Diphenhydramine

Source: Wikipedia, the free encyclopedia.
Not to be confused with dimenhydrinate.

Diphenhydramine
Nytol, others
AHFS/Drugs.comMonograph
MedlinePlusa682539
License data
Pregnancy
category
  • AU: A
first-generation antihistamine (ethanolamine), anticholinergic, hallucinogen (deliriant)
ATC code
Legal status
Legal status
  • AU: S2 (Pharmacy medicine)
  • CA: OTC
  • UK: P (
    Pharmacy medicines)[3]
  • US: OTC
  • UN: Unscheduled
Pharmacokinetic data
Bioavailability40–60%[4]
Protein binding98–99%
MetabolismLiver (CYP2D6, others)[8][9]
Elimination half-lifeRange: 2.4–13.5 h[5][4][6]
ExcretionUrine: 94%[7]
Feces: 6%[7]
Identifiers
  • 2-(diphenylmethoxy)-N,N-dimethylethanamine
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 (DPH) is an

injected into a muscle, or applied to the skin.[10] Maximal effect is typically around two hours after a dose, and effects can last for up to seven hours.[10]

Common side effects include sleepiness, poor coordination and an upset stomach.[10] Its use is not recommended in young children or the elderly.[10][11] There is no clear risk of harm when used during pregnancy; however, use during breastfeeding is not recommended.[12] It is a first-generation H1-antihistamine and it works by blocking certain effects of histamine, which produces its antihistamine and sedative effects.[10][2] Diphenhydramine is also a potent anticholinergic, which means it also works as a deliriant at much higher than recommended doses as a result.[13] Its sedative and deliriant effects have led to some cases of recreational use.[14][2]

Diphenhydramine was first developed by

generic medication.[10] It is sold under the brand name Benadryl, among others.[10] In 2021, it was the 242nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.[17][18]

Medical uses

Diphenhydramine tablets

Diphenhydramine is a first-generation antihistamine used to treat a number of conditions including

local anesthetics such as lidocaine.[21]

Allergies

Diphenhydramine is effective in treatment of allergies.[22] As of 2007, it was the most commonly used antihistamine for acute allergic reactions in the emergency department.[23]

By injection it is often used in addition to epinephrine for anaphylaxis,[24] although as of 2007 its use for this purpose had not been properly studied.[25] Its use is only recommended once acute symptoms have improved.[22]

A bottle of topical "Itch-Stopping Gel" diphenhydramine

Topical formulations of diphenhydramine are available, including creams, lotions, gels, and sprays. These are used to relieve itching and have the advantage of causing fewer systemic effects (e.g., drowsiness) than oral forms.[26]

Movement disorders

Diphenhydramine is used to treat akathisia and Parkinson's disease–like extrapyramidal symptoms caused by antipsychotics.[27] It is also used to treat acute dystonia including torticollis and oculogyric crisis caused by first generation antipsychotics.

Sleep

Because of its

Advil PM. Diphenhydramine can cause minor psychological dependence.[28] Diphenhydramine has also been used as an anxiolytic.[29]

Diphenhydramine has also been used off-prescription by parents in an attempt to make their children sleep and to sedate them on long-distance flights.[30] This has been met with criticism, both by doctors and by members of the airline industry, because sedating passengers may put them at risk if they cannot react efficiently to emergencies,[31] and because the drug's side effects, especially the chance of a paradoxical reaction, may make some users hyperactive. Addressing such use, the Seattle Children's hospital argued, in a 2009 article, "Using a medication for your convenience is never an indication for medication in a child."[32]

The

network meta-analysis of medications for the treatment of insomnia published in 2022 found little evidence to inform the use of diphenhydramine for insomnia.[34]

Nausea

Diphenhydramine also has antiemetic properties, which make it useful in treating the nausea that occurs in vertigo and motion sickness. However, when taken above recommended doses, it can cause nausea (especially above 200 mg).[35]

Special populations

Diphenhydramine is not recommended for people older than 60 and children younger than six, unless a physician is consulted.

Beers list of drugs to avoid in the elderly.[38][39]

Diphenhydramine is excreted in breast milk.[40] It is expected that low doses of diphenhydramine taken occasionally will cause no adverse effects in breastfed infants. Large doses and long-term use may affect the baby or reduce breast milk supply, especially when combined with sympathomimetic drugs, such as pseudoephedrine, or before the establishment of lactation. A single bedtime dose after the last feeding of the day may minimize harmful effects of the medication on the baby and on the milk supply. Still, non-sedating antihistamines are preferred.[41]

Paradoxical reactions to diphenhydramine have been documented, particularly in children, and it may cause excitation instead of sedation.[42]

Topical diphenhydramine is sometimes used especially for people in hospice. This use is without indication and topical diphenhydramine should not be used as treatment for nausea because research has not shown that this therapy is more effective than others.[43]

There were no documented cases of clinically apparent acute liver injury caused by normal doses of diphenhydramine.[44]

Adverse effects

The most prominent side effect is sedation. A typical dose creates driving impairment equivalent to a blood-alcohol level of 0.10, which is higher than the 0.08 limit of most drunk-driving laws.[23]

Diphenhydramine is a potent

QT prolongation.[46]

Some individuals experience an

allergic reaction to diphenhydramine in the form of hives.[47][48]

Conditions such as restlessness or akathisia can worsen from increased levels of diphenhydramine, especially with recreational dosages.[42] Normal doses of diphenhydramine, like other first generation antihistamines, can also make symptoms of restless legs syndrome worse.[49] As diphenhydramine is extensively metabolized by the liver, caution should be exercised when giving the drug to individuals with hepatic impairment.

