascular permeability | 1 |
| positive regulation of vasoconstriction | 1 |
| regulation of synaptic plasticity | 1 |
| cellular response to histamine | 1 |
| signal transduction | 1 |
| phospholipase C-activating serotonin receptor signaling pathway | 1 |
Indications & clinical
Indications
2 indications (2 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 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 1.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT06312254 | Not specified | COMPLETED | Pharmacological Modulation of Peripheral Nerve Excitability |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
295 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| ACLIDINIUM BROMIDE | ChEMBL + PubChem | Phase 4 (approved) | HRH1 |
| DESLORATADINE | ChEMBL + PubChem | Phase 4 (approved) | HRH1 |
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | HRH1 |
| PALIPERIDONE | ChEMBL + PubChem | Phase 4 (approved) | HRH1 |
| PRAMIPEXOLE | ChEMBL + PubChem | Phase 4 (approved) | HRH1 |
| ABEMACICLIB | ChEMBL | Phase 4 (approved) | HRH1 |
| ACETOPHENAZINE | ChEMBL | Phase 4 (approved) | HRH1 |
| ACRIVASTINE | ChEMBL | Phase 4 (approved) | HRH1 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | HRH1 |
| AMISULPRIDE | ChEMBL | Phase 4 (approved) | HRH1 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | HRH1 |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | HRH1 |
| AMSACRINE | ChEMBL | Phase 4 (approved) | HRH1 |
| ANTAZOLINE | ChEMBL | Phase 4 (approved) | HRH1 |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | HRH1 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | HRH1 |
| ASENAPINE | ChEMBL | Phase 4 (approved) | HRH1 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | HRH1 |
| ATOMOXETINE | ChEMBL | Phase 4 (approved) | HRH1 |
| AZATADINE | ChEMBL | Phase 4 (approved) | HRH1 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | HRH1 |
| BENFLUOREX | ChEMBL | Phase 4 (approved) | HRH1 |
| BENPERIDOL | ChEMBL | Phase 4 (approved) | HRH1 |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | HRH1 |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | HRH1 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | HRH1 |
| BETAMETHASONE PHOSPHORIC ACID | ChEMBL | Phase 4 (approved) | HRH1 |
| BIPERIDEN | ChEMBL | Phase 4 (approved) | HRH1 |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | HRH1 |
| BROMPERIDOL | ChEMBL | Phase 4 (approved) | HRH1 |
| BROMPHENIRAMINE | ChEMBL | Phase 4 (approved) | HRH1 |
| BUCLIZINE | ChEMBL | Phase 4 (approved) | HRH1 |
| BUPROPION | ChEMBL | Phase 4 (approved) | HRH1 |
| BUSPIRONE | ChEMBL | Phase 4 (approved) | HRH1 |
| BUTRIPTYLINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CABERGOLINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | HRH1 |
| CAPTOPRIL | ChEMBL | Phase 4 (approved) | HRH1 |
| CARBINOXAMINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CARIPRAZINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CETIRIZINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CHLORDIAZEPOXIDE | ChEMBL | Phase 4 (approved) | HRH1 |
| CHLORPHENIRAMINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CHLORPHENTERMINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CHLORPROTHIXENE | ChEMBL | Phase 4 (approved) | HRH1 |
| CINACALCET | ChEMBL | Phase 4 (approved) | HRH1 |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CISAPRIDE | ChEMBL | Phase 4 (approved) | HRH1 |
| CITALOPRAM | ChEMBL | Phase 4 (approved) | HRH1 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CLOFAZIMINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | HRH1 |
| CLOZAPINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CYCLIZINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CYCLOBENZAPRINE | ChEMBL | Phase 4 (approved) | HRH1 |
| CYPROHEPTADINE | ChEMBL | Phase 4 (approved) | HRH1 |
| DAUNORUBICIN | ChEMBL | Phase 4 (approved) | HRH1 |
| DESIPRAMINE | ChEMBL | Phase 4 (approved) | HRH1 |
Related Atlas pages
- Genes: HRH1
- Diseases: allergic disease
- Drugs: Aclidinium Bromide, Desloratadine, Dihydroergotamine, Paliperidone, Pramipexole, Abemaciclib, Acetophenazine, Acrivastine, Amiodarone, Amisulpride, Amitriptyline, Amoxapine, Amsacrine, Antazoline, Apomorphine, Aripiprazole, Asenapine, Astemizole, Atomoxetine, Azatadine, Azelastine, Benfluorex, Benperidol, Benzbromarone, Benztropine, Bepridil, Betamethasone Phosphoric Acid, Biperiden, Brexpiprazole, Bromperidol, Brompheniramine, Buclizine, Bupropion, Buspirone, Butriptyline, Cabergoline, Candesartan Cilexetil, Captopril, Carbinoxamine, Cariprazine, Cetirizine, Chlordiazepoxide, Chlorpheniramine, Chlorphentermine, Chlorpromazine, Chlorprothixene, Cinacalcet, Cinnarizine, Cisapride, Citalopram, Clemastine, Clofazimine, Clomipramine, Clotrimazole, Clozapine, Cyclizine, Cyclobenzaprine, Cyproheptadine, Daunorubicin, Desipramine