Azilsartan
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Also known as TAK-536AZILSARTAN (TAK-536)
Summary
Azilsartan (CHEMBL57242) is an approved small-molecule angiotensin receptor antagonist targeting AGTR1; indicated across 6 conditions including hypertensive disorder and essential hypertension.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Targets: 1 (AGTR1)
- Indications: 6 conditions
- Clinical trials: 27
- Chemistry: 456.4 Da · C25H20N4O5
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL57242 |
| Name | Azilsartan |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | yes |
| PubChem CID | 135415867 |
| ChEBI | CHEBI:68850 |
| Molecular formula | C25H20N4O5 |
| Molecular weight | 456.4 |
| InChIKey | KGSXMPPBFPAXLY-UHFFFAOYSA-N |
SMILES: CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NOC(=O)N5)C(=O)O
IUPAC name: 2-ethoxy-3-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
ChEBI definition: A benzimidazolecarboxylic acid that is benzimidazole-7-carboxylic acid substituted at position 2 by a methoxy group and at position 1 by a 2’-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl group. Used (as the prodrug, azilsartan medoxomil) for treatment of hypertension.
Pharmacological roles (ChEBI): angiotensin receptor antagonist, antihypertensive agent.
Also known as: Azilsartan, TAK-536, AZILSARTAN, AZILSARTAN (TAK-536), Azilsartan (TAK-536)
Patent coverage: 974 distinct patent families (2,356 SureChEMBL compound mentions), from 5 matched compound structure(s). One matched structure accounts for 1,992 (85%) 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 |
|---|---|---|---|---|---|
| AGTR1 | AT1 receptor | Antagonist | 8.13 | 0.4% | P30556 |
Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Type-1 angiotensin II receptor.
Bioactivity
ChEMBL activities: 1 potent at pChembl ≥ 5 of 1 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P25104 | 6.38 | IC50 | 420 | nM | CHEMBL_ACT_164307 |
Target pathways
Aggregated over 1 target gene(s): AGTR1.
Top Reactome pathways
11 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 1 | AGTR1 |
| Membrane Trafficking | 1 | AGTR1 |
| Signaling by GPCR | 1 | AGTR1 |
| Class A/1 (Rhodopsin-like receptors) | 1 | AGTR1 |
| Peptide ligand-binding receptors | 1 | AGTR1 |
| GPCR downstream signalling | 1 | AGTR1 |
| G alpha (q) signalling events | 1 | AGTR1 |
| GPCR ligand binding | 1 | AGTR1 |
| Vesicle-mediated transport | 1 | AGTR1 |
| Cargo recognition for clathrin-mediated endocytosis | 1 | AGTR1 |
| Clathrin-mediated endocytosis | 1 | AGTR1 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| regulation of cell growth | 1 |
| kidney development | 1 |
| renin-angiotensin regulation of aldosterone production | 1 |
| maintenance of blood vessel diameter homeostasis by renin-angiotensin | 1 |
| regulation of systemic arterial blood pressure by renin-angiotensin | 1 |
| inflammatory response | 1 |
| G protein-coupled receptor signaling pathway | 1 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| positive regulation of cytosolic calcium ion concentration | 1 |
| Rho protein signal transduction | 1 |
| positive regulation of macrophage derived foam cell differentiation | 1 |
| regulation of vasoconstriction | 1 |
| calcium-mediated signaling | 1 |
| low-density lipoprotein particle remodeling | 1 |
| regulation of renal sodium excretion | 1 |
Indications & clinical
Indications
6 indications (0 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 |
|---|---|---|---|
| hypertensive disorder | 3 | MONDO:0005044 | EFO:0000537 |
| essential hypertension | 3 | MONDO:0001134 | MONDO:0001134 |
| type 2 diabetes mellitus | 3 | MONDO:0005148 | MONDO:0005148 |
| severe acute respiratory syndrome | 3 | MONDO:0005091 | EFO:0000694 |
| diabetes mellitus | 2 | MONDO:0005015 | EFO:0000400 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 27.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 7 |
