1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}propan-1-one

• ChemBase ID: 657
• Molecular Formular: C20H24N2OS
• Molecular Mass: 340.48236
• Monoisotopic Mass: 340.1609344
• SMILES: S1c2c(N(CC(N(C)C)C)c3c1cccc3)cc(cc2)C(=O)CC
• Canonical SMILES: CCC(=O)c1ccc2c(c1)N(CC(N(C)C)C)c1c(S2)cccc1
• InChI: InChI=1S/C20H24N2OS/c1-5-18(23)15-10-11-20-17(12-15)22(13-14(2)21(3)4)16-8-6-7-9-19(16)24-20/h6-12,14H,5,13H2,1-4H3
• InChIKey: UVOIBTBFPOZKGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl}propan-1-one
• IUPAC Traditional name: propiomazine
• Brand Name: Largon; Phenoctyl; Propiomazina [INN-Spanish]; Propiomazine [Usan:Ban:Inn]; Propiomazinum [INN-Latin]; Propionylpromethazine
• Synonyms: Propiomazine

Database IDs

• CAS Number: 362-29-8
• PubChem SID: 46506205; 160964120
• PubChem CID: 4940
• CHEBI ID: 8491
• ATC CODE: N05CM06
• CHEMBL: 1201210
• Chemspider ID: 4771
• DrugBank ID: DB00777
• KEGG ID: D02361
• Unique Ingredient Identifier: 242Z0PM79Y
• Wikipedia Title: Propiomazine

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.642542
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8091987
• LogD (pH = 7.4): 3.579675
• Log P: 4.5457544
• Molar Refractivity: 103.5346 cm^3
• Polarizability: 39.702175 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.53
• LOG S: -4.69
• Solubility (Water): 7.03e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.454 mg/L
• Hydrophobicity(logP): 4.5

Pharmacology Properties

• Admin Routes: Intramuscular, intravenous

DETAILS

DrugBank - DB00777

• Drug Groups: approved
• Description: Propiomazine, an atypical antipsychotic agent, is used to treat both negative and positive symptoms of schizophrenia, acute mania with bipolar disorder, agitation, and psychotic symptoms in dementia. Future uses may include the treatment of obsessive-compulsive disorder and severe behavioral disorders in autism. Structurally and pharmacologically similar to clozapine, propiomazine binds to alpha(1), dopamine, histamine H1, muscarinic, and serotonin type 2 (5-HT2) receptors.
• Indication: Propiomazine is largely used for its antihistamininc sleep inducing effects in treating insomnia.
• Pharmacology: Although propiomazine is a phenothiazine, it is not used as an antipsychotic. It posesses antihistamine effects and is mostly used as a sedative in treating insomnia.
• Toxicity: Rare, serious side effects include convulsions (seizures); difficult or unusually fast breathing; fast or irregular heartbeat or pulse; fever (high); high or low blood pressure; loss of bladder control; muscle stiffness (severe); unusual increase in sweating; unusually pale skin; and unusual tiredness or weakness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Unknown, but most likely hepatic as with other phenothiazines.
• Protein Binding: 81%
• External Links: Wikipedia