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20-September-2008 09:55:57 - Diphenhydramine Diphenhydramine Systematic IUPAC name 2-benzhydryloxy-N,N-dimethyl-ethanamine Identifiers CAS number 58-73-1 ATC code D04AA32 D04AA33, R06AA02 PubChem 3100 DrugBank APRD00587 Chemical data Formula C17H21NO Mol. mass 255.355 g/mol Pharmacokinetic data Bioavailability 86% bound to plasma protein Protein binding 98 to 99% Metabolism Various cytochrome P450 liver enzymes cyp 2D6 80% ,cyp 3A4 10% Half life 2-8 hours Excretion 94% through the urine, 6% through feces Therapeutic considerations Pregnancy cat. B Legal status Over-the-counter, non-regulated Routes Oral, parenteral IM, suppository Indicated for: Antihistaminic Motion sickness Sedative/Hypnotic Other uses: Halting allergic reactions, controlling extrapyramidal side-effects induced by antipsychotics Contraindications: Use in neonates and premature infants Use in nursing mothers Use as a local anesthetic Use in people with hypersensitivity to diphenhydramine hydrochloride and other antihistamines of similar chemical structure Non-medical use/abuse: Used as a deliriant/hallucinogen Side effects: Severe: Myocardial infarction Heart Attack, serious ventricular dysrhythmias, coma and death Atypical sensations: Feelings of heaviness, hearing disturbance Cardiovascular: Hypertension in sensitive individuals Ear, nose, and throat: Dryness of the nose and throat, heartburn Endocrinal: Increased or decreased appetite Eye: Dryness of the eyes, redness of the eyes, yellowing of the eyes Gastrointestinal: Constipation, nausea Hematological: Hepatotoxicity in extremely large dosages Musculoskeletal: Incoordination, slow muscle response, fasciculations twitching, restlessness, extrapyramidal side-effects, restless-leg syndrome Neurological: Confusion, clouded thinking, drowsiness, hallucinations, delirium, euphoria, short-term memory loss Psychological: Agitation, anxiety, emotional lability, depression, excitability especially in children, paranoia Respiratory: Decreased respiration Skin: Photosensitivity, flushing Urogenital and reproductive: Urinary retention, sexual dysfunction, vaginal dryness, decreased libido Miscellaneous: ? Diphenhydramine hydrochloride trade name Benadryl as produced by Johnson Johnson, or Dimedrol outside the U.S. Canada. Nytol as a sleeping pill is an over-the-counter OTC antihistamine, antiemetic, sedative, and hypnotic. It may also be used for the treatment of extrapyramidal side effects of typical antipsychotics, such as the tremors that haloperidol can cause. It is a member of the ethanolamine class of antihistaminergic agents. Diphenhydramine is an anticholinergic, possessing 58 per cent of the anti-muscarinic power of atropine and was discovered during the search for synthetic alternatives to scopolamine which would be easier to work with. Diphenhydramine was one of the first known antihistamines, invented in 1943 by Dr. George Rieveschl.1 It became the first FDA-approved prescription antihistamine in 1946.2 The brand Benadryl is currently trademarked in the United States by Pfizer; however, many drug store chains and retail outlets manufacture less-costly generic versions under their own store brands. Contents 1 Pharmacological action 2 Common use and dosage 3 Side effects 4 Recreational use 5 See also 6 External links 7 References 7.1 Notes 7.2 Sources Pharmacological action This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. December 2007 Diphenhydramine dye fen hye' dra meen works by blocking the effect of histamine at H1 receptor sites. This results in effects such as the reduction of smooth muscle contraction, making diphenhydramine a popular choice for treatment of the symptoms of allergic rhinitis, hives, motion sickness, and insect bites and stings. In the 1960s it was found that diphenhydramine inhibits reuptake of the neurotransmitter serotonin. 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. A similar search had previously led to the synthesis of the first SSRI zimelidine from chlorpheniramine, also an antihistamine. Common use and dosage As an antihistamine, recommended doses for adults is 25-50 mg diphenhydramine every 6-8 hours, not to exceed 50-100 mg every 4-6 hours.3 Diphenhydramine is a first-generation antihistamine drug. Despite being one of the oldest antihistamines on the market, it is largely the most effective antihistamine available either by prescription or over-the-counter, and has been shown to exceed the effectiveness of even the latest prescription drugs.4 Consequently, it is frequently used when an allergic reaction requires fast, effective reversal of the often dangerous effects of a massive histamine release. Diphenhydramine has sedative properties. The drug is also used as a sleep aid and is an ingredient in many sleep aids, such as Unisom gelcaps however, the tablet form of Unisom contains Doxylamine, a different active ingredient5, and