| Not specified | 7 |
| PHASE1 | 6 |
| PHASE4 | 3 |
| PHASE2 | 3 |
| PHASE2/PHASE3 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT01609959 | PHASE4 | COMPLETED | New Angiotensin II Receptor Blocker Azilsartan Study for Stronger Blood Pressure Lowering |
| NCT02079805 | PHASE4 | COMPLETED | A Study to Explore the Effects of Azilsartan Compared to Telmisartan on Insulin Resistance of Patients With Essential Hypertension on Type 2 Diabetes Mellitus by HOMA-R |
| NCT02400775 | PHASE4 | WITHDRAWN | A Study to Evaluate the Effects of Azilsartan on Coronary Artery Plaque in Essential Hypertensive Patients With Stable Angina and Dyslipidemia. |
| NCT00376181 | PHASE3 | TERMINATED | Efficacy, Safety and Tolerability of Pioglitazone-Azilsartan in Subjects With Type 2 Diabetes Mellitus |
| NCT02235519 | PHASE2/PHASE3 | UNKNOWN | Pleiotropic Effects of Azilsartan Medoxomil Over Insulin Resistance in Obese, Diabetic and Hypertensive Patients |
| NCT02407210 | PHASE3 | UNKNOWN | Efficacy and Safety of Azilsartan Compared to Olmesartan Medoxomil in Chinese Participants With Grade I or II Essential Hypertension |
| NCT02451150 | PHASE3 | COMPLETED | A Phase 3 Pharmacokinetic Study of TAK-536 (Azilsartan) in Pediatric Patients 6 to Less Than 16 Years With Hypertension |
| NCT02609490 | PHASE3 | COMPLETED | Azilsartan in Chinese Patients With Mild and Moderate Hypertension |
| NCT02791438 | PHASE3 | COMPLETED | A Phase 3 Long-term Study of TAK-536 in Pediatric Patients 6 to Less Than 16 Years With Hypertension |
| NCT04606563 | PHASE3 | TERMINATED | Host Response Mediators in Coronavirus (COVID-19) Infection - Is There a Protective Effect of Losartan and Other ARBs on Outcomes of Coronavirus Infection? |
| NCT04668157 | PHASE3 | COMPLETED | A Study of TAK-536 in Children From 2 to Less Than 6 Years Old With High Blood Pressure |
| NCT00759551 | PHASE2 | COMPLETED | Efficacy and Safety of Azilsartan in Subjects With Essential Hypertension |
| NCT00762736 | PHASE2 | COMPLETED | Efficacy and Safety of Pioglitazone and Azilsartan in Treating Subjects With Type 2 Diabetes Mellitus |
| NCT01289132 | PHASE2 | COMPLETED | Efficacy and Safety of Azilsartan in Participants With Mild to Moderate Uncomplicated Essential Hypertension |
| NCT01985152 | PHASE1 | UNKNOWN | A Phase Ⅰa Study of Azilsartan Trimethylethanolamine in Healthy Volunteers |
| NCT02401464 | PHASE1 | COMPLETED | A Bioequivalence Study of TAK-536 Pediatric Formulation |
| NCT02786082 | PHASE1 | COMPLETED | Pharmacokinetics Study of Azilsartan Tablets in Chinese Healthy Volunteers |
| NCT03042299 | PHASE1 | COMPLETED | A Phase 1, Bio-equivalence Study of TAK-536 Pediatric Formulation |
| NCT03434977 | PHASE1 | COMPLETED | A Phase 1 Food Effect Study of Azilsartan (TAK-536) Pediatric Formulation |
| NCT03652792 | PHASE1 | COMPLETED | Bioequivalence Study of Azilsartan Tablets in Chinese Healthy Volunteers |
| NCT01762501 | Not specified | COMPLETED | Azilsartan Circadian and Sleep Pressure |
| NCT01774591 | Not specified | COMPLETED | Effect of Azilsartan on Aldosterone in Postmenopausal Females |
| NCT02092025 | Not specified | COMPLETED | Azilsartan Tablets Special Drug Use Surveillance: Long-term Use |
| NCT02100319 | Not specified | COMPLETED | Azilsaltan Tablets (Azilva Tablets) Special Drug Use Surveillance Hypertension Complicated by Diabetes |
| NCT02181816 | Not specified | COMPLETED | Azilsartan/Amlodipine Combination Tablets LD & HD Specified Drug-use Survey Long-term Use Survey |
| NCT05107960 | Not specified | COMPLETED | A Study of Azilsartan in Children From 6 to Less Than 16 Years Old With High Blood Pressure |
| NCT05753696 | Not specified | UNKNOWN | Azilsartan in Patients With Diabetic Kidney Disease and Hypertension |
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
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.
