Diphenhydramine

Diphenhydramine
Clinical data
Pronunciation/ˌdfɛnˈhdrəmn/
Trade namesBenadryl, Unisom, Nytol, others
AHFS/Drugs.comMonograph
MedlinePlusa682539
License data
Pregnancy
category
  • AU: A
Dependence
liability
Low[1][2]
Routes of
administration
By mouth, intramuscular, intravenous, topical, rectal
Drug classFirst-generation antihistamine, antimuscarinic, hallucinogen (deliriant)
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) / S2 (Pharmacy Medicine) / S3 (Pharmacist Only Medicine)
  • CA: OTC
  • UK: P (Pharmacy medicines)[3]
  • US: OTC / Rx-only[4]
  • UN: Unscheduled
Pharmacokinetic data
Bioavailability40–60%[5]
Protein binding98–99%
MetabolismLiver (CYP2D6, others)[9][10]
Elimination half-lifeRange: 2.4–13.5 h[6][5][7]
ExcretionUrine: 94%[8]
Feces: 6%[8]
Identifiers
  • 2-(diphenylmethoxy)-N,N-dimethylethanamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.360 Edit this at Wikidata
Chemical and physical data
FormulaC17H21NO
Molar mass255.361 g·mol−1
3D model (JSmol)
  • O(CCN(C)C)C(c1ccccc1)c2ccccc2
  • InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3 checkY
  • Key:ZZVUWRFHKOJYTH-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Diphenhydramine, sold under the brand name Benadryl among others, is an antihistamine and sedative. It is a first-generation H1-antihistamine and it works by blocking certain effects of histamine, which produces its antihistamine and sedative effects.[11][2] Diphenhydramine is also a potent anticholinergic.[12] It is mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremors in parkinsonism, and nausea.[11] It is taken by mouth, injected into a vein, injected into a muscle, or applied to the skin.[11] Maximal effect is typically around two hours after a dose, and effects can last for up to seven hours.[11]

Common side effects include sleepiness, poor coordination, and upset stomach.[11] There is no clear risk of harm when used during pregnancy; however, use during breastfeeding is not recommended.[13]

It was developed by George Rieveschl and put into commercial use in 1946.[14][15] It is available as a generic medication,[11][11] In 2022, it was the 258th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[16][17]

Its sedative and deliriant effects have led to some cases of recreational use.[18][2]

  1. ^ Hubbard JR, Martin PR (2001). Substance Abuse in the Mentally and Physically Disabled. CRC Press. p. 26. ISBN 978-0-8247-4497-7.
  2. ^ a b c Saran JS, Barbano RL, Schult R, Wiegand TJ, Selioutski O (October 2017). "Chronic diphenhydramine abuse and withdrawal: A diagnostic challenge". Neurology. Clinical Practice. 7 (5): 439–441. doi:10.1212/CPJ.0000000000000304. PMC 5874453. PMID 29620065.
  3. ^ "Benylin Chesty Coughs (Original) - Summary of Product Characteristics (SmPC)". (emc). 24 February 2022. Archived from the original on 30 December 2022. Retrieved 29 December 2022.
  4. ^ "Diphenhydramine- diphenhydramine hydrochloride injection, solution". DailyMed. 11 November 2019. Retrieved 18 May 2024.
  5. ^ a b Cite error: The named reference pmid2866055 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference AHFS was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference pmid2391399 was invoked but never defined (see the help page).
  8. ^ a b Garnett WR (February 1986). "Diphenhydramine". American Pharmacy. NS26 (2): 35–40. doi:10.1016/s0095-9561(16)38634-0. PMID 3962845.
  9. ^ Cite error: The named reference pmid19153052 was invoked but never defined (see the help page).
  10. ^ "Showing Diphenhydramine (DB01075)". DrugBank. Archived from the original on 31 August 2009. Retrieved 5 September 2009.
  11. ^ a b c d e f g "Diphenhydramine Hydrochloride". Drugs.com. American Society of Health-System Pharmacists. 6 September 2016. Archived from the original on 15 September 2016. Retrieved 28 September 2016.
  12. ^ Ayd FJ (2000). Lexicon of Psychiatry, Neurology, and the Neurosciences. Lippincott Williams & Wilkins. p. 332. ISBN 978-0-7817-2468-5. Archived from the original on 8 September 2017.
  13. ^ "Diphenhydramine Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 2 October 2016. Retrieved 28 September 2016.
  14. ^ Dörwald FZ (2013). Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. p. 225. ISBN 978-3-527-64565-7. Archived from the original on 2 October 2016.
  15. ^ "Benadryl". Ohio History Central. Archived from the original on 17 October 2016. Retrieved 28 September 2016.
  16. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  17. ^ "Diphenhydramine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  18. ^ Cite error: The named reference Thomas2008 was invoked but never defined (see the help page).

From Wikipedia, the free encyclopedia · View on Wikipedia

Developed by razib.in