Antihistamine medication
Pharmaceutical compound
Diphenhydramine Pronunciation Trade names Benadryl , Unisom, Nytol, othersAHFS /Drugs.com Monograph MedlinePlus a682539 License data
Pregnancy category Dependence liability Low[ 1] [ 2] Routes of administration By mouth , intramuscular , intravenous , topical , rectal Drug class First-generation antihistamine , antimuscarinic , hallucinogen (deliriant )ATC code Legal status
Bioavailability 40–60%[ 5] Protein binding 98–99% Metabolism Liver (CYP2D6 , others)[ 9] [ 10] Elimination half-life Range: 2.4–13.5 h [ 6] [ 5] [ 7] Excretion Urine : 94%[ 8] Feces : 6%[ 8]
2-(diphenylmethoxy)-N ,N -dimethylethanamine
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.000.360 Formula C 17 H 21 N O Molar mass 255.361 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
Y Key:ZZVUWRFHKOJYTH-UHFFFAOYSA-N
Y
N Y (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]
^ Hubbard JR, Martin PR (2001). Substance Abuse in the Mentally and Physically Disabled . CRC Press. p. 26. ISBN 978-0-8247-4497-7 .
^ 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 .
^ "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 .
^ "Diphenhydramine- diphenhydramine hydrochloride injection, solution" . DailyMed . 11 November 2019. Retrieved 18 May 2024 .
^ a b Cite error: The named reference pmid2866055
was invoked but never defined (see the help page ).
^ Cite error: The named reference AHFS
was invoked but never defined (see the help page ).
^ Cite error: The named reference pmid2391399
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^ a b Garnett WR (February 1986). "Diphenhydramine". American Pharmacy . NS26 (2): 35–40. doi :10.1016/s0095-9561(16)38634-0 . PMID 3962845 .
^ Cite error: The named reference pmid19153052
was invoked but never defined (see the help page ).
^ "Showing Diphenhydramine (DB01075)" . DrugBank. Archived from the original on 31 August 2009. Retrieved 5 September 2009 .
^ 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 .
^ 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.
^ "Diphenhydramine Pregnancy and Breastfeeding Warnings" . Drugs.com . Archived from the original on 2 October 2016. Retrieved 28 September 2016 .
^ 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.
^ "Benadryl" . Ohio History Central . Archived from the original on 17 October 2016. Retrieved 28 September 2016 .
^ "The Top 300 of 2022" . ClinCalc . Archived from the original on 30 August 2024. Retrieved 30 August 2024 .
^ "Diphenhydramine Drug Usage Statistics, United States, 2013 - 2022" . ClinCalc . Retrieved 30 August 2024 .
^ Cite error: The named reference Thomas2008
was invoked but never defined (see the help page ).