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Promazine

From Wikipedia, the free encyclopedia
Chemical compound

Not to be confused withBromazine.
Pharmaceutical compound
Promazine
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa600010
Drug classTypical antipsychotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding94%
Eliminationhalf-life20-40 hr
Identifiers
  • N,N-dimethyl-3-(10H-phenothiazin-10-yl)-propan-1-amine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.347Edit 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 nameSparine among others),[2] is used as a short-term add-on treatment forpsychomotor agitation.[3][4] Its approved uses in people is limited, but is used as atranquilizer inveterinary medicine.[3] It has weakantipsychotic effects but is generally not used to treatpsychoses.[3]

It acts similar tochlorpromazine and causessedation.[3] It has predominantlyanticholinergic side effects, thoughextrapyramidal side effects are not uncommon. It belongs to thetypical antipsychotic andphenothiazine 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 forpsychomotor 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 causehypotension,hypothermia,tachycardia, andarrhythmia.[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 withopioids orα2 adrenoreceptor agonists, such asclonidine, or both.[8][9] It can be used alone when performing a non-painful procedure such as thefitting a horseshoe.[9]Low blood pressure,fast heart rate andparalysis of the penis are side effects.[7] It is also anantiemetic,antispasmodic andhypothermic agent.[8] Additionally it is used to lowerblood pressure in animals withlaminitis andkidney failure.[8] It is available in the US for veterinary use under the namesPromazine andTranquazine.[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. Retrieved2023-08-16.
  2. ^ab"Promazine (Primazine, Prozine)".Davis's Drug Guide. Retrieved6 August 2021.
  3. ^abcdDavis C (2007). "Promazine". In Enna SJ, Bylund DB (eds.).XPharm: The Comprehensive Pharmacology Reference. Elsevier. pp. 1–6.doi:10.1016/B978-008055232-3.62472-9.ISBN 978-0-08-055232-3.
  4. ^abcde"BNF".NICE. Retrieved4 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. ^abHendrickson 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. ^abcd"Promazine".Equimed - Horse Health Matters. 20 January 2014. Archived fromthe original on 4 August 2021. Retrieved4 August 2021.
  9. ^abRinger 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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mAChRsTooltip Muscarinic acetylcholine receptors
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(andprodrugs)
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