N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-sulfonamide

• ChemBase ID: 1398
• Molecular Formular: C22H30N4O2S2
• Molecular Mass: 446.6292
• Monoisotopic Mass: 446.18101822
• SMILES: S1c2c(N(CCCN3CCN(CC3)C)c3c1cccc3)cc(S(=O)(=O)N(C)C)cc2
• Canonical SMILES: CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)S(=O)(=O)N(C)C
• InChI: InChI=1S/C22H30N4O2S2/c1-23(2)30(27,28)18-9-10-22-20(17-18)26(19-7-4-5-8-21(19)29-22)12-6-11-25-15-13-24(3)14-16-25/h4-5,7-10,17H,6,11-16H2,1-3H3
• InChIKey: VZYCZNZBPPHOFY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-dimethyl-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine-2-sulfonamide
• IUPAC Traditional name: thioproperazine
• Brand Name: Vontil; Sulfenazin; Megeptil; Mazeptyl; Mazeptil; Majeptyl; Cephalmin
• Synonyms: Tioproferazina [inn-spanish]; Thiproperazine; Thioproperazinum [inn-latin]; Thioproperazin; Thioperazine; Thioproperazine

Database IDs

• CAS Number: 316-81-4
• PubChem SID: 46507111; 160964858
• PubChem CID: 9429
• CHEBI ID: 59120
• ATC CODE: N05AB08
• CHEMBL: 609109
• Chemspider ID: 9058
• DrugBank ID: DB01622
• KEGG ID: D08585
• Wikipedia Title: Thioproperazine

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.055762142
• LogD (pH = 7.4): 1.823456
• Log P: 2.831458
• Molar Refractivity: 126.9529 cm^3
• Polarizability: 49.376232 Å^3
• Polar Surface Area: 47.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.09
• LOG S: -3.89
• Solubility (Water): 5.69e-02 g/l

DETAILS

DrugBank - DB01622

• Drug Groups: approved
• Description: Thioproperazine is a potent neuroleptic with antipsychotic properties. Thioproperazine has a marked cataleptic and antiapomorphine activity associated with relatively slight sedative, hypothermic and spasmolytic effects. It is virtually without antiserotonin and hypotensive action and has no antihistaminic property. It is used for the treatment of all types of acute and chronic schizophrenia, including those which did not respond to the usual neuroleptics; manic syndromes.; Overdosage may result in severe extrapyramidal symptoms with dysphagia, marked sialorrhea, persistent and rapidly increasing hyperthermia, pulmonary syndrome, state of shock with pallor and profuse sweating, which may be followed by collapse and coma. LD50 in mice is 70 mg/kg I.V., 120 mg/kg I.P., 500 mg/kg S.C. and 830 mg/kg P.O.
• Indication: For the treatment of all types of acute and chronic schizophrenia, including those which did not respond to the usual neuroleptics; manic syndromes.
• Pharmacology: Thioproperazine is a potent neuroleptic with antipsychotic properties. Thioproperazine has a marked cataleptic and antiapomorphine activity associated with relatively slight sedative, hypothermic and spasmolytic effects. It is virtually without antiserotonin and hypotensive action and has no antihistaminic property.
• Toxicity: Overdosage may result in severe extrapyramidal symptoms with dysphagia, marked sialorrhea, persistent and rapidly increasing hyperthermia, pulmonary syndrome, state of shock with pallor and profuse sweating, which may be followed by collapse and coma. LD50 in mice is 70 mg/kg I.V., 120 mg/kg I.P., 500 mg/kg S.C. and 830 mg/kg P.O.
• Affected Organisms: Humans and other mammals