Anticholinergic use later in life is associated with an increased risk for cognitive decline and dementia among older people.[50]

Contraindications

Diphenhydramine is contraindicated in premature infants and neonates, as well as people who are breastfeeding. It is a pregnancy Category B drug. Diphenhydramine has additive effects with alcohol and other CNS depressants. Monoamine oxidase inhibitors prolong and intensify the anticholinergic effect of antihistamines.[51]

Overdose

Diphenhydramine is one of the most commonly misused over-the-counter drugs in the United States.[52] In cases of extreme overdose, if not treated in time, acute diphenhydramine poisoning may have serious and potentially fatal consequences. Overdose symptoms may include:[53]

Acute poisoning can be fatal, leading to cardiovascular collapse and death in 2–18 hours, and in general is treated using a symptomatic and supportive approach.

cardiac arrhythmias such as torsades de pointes.[55]
No specific
seizures in people who are prone to these symptoms.[56]

Interactions

Alcohol may increase the drowsiness caused by diphenhydramine.[57][58]

Pharmacology

Pharmacodynamics


Diphenhydramine[59]
Site Ki (nM) Species Ref
SERTTooltip Serotonin transporter ≥3,800 Human [60][61]
NETTooltip Norepinephrine transporter 960–2,400 Human [60][61]
DATTooltip Dopamine transporter 1,100–2,200 Human [60][61]
5-HT2C 780 Human [61]
α1B 1,300 Human [61]
α2A 2,900 Human [61]
α2B 1,600 Human [61]
α2C 2,100 Human [61]
D2
 20,000 Rat [62]
H1 9.6–16 Human [63][61]
H2 >100,000 Canine [64]
H3 >10,000 Human [61][65][66]
H4 >10,000 Human [66]
M1 80–100 Human [67][61]
M2 120–490 Human [67][61]
M3 84–229 Human [67][61]
M4 53–112 Human [67][61]
M5 30–260 Human [67][61]
VGSC
Tooltip Voltage-dependent sodium channel		 48,000–86,000 Rat [68]
hERG
Tooltip Human Ether-à-go-go-Related Gene		 27,100 (
IC50
Tooltip Half-maximal inhibitory concentration)		 Human [69]
Values are Ki (nM), unless otherwise noted. The smaller the value, the more strongly the drug binds to the site.

Diphenhydramine, available in various salt forms,[70] such as citrate,[71][72] hydrochloride,[73] and salicylate,[74] exhibits distinct molecular weights and pharmacokinetic properties. Specifically, diphenhydramine hydrochloride and diphenhydramine citrate possess molecular weights of 291.8 g/mol[75] and 447.5 g/mol,[76] respectively. These variations in molecular weight influence the dissolution rates and absorption characteristics of each salt form. Consequently, a dose of 25 mg diphenhydramine hydrochloride is therapeutically equivalent to 38 mg of diphenhydramine citrate. As such, dosage adjustments are necessary to account for these differences when switching between salt forms.[77]

Diphenhydramine, while traditionally known as an antagonist, acts primarily as an inverse agonist of the histamine H1 receptor.[78] It is a member of the ethanolamine class of antihistaminergic agents.[37] By reversing the effects of histamine on the capillaries, it can reduce the intensity of allergic symptoms. It also crosses the blood–brain barrier and inversely agonizes the H1 receptors centrally.[78] Its effects on central H1 receptors cause drowsiness.

Diphenhydramine is a potent

anticholinergic syndrome.[79] The utility of diphenhydramine as an antiparkinson
agent is the result of its blocking properties on the muscarinic acetylcholine receptors in the brain.

