Diphenhydramine Pronunciation Trade names Benadryl , Unisom, Nytol, othersAHFS/Drugs.com Monograph MedlinePlus a682539 License data
Pregnancy category Dependence liability Very low[1] Routes of administration By mouth, intramuscular, intravenous , topical, rectal ATC code Legal status
AU : S2 (Pharmacy medicine)
UK : General sales list (GSL, OTC)
US : OTC
Bioavailability 40–60%[4] Protein binding 98–99% Metabolism Liver (CYP2D6, others)[2] [3] Elimination half-life Range: 2.4–13.5 h [5] [4] [6] Excretion Urine : 94%[7] Feces : 6%[7]
2-(diphenylmethoxy)-N ,N -dimethylethanamine
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL ECHA InfoCard 100.000.360 Formula C 17 H 21 N O Molar mass 255.36 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
Diphenhydramine (DPH ) is an antihistamine medication. It is mainly used to treat allergies .[8] It can also be used to treat insomnia , the common cold , tremor in parkinsonism, and nausea .[8] It is taken by mouth, injected into a vein, injected into a muscle, or put on the skin.[8] It works best two hours after taking, and works for up to seven hours.[8]
Common side effects include sleepiness , bad balance and a bad stomach .[8] It should not be used in young children or the elderly .[8] [9] It can be used while pregnant , but not when breastfeeding .[10] It works by blocking some effects of histamine from working at the H1 receptor.[8] Diphenhydramine is also an anticholinergic, and is a deliriant at high doses.[11]
Diphenhydramine was first made by George Rieveschl and was first used in 1946.[12] [13] It is available as a generic medication.[8] It is also sold under the brand name Benadryl , as well as others.[8] It was the 241st most commoly prescribed medication in the United States in 2017.[14] [15]
↑ Hubbard, John R.; Martin, Peter R. (2001). Substance Abuse in the Mentally and Physically Disabled . CRC Press. p. 26. ISBN 9780824744977 .
↑ Krystal AD (August 2009). "A compendium of placebo-controlled trials of the risks/benefits of pharmacological treatments for insomnia: the empirical basis for U.S. clinical practice". Sleep Med Rev . 13 (4): 265–74. doi :10.1016/j.smrv.2008.08.001 . PMID 19153052 .
↑ "Showing Diphenhydramine (DB01075)" . DrugBank. Archived from the original on 31 August 2009. Retrieved 5 September 2009 .
↑ 4.0 4.1 Paton DM, Webster DR (1985). "Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines)". Clinical Pharmacokinetics . 10 (6): 477–97. doi :10.2165/00003088-198510060-00002 . PMID 2866055 . S2CID 33541001 .
↑ AHFS Drug Information . Published by authority of the Board of Directors of the American Society of Hospital Pharmacists. 1990.
↑ Simons KJ, Watson WT, Martin TJ, Chen XY, Simons FE (July 1990). "Diphenhydramine: pharmacokinetics and pharmacodynamics in elderly adults, young adults, and children" . Journal of Clinical Pharmacology . 30 (7): 665–71. doi :10.1002/j.1552-4604.1990.tb01871.x . PMID 2391399 . S2CID 25452263 .
↑ 7.0 7.1 Garnett WR (February 1986). "Diphenhydramine". American Pharmacy . NS26 (2): 35–40. doi :10.1016/s0095-9561(16)38634-0 . PMID 3962845 .
↑ 8.0 8.1 8.2 8.3 8.4 8.5 8.6 8.7 8.8 "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 .
↑ Schroeck JL, Ford J, Conway EL, Kurtzhalts KE, Gee ME, Vollmer KA, Mergenhagen KA (November 2016). "Review of Safety and Efficacy of Sleep Medicines in Older Adults" . Clinical Therapeutics . 38 (11): 2340–2372. doi :10.1016/j.clinthera.2016.09.010 . PMID 27751669 .
↑ "Diphenhydramine Pregnancy and Breastfeeding Warnings" . Drugs.com . Archived from the original on 2 October 2016. Retrieved 28 September 2016 .
↑ Ayd, Frank J. (2000). Lexicon of Psychiatry, Neurology, and the Neurosciences . Lippincott Williams & Wilkins. p. 332. ISBN 978-0-7817-2468-5 .
↑ Dörwald, Florencio Zaragoza (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 .
↑ "Benadryl" . Ohio History Central . Archived from the original on 17 October 2016. Retrieved 28 September 2016 .
↑ "The Top 300 of 2020" . ClinCalc . Retrieved 11 April 2020 .
↑ "Diphenhydramine Hydrochloride - Drug Usage Statistics" . ClinCalc . Archived from the original on 29 April 2017. Retrieved 11 April 2020 .
