Wikipedia

Promethazine

sedating antihistamine

Promethazine, dem sell under de brand name Phenergan among odas, be a first-generation antihistamine, sedative, den antiemetic dem use to treat allergies, nausea, den vomiting. E sanso fi help plus sam symptoms dem associate plus de common cold[1] den sanso fi be used for sedating people wey be agitated anaa anxious, an effect wey lead to sam recreational use (especially plus codeine).[2][3][4] Dem dey take promethazine by mouth (oral), as a rectal suppository, anaa by injection into a muscle (IM).[1]

(±)-promethazine
group of stereoisomers, type of chemical entity
Subclass ofphenothiazine, Medication Edit
Native labelPromethazine Edit
Chemical formulaC₁₇H₂₀N₂S Edit
Canonical SMILESCC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C Edit
Active ingredient inPhenergan, Phenadoz, Promethegan Edit
World Health Organisation international non-proprietary namepromethazine Edit
Medical condition treatedvomiting, motion sickness, postoperative complications, pain Edit
Physically dey interact plusHistamine receptor H1 Edit
Pregnancy categoryAustralian pregnancy category C, US pregnancy category C Edit
LiverTox likelihood scoreLiverTox toxicity likelihood category E Edit
Subject has roleantipruritic, dopamine antagonist, H1 antagonist, anti-allergic agents Edit
MCN code2934.30.30 Edit

Common side effects of promethazine dey include confusion den sleepiness;[1] consumption of alcohol anaa oda sedatives fi make dese symptoms worse.[1] E be unclear if use of promethazine during pregnancy anaa breastfeeding be safe.[1][5] Use of promethazine no be recommended insyd those less dan two years old, secof potentially negative effects on breathing.[1] Use of promethazine by injection into a vein no be recommended, secof potential skin damage.[1] Promethazine dey insyd de phenothiazine family of medications.[1] E sanso be a strong anticholinergic den at high anaa toxic doses fi act as a deliriant.[6]

Dem make promethazine insyd de 1940s by a team of scientists wey komot Rhône-Poulenc laboratories.[7] Na e be approved for medical use insyd de United States insyd 1951.[1] E be a generic medication wey be available under chaw brand names globally.[8] Insyd 2023, na e be de 230th most commonly prescribed medication insyd de United States, plus more dan 1 million prescriptions;[9][10] den de combination plus dextromethorphan be de 252nd most commonly prescribed medication insyd de United States, plus more dan 1 million prescriptions.[11][12]

Pharmacology

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Anoda notable use of promethazine be as a local anesthetic, by blockage of sodium channels.[13]

Binding to receptors in nM (Ki)
receptor Ki (nM) ref
α1A-adrenoceptor (Rat) 32 [14]
α1B-adrenoceptor (Rat) 21 [14]
α1D-adrenoceptor (Human) 90 [14]
α2A-adrenoceptor (Human) 256 [14]
α2B-adrenoceptor (Human) 24 [14]
α2C-adrenoceptor (Human) 353 [14]
Calmodulin (Human) 60000 [15][14][16]
Calmodulin (Bovine) 50000 [15][16][14]
Chloroquine resistance transporter (Plasmodium falciparum) 85000 [17][14]
D1 receptor (Human) 1372 [14]
D2 receptor (Human) 260 [14]
D3 receptor (Human) 190 [14]
H1 receptor (Human) 0.33[14]-1.4[18] [18][14]
H2 receptor (Human) 1146 [14]
M1 receptor (Human) 3.32 [14]
M2 receptor (Human) 12 [14]
M3 receptor (Human) 4.15 [14]
M4 receptor (Human) 1.06 [14]
M5 receptor (Human) 3.31 [14]
NET (Norephinephrine transporter) (Human) 4203 [14]
Prion protein (Human) 8000 [19][14]
5-HT1A receptor (Rat) 1484 [14]
5-HT2A receptor (Human) 19 [14]
5-HT2B receptor (Human) 43 [14]
5-HT2C receptor (Human) 6.48 [14]
5-HT6 receptor (Human) 1128 [14]
SERT (Serotonin transporter) (Human) 2130 [14]
Sigma1 receptor (Human) 120 [14]
OCT1 (Human) 35100 [20][14]

