Naratriptan
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Also known as SID174006312Naratriptan HCl
Summary
Naratriptan (CHEMBL1278) is an approved small-molecule serotonergic agonist (ATC N02CC02) targeting HTR1A, HTR1B, and HTR1D; indicated across 2 conditions including migraine disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: N02CC02
- Targets: 5 (HTR1A, HTR1B, HTR1D…)
- Indications: 2 conditions
- Clinical trials: 9
- Chemistry: 335.5 Da · C17H25N3O2S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1278 |
| Name | Naratriptan |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 4440 |
| ChEBI | CHEBI:7478 |
| ATC | N02CC02 |
| Molecular formula | C17H25N3O2S |
| Molecular weight | 335.5 |
| InChIKey | AMKVXSZCKVJAGH-UHFFFAOYSA-N |
SMILES: CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C
IUPAC name: N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
Pharmacological roles (ChEBI): serotonergic agonist, vasoconstrictor agent.
Also known as: Naratriptan, naratriptan, SID174006312, NARATRIPTAN, Naratriptan HCl
Parent form; salt/anhydrous children: CHEMBL1200601
Patent coverage: 3,067 distinct patent families (12,474 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 12,445 (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 |
|---|---|---|---|---|---|
| HTR1A | 5-HT1A receptor | Full agonist | 7.6 | 0% | P08908 |
| HTR1B | 5-HT1B receptor | Partial agonist | 8.1 | 0.2% | P28222 |
| HTR1D | 5-HT1D receptor | Full agonist | 9 | 0% | P28221 |
| HTR1E | 5-ht1e receptor | Full agonist | 7.7 | 0% | P28566 |
| HTR1F | 5-HT1F receptor | Full agonist | 8.2 | 0.1% | P30939 |
Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: 5-hydroxytryptamine receptor 1B, 5-hydroxytryptamine receptor 1D, 5-hydroxytryptamine receptor 1A.
Bioactivity
ChEMBL activities: 6 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| HTR1B | 8.82 | Ki | 1.5 | nM | CHEMBL_ACT_25553868 |
| HTR1D | 8.82 | Ki | 1.5 | nM | CHEMBL_ACT_25553873 |
| HTR1D | 8.8 | EC50 | 1.6 | nM | CHEMBL_ACT_771450 |
| HTR1D | 8.64 | Ki | 2.3 | nM | CHEMBL_ACT_771447 |
| HTR1B | 8.48 | Ki | 3.3 | nM | CHEMBL_ACT_771449 |
| HTR1A | 7.35 | Ki | 45 | nM | CHEMBL_ACT_771448 |
Target pathways
Aggregated over 5 target gene(s): HTR1A, HTR1B, HTR1D, HTR1E, HTR1F.
Top Reactome pathways
8 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 5 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| Signaling by GPCR | 5 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| Class A/1 (Rhodopsin-like receptors) | 5 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| Amine ligand-binding receptors | 5 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| Serotonin receptors | 5 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| GPCR ligand binding | 5 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| GPCR downstream signalling | 4 | HTR1B, HTR1D, HTR1E, HTR1F |
| G alpha (i) signalling events | 4 | HTR1B, HTR1D, HTR1E, HTR1F |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| G protein-coupled receptor signaling pathway | 5 |
| G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger | 5 |
| adenylate cyclase-inhibiting serotonin receptor signaling pathway | 5 |
| chemical synaptic transmission | 5 |
| signal transduction | 5 |
| adenylate cyclase-activating G protein-coupled receptor signaling pathway | 4 |
| adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway | 4 |
| regulation of behavior | 3 |
| vasoconstriction | 2 |
| behavioral fear response | 1 |
| serotonin receptor signaling pathway | 1 |
| gamma-aminobutyric acid signaling pathway | 1 |
| positive regulation of cell population proliferation | 1 |
| regulation of serotonin secretion | 1 |
| regulation of vasoconstriction | 1 |
Indications & clinical
Indications
2 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 |
|---|---|---|---|
| migraine disorder | 4 | MONDO:0005277 | MONDO:0005277 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 9.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 4 |
| PHASE4 | 2 |
| PHASE3 | 2 |
| PHASE1/PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00282165 | PHASE4 | TERMINATED | Efficacy of a Triptan in the Treatment of Hostility and Aggression Among Convicts With a Psychiatric Treatment Order |
| NCT00487578 | PHASE4 | TERMINATED | Naratriptan for the Treatment of Post Traumatic Headache Associated With Cognitive Dysfunction |
| NCT01390324 | PHASE3 | WITHDRAWN | Efficacy and Safety of a Fixed-dose Combination of Naratriptan and Naproxen in Acute Treatment of Migraine |
| NCT01726920 | PHASE3 | WITHDRAWN | Efficacy and Safety of a Fixed-dose Combination of Naratriptan and Naproxen in Acute Treatment of Migraine. |
| NCT03066544 | PHASE1/PHASE2 | UNKNOWN | Status Migrainosus - Differentiating Between Responders and Non-responders |
| NCT01059604 | Not specified | COMPLETED | Sumatriptan and Naratriptan Pregnancy Registry |
| NCT01161654 | Not specified | COMPLETED | Bioequivalency Study of Naratriptan Hydrochloride 2.5 mg Under Fed Conditions |
| NCT01332383 | Not specified | COMPLETED | Special Drug Use Investigation for AMERGE® Tablet (Long-term) |
| NCT01376193 | Not specified | COMPLETED | Drug Use Investigation for AMERGE (Naratriptan Hydrochloride) Tablet |
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.
