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Alimemazine

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Alimemazine
Systematic (IUPAC) name
N,N,2-trimethyl-3-phenothiazin-10-yl-propan-1-amine
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a600010
Pregnancy cat. C(AU)
Legal status  ?
Routes Oral
Pharmacokinetic data
Metabolism Hepatic
Half-life 5 hrs
Identifiers
CAS number 84-96-8
ATC code D04AA10 R06AD02, R06AD05
PubChem CID 5574
DrugBank APRD00258
ChemSpider 5373 YesY
UNII 76H78MJJ52 YesY
KEGG D07125 YesY
ChEMBL CHEMBL829 YesY
Chemical data
Formula C18H22N2S 
Mol. mass 298.447 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Alimemazine (INN), also known as trimeprazine (former BAN and USAN; trade names Nedeltran, Panectyl, Repeltin, Therafene, Theraligene, Theralen, Theralene, Vallergan, Vanectyl, or 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).[1] It also acts as a sedative, hypnotic and anti-emetic for prevention of motion sickness. Although it is structurally related to drugs such as chlorpromazine (Thorazine), it is not used as an anti-psychotic treatment.[2] It is no longer available in the United States.[3] The elimination half-life is approximately 5 hours.[4]

In veterinary use, the combination of alimemazine and prednisolone is licensed as an anti-pruritic and anti-tussive in dogs.

[edit] Chemistry

Alimemazine is synthesized by alkylating phenothiazine with 1-dimethylamino-2-metylpropylchloride.[5]

[edit] References

  1. ^ "PubChem CID 78032". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=78032. 
  2. ^ "Drugbank:Trimeprazine". http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00258.txt. 
  3. ^ "MedlinePlus:Trimeprazine". http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a601126.html. 
  4. ^ Hu OY; Gfeller E, Perrin JH, Curry SH (March 1986). "Relative bioavailability of trimeprazine tablets investigated in man using HPLC with electrochemical detection". J Pharm Pharmacol 38 (3): 172–6. PMID 2871150. 
  5. ^ R.M. Jzcob, J.G. Robert, U.S. Patent 2,837,518 (1958)
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