(9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide

• ChemBase ID: 1399
• Molecular Formular: C23H29N3O2S2
• Molecular Mass: 443.62526
• Monoisotopic Mass: 443.17011918
• SMILES: S(=O)(=O)(N(C)C)c1cc2/C(=C\CCN3CCN(CC3)C)/c3c(Sc2cc1)cccc3
• Canonical SMILES: CN1CCN(CC1)CC/C=C\1/c2ccccc2Sc2c1cc(cc2)S(=O)(=O)N(C)C
• InChI: InChI=1S/C23H29N3O2S2/c1-24(2)30(27,28)18-10-11-23-21(17-18)19(20-7-4-5-9-22(20)29-23)8-6-12-26-15-13-25(3)14-16-26/h4-5,7-11,17H,6,12-16H2,1-3H3/b19-8-
• InChIKey: GFBKORZTTCHDGY-UWVJOHFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9Z)-N,N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide
• IUPAC Traditional name: thiothixene
• Brand Name: Navan; Navaron; Orbinamon; Navane
• Synonyms: Thiothixine; Tiotixene; Tiotixeno [inn-spanish]; Tiotixenum [inn-latin]; Cis-thiothixene; (e)-thiothixene; Thiothixene

Database IDs

• CAS Number: 5591-45-7
• PubChem SID: 46505564; 160964859
• PubChem CID: 941651

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.4381266
• LogD (pH = 7.4): 2.17915
• Log P: 3.3624241
• Molar Refractivity: 137.8545 cm^3
• Polarizability: 49.91193 Å^3
• Polar Surface Area: 43.86 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.01
• LOG S: -4.5
• Solubility (Water): 1.39e-02 g/l

DETAILS

DrugBank - DB01623

• Drug Groups: approved
• Description: A thioxanthine used as an antipsychotic agent. Its effects are similar to the phenothiazine antipsychotics. [PubChem]
• Indication: For the management of schizophrenia.
• Pharmacology: Thiothixene is an antipsychotic of the thioxanthene series. Navane possesses certain chemical and pharmacological similarities to the piperazine phenothiazines and differences from the aliphatic group of phenothiazines. Although widely used in the treatment of schizophrenia for several decades, thiothixene is seldom used today in favor of atypical antipsychotics such as risperidone.
• Toxicity: Symptoms of overdose include central nervous system depression, coma, difficulty swallowing, dizziness, drowsiness, head tilted to the side, low blood pressure, muscle twitching, rigid muscles, salivation, tremors, walking disturbances, and weakness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 10-20 hours
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com