Urapidil
drugOn this page
Also known as EbrantilNSC-310405SID11111935SID11114211SID26752246SID90341686SID11111936SID99361071SID104171260SID144203849
Summary
Urapidil (CHEMBL279229) is a phase-3 clinical-stage small molecule (ATC C02CA06); indicated across 4 conditions including hypertensive disorder and preeclampsia.
At a glance
- Status: Max clinical phase 3 (not approved)
- Modality: Small molecule
- ATC class: C02CA06
- Indications: 4 conditions
- Clinical trials: 10
- Chemistry: 387.5 Da · C20H29N5O3
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL279229 |
| Name | Urapidil |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | no |
| PubChem CID | 5639 |
| ATC | C02CA06 |
| Molecular formula | C20H29N5O3 |
| Molecular weight | 387.5 |
| InChIKey | ICMGLRUYEQNHPF-UHFFFAOYSA-N |
SMILES: CN1C(=CC(=O)N(C1=O)C)NCCCN2CCN(CC2)C3=CC=CC=C3OC
IUPAC name: 6-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-1,3-dimethylpyrimidine-2,4-dione
Also known as: Ebrantil, NSC-310405, Urapidil, SID11111935, SID11114211, SID26752246, SID90341686, SID11111936, SID99361071, SID104171260, SID144203849, URAPIDIL
Parent form; salt/anhydrous children: CHEMBL1256716
Patent coverage: 2,088 distinct patent families (7,581 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 7,232 (95%) 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
Broader ChEMBL bioactivity targets: 22 (assay-derived). Sample: Microtubule-associated protein tau, Prelamin-A/C, 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Adrenergic receptor alpha-1, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Thyrotropin receptor, Beta-2 adrenergic receptor, Beta-1 adrenergic receptor.
Bioactivity
ChEMBL activities: 19 potent at pChembl ≥ 5 of 31 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| ADRA1A | 8.37 | AC50 | 4.3 | nM | CHEMBL_ACT_25138152 |
| MAPK1 | 7.8 | Potency | 15.8 | nM | CHEMBL_ACT_4522384 |
| P15823 | 6.89 | Ki | 127.9 | nM | CHEMBL_ACT_18530190 |
| HTR1A | 6.67 | Ki | 213 | nM | CHEMBL_ACT_18530187 |
| HTR1A | 6.58 | AC50 | 260 | nM | CHEMBL_ACT_25165670 |
| HTR1A | 6.31 | AC50 | 491.9 | nM | CHEMBL_ACT_25164624 |
| LMNA | 6.3 | Potency | 501.2 | nM | CHEMBL_ACT_3661669 |
| ADRA1A | 6.24 | AC50 | 570 | nM | CHEMBL_ACT_25218371 |
| ADRB1 | 6.1 | AC50 | 790 | nM | CHEMBL_ACT_25122173 |
| ADRB2 | 6.1 | AC50 | 800 | nM | CHEMBL_ACT_25123195 |
| DRD3 | 5.85 | AC50 | 1400 | nM | CHEMBL_ACT_25193932 |
| ADRA2C | 5.57 | AC50 | 2700 | nM | CHEMBL_ACT_25148293 |
| HRH1 | 5.37 | AC50 | 4300 | nM | CHEMBL_ACT_25212925 |
| DRD2 | 5.23 | AC50 | 5900 | nM | CHEMBL_ACT_25140747 |
| CYP2C19 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_4005914 |
| CYP2C19 | 5.1 | AC50 | 7943 | nM | CHEMBL_ACT_6056450 |
| SLC6A4 | 5.02 | AC50 | 9500 | nM | CHEMBL_ACT_25150729 |
| PDE3A | 5.02 | AC50 | 9500 | nM | CHEMBL_ACT_25191108 |
| ADRA2B | 5.01 | AC50 | 9800 | nM | CHEMBL_ACT_25144102 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
4 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 |
| preeclampsia | 3 | MONDO:0005081 | EFO:0000668 |
| stroke disorder | 3 | MONDO:0005098 | EFO:0000712 |
| cerebrovascular disorder | 3 | MONDO:0011057 | EFO:0003763 |
Clinical trials
Total trials: 10.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 4 |
| PHASE3 | 3 |
| PHASE4 | 2 |
| PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT03300479 | PHASE4 | WITHDRAWN | Clevidipine (Cleviprex®) Compared With Urapidil (Ebrantil®) |
| NCT03529149 | PHASE4 | UNKNOWN | TCD Monitoring Technology Guides the Precise Control of Blood Pressure After EVT |
| NCT00409253 | PHASE3 | UNKNOWN | Treatment of Severe Hypertension During Pre-Eclampsia: A Preliminary Equivalence Study Between Urapidil and Nicardipine |
| NCT02558023 | PHASE3 | TERMINATED | The Treatment of Hypertension Associated With Severe Preeclampsia (PE). A Trial of Urapidil Versus Nicardipine |
| NCT03790800 | PHASE3 | COMPLETED | Intensive Ambulance-delivered Blood Pressure Reduction in Hyper-Acute Stroke Trial |
| NCT03001739 | PHASE1 | UNKNOWN | Intensive Blood PRessure Control in Patients With Acute Type B AortIc Dissection |
| NCT06635707 | Not specified | NOT_YET_RECRUITING | Efficacy and Safety Study of Urapidil Alone or With Esmolol in Treating Acute Hypertensive Intracerebral Hemorrhage |
| NCT00226096 | Not specified | COMPLETED | Intensive Blood Pressure Reduction in Acute Cerebral Haemorrhage |
| NCT02857153 | Not specified | UNKNOWN | Effect of High vs. Low MAP Levels on Clinical Outcomes in Elderly Patients During Noncardiothoracic Surgery |
| NCT03497351 | Not specified | COMPLETED | Effects of Different Kinds of Hypotensive Drugs on Dynamic Hemodynamic Changing in Patients Under Surgeries |
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).