140 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| CRIZOTINIB | ChEMBL + PubChem | Phase 4 (approved) | AGTR1 |
| LOSARTAN | ChEMBL + PubChem | Phase 4 (approved) | AGTR1 |
| OLMESARTAN MEDOXOMIL | ChEMBL + PubChem | Phase 4 (approved) | AGTR1 |
| RIFAMPIN | ChEMBL + PubChem | Phase 4 (approved) | AGTR1 |
| SPARSENTAN | ChEMBL + PubChem | Phase 4 (approved) | AGTR1 |
| TEGASEROD | ChEMBL + PubChem | Phase 4 (approved) | AGTR1 |
| ALFACALCIDOL | ChEMBL | Phase 4 (approved) | AGTR1 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | AGTR1 |
| ANGIOTENSIN II | ChEMBL | Phase 4 (approved) | AGTR1 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | AGTR1 |
| BALSALAZIDE | ChEMBL | Phase 4 (approved) | AGTR1 |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | AGTR1 |
| BUTOCONAZOLE | ChEMBL | Phase 4 (approved) | AGTR1 |
| CALCITRIOL | ChEMBL | Phase 4 (approved) | AGTR1 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | AGTR1 |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | AGTR1 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | AGTR1 |
| DABIGATRAN ETEXILATE | ChEMBL | Phase 4 (approved) | AGTR1 |
| DESOGESTREL | ChEMBL | Phase 4 (approved) | AGTR1 |
| DISULFIRAM | ChEMBL | Phase 4 (approved) | AGTR1 |
| DOFETILIDE | ChEMBL | Phase 4 (approved) | AGTR1 |
| DONEPEZIL | ChEMBL | Phase 4 (approved) | AGTR1 |
| EFAVIRENZ | ChEMBL | Phase 4 (approved) | AGTR1 |
| EPALRESTAT | ChEMBL | Phase 4 (approved) | AGTR1 |
| EPROSARTAN | ChEMBL | Phase 4 (approved) | AGTR1 |
| FELODIPINE | ChEMBL | Phase 4 (approved) | AGTR1 |
| FENTICONAZOLE | ChEMBL | Phase 4 (approved) | AGTR1 |
| GUAIFENESIN | ChEMBL | Phase 4 (approved) | AGTR1 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | AGTR1 |
| IBANDRONIC ACID | ChEMBL | Phase 4 (approved) | AGTR1 |
| INDOCYANINE GREEN ACID FORM | ChEMBL | Phase 4 (approved) | AGTR1 |
| IRBESARTAN | ChEMBL | Phase 4 (approved) | AGTR1 |
| IVACAFTOR | ChEMBL | Phase 4 (approved) | AGTR1 |
| LEFLUNOMIDE | ChEMBL | Phase 4 (approved) | AGTR1 |
| LOVASTATIN | ChEMBL | Phase 4 (approved) | AGTR1 |
| MILTEFOSINE | ChEMBL | Phase 4 (approved) | AGTR1 |
| NIFEDIPINE | ChEMBL | Phase 4 (approved) | AGTR1 |
| NIMESULIDE | ChEMBL | Phase 4 (approved) | AGTR1 |
| NITAZOXANIDE | ChEMBL | Phase 4 (approved) | AGTR1 |
| NORGESTIMATE | ChEMBL | Phase 4 (approved) | AGTR1 |
| NOSCAPINE | ChEMBL | Phase 4 (approved) | AGTR1 |
| OXYMETHOLONE | ChEMBL | Phase 4 (approved) | AGTR1 |
| PIMOZIDE | ChEMBL | Phase 4 (approved) | AGTR1 |
| PONATINIB | ChEMBL | Phase 4 (approved) | AGTR1 |
| PRAZOSIN | ChEMBL | Phase 4 (approved) | AGTR1 |
| PROPRANOLOL | ChEMBL | Phase 4 (approved) | AGTR1 |
| PYRVINIUM | ChEMBL | Phase 4 (approved) | AGTR1 |
| RIMONABANT | ChEMBL | Phase 4 (approved) | AGTR1 |
| RITONAVIR | ChEMBL | Phase 4 (approved) | AGTR1 |
| ROCURONIUM | ChEMBL | Phase 4 (approved) | AGTR1 |
| ROSIGLITAZONE | ChEMBL | Phase 4 (approved) | AGTR1 |
| SARALASIN | ChEMBL | Phase 4 (approved) | AGTR1 |
| SELEXIPAG | ChEMBL | Phase 4 (approved) | AGTR1 |
| SIMVASTATIN | ChEMBL | Phase 4 (approved) | AGTR1 |
| SORAFENIB | ChEMBL | Phase 4 (approved) | AGTR1 |
| SULCONAZOLE | ChEMBL | Phase 4 (approved) | AGTR1 |
| SUNITINIB | ChEMBL | Phase 4 (approved) | AGTR1 |
| TELMISARTAN | ChEMBL | Phase 4 (approved) | AGTR1 |
| TELOTRISTAT | ChEMBL | Phase 4 (approved) | AGTR1 |
| TELOTRISTAT ETHYL | ChEMBL | Phase 4 (approved) | AGTR1 |
Related Atlas pages
- Genes: AGTR1
- Diseases: hypertensive disorder, essential hypertension, type 2 diabetes mellitus, severe acute respiratory syndrome
- Drugs: Crizotinib, Losartan, Olmesartan Medoxomil, Rifampin, Sparsentan, Tegaserod, Alfacalcidol, Amitriptyline, Angiotensin Ii, Aripiprazole, Balsalazide, Benzbromarone, Butoconazole, Calcitriol, Candesartan Cilexetil, Carvedilol, Clotrimazole, Dabigatran Etexilate, Desogestrel, Disulfiram, Dofetilide, Donepezil, Efavirenz, Epalrestat, Eprosartan, Felodipine, Fenticonazole, Guaifenesin, Haloperidol, Ibandronic Acid, Indocyanine Green Acid Form, Irbesartan, Ivacaftor, Leflunomide, Lovastatin, Miltefosine, Nifedipine, Nimesulide, Nitazoxanide, Norgestimate, Noscapine, Oxymetholone, Pimozide, Ponatinib, Prazosin, Propranolol, Pyrvinium, Rimonabant, Ritonavir, Rocuronium, Rosiglitazone, Saralasin, Selexipag, Simvastatin, Sorafenib, Sulconazole, Sunitinib, Telmisartan, Telotristat, Telotristat Ethyl