most notably Tylenol PM where it is combined with acetaminophen paracetamol, and Nytol and Sominex which have diphenhydramine as the only active ingredient. Several generic and store brands of antihistamines and sleep aids also contain solely diphenhydramine, such as Tylenol Simply Sleep. Diphenhydramine is widely used in nonprescription sleep aids with a maximum recommended dose of 50mg as the hydrochloride salt being mandated by the FDA. In the United Kingdom, Australia, New Zealand, South Africa, and other countries, a 50 to 100mg recommended dose is permitted, though in the case of New Zealand the purchaser is required to provide the pharmacist with their name, address and other personal identification to be later logged in a national police data base following any purchase of over the counter medications containing diphenhydramine such as Unisom.citation needed There are also topical formulations of diphenhydramine available, including creams, lotions, gels, and sprays. They are used to relieve itching, and have the advantage of causing much less systemic effect i.e. drowsiness than oral forms.citation needed Side effects Like many other first-generation antihistamines, diphenhydramine is a potent anticholinergic agent. This leads to profound drowsiness as a very common side-effect, along with the possibilities of motor impairment ataxia, dry mouth and throat, flushed skin, rapid or irregular heartbeat tachycardia, blurred vision at nearpoint owing to lack of accommodation cycloplegia, abnormal sensitivity to bright light photophobia, pupil dilation mydriasis, urinary retention ischuria, constipation, difficulty concentrating, short-term memory loss, visual disturbances, hallucinations, irritability, itchy skin, confusion, erectile dysfunction, and delirium. Some side effects such as twitching may be delayed until the drowsiness begins to cease and the person is in more of an awakening mode. Diphenhydramine also has local anesthetic properties, and has been used for patients allergic to common local anesthetics like lidocaine.6 Severe, prolonged twitching and muscle spasm have also been experienced. The most common cardiac dysrhythmias associated with diphenhydramine overdose are sinus bradycardia, elongated S-T segment interval, and premature ventricular contraction. Diphenhydramine is similar in its effects to dimenhydrinate Dramamine, its 8-chlorotheophylline salt, although the latter is approximately 60% the potency in terms of required dosage and is slightly less sedating. Some patients have an allergic reaction to diphenhydramine in the form of hives. 7 8 Since 2002 the US FDA requires special labeling: avoid using multiple products including Diphenhydramine, or using topical forms to treat poison ivy Urushiol-induced contact dermatitis.1 2 Recreational use Diphenhydramine is used both clinically and recreationally in conjunction with opioids to relieve itching and act as an analgesia potentiator 9 in a dose of 100-800 mg depending on body size and length of diphenhydramine use. It is used recreationally as a deliriant, depressant, or booster for alcohol. Mixing medications with sedating antihistamines other than under medical supervision can be quite dangerous.citation needed Those who use diphenhydramine recreationally take a higher dose than recommended. In smaller recreational doses 100-250mg the side effects are mild and are mainly limited to sleepiness and labored breath. The mental effects of higher doses 250+mg are described by many as dreaming while awake10 involving visual and auditory hallucinations that, unlike those experienced with most psychedelic drugs, often cannot be readily distinguished from reality. People who consume a high recreational dose can possibly find themselves in a hallucination which places them in a familiar situation with people and friends and rooms they know, while in reality being in a totally different setting. Inexperienced users of hallucinogens are liable to panic. Many users report a side effect profile consistent with atropine intoxication.citation needed This is due to antagonism of muscarinic acetylcholine receptors in both the central and autonomic nervous system which inhibits various signal transduction pathways. In the CNS, diphenhydramine readily crosses the blood-brain barrier, exerting effects within the visual and auditory cortex. Other CNS effects occur within the limbic system and hippocampus, causing confusion and temporary amnesia. Toxicology also manifests in the autonomic nervous system, primarily at the neuromuscular junction, resulting in ataxia and extrapyramidal side-effects, and at sympathetic post-ganglionic junctions, causing urinary retention, pupil dilation, tachycardia, irregular urination, and dry skin and mucous membranes. Considerable overdosage can lead to myocardial infarction heart attack, serious ventricular dysrhythmias, coma and death.citation needed Such a side-effect