Home > Compound List > Product Information
Diphenhydramine_Molecular_structure_CAS_58-73-1)
Click picture or here to close

Diphenhydramine

Catalog No. DB01075 Name DrugBank
CAS Number 58-73-1 Website http://www.ualberta.ca/
M. F. C17H21NO Telephone (780) 492-3111
M. W. 255.35474 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 946

SYNONYMS

IUPAC name
[2-(diphenylmethoxy)ethyl]dimethylamine
IUPAC Traditional name
diphenhydramine
Brand Name
Antitussive
Dimedrol
Diabenyl
Antomin
Diphenhist Captabs
Benzhydraminum
Amidryl
Bagodryl
Benylin
Benzhydryl
Dermodrin
Diphenhist
Ibiodral
Mephadryl
Sleep-Eze D
Syntodril
Alledryl
Aller-Med
Allergeval
Allergical
Allergival
Automin
Belix
Bena
Benadryl Allergy
Benodine
Benzhydramine
Dabylen
Debendrin
Dibenil
Dimedryl
Diphen
Histaxin
Hyadrine
Hydramine
Medidryl
Nytol Quickgels
Rigidyl
Soverin
Twilite Caplets
Allerdryl
Allergan B
Allergin
Allermax Caplets
Ambodryl
Antistominum
Banophen
Banophen Caplets
Baramine
Ben-Allergin
Benachlor
Benadryl
Benadryl Preservative Free
Benapon
Benodin
Benzantine
Benzhydril
Benzhydroamina
Betramin
Compoz
Desentol
Diabylen
Dibondrin
Difedryl
Difenhydramin
Difenidramina
Dihidral
Diphen Cough
Dormarex 2
Drylistan
Dylamon
Etanautine
Nausen
Nytol Quickcaps
Restamin
Rigidil
Siladryl
Silphen
Sleep-Eze D Extra Strength
Sominex
Syntedril
Torinal
Unisom Sleepgels Maximum Strength
Vena
Vicks Formula 44
Aleryl
Allergina
Beldin
Benadrin
Benylan
Dermistina
Dibendrin
Diphantine
Dryistan
Genahist
Hyrexin
Nervine Nighttime Sleep-Aid
Novamina
Probedryl
Synonyms
Diphenhydramine Hcl
Diphenhydramine Base
Diphenhydramine Salicylate
Diphenylhydramine

DATABASE IDS

PubChem CID 3100
PubChem SID 46505484
CAS Number 58-73-1

PROPERTIES

Hydrophobicity(logP) 3.27 [HANSCH,C ET AL. (1995)]
Solubility 3.06 mg/mL at 37 oC [BEILSTEIN]

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.
Indication For the treatment of symptoms associated with Vertigo/Meniere's disease, nausea and vomiting, motion sickness and insect bite.
Pharmacology Diphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, diphenhydramine competes with free histamine for binding at HA-receptor sites. Diphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of diphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Toxicity LD50=500 mg/kg (orally in rats). Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular dysrhythmias, coma and death.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic and renal
Absorption Quickly absorbed with maximum activity occurring in approximately one hour.
Half Life 1-4 hours
Protein Binding 98 to 99%
Elimination Little, if any, is excreted unchanged in the urine; most appears as the degradation products of metabolic transformation in the liver, which are almost completely excreted within 24 hours.
References
Raphael GD, Angello JT, Wu MM, Druce HM: Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2006 Apr;96(4):606-14. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • Raphael GD, Angello JT, Wu MM, Druce HM: Efficacy of diphenhydramine vs desloratadine and placebo in patients with moderate-to-severe seasonal allergic rhinitis. Ann Allergy Asthma Immunol. 2006 Apr;96(4):606-14. Pubmed