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Promazine

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Not to be confused with Bromazine.
Promazine
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa600010
Drug classTypical antipsychotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding94%
Elimination half-life20-40 hr
Identifiers
  • N,N-dimethyl-3-(10H-phenothiazin-10-yl)-propan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.347 Edit this at Wikidata
Chemical and physical data
FormulaC17H20N2S
Molar mass284.42 g·mol−1
3D model (JSmol)
  • CN(C)CCCN1c2ccccc2Sc3c1cccc3
  • InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3 checkY
  • Key:ZGUGWUXLJSTTMA-UHFFFAOYSA-N checkY
  (verify)

Promazine (brand name Sparine among others),[2] is used as a short-term add-on treatment for psychomotor agitation.[3][4] Its approved uses in people is limited, but is used as a tranquilizer in veterinary medicine.[3] It has weak antipsychotic effects but is generally not used to treat psychoses.[3]

It acts similar to chlorpromazine and causes sedation.[3] It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon. It belongs to the typical antipsychotic and phenothiazine class of drugs.[5]

Promazine was approved for medical use in the United States in the 1950s, although it is no longer commercially available there.[2][6]

Uses[edit]

Promazine is a short-term add-on treatment for psychomotor agitation.[4]

Adverse effects[edit]

Common side effects include agitation, amenorrhea, arrhythmias, constipation, drowsiness and dizziness, dry mouth, impotence, tiredness, galactorrhoea, gynecomastia, hyperglycemia, insomnia, hypotension, prolonged QT, seizures, tremor, vomiting and weight gain, among others.[4]

Overdose[edit]

In overdose, it may cause hypotension, hypothermia, tachycardia, and an arrythmias.[4]

Sudden death may occur, although rare.[4]

Other animals[edit]

Promazine, given as promazine hydrochloride, is one of the primary tranquilizers used by veterinarians as a pre-anaesthesia injection in horses.[7][8] It does not provide analgesia and is not a very strong sedative, hence it is used combined with opioids or α2 adrenoreceptor agonists, such as clonidine, or both.[8][9] It can be used alone when performing a non-painful procedure such as the fitting a horseshoe.[9] Low blood pressure, fast heart rate and paralysis of the penis are side effects.[7] It is also an antiemetic, antispasmodic and hypothermic agent.[8] Additionally it is used to lower blood pressure in animals with laminitis and kidney failure.[8] It is available in the US for veterinary use under the names Promazine and Tranquazine.[citation needed]

Synthesis[edit]

Synthesis:[10][11][12] Patents:[13][14] ~75%:[15]

References[edit]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ a b "Promazine (Primazine, Prozine)". Davis's Drug Guide. Retrieved 6 August 2021.
  3. ^ a b c d Davis C (2007). "Promazine". In Enna SJ, Bylund DB (eds.). X Pharm: The Comprehensive Pharmacology Reference. Elsevier. pp. 1–6. doi:10.1016/B978-008055232-3.62472-9. ISBN 978-0-08-055232-3.
  4. ^ a b c d e "BNF". NICE. Retrieved 4 August 2021.
  5. ^ Pagliaro LA, Pagliaro AM (1999). "PPDR: Promazine". Psychologist's Neuropsychotropic Desk Reference. Philadelphia: Brunner/Mazel. p. 535. ISBN 978-1-138-00968-4.
  6. ^ "Drugs@FDA: FDA-Approved Drugs". New Drug Application (NDA): 010942 Sparine. U.S. Food and Drug Administration.
  7. ^ a b Hendrickson DA (2007). "2. Anaesthesia and fluid therapy". Techniques in Large Animal Surgery (3rd ed.). Blackwell Publishing. p. 16. ISBN 978-0-7817-8255-5.
  8. ^ a b c d "Promazine". Equimed - Horse Health Matters. 20 January 2014. Archived from the original on 4 August 2021. Retrieved 4 August 2021.
  9. ^ a b Ringer SK, Mama KR (2019). "23. Chemical restraint for standing procedures". In Auer JA, Stick JA (eds.). Equine Surgery (5th ed.). St Louis, Missouri: Elsevier. pp. 351–352. ISBN 978-0-323-48420-6.
  10. ^ Wirth W (August 1958). "[The pharmacological action of promazine]". Arzneimittel-Forschung. 8 (8): 507–511. PMID 13584240.
  11. ^ Szabo WA, Chung RH, Tam CC, Tishler M (February 1980). "Synthetic applications and mechanism of the pyrolysis of phenothiazine carbamates". The Journal of Organic Chemistry. 45 (4): 744–746. doi:10.1021/jo01292a048.
  12. ^ Schmolka SJ, Zimmer H (1984). "N -Dimethylaminopropylation in a Solid-Liquid Two Phase System: Synthesis of Chlorpromazine, its Analogs, and Related Compounds". Synthesis. 1984 (1): 29–31. doi:10.1055/s-1984-30719. S2CID 95682513.
  13. ^ US 2519886, Charpentier P, issued 1950, assigned to Rhône-Poulenc. 
  14. ^ US 3100772, Kantor ML, Samuel T, issued 1963, assigned to Wyeth LLC. 
  15. ^ Dahl T, Tornøe CW, Bang-Andersen B, Nielsen P, Jørgensen M (15 February 2008). "Palladium-Catalyzed Three-Component Approach to Promazine with Formation of One Carbon–Sulfur and Two Carbon–Nitrogen Bonds". Angewandte Chemie International Edition. 47 (9): 1726–1728. doi:10.1002/anie.200705209. PMID 18213669.
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