Chemistry:Promazine

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Short description: Chemical compound
Promazine
Promazine.svg
Promazine3d.png
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa600010
Drug classTypical antipsychotic
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
Pharmacokinetic data
Protein binding94%
Elimination half-life20-40 hr
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC17H20N2S
Molar mass284.42 g·mol−1
3D model (JSmol)
  (verify)

Promazine (brand name Sparine among others),[1] is used as a short-term add-on treatment for psychomotor agitation.[2][3] Its approved uses in people is limited, but is used as a tranquilizer in veterinary medicine.[2] It has weak antipsychotic effects but is generally not used to treat psychoses.[2]

It acts similar to chlorpromazine and causes sedation.[2] It has predominantly anticholinergic side effects, though extrapyramidal side effects are not uncommon. It belongs to the typical antipsychotic and phenothiazine class of drugs.[4]

Promazine was approved for medical use in the United States in the 1950s, although it is no longer commercially available there.[1][5]

Uses

Promazine is a short-term add-on treatment for psychomotor agitation.[3]

Adverse effects

Common side effects include agitation, absent menstruation, arrhythmias, constipation, drowsiness and dizziness, dry mouth, problems with erection, tiredness, milky nipple discharge, large breasts, high sugars, difficulty sleeping, low blood pressure, prolonged QT, fits, shaking, vomiting and weight gain, among others.[3]

Overdose

In overdose, it may cause blood pressure to drop, lowering of body temperature, increased heart rate, and an irregular heart beat.[3]

Sudden death may occur, although rare.[3]

Other animals

Promazine, given as promazine hydrochloride, is one of the primary tranquilizers used by veterinarians as a pre-anaesthesia injection in horses.[6][7] 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.[7][8] It can be used alone when performing a non-painful procedure such as the fitting a horseshoe.[8] Low blood pressure, fast heart rate and paralysis of the penis are side effects.[6] It is also an antiemetic, antispasmodic and hypothermic agent.[7] Additionally it is used to lower blood pressure in animals with laminitis and kidney failure.[7] It is available in the US for veterinary use under the names Promazine and Tranquazine.[citation needed]

Synthesis

Synthesis:[9][10][11] Patents:[12][13] ~75%:[14]

References

  1. ↑ 1.0 1.1 "Promazine (Primazine, Prozine)" (in en). Davis's Drug Guide. https://www.drugguide.com/ddo/view/Davis-Drug-Guide/109132/all/promazine. 
  2. ↑ 2.0 2.1 2.2 2.3 "Promazine". X Pharm: The Comprehensive Pharmacology Reference. Elsevier. 2007. pp. 1–6. doi:10.1016/B978-008055232-3.62472-9. ISBN 978-0-08-055232-3. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "BNF". https://bnf.nice.org.uk/drug/promazine-hydrochloride.html. 
  4. ↑ "PPDR: Promazine". Psychologist's Neuropsychotropic Desk Reference. Philadelphia: Brunner/Mazel. 1999. p. 535. ISBN 978-1-138-00968-4. https://books.google.com/books?id=n2e2aAYnZYkC&pg=PA535. 
  5. ↑ "Drugs@FDA: FDA-Approved Drugs". New Drug Application (NDA): 010942 Sparine. U.S. Food and Drug Administration. https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=010942. 
  6. ↑ 6.0 6.1 "2. Anaesthesia and fluid therapy" (in en). Techniques in Large Animal Surgery (3rd ed.). Blackwell Publishing. 2007. p. 16. ISBN 978-0-7817-8255-5. https://books.google.com/books?id=J4hp2713DJAC&pg=PA16. 
  7. ↑ 7.0 7.1 7.2 7.3 "Promazine" (in en). Equimed - Horse Health Matters. 20 January 2014. https://equimed.com/drugs-and-medications/reference/promazine. 
  8. ↑ 8.0 8.1 "23. Chemical restraint for standing procedures" (in en). Equine Surgery (5th ed.). St Louis, Missouri: Elsevier. 2019. pp. 351–352. ISBN 978-0-323-48420-6. https://books.google.com/books?id=0mRgDwAAQBAJ&pg=PA351. 
  9. ↑ "[The pharmacological action of promazine]". Arzneimittel-Forschung 8 (8): 507–511. August 1958. PMID 13584240. 
  10. ↑ "Synthetic applications and mechanism of the pyrolysis of phenothiazine carbamates". The Journal of Organic Chemistry 45 (4): 744–746. February 1980. doi:10.1021/jo01292a048. 
  11. ↑ "N -Dimethylaminopropylation in a Solid-Liquid Two Phase System: Synthesis of Chlorpromazine, its Analogs, and Related Compounds". Synthesis 1984 (1): 29–31. 1984. doi:10.1055/s-1984-30719. 
  12. ↑ Charpentier P, US patent 2519886, issued 1950, assigned to Rhône-Poulenc.
  13. ↑ Kantor ML, Samuel T, US patent 3100772, issued 1963, assigned to Wyeth LLC.
  14. ↑ "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. 15 February 2008. doi:10.1002/anie.200705209. PMID 18213669. 



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