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Identification
Name Dimenhydrinate
Accession Number DB00985 (APRD00924)
Type small molecule
Groups approved
Description

Dimenhydrinate (Dramamine, Gravol and Vertirosan) is an over-the-counter drug used to prevent motion sickness. It is closely related to diphenhydramine HCl, or Benadryl. It is primarily a H1-antagonist, but also possesses an antimuscarinic effect.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Diphenhydrinate
Salts Not Available
Brand names
Name Company
Amosyt
Anautine
Andramine
Antemin
Aviomarin
Chloranautine
Diamarin
Dimate
Dimenest
Dimentabs
Dramalen
Dramamin
Dramarin
Dramilin
Dramyl
Dromyl
Eldodram
Gravinol
Gravol
Hydrinate
Menhydrinate
Neo-Navigan
Novamine
Permital
Reise-Engletten
Supremal
Teodramin
Travelin
Travelmin
Troversin
Vomex A
Xamamina
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Brand mixtures Not Available
Categories
  • Antiemetics
  • Histamine H1 Antagonists
CAS number 523-87-5
Weight Average: 469.964
Monoisotopic: 469.188067494
Chemical Formula C24H28ClN5O3
InChI Key InChIKey=DKHVTDUUNTVKOW-UHFFFAOYSA-N
InChI
InChI=1S/C17H21NO.C7H7ClN4O2/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h3-12,17H,13-14H2,1-2H3;1-2H3,(H,9,10,13)
Plain Text
IUPAC Name
8-chloro-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-ide; [2-(diphenylmethoxy)ethyl]dimethylazanium
SMILES
CN1C2=C([N-]C(Cl)=N2)C(=O)N(C)C1=O.C[NH+](C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Xanthines
  • Diphenylmethanes
Substructures
  • Anions
  • Benzyl Alcohols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Xanthines
  • Aryl Halides
  • Pyrimidines and Derivatives
  • Aliphatic and Aryl Amines
  • Diphenylmethanes
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Purines and Purine Derivatives
  • Cyanamides
  • Phenols and Derivatives
  • Cations
Pharmacology
Indication Used for treating vertigo, motion sickness, and nausea associated with pregnancy.
Pharmacodynamics Dimenhydrinate is an antiemetics drug combination that contains diphenhydramine and theophylline. It is not effective in the treatment of nausea associated with cancer chemotherapy. Dimenhydrinate directly inhibits the stimulation of certain nerves in the brain and inner ear to suppress nausea, vomiting, dizziness, and vertigo. Diphenhydramine and dimenhydinate both reduce vestibular neuronal excitation due to angular or linear acceleration motions.
Mechanism of action The mechanism by which some antihistamines exert their antiemetic, anti–motion sickness, and antivertigo effects is not precisely known but may be related to their central anticholinergic actions. They diminish vestibular stimulation and depress labyrinthine function. An action on the medullary chemoreceptive trigger zone may also be involved in the antiemetic effect. Dimenhydrinate is a competitive antagonist at the histamine H1 receptor, which is widely distributed in the human brain. Dimenhydrinate's anti-emetic effect is probably due to H1 antagonism in the vestibular system in the brain.
Absorption Well absorbed after oral administration.
Volume of distribution Not Available
Protein binding 98 to 99%.
Metabolism Hepatic (cytochrome P-450 system).
Route of elimination Not Available
Half life 1 to 4 hours
Clearance Not Available
Toxicity Symptoms of overdose include delerium, hallucinations, and excitment. Patients may be violent and confused.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Watson laboratories inc
  • Wyeth ayerst laboratories
  • Alra laboratories inc
  • Heather drug co inc
  • Nexgen pharma inc
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Liquid Intramuscular
Liquid Intravenous
Liquid Oral
Solution Intramuscular
Solution Intravenous
Suppository Rectal
Syrup Oral
Tablet Oral
Tablet, multilayer Oral
Prices
Unit description Cost Unit
Dimenhydrinate 50 mg/ml vial 5.7 USD ml
Dimenhydrinate I.M. 50 mg/ml 1.17 USD ml
Meclizine 12.5 mg tablet 0.62 USD tablet
Dramamine less drowsy tablet 0.42 USD tablet
Dimenhydrinate I.V. 10 mg/ml 0.32 USD ml
Dramamine 50 mg tablet 0.28 USD tablet
Novamine 15% iv solution 0.09 USD ml
Dimenhydrinate 100% powder 0.07 USD g
Driminate 50 mg tablet 0.05 USD tablet
Dimenhydrinate 50 mg tablet 0.03 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 204.5 °C PhysProp
water solubility 3000 mg/L MERCK INDEX (1996); approx.
logP -0.39 Not Available
Predicted Properties
Property Value Source
water solubility 1.25e-03 g/l ALOGPS
logP 2.67 ALOGPS
logP 3.65 ChemAxon
logS -5.6 ALOGPS
pKa (strongest basic) 8.87 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 13.67 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 90.94 ChemAxon
polarizability 30.28 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Takeda N, Morita M, Hasegawa S, Horii A, Kubo T, Matsunaga T: Neuropharmacology of motion sickness and emesis. A review. Acta Otolaryngol Suppl. 1993;501:10-5. Pubmed
  2. Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. Pubmed
  3. Jaju BP, Wang SC: Effects of diphenhydramine and dimenhydrinate on vestibular neuronal activity of cat: a search for the locus of their antimotion sickness action. J Pharmacol Exp Ther. 1971 Mar;176(3):718-24. Pubmed
External Links
Resource Link
KEGG Drug D00520 Link_out
PubChem Compound 441281 Link_out
PubChem Substance 46504881 Link_out
ChemSpider 390044 Link_out
ChEBI 4604 Link_out
ChEMBL 4604 Link_out
Therapeutic Targets Database DAP000333 Link_out
PharmGKB PA449338 Link_out
Drug Product Database 2241532 Link_out
Drugs.com http://www.drugs.com/cdi/dimenhydrinate.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Dimenhydrinate Link_out
ATC Codes
  • R06AA02
AHFS Codes
  • 56:22.08
PDB Entries Not Available
FDA label Not Available
MSDS show (72 KB)
Interactions
Drug Interactions
Drug Interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Rivastigmine Possible antagonism of action
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Dimenhydrinate, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Trimethobenzamide Trimethobenzamide and Dimenhydrinate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Dimenhydrinate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Trospium Trospium and Dimenhydrinate, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Avoid alcohol.
  • Take with food.
Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19