References

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  1. 1 2 3 4 5 6 7 8 9 "Promethazine Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 24 October 2018.
  2. ↑ Agnich LE, Stogner JM, Miller BL, Marcum CD (September 2013). "Purple drank prevalence and characteristics of misusers of codeine cough syrup mixtures" (PDF). Addictive Behaviors. 38 (9): 2445–9. doi:10.1016/j.addbeh.2013.03.020. PMID 23688907.
  3. ↑ British national formulary: BNF 74 (74 ed.). British Medical Association. 2017. p. 276. ISBN 978-0-85711-298-9.
  4. ↑ Malamed SF (2009). Sedation: A Guide to Patient Management (in English). Elsevier Health Sciences. p. 113. ISBN 978-0-323-07596-1.
  5. ↑ British national formulary: BNF 74 (74 ed.). British Medical Association. 2017. p. 276. ISBN 978-0-85711-298-9.
  6. ↑ Page CB, Duffull SB, Whyte IM, Isbister GK (February 2009). "Promethazine overdose: clinical effects, predicting delirium and the effect of charcoal". QJM. 102 (2): 123–131. doi:10.1093/qjmed/hcn153. PMID 19042969. S2CID 17677540.
  7. ↑ Li JJ (2006). Laughing Gas, Viagra, and Lipitor: The Human Stories behind the Drugs We Use. United Kingdom: Oxford University Press. p. 146. ISBN 978-0-19-988528-2. Retrieved 9 July 2016.
  8. ↑ "Promethazine international brands". Drugs.com. Retrieved 17 July 2017.
  9. ↑ "The Top 300 of 2023". ClinCalc. Archived from the original on 17 August 2025. Retrieved 17 August 2025.
  10. ↑ "Promethazine Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
  11. ↑ "The Top 300 of 2023". ClinCalc. Archived from the original on 17 August 2025. Retrieved 17 August 2025.
  12. ↑ "Dextromethorphan; Promethazine Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
  13. ↑ Prasad JP (2010). Conceptual Pharmacology. Universities Press. pp. 295, 303, 598. ISBN 978-81-7371-679-9. Retrieved 27 November 2011.
  14. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 "promethazine | Ligand Activity Charts | IUPHAR/BPS Guide to PHARMACOLOGY". www.guidetopharmacology.org (in English). Retrieved 18 May 2023.
  15. 1 2 Bruno C, Cavalluzzi MM, Rusciano MR, Lovece A, Carrieri A, Pracella R, Giannuzzi G, Polimeno L, Viale M, Illario M, Franchini C, Lentini G (June 2016). "The chemosensitizing agent lubeluzole binds calmodulin and inhibits Ca(2+)/calmodulin-dependent kinase II". European Journal of Medicinal Chemistry. 116: 36–45. doi:10.1016/j.ejmech.2016.03.045. PMID 27043269.
  16. 1 2 Bolshan Y, Getlik M, Kuznetsova E, Wasney GA, Hajian T, Poda G, Nguyen KT, Wu H, Dombrovski L, Dong A, Senisterra G, Schapira M, Arrowsmith CH, Brown PJ, Al-Awar R, Vedadi M, Smil D (March 2013). "Synthesis, Optimization, and Evaluation of Novel Small Molecules as Antagonists of WDR5-MLL Interaction". ACS Medicinal Chemistry Letters. 4 (3): 353–357. doi:10.1021/ml300467n. PMC 4027439. PMID 24900672.
  17. ↑ Deane KJ, Summers RL, Lehane AM, Martin RE, Barrow RA (May 2014). "Chlorpheniramine Analogues Reverse Chloroquine Resistance in Plasmodium falciparum by Inhibiting PfCRT". ACS Medicinal Chemistry Letters. 5 (5): 576–581. doi:10.1021/ml5000228. PMC 4027738. PMID 24900883.
  18. 1 2 Nakai T, Kitamura N, Hashimoto T, Kajimoto Y, Nishino N, Mita T, Tanaka C (August 1991). "Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia". Biological Psychiatry. 30 (4): 349–356. doi:10.1016/0006-3223(91)90290-3. PMID 1912125. S2CID 9715772.
  19. ↑ Vogtherr M, Grimme S, Elshorst B, Jacobs DM, Fiebig K, Griesinger C, Zahn R (August 2003). "Antimalarial drug quinacrine binds to C-terminal helix of cellular prion protein". Journal of Medicinal Chemistry. 46 (17): 3563–3564. doi:10.1021/jm034093h. PMID 12904059.
  20. ↑ Ahlin G, Karlsson J, Pedersen JM, Gustavsson L, Larsson R, Matsson P, Norinder U, Bergström CA, Artursson P (October 2008). "Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1". Journal of Medicinal Chemistry. 51 (19): 5932–5942. doi:10.1021/jm8003152. PMID 18788725.
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