Diphenhydramine also acts as an intracellular

endogenous opioids, in rats.[81] The drug has also been found to act as an inhibitor of histamine N-methyltransferase (HNMT).[82][83]

Overview of diphenhydramine targets and effects
Biological target Mode of action Effect
H1 receptor Inverse agonist Allergy reduction; Sedation
mACh receptors
Antagonist
Anticholinergic; Antiparkinson
Sodium channels Blocker Local anesthetic

Pharmacokinetics

Oral bioavailability of diphenhydramine is in the range of 40% to 60%, and peak plasma concentration occurs about 2 to 3 hours after administration.[4]

The primary route of metabolism is two successive

oxidized to the carboxylic acid.[4] Diphenhydramine is metabolized by the cytochrome P450 enzymes CYP2D6, CYP1A2, CYP2C9, and CYP2C19.[8]

The

elimination half-life of diphenhydramine has not been fully elucidated, but appears to range between 2.4 and 9.3 hours in healthy adults.[5] A 1985 review of antihistamine pharmacokinetics found that the elimination half-life of diphenhydramine ranged between 3.4 and 9.3 hours across five studies, with a median elimination half-life of 4.3 hours.[4] A subsequent 1990 study found that the elimination half-life of diphenhydramine was 5.4 hours in children, 9.2 hours in young adults, and 13.5 hours in the elderly.[6] A 1998 study found a half-life of 4.1 ± 0.3 hours in young men, 7.4 ± 3.0 hours in elderly men, 4.4 ± 0.3 hours in young women, and 4.9 ± 0.6 hours in elderly women.[84] In a 2018 study in children and adolescents, the half-life of diphenhydramine was 8 to 9 hours.[85]

Chemistry

Diphenhydramine is a

derivative. Analogues of diphenhydramine include orphenadrine, an anticholinergic, nefopam, an analgesic, and tofenacin, an antidepressant
.

Detection in body fluids

Diphenhydramine can be quantified in blood, plasma, or serum.[86] Gas chromatography with mass spectrometry (GC-MS) can be used with electron ionization on full scan mode as a screening test. GC-MS or GC-NDP can be used for quantification.[86] Rapid urine drug screens using immunoassays based on the principle of competitive binding may show false-positive methadone results for people having ingested diphenhydramine.[87] Quantification can be used to monitor therapy, confirm a diagnosis of poisoning in people who are hospitalized, provide evidence in an impaired driving arrest, or assist in a death investigation.[86]

History

Diphenhydramine was discovered in 1943 by George Rieveschl, a former professor at the University of Cincinnati.[88][89] In 1946, it became the first prescription antihistamine approved by the U.S. FDA.[90]

In the 1960s, diphenhydramine was found to weakly inhibit reuptake of the neurotransmitter serotonin.[80] This discovery led to a search for viable antidepressants with similar structures and fewer side effects, culminating in the invention of fluoxetine (Prozac), a selective serotonin reuptake inhibitor (SSRI).[80][91] A similar search had previously led to the synthesis of the first SSRI, zimelidine, from brompheniramine, also an antihistamine.[92]

In 1975, diphenhydramine was still available only by prescription in the U.S. and required medical supervision.[93]

Society and culture

Diphenhydramine is deemed to have limited abuse potential in the United States owing to its potentially serious side-effect profile and limited euphoric effects, and is not a controlled substance. Since 2002, the U.S. FDA has required special labeling warning against use of multiple products that contain diphenhydramine.[94] In some jurisdictions, diphenhydramine is often present in postmortem specimens collected during investigation of sudden infant deaths; the drug may play a role in these events.[95][96]

Diphenhydramine is among prohibited and controlled substances in the

Republic of Zambia,[97] and travelers are advised not to bring the drug into the country. Several Americans have been detained by the Zambian Drug Enforcement Commission for possession of Benadryl and other over-the-counter medications containing diphenhydramine.[98]

Recreational use

Although diphenhydramine is widely used and generally considered to be safe for occasional usage, multiple cases of abuse and addiction have been documented.[14] Because the drug is cheap and sold over the counter in most countries, adolescents without access to more sought-after illicit drugs, are particularly at risk.[99] People with mental health problems—especially those with schizophrenia—are also prone to abuse the drug, which is self-administered in large doses to treat extrapyramidal symptoms caused by the use of antipsychotics.[100]

Recreational users report calming effects, mild euphoria, and hallucinations as the desired effects of the drug.[100][101] Research has shown that antimuscarinic agents, including diphenhydramine, "may have antidepressant and mood-elevating properties".[102] A study conducted on adult males with a history of sedative abuse found that subjects who were administered a high dose (400 mg) of diphenhydramine reported a desire to take the drug again, despite also reporting negative effects, such as difficulty concentrating, confusion, tremors, and blurred vision.[103]

In 2020, an Internet challenge emerged on social media platform TikTok involving deliberately overdosing on diphenhydramine; dubbed the Benadryl challenge, the challenge encourages participants to consume dangerous amounts of Benadryl for the purpose of filming the resultant psychoactive effects the hallucinations can include a visit from the "Hat Man" as recreational users call him, and has been implicated in several hospitalizations[104] and at least two deaths.[105][106][107]

Names

Diphenhydramine is sold under the brand name

generic medication
.

Procter & Gamble markets an over-the-counter formulation of diphenhydramine as a sleep aid under the brand ZzzQuil.[109]

Prestige Brands markets an over-the-counter formulation of diphenhydramine as a sleep aid in the U.S. under the name Sominex.[110]

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Further reading

External links

Media related to Diphenhydramine at Wikimedia Commons