Alimemazine

Alimemazine

Systematic (IUPAC) name
N,N,2-trimethyl-3-phenothiazin-10-yl-propan-1-amine
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	AU: C
Routes of administration	Oral
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	4.78 ± 0.59 hours[1]
Identifiers
CAS Number	84-96-8
ATC code	R06AD01 (WHO)
PubChem	CID 5574
IUPHAR/BPS	7237
DrugBank	DB01246
ChemSpider	5373
UNII	76H78MJJ52
KEGG	D07125
ChEMBL	CHEMBL829
Chemical data
Formula	C18H22N2S
Molar mass	298.447 g/mol
SMILES S2c1ccccc1N(c3c2cccc3)CC(C)CN(C)C
InChI InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3 Key:ZZHLYYDVIOPZBE-UHFFFAOYSA-N
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Alimemazine (INN), also known as trimeprazine (USAN and former BAN); brand names Nedeltran, Panectyl, Repeltin, Therafene, Theraligene, Theralen, Theralene, Vallergan, Vanectyl, and Temaril), commonly provided as a tartrate salt, is a phenothiazine derivative that is used as an antipruritic (it prevents itching from causes such as eczema or poison ivy, by acting as an antihistamine).^[2] It also acts as a sedative, hypnotic, and antiemetic for prevention of motion sickness. Although it is structurally related to drugs such as chlorpromazine, it is not used as an antipsychotic.^[3] In the Russian Federation, it is marketed under the brand name Teraligen for the treatment of anxiety disorders (including GAD), organic mood disorders, sleep disturbances, personality disorders accompanied by asthenia and depression, somatoform autonomic dysfunction and various neuroses.^[4]

Alimemazine is not approved for use in humans in the United States. The combination of alimemazine and prednisolone (commonly sold under the brand name Temaril-P) is licensed as an antipruritic and antitussive in dogs.

References

1. Hu OY, Gfeller E, Perrin JH, Curry SH (March 1986). "Relative bioavailability of trimeprazine tablets investigated in man using HPLC with electrochemical detection". The Journal of Pharmacy and Pharmacology 38 (3): 172–6. doi:10.1111/j.2042-7158.1986.tb04539.x. PMID 2871150.
2. "PubChem CID 78032".
3. "Drugbank:Trimeprazine".
4. "Russian Register of Medicines: “Teraligen” film-coated tablets (alimemazine tartrate) Patient Information Leaflet (in Russian). Revised September 2013.".