Chlorpheniramine
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Also known as ChlorphenamineClorfenaminaIsoclorSID90340572SID50110994Chlorpheniramine (+/-)SID174007153SID174006626(+)-chlorpheniramine(-)-chlorpheniramineDEXCHLORPHENIRAMINE MALEATE
Summary
Chlorpheniramine (CHEMBL505) is an approved small-molecule anti-allergic agent (ATC R06AB54) targeting HRH1; indicated across 5 conditions including allergic disease and influenza.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: R06AB54 (+1 more)
- Targets: 1 (HRH1)
- Indications: 5 conditions
- Clinical trials: 6
- Chemistry: 274.79 Da · C16H19ClN2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL505 |
| Name | Chlorpheniramine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 2725 |
| ChEBI | CHEBI:52010 |
| ATC | R06AB54, R06AB04 |
| Molecular formula | C16H19ClN2 |
| Molecular weight | 274.79 |
| InChIKey | SOYKEARSMXGVTM-UHFFFAOYSA-N |
SMILES: CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2
IUPAC name: 3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
ChEBI definition: A tertiary amino compound that is propylamine which is substituted at position 3 by a pyridin-2-yl group and a p-chlorophenyl group and in which the hydrogens attached to the nitrogen are replaced by methyl groups. A histamine H1 antagonist, it is used to relieve the symptoms of hay fever, rhinitis, urticaria, and asthma.
Pharmacological roles (ChEBI): anti-allergic agent, H1-receptor antagonist, antipruritic drug, histamine antagonist, serotonin uptake inhibitor, antidepressant.
Also known as: Chlorphenamine, Chlorpheniramine, Clorfenamina, Isoclor, chlorpheniramine, SID90340572, SID50110994, Chlorpheniramine (+/-), SID174007153, SID174006626, (+)-chlorpheniramine, CHLORPHENIRAMINE
Parent form; salt/anhydrous children: CHEMBL180454, CHEMBL1659, CHEMBL1201659
Patent coverage: 14,163 distinct patent families (40,315 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 40,309 (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 | Antagonist | 8.15 | 0% | P35367 |
Broader ChEMBL bioactivity targets: 23 (assay-derived). Sample: Lethal(3)malignant brain tumor-like protein 1, Lethal(3)malignant brain tumor-like protein 3, MBT domain-containing protein 1, Solute carrier family 22 member 2, Chloroquine resistance transporter, 5-hydroxytryptamine receptor 2B, Histamine H2 receptor, Alpha-2B adrenergic receptor, Muscarinic acetylcholine receptor M5, Solute carrier family 22 member 1.
Bioactivity
ChEMBL activities: 23 potent at pChembl ≥ 5 of 35 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| HRH1 | 9.04 | Ki | 0.92 | nM | CHEMBL_ACT_13876516 |
| P31390 | 8.7 | Ki | 2 | nM | CHEMBL_ACT_308778 |
| HRH1 | 8.35 | Ki | 4.47 | nM | CHEMBL_ACT_13876482 |
| P31390 | 8.26 | Ki | 5.5 | nM | CHEMBL_ACT_476813 |
| P31390 | 8.26 | Ki | 5.5 | nM | CHEMBL_ACT_921213 |
| HRH1 | 8.15 | Ki | 7 | nM | CHEMBL_ACT_6175689 |
| P31389 | 8.06 | IC50 | 8.8 | nM | CHEMBL_ACT_985586 |
| HRH1 | 7.48 | AC50 | 33 | nM | CHEMBL_ACT_25211981 |
| HRH1 | 7.25 | AC50 | 56 | nM | CHEMBL_ACT_25116904 |
| HRH1 | 7.18 | IC50 | 66 | nM | CHEMBL_ACT_2515911 |
| HRH2 | 6.38 | AC50 | 412.3 | nM | CHEMBL_ACT_25114319 |
| KCNH2 | 5.96 | IC50 | 1100 | nM | CHEMBL_ACT_1449633 |
| SLC6A4 | 5.96 | AC50 | 1100 | nM | CHEMBL_ACT_25149824 |
| HTR2A | 5.93 | AC50 | 1186 | nM | CHEMBL_ACT_25173433 |
| SLC6A3 | 5.84 | AC50 | 1460 | nM | CHEMBL_ACT_25123430 |
| HTR2B | 5.39 | AC50 | 4060 | nM | CHEMBL_ACT_25163973 |
| ADRA2B | 5.31 | AC50 | 4900 | nM | CHEMBL_ACT_25143183 |
| CHRM2 | 5.26 | AC50 | 5519 | nM | CHEMBL_ACT_25195133 |
| CHRM5 | 5.21 | AC50 | 6118 | nM | CHEMBL_ACT_25137379 |
| ADRA1A | 5.15 | AC50 | 7008 | nM | CHEMBL_ACT_25137621 |
| SLC6A2 | 5.11 | AC50 | 7700 | nM | CHEMBL_ACT_25144488 |
| CHRM1 | 5.03 | AC50 | 9300 | nM | CHEMBL_ACT_25134920 |
| SCN1A | 5 | IC50 | 10000 | nM | CHEMBL_ACT_377987 |
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
5 indications (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 |
| influenza | 3 | MONDO:0005812 | EFO:0007328 |
| seasonal allergic rhinitis | 2 | MONDO:0005324 | EFO:0003956 |
| sunburn | 2 | MONDO:0005326 | EFO:0003958 |
| chronic hepatitis B virus infection | 2 | MONDO:0005366 | EFO:0004239 |
Clinical trials
Total trials: 6.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 2 |
| Not specified | 2 |
| PHASE4 | 1 |
| PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT03583567 | PHASE4 | COMPLETED | Effect of Anti-histamine in Prevention Systolic Hypotension After Protamine |
| NCT04688736 | PHASE2 | RECRUITING | Efficacy of Placebo Versus Chlorpheniramine for the Prevention of Allergic Transfusion Reactions. |
| NCT02065336 | PHASE2 | TERMINATED | A Multicenter Study to Determine the Depth and Duration of Hepatitis B Surface Antigen (HBsAg) Reduction After Single or Multiple Doses of ARC-520, in Combination With Entecavir in Patients With Chronic Hepatitis B Virus (HBV) Infection |
| NCT00837837 | PHASE1 | COMPLETED | Study Evaluating Chlorpheniramine Maleate Liquid in Children and Adolescents |
| NCT01209455 | Not specified | COMPLETED | Mechanisms of N-acetylcysteine Mediated Vascular Adverse Effects |
| NCT03940391 | Not specified | UNKNOWN | Effect of the Antihistamine Injection to Prevent Paradoxical Reaction During Sedative Endoscopy |
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 |
| 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 |
| DEXBROMPHENIRAMINE | ChEMBL | Phase 4 (approved) | HRH1 |
Related Atlas pages
- Genes: HRH1
- Diseases: allergic disease, influenza
- 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, Chlorphentermine, Chlorpromazine, Chlorprothixene, Cinacalcet, Cinnarizine, Cisapride, Citalopram, Clemastine, Clofazimine, Clomipramine, Clotrimazole, Clozapine, Cyclizine, Cyclobenzaprine, Cyproheptadine, Daunorubicin, Desipramine, Dexbrompheniramine