Naftopidil

Summary

Naftopidil (CHEMBL142635) is an approved small molecule; indicated across 1 condition including hyperplasia.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Indications: 1 condition
• Clinical trials: 6
• Chemistry: 392.5 Da · C24H28N2O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL142635
Name	Naftopidil
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	4418
Molecular formula	C24H28N2O3
Molecular weight	392.5
InChIKey	HRRBJVNMSRJFHQ-UHFFFAOYSA-N

SMILES: COC1=CC=CC=C1N2CCN(CC2)CC(COC3=CC=CC4=CC=CC=C43)O

IUPAC name: 1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-naphthalen-1-yloxypropan-2-ol

Also known as: Flivas, Naftopidil, NSC-759293, SID26719853, SID26751791, SID90340768, SID49681769, SID104171197, SID50104483, SID144203756, SID170466026, NAFTOPIDIL

Parent form; salt/anhydrous children: CHEMBL1257069, CHEMBL1532139, CHEMBL1593765

Patent coverage: 1,026 distinct patent families (3,611 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 3,547 (98%) 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: 39 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Microtubule-associated protein tau, Prelamin-A/C, Inositol monophosphatase 1, 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Adrenergic receptor alpha-1, Alpha-2C adrenergic receptor, Histamine H2 receptor, Alpha-2B adrenergic receptor, Equilibrative nucleoside transporter 1, Glucocorticoid receptor, D(1A) dopamine receptor, Adrenergic receptor alpha-2, Beta-1 adrenergic receptor, 5-hydroxytryptamine receptor 1A, D(2) dopamine receptor, Acetylcholinesterase, Sodium-dependent noradrenaline transporter, Alpha-1D adrenergic receptor.

Bioactivity

ChEMBL activities: 54 potent at pChembl ≥ 5 of 65 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ADRA1D	8.92	Ki	1.2	nM	CHEMBL_ACT_18496948
ADRA1A	8.43	Ki	3.7	nM	CHEMBL_ACT_1431018
ADRA1A	8.43	Ki	3.71	nM	CHEMBL_ACT_18496946
ADRA1A	8.23	Ki	5.89	nM	CHEMBL_ACT_12411233
ADRA1A	8.23	Ki	5.88	nM	CHEMBL_ACT_12411277
HTR1A	8.07	AC50	8.6	nM	CHEMBL_ACT_25165401
P23944	7.93	Kd	11.75	nM	CHEMBL_ACT_15211918
P23944	7.93	Kd	11.75	nM	CHEMBL_ACT_18496918
ADRA1B	7.7	Ki	19.95	nM	CHEMBL_ACT_18496947
ADRA1A	7.7	AC50	20	nM	CHEMBL_ACT_25234699
P43140	7.48	Kd	33.11	nM	CHEMBL_ACT_15211892
P43140	7.48	Kd	33.11	nM	CHEMBL_ACT_18496904
P15823	7.41	Ki	39	nM	CHEMBL_ACT_994643
DRD3	7.4	AC50	40	nM	CHEMBL_ACT_25194889
HTR2B	7.33	AC50	47	nM	CHEMBL_ACT_25164209
ADRA1D	7.26	IC50	55.2	nM	CHEMBL_ACT_16412545
ADRA1D	7.26	IC50	55.2	nM	CHEMBL_ACT_18584604
P23944	6.84	Kd	143.2	nM	CHEMBL_ACT_18994268
P15823	6.75	Kd	177.8	nM	CHEMBL_ACT_15211905
P15823	6.75	Kd	177.8	nM	CHEMBL_ACT_18496911
ADRA2C	6.7	AC50	200	nM	CHEMBL_ACT_25148246
ADRA2A	6.54	AC50	290	nM	CHEMBL_ACT_25156806
ADRA2B	6.52	AC50	300	nM	CHEMBL_ACT_25144059
DRD3	6.38	AC50	420	nM	CHEMBL_ACT_25193888
ADRA1A	6.34	AC50	460	nM	CHEMBL_ACT_25218335
ADRA1A	6.27	AC50	542.6	nM	CHEMBL_ACT_25138133
ADRA1A	6.26	IC50	555	nM	CHEMBL_ACT_16412481
ADRA1A	6.26	IC50	555	nM	CHEMBL_ACT_18584592
ADRA1B	6.2	IC50	634	nM	CHEMBL_ACT_16412522
ADRA1B	6.2	IC50	634	nM	CHEMBL_ACT_18584598
HRH1	6.12	AC50	750	nM	CHEMBL_ACT_25212879
HTR2B	6.08	AC50	840	nM	CHEMBL_ACT_25227867
KCNH2	6.06	AC50	870	nM	CHEMBL_ACT_25118375
OPRM1	6.05	AC50	900	nM	CHEMBL_ACT_25158552
LMNA	6.05	Potency	891.3	nM	CHEMBL_ACT_3657516
DRD2	6	AC50	1000	nM	CHEMBL_ACT_25140701
P54833	6	Ki	1000	nM	CHEMBL_ACT_994646
ADRB1	5.96	AC50	1100	nM	CHEMBL_ACT_25122128
HTR1A	5.92	AC50	1200	nM	CHEMBL_ACT_25216267
HRH2	5.89	AC50	1300	nM	CHEMBL_ACT_25169673
SLC6A4	5.84	AC50	1430	nM	CHEMBL_ACT_25151704
P19328	5.8	Ki	1600	nM	CHEMBL_ACT_994644
DRD1	5.68	AC50	2080	nM	CHEMBL_ACT_25115587
OPRK1	5.66	AC50	2200	nM	CHEMBL_ACT_25129762
P97697	5.6	Potency	2512	nM	CHEMBL_ACT_4411368
ADRA2A	5.43	AC50	3700	nM	CHEMBL_ACT_25220238
SLC6A3	5.35	AC50	4460	nM	CHEMBL_ACT_25125336
SLC6A3	5.26	AC50	5500	nM	CHEMBL_ACT_25124309
SLC6A2	5.22	AC50	6010	nM	CHEMBL_ACT_25146377
P22002	5.2	AC50	6300	nM	CHEMBL_ACT_25119878
NR3C1	5.05	AC50	8900	nM	CHEMBL_ACT_25176174
MAPK1	5.05	Potency	8912	nM	CHEMBL_ACT_4737632
HTR2A	5.04	AC50	9200	nM	CHEMBL_ACT_25225499
SLC6A2	5.02	AC50	9600	nM	CHEMBL_ACT_25145355

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 disease in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
hyperplasia	3	MONDO:0005043	EFO:0000536

Clinical trials

Total trials: 6.

Phase distribution

Phase	Trials
PHASE3	3
PHASE4	2
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01922375	PHASE4	COMPLETED	Clinical Trial to Evaluate the Efficacy and Safety of Naftopidil in Male Patients With Lower Urinary Tract Symptoms Associated With Benign Prostatic Hyperplasia
NCT02011737	PHASE4	UNKNOWN	Naftopidil 75mg for Improving Clearance of Urinary Stones
NCT01203371	PHASE3	WITHDRAWN	Efficacy And Safety Study Of Naftopidil to Patients Treatment With LUTS
NCT01952314	PHASE3	COMPLETED	Medical Expulsive Therapy for Ureter Stone Using Naftopidil
NCT01959074	PHASE3	COMPLETED	The Effect of Naftopidil for the Double-J Stent Discomfort
NCT00967772	PHASE1	COMPLETED	The Safety/Tolerability and Pharmacokinetics (PKs) of Naftopidil in Korean Healthy Male Volunteers

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).