profile is thought to give ethanolamine-class antihistamines a relatively low abuse liability. The specific antidote for diphenhydramine poisoning is physostigmine, usually given by IV in hospital. See also Akathisia Acrivastine UK Benadryl Benadryl Allergy Relief Cetirizine UK Benadryl Once-A-Day External links Prescription Information PDF DiphenhydrAMINE University of Maryland Medical Center - Includes comprehensive dosage recommendations Diphenhydramine entry for recreational use at Drugs-Wiki Man 'took own life' in courtroom - suicide by Diphenhydramine - BBC News References Notes ^ George Rieveschl, 91, Allergy Reliever, Dies - New York Times ^ James Ritchie. UC prof, Benadryl inventor dies. Business Courier of Cincinnati. Retrieved on 2007-10-23. ^ http://www.nhtsa.dot.gov/people/injury/research/job185drugs/diphenhydramine.htm ^ Raphael GD, Angello JT, Wu MM, Druce HM 2006. Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol 96 4: 606-614. PMID 16680933. ^ Chattem: Unisom. ^ Postgraduate Medicine: Local anesthesia ^ Heine, A. 1996. Diphenhydramine: a forgotten allergen? Contact Dermatitis, 355, 311-2. ^ Coskey, R.J. 1983. Contact dermatitis caused by diphenhydramine hydrochloride. Journal of the Americal Academy of Dermatology, 82, 204-6. ^ Diphenhydramine potentiates narcotic but not endogenous opioid analgesia.. ^ Diphenhydramine Reports http://www.erowid.org/experiences/subs/exp_Diphenhydramine.shtml Sources Bruce G. Charlton, Self-management of psychiatric symptoms using over-the-counter OTC psychopharmacology: the S-DTM therapeutic model - self-diagnosis, self-treatment, self-monitoring. Medical Hypotheses 2005; 65: 823-828. J.A. Lieberman, History of the use of antidepressants in primary care. Primary Care Companion, Journal of Clinical Psychiatry 2003; 5 supplement 7. v d e Histamine antagonists H1 or non-selective Alkylamines Bepotastine Bamipine Brompheniramine Chlorpheniramine Dexbrompheniramine Dexchlorpheniramine Dimethindene Metron S Pheniramine Pyrrobutamine Talastine Thenaldine Tolpropamine Triprolidine Ethanolamines Aminoalkyl ethers Bietanautine Bromazine/Bromodiphenhydramine Carbinoxamine Chlorphenoxamine Clemastine Diphenylpyraline Diphenhydramine Doxylamine Embramine p-Methyldiphenhydramine Moxastine Orphenadrine Phenyltoloxamine Setastine Ethylenediamines Chloropyramine Chlorothen Histapyrrodine Methafurylene Mepyramine Methapyrilene Pyrilamine Talastine Thenyldiamine Thonzylamine Tripelennamine Pyribenzamine Phenothiazine Tricyclics Ahistan Etymemazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine Thiazinamium Other Tricyclics Azatadine Clobenzepam Cyproheptadine Deptropine Isothipendyl Loratidine Piperazine Buclizine Chlorcyclizine Cinnarizine Clocinizine Hydroxyzine Niaprazine Oxatomide Benzhydryl compounds Cyclizine, Meclizine Others including selective, 2nd gen, 3rd gen Antazoline Astemizole Azatadine Azelastine Bepottastine Bamipine Cetoxine Clemizole Clobenztropine Deptropine Desloratadine Dimebon Ebastine Emedastine Epinastine Ketotifen Levocabastine Loratadine Mebhydrolin Mizolastine Phenindamine Pimethixene Pyrrobutamine Rupatadine Thenalidine Tritoqualine Alkylamine Acrivastine Tricyclic Olopatadine Piperazine Levocetirizine, Cetirizine Benzhydryl compounds Fexofenadine, Terfenadine H2 Cimetidine Famotidine Ranitidine Roxatidine Lafutidine Niperotidine Nizatidine H3 A-349,821 ABT-239 Burimamide Ciproxifan Clobenpropit Conessine Impentamine Iodophenpropit Thioperamide VUF-5681 H4 JNJ 7777120 Thioperamide VUF-6002 v d e Antipruritics D04 Antihistamines for topical use Thonzylamine - Mepyramine - Thenalidine - Tripelennamine - Chloropyramine - Promethazine - Tolpropamine - Dimetindene - Clemastine - Bamipine - Isothipendyl - Diphenhydramine - Chlorphenoxamine Anesthetics for topical use Lidocaine - Cinchocaine - Oxybuprocaine - Benzocaine - Quinisocaine - Tetracaine - Pramocaine v d e Deliriants anticholinergic hallucinogens Tropanes Atropine, Hyoscyamine, Scopolamine Benzilates Benactyzine, Ditran, EA-3167, N-Ethyl-3-piperidyl benzilate, N-Methyl-3-piperidyl benzilate, 3-Quinuclidinyl benzilate Antihistamines Benzhydryl compounds Cyclizine, Dimenhydrinate, Diphenhydramine, Doxylamine, Promethazine Others Benzydamine, Dicyclomine, Biperiden, Trihexyphenidyl Retrieved from http://en..org/wiki/Diphenhydramine Categories: Antihistamines | Antiemetics | Deliriants | H1 receptor antagonists | Muscarinic antagonists | Sedatives | Hypnotics | Tardive dyskinesiaHidden categories: Articles needing additional references from December 2007 | All articles with statements | Articles with statements since December 2007 | Articles with statements since April 2008 | Articles with statements since January 2008 | Articles with statements since May 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch 日本語 Polski РуÑ?Ñ?кий ไทย This page was last modified on 13 August 2008, at 20:48
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