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| Clinical data | |
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| Trade names | Torecan, Norzine |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
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| Pharmacokinetic data | |
| Protein binding | 60% |
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| ECHA InfoCard | 100.014.381 |
| Chemical and physical data | |
| Formula | C22H29N3S2 |
| Molar mass | 399.62 g·mol−1 |
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Thiethylperazine (Torecan,Norzine) is anantiemetic[1] of thephenothiazine class. It is an antagonist ofdopamine receptors (DRD1,DRD2,DRD4) as well as of5-HT2A,5-HT2C receptors,mAChRs (1 through 5),α1 adrenergic receptor andH1 receptor.
Thiethylperazine activates the transport proteinABCC1 that clearsbeta-amyloid from brains of mice.[2]
Thiethylperazine is highly lipofilic and it binds with membranes and serum proteins (over 85%).[3] It accumulates in organs with high blood flow and penetrates the placenta. It cannot be removed with dialysis.
It is mainly metabolized in the liver and only 3% is eliminated unchanged. Thiethylperazine'shalf-life is 12 h.
In toxic doses above the terapeutic window, it increases the rate of cleft palate occurrence.
Theithylperazine may possessantipsychotic activity[4] due to the antagonism of 5-HT2 and D2 receptors. It can causeextrapyramidal symptoms.[citation needed] Nevertheless, it was never marketed as an antipsychotic.
One cause of acutedystonia occurred in a 19-year-old male patient after discontinuation of this drug.[5]
Signs of acute thiethylperazine overdose include extrapyramidal symptoms, confusion,convulsions,respiratory depression, andhypotension.
One synthesis of thiethylperazine begins with aGoldberg reaction between 3-(ethylsulfanyl)aniline (1) and2-chlorobenzoic acid (2) to give the diarylamine3.[6][7][8] The carboxyl in the anthranilic acidresidue, having performed its activating function, is then thermolytically removed to form (4). Upon treatment with sulfur and iodine, we get predominantly thephenothiazine (5). The reaction may well be aided by the presence of the electron donatingthioether at thepara-position. Alkylation with 1-(γ-chloropropyl)-4-methylpiperazine (6) in the presence of sodamide affords thiethylperazine (7).
