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
Show more names
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
- Formal charge
- 0
- Complexity
- 577
Experimental & physicochemical properties
Collision Cross Section
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)
- form
- solid
- color
- light yellow
- Water Solubility
- 32 mg/L · 32mg/L(22 ºC)
- InChI
- 1S/C23H26FN3O2/c24-19-10-8-18(9-11-19)21(28)7-4-14-26-15-12-23(13-16-26)22(29)25-17-27(23)20-5-2-1-3-6-20/h1-3,5-6,8-11H,4,7,12-17H2,(H,25,29)
- InChIKey
- DKGZKTPJOSAWFA-UHFFFAOYSA-N
- SMILES
- Fc1ccc(cc1)C(=O)CCCN2CCC3(CC2)N(CNC3=O)c4ccccc4
- FDA UNII
- 4 X6E73CJ0Q · 4X6E73CJ0Q
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 302 · H302-H361
- Precautionary statements
- 201 · P201-P301+P312+P330-P308+P313
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-63
- Safety Statements
- 36 · 36/37
- WGK Germany
- 3 · 3
- RTECS
- 8925000 · XX8925000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralRepr · Acute Tox. 4 OralRepr. 2
Safety & regulation
GHS classification
GHS Classification
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
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
- hazard_code
- Xn
- safety_code
- 36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H361
- Hazard Classifications
- Acute Tox. 4 OralRepr. 2
- Precautionary statements
- P201-P301+P312+P330-P308+P313
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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
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
Upstream raw materials
Downstream products
Suppliers33 total
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
Linked notes
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