415 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| ERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| IMIPRAMINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| RISPERIDONE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| RIZATRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| SUMATRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| ZOLMITRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| SEROTONIN | ChEMBL + PubChem | Phase 3 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| YOHIMBINE | ChEMBL + PubChem | Phase 3 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| MEBUFOTENIN | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| CLOZAPINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1E, HTR1F |
| ELETRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1E, HTR1F |
| OLANZAPINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1E, HTR1F |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E |
| FROVATRIPTAN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E |
| PSILOCIN | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1D, HTR1E |
| CYPROHEPTADINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR1F |
| LASMIDITAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1D, HTR1E, HTR1F |
| METHYLERGONOVINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR1F |
| PRAMIPEXOLE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1E |
| QUETIAPINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR1F |
| SORAFENIB | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR1F |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| AZELASTINE | ChEMBL | Phase 4 (approved) | HTR1B, HTR1D, HTR1E |
| CARIPRAZINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| KETANSERIN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| NEFAZODONE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| OXYMETAZOLINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| SALMETEROL | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| SILODOSIN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| VILAZODONE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| XYLOMETAZOLINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D |
| ACETRYPTINE | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1D |
| GSK163090 | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1D |
| LYSERGIDE | ChEMBL | Phase 2 | HTR1A, HTR1D, HTR1E |
| RITANSERIN | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1E |
| ASENAPINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E |
| CANNABIDIOL | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E |
| PALIPERIDONE | ChEMBL + PubChem | Phase 4 (approved) | HTR1B, HTR1D |
| ZIPRASIDONE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E |
| CINACALCET | ChEMBL | Phase 4 (approved) | HTR1A, HTR1D |
| LOPERAMIDE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1D |
| MIANSERIN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1D |
| PINDOLOL | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B |
| PRAZOSIN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1D |
| SERTINDOLE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B |
| TEGASEROD | ChEMBL | Phase 4 (approved) | HTR1A, HTR1D |
| LATREPIRDINE | ChEMBL | Phase 3 | HTR1D, HTR1E |
| ALNIDITAN | ChEMBL | Phase 2 | HTR1A, HTR1D |
| MAZAPERTINE | ChEMBL | Phase 2 | HTR1A, HTR1B |
| NIGULDIPINE | ChEMBL | Phase 2 | HTR1A, HTR1B |
| PENFLURIDOL | ChEMBL | Phase 2 | HTR1A, HTR1D |
| SPIRAMIDE | ChEMBL | Phase 2 | HTR1A, HTR1D |
| ACEMETACIN | ChEMBL | Phase 4 (approved) | HTR1A |
| ACETOPHENAZINE | ChEMBL | Phase 4 (approved) | HTR1A |
| ACETYLCHOLINE | ChEMBL | Phase 4 (approved) | HTR1A |
| ALMOTRIPTAN | ChEMBL | Phase 4 (approved) | HTR1A |
| AMILORIDE | ChEMBL | Phase 4 (approved) | HTR1A |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | HTR1A |
| AMLODIPINE | ChEMBL | Phase 4 (approved) | HTR1A |
Related Atlas pages
- Genes: HTR1A, HTR1B, HTR1D, HTR1E, HTR1F
- Diseases: migraine disorder
- Drugs: Dihydroergotamine, Ergotamine, Imipramine, Risperidone, Rizatriptan, Sumatriptan, Zolmitriptan, Serotonin, Yohimbine, Clozapine, Eletriptan, Olanzapine, Brexpiprazole, Frovatriptan, Cyproheptadine, Lasmiditan, Methylergonovine, Pramipexole, Quetiapine, Sorafenib, Aripiprazole, Azelastine, Cariprazine, Ketanserin, Nefazodone, Oxymetazoline, Salmeterol, Silodosin, Vilazodone, Xylometazoline, Asenapine, Cannabidiol, Paliperidone, Ziprasidone, Cinacalcet, Loperamide, Mianserin, Pindolol, Prazosin, Sertindole, Tegaserod, Latrepirdine, Acemetacin, Acetophenazine, Acetylcholine, Almotriptan, Amiloride, Amitriptyline, Amlodipine