Product Name

Thiothixene

CAS Number

5591-45-7

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Product Name:
Thiothixene
CAS Number:
5591-45-7
Indication:
For the management of schizophrenia.
Mode of Action:

Thiothixene acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 – different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism – controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects).

Pharmacodynamics:

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.

IUPAC:
(9Z)-N, N-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]-9H-thioxanthene-2-sulfonamide
ATC:
N05AF04
PubChem:
941651
DrugBank:
DB01623
Formula:
C23-H29-N3-O2-S2
Molecular Mass:
443.6331
Synonyms:
2-(Dimethylsulfamoyl)-(9-(4-methyl-1-piperazinyl)propylidene)thioxanthene, 9H-Thioxanthene-2-sulfonamide, N,N-dimethyl-9-(3-(4-methyl-1-piperazinyl)propylidene)-, 9H-Thioxanthene-2-sulfonamide, N,N-dimethyl-9-(3-(4-methyl-1-piperazinyl)propylidene)-, (Z)-, CP-12,252-1, CP-12,252-1 base, EINECS 227-001-0, HSDB 3402, N,N-Dimethyl-9-(3-(4-methyl-1-piperazinyl)propylidene)thioxanthene-2-sulfonamide, Navane, Navaron, NSC 108165, Orbinamon, P 4657B, P-4657 B, P-4657-B, Thiothixene, Thioxanthene-2-sulfonamide, N,N-dimethyl-9-(3-(4-methyl-1-piperazinyl)propylidene)-, Tiotixene
SMILES:
c12C(c3c(cccc3)Sc1ccc(c2)S(N(C)C)(=O)=O)=CCCN1CCN(C)CC1
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+

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