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Basic information
- CAS
144598-75-4- Standard SMILES
Cc1nc2n(c(=O)c1CCN1CCC(c3noc4cc(F)ccc34)CC1)CCCC2O- InChIKey
PMXMIIMHBWHSKN-UHFFFAOYSA-N- Molecular formula
- C23H27FN4O3
- Average molar mass
- 426.492 g/mol
- Monoisotopic mass
- 426.20671894
Names & identifiers
- Preferred name
- Paliperidone
- IUPAC
- 3-{2-[4-(6-Fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl}-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one
- English name
- Paliperidone
- Molecular formula
- C23H27FN4O3
- Molecular weight
- 426.48
Names & synonyms
9-HYDROXYRISPERIDONE3-(2-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-onePalliperidonePaliperidone (Invega)r76477NSC8646RO 76477NSC 8646NSC-8646iperidone
Database identifiers
- CAS
144598-75-4- PubChem CID
- 115237
- DTXSID
DTXSID7049059- ChEMBL
CHEMBL1621- ChEBI
CHEBI:83804- UNII
- 838F01T721
- EC Number
- 620-493-1
- Nikkaji
- J508.304D
Properties
Physicochemical properties
- Melting point
- 158 · 158-160°C
- Boiling point
- 612.3 · 612.3±65.0 °C(Predicted)
- Density
- 1.45 · 1.45±0.1 g/cm3(Predicted)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- solubility
- 2 mg/mL, · DMSO: soluble2mg/mL, clear (warmed)
- pka
- 13 · 13.00±0.60(Predicted)
- form
- powder
- color
- white to brown
- Henry's Law Constant
- 1.2 · 1.2×1015 mol/(m3Pa) at 25℃, HSDB (2015)
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
- InChI
- InChI=1S/C23H27FN4O3/c1-14-17(23(30)28-9-2-3-19(29)22(28)25-14)8-12-27-10-6-15(7-11-27)21-18-5-4-16(24)13-20(18)31-26-21/h4-5,13,15,19,29H,2-3,6-12H2,1H3
- InChIKey
- PMXMIIMHBWHSKN-UHFFFAOYSA-N
- SMILES
- C12C(O)CCCN1C(=O)C(CCN1CCC(C3C4=C(ON=3)C=C(F)C=C4)CC1)=C(C)N=2
- CAS DataBase Reference
- 144598 · 144598-75-4(CAS DataBase Reference)
- FDA UNII
- 838 F01T721 · 838F01T721
- ATC code
- 5 AX13 · N05AX13
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 77 · NA.77
- Protein binding
- 74 % · 74%
- Excreted unchanged in urine
- 59 % · 59%
- Volume of distribution
- 487 Litrebr/> · 487 Litrebr/>
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- UV1164720
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29349990
- Toxicity
- rat,LD50,oral,65mg/kg (65mg/kg),Drug Development Research. Vol. 33, Pg. 399, 1994.
- risk_code
- 25-39/23/24/25-23/24/25-11
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T,F
- safety_code
- 45-36/37-16
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P310
- Hazardous Substances Data
- 144598-75-4(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionPaliperidone, (±)-3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one(Invega), is essentially insoluble in water and is available asextended-release tablets. Paliperidone is delivered at a constantrate using an osmotic drug release device (OsmoticRelease Oral Systems [OROS]). Paliperidone is FDA-approved for schizophrenia aged 12–17. However, the pharmacologic portfolio, extrapolation from adult studies, and the long track record of the parent drug, risperidone in child/adolescent psychiatric (CAP) population might expand its therapeutic potential.
UsesThis medication is used to treat certain mental/mood disorders (such as schizophrenia, schizoaffective disorder). This medication can decrease hallucinations and help you to think more clearly and positively about yourself, feel less agitated, and take a more active part in everyday life. Paliperidone belongs to a class of drugs called atypical antipsychotics. It works by helping to restore the balance of certain natural substances in the brain.
DescriptionPaliperidone, the C-9 hydroxylated active metabolite of the antipsychotic agent risperidone, is the newest atypical antipsychotic to join the market following the introductions of olanzapine (ZyprexaTM), risperidone (RisperdalTM), quetiapine(SeroquelTM), and ziprasidone (GeodonTM). Compared to its parent, paliperidone has improved PK properties and a reduced potential for drug interactions. In terms of receptor affinity, the two drugs are equipotent.
UsesA metabolite of Risperidone, a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist
UsesPaliperidone(Invega) is an atypical antipsychotic. Chemically, paliperidone is the primary active metabolite of the older atypical antipsychotic risperidone. It is indicated for the acute and maintenance treatment of schizophrenia
General DescriptionPaliperidone, (±)-3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one(Invega), is essentially insoluble in water and is available asextended-release tablets. Paliperidone is delivered at a constantrate using an osmotic drug release device (OsmoticRelease Oral Systems [OROS]). The absolute bioavailabilityof paliperidone is 28%, and studies in healthy subjects on ahigh-fat, high-calorie meal showed an increase in AUC.Paliperidone is 74% bound to plasma proteins. After a single,1-mg dose of C-paliperidone, 59% of the dose was excretedin the urine as unchanged drug, and 32% of the dose was recoveredas metabolites. Most of the drug (80%) is excreted bythe kidneys. Paliperidone is metabolized by dealkylation, hydroxylation,dehydrogenation, and scission of the benzoxazolering. None of these metabolic pathways account for morethan 10% of the dose. The terminal elimination half-life ofpaliperidone is 23 hours.
Related reactions
17 records
Compound notes
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