Spiperone

HCID 5265CAS 749-02-0

Basic information

Standard SMILES
O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1
InChIKey
DKGZKTPJOSAWFA-UHFFFAOYSA-N
Molecular formula
C23H26FN3O2
Average molar mass
395.5 g/mol
Monoisotopic mass
395.20090529

Overview

Spiperone is an azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively. It has a role as a psychotropic drug, an antipsychotic agent, an alpha-adrenergic antagonist, a serotonergic antagonist and a dopaminergic antagonist. It is a member of piperidines, an azaspiro compound, an organofluorine compound, a tertiary amino compound and an aromatic ketone.

Names & identifiers

Preferred name
Spiperone
IUPAC
8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
English name
SPIPERONE
Molecular formula
C23H26FN3O2
Molecular weight
395.47

Names & synonyms

spiperone749-02-0SpiropitanSpiroperidolEspiperonaSpiperonum8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-oneR 5147DTXSID50452058-(3-(p-Fluorobenzoyl)propyl)-1-phenyl-1,3,8-triazaspiro(4.5)decan-4-one8-(3-p-Fluorobenzoyl-1-propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro(4,5)decaneR-5147
Show more names
r5147SpiperonLuopenglongSpiperone-d5SpiperoneHClSpiroperidoneSpiperone, 10 mM in DMSO
NSC-1709834X6E73CJ0Q1,3,8-Triazaspiro(4.5)decan-4-one, 8-(4-(4-fluorophenyl)-4-oxobutyl)-1-phenyl-CHEBI:9233DTXCID30252058-(4-(4-Fluorophenyl)-4-oxobutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one8-[3-(p-Fluorobenzoyl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-oneSpiroperone

Database identifiers

CAS
749-02-0
PubChem CID
5265
DTXSID
DTXSID5045205
ChEMBL
CHEMBL267930
ChEBI
CHEBI:9233
UNII
4X6E73CJ0Q
EC Number
212-024-0
Nikkaji
J3.320K

Properties

Computed structural properties

XLogP
3
Topological polar surface area
52.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
6
Heavy atoms
29

Experimental & physicochemical properties

Solubility50.1 [ug/mL] (The mean of the results at pH 7.4)
Collision Cross Section · 2 items

193.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

199.03 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
190 · 190-193.60C
Boiling point
630.6 · 630.6±55.0 °C(Predicted)
Density
1.1714 · 1.1714 (estimate)
storage temp.
Store at RT
solubility
2 O: · H2O: slightly soluble0.2mg/mL
pka
8.31 · pKa 8.31 (Uncertain);9.09 (Uncertain)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (98.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 68 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (98.5%)

Safety data

PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
XX8925000
risk_code
22-63
Signal word
Warning
Symbol(GHS)
GHS07,GHS08

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

Applications · 3 items

UsesSpiperone is an antipsychotic.

Usesantibacterial

General DescriptionSpiperone is a butyrophenone antipsychotic agent. It induces calcium-dependent chloride secretion in the airway and functions as a potential therapeutic target for cystic fibrosis.

Upstream & downstream products

Suppliers33 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]

Additional notes

DefinitionChEBI: An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.

Related reactions

13 records

Linked notes

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