Basic information
- CAS
57149-07-2- Standard SMILES
COc1ccccc1N1CCN(CC(O)COc2cccc3ccccc23)CC1- InChIKey
HRRBJVNMSRJFHQ-UHFFFAOYSA-N- Molecular formula
- C24H28N2O3
- Average molar mass
- 392.5 g/mol
- Monoisotopic mass
- 392.20999276
Overview
Naftopidil is a member of piperazines.
Names & identifiers
- Preferred name
- Naftopidil
- IUPAC
- 1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-naphthalen-1-yloxypropan-2-ol
- English name
- Naftopidil dihydrochloride
- Molecular formula
- C24H28N2O3
- Molecular weight
- 392.49
Names & synonyms
naftopidil57149-07-2FlivasNaftopidilumDTXSID50451761-(4-(2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-olR9PHW59SFNNSC-759293DTXCID30251761-[4-(2-methoxyphenyl)piperazin-1-yl]-3-(naphthalen-1-yloxy)propan-2-ol1-(4-(2-methoxyphenyl)-1-piperazinyl)-3-(1-naphthyloxy)-2-propanol1-[4-(2-Methoxyphenyl)-1-piperazinyl]-3-(1-naphthyloxy)-2-propanol
Show more names
BM-15275NaftopilNaftopiilNafTopIDi1NafitopidilNaftopidil>
RefChem:831691(2RS)-1-(4-(2-Methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy)propan-2-olNaftopidil [INN]KT-6114-(2-methoxyphenyl)-alpha-[(1-naphthalenyloxy)methyl]-1-piperazineethanol(+/-)-NaftopidilAvishotMFCD00242741
Database identifiers
- CAS
57149-07-2- PubChem CID
- 4418
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 45.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 7
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 483
Physicochemical properties
- Melting point
- 127 °C · 127 °C
- Boiling point
- 517.2 °C · 517.2°C (rough estimate)
- Density
- 1.1592 · 1.1592 (rough estimate)
- refractive index
- 1.63 · 1.6300 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 10 mg/mL · methanol: >10 mg/mL
- pka
- 14.01 · 14.01±0.20(Predicted)
- form
- solid
- color
- white
- Merck
- 14 · 14,6356
- InChI
- InChI=1S/C24H28N2O3/c1-28-24-11-5-4-10-22(24)26-15-13-25(14-16-26)17-20(27)18-29-23-12-6-8-19-7-2-3-9-21(19)23/h2-12,20,27H,13-18H2,1H3
- InChIKey
- HRRBJVNMSRJFHQ-UHFFFAOYSA-N
- SMILES
- C12C=CC=CC1=CC=CC=2OCC(O)CN1CCN(C2C=CC=CC=2OC)CC1
- CAS DataBase Reference
- 57149 · 57149-07-2(CAS DataBase Reference)
- FDA UNII
- 9 PHW59SFN · R9PHW59SFN
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
Warning
H361 (50%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesRepr. 2 (50%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- TL9336500
- ridadr
- 3077
- hs_code
- 29335990
- Toxicity
- LD50 in mice, rats (g/kg): 1.3, 6.4 orally (Himmel)
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H361
- Precautionary statements
- P201-P202-P281-P308+P313-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Applications
DescriptionNaftopidil was launched in Japan for the treatment of dysuria associated with benign prostatic hypertrophy (BPH). It can be prepared by a two step route starting with α-naphthol. Naftopidil is a potent postsynaptic-selective alpha-l-antagonist with a slightly higher affinity for the human prostatic than for the aortic alpha-adrenoceptor. It also shows a 5-HT1A agonistic effect, as well as a weak calcium antagonistic activity, but no alpha-2 or beta-adrenoreceptor affinity. In experiments with rats or rabbits, Naftopidil was shown to be more potent and selective for the urodynamic effect than the hypotensive effect. Aromatic or aliphatic hydroxylation are the major routes of metabolism, producing metabolites with a profile similar to the parent compound.
UsesNaftopidil is an α-1-adrenergic receptor antagonist. Naftopidil is used as an antihypertensive.
UsesA α-1-Adrenergic receptor antagonist, antihypertensive.
Usesantihypertensive, alpha-blocker, 5HT1a agonist
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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