Cough and cold preparations (R05)
Expectorants
Potassium iodide
Althea root
Antimony pentasulfide
Creosote
Guaiacolsulfonate
Guaifenesin (+ oxomemazine)
Ipecacuanha (Syrup of ipecac)
Levoverbenone
Senega
Tyloxapol
Ammonium Chloride
Mucolytics
Acetylcysteine #
Ambroxol
Bromhexine
Carbocisteine
Domiodol
Dornase alfa
Eprazinone
Erdosteine
Letosteine
Mannitol
Mesna
Neltenexine
Sobrerol
Stepronin
Cough suppressants
Opium alkaloids,opioids , and derivatives
Codeine #
Dextromethorphan
Heroin
Hydrocodone
Laudanum
Methadone
Acetyldihydrocodeine
Benzylmorphine
Butorphanol
Dihydrocodeine
Dimemorfan
Droxypropine
Ethylmorphine
Hydromorphone
Isoaminile
Levomethadone
Levopropoxyphene
Nicocodeine
Nicodicodeine
Normethadone
Noscapine
Pholcodine
Thebacon
Tipepidine
Other
Benzonatate
Diphenhydramine
Alloclamide
Benproperine
Bibenzonium bromide
Butamirate
Clobutinol
Clofedanol
Cloperastine
Dibunate
Dimethoxanate
Dropropizine
Fedrilate
Fominoben
Glaucine
Levodropropizine
Meprotixol
Moguisteine
Morclofone
Nepinalone
Oxolamine
Oxeladin
Pentoxyverine
Pipazetate
Prenoxdiazine
Piperidione
Zipeprol
Drug culture
Cannabis culture
420
Cannabis consumption
Cannabis cultivation
Cannabis edible
Cannabis rights
Cannabis rights leaders
List of cannabis rights organizations
Cannabis smoking
Cannabis Social Club
Cannabis tea
Cannabis vaping
Head shop
Legal history of cannabis in the United States
Legality of cannabis
Marijuana Policy Project
Medical cannabis
NORML
Cannabis and religion
Stoner film
Coffee culture Drinking culture Psychedelia
Psychonautics
Art
Drug
Era
Experience
Literature
Music
Microdosing
Smart shop
Therapy
Smoking culture
Cigarette card
Fashion cigarettes
Cloud-chasing
Loosie
Smokeasy
Smoking fetishism
Tobacco smoking
Other
Legality of drug use
International
International Drug Control Conventions
1961 Narcotic Drugs
1971 Psychotropic Substances
1988 Drug Trafficking
Other treaties addressing drugs
Law of the Sea Convention
Convention Against Doping
Council of the European Union decisions on designer drugs
State level
Drug policy
Policy reform
Demand reduction
Drug Policy Alliance
Harm reduction
Law Enforcement Action Partnership
Liberalization
Students for Sensible Drug Policy
Transform Drug Policy Foundation
Drug policy by country
Australia
Canada
Germany
India
Netherlands
Portugal
Slovakia
Soviet Union
Sweden
Switzerland
United States
Drug legality
Alcohol legality
Anabolic steroid legality
Cannabis legality
Cocaine legality
Methamphetamine legality
Psilocybin mushrooms legality
Salvia legality
Other
Other
Drug production and trade
Drug production
Coca production in Colombia
Drug precursors
Opium production in Afghanistan
Rolling meth lab
Drug trade
Issues with drug use Harm reduction
Drug checking
Drug legalization
Drug rehabilitation
Needle and syringe programmes
Opioid replacement therapy
Pharmacovigilance
Reagent testing
Regulation of therapeutic goods
Responsible drug use
Substance abuse prevention
Supervised injection site
Countries by drug use
Alcohol consumption
Cocaine use
Cannabis
Opiates use
Tobacco consumption
GABAA
GABAB
1,4-Butanediol
4-Fluorophenibut
Aceburic acid
Baclofen
GABOB
GHB (sodium oxybate )
GBL
GVL
Phenibut
Tolibut
H1
Antihistamines Antidepressants
Serotonin antagonists and reuptake inhibitors
Etoperidone
Nefazodone
Trazodone
Tricyclic antidepressants
Amitriptyline
Doxepin
Trimipramine, etc.
Tetracyclic antidepressants
Mianserin
Mirtazapine, etc.
Antipsychotics
Typical antipsychotics
Atypical antipsychotics
α2 -Adrenergic
Clonidine
Detomidine
Dexmedetomidine
Lofexidine
Medetomidine
Romifidine
Tizanidine
Xylazine
5-HT2A
Antidepressants
Trazodone
Tricyclic antidepressants
Amitriptyline
Doxepin
Trimipramine, etc.
Tetracyclic antidepressants
Mianserin
Mirtazapine, etc.
Antipsychotics
Typical antipsychotics
Atypical antipsychotics
Others
Melatonin Orexin
Daridorexant
Lemborexant
Suvorexant
α2 δ VDCC
Gabapentin
Gabapentin enacarbil
Mirogabalin
Phenibut
Pregabalin
Others
Cannabidiol
Chlorophenylalkyldiols
Fenpentadiol
Metaglycodol
Phenaglycodol
Diethylpropanediol
Evoxine
Fenadiazole
Guaifenesin-related muscle relaxants
Chlorphenesin
Mephenesin
Mephenoxalone
Metaxalone
Methocarbamol
Midaflur
Opioids (e.g., morphine )
Passion flower
Scopolamine
Trazodone
UMB68
Valnoctamide
Antiemetics (A04)
5-HT3 serotonin ion channel antagonists
Alosetron
Azasetron
Bemesetron
Cilansetron
Clozapine
Dazopride
Dolasetron
Granisetron
Lerisetron
Metoclopramide
Mianserin
Mirtazapine
Olanzapine
Ondansetron
Palonosetron (+netupitant)
Quetiapine
Ramosetron
Ricasetron
Tropisetron
Zatosetron
5-HT serotonin G-protein receptor antagonists CB1 agonists (cannabinoids ) D2 /D3 antagonists
Alizapride
Bromopride
Chlorpromazine
Clebopride
Domperidone
Haloperidol
Hydroxyzine
Itopride
Metoclopramide
Metopimazine
Prochlorperazine
Thiethylperazine
Trimethobenzamide
H1 antagonists (antihistamines) mACh antagonists (anticholinergics) NK1 antagonists
Aprepitant
Fosaprepitant
Maropitant
Netupitant
Rolapitant
Others