Dimenhydrinate

Identification

Summary

Dimenhydrinate is a medication used to prevent and treat nausea, vomiting, vertigo, and motion sickness.

Brand Names

Dramamine, Driminate, Gravol

Generic Name

Dimenhydrinate

DrugBank Accession Number

DB00985

Background

Dimehydrinate was first described in the literature in 1949,⁵ and patented in 1950.¹¹ Early research into dimenhydrinate focused on its role as an antihistamine for urticaria; the treatment of motion sickness was an accidental discovery.⁷

Dimenhydrinate, also known as B-dimethylaminoethyl benzohydrol ether 8-chlorotheophyllinate, is indicated to prevent nausea, vomiting, and dizziness caused by motion sickness.^9,10,11 Dimenhydrinate is a combination of Diphenhydramine and 8-chlorotheophylline in a salt form, with 53%-55.5% dried diphenhydramine, and 44%-47% died 8-chlorotheophylline.¹⁰

The antiemetic properties of dimenhydrinate are primarily thought to be produced by diphenhydramine's antagonism of H1 histamine receptors in the vestibular system² while the excitatory effects are thought to be produced by 8-chlorotheophylline's adenosine receptor blockade.³

When used in large doses, dimenhydrinate has been shown to cause a "high" characterized by hallucinations, excitement, incoordination, and disorientation.¹

Dimenhydrinate was granted FDA approval on 31 May 1972.⁸

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 469.97
Monoisotopic: 469.1880675
Chemical Formula: C₂₄H₂₈ClN₅O₃

Synonyms

(O-benzhydryl(dimethylamino)ethanol) 8-chlorotheophyllinate
8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione - 2-(diphenylmethoxy)-N,N-dimethylethanamine (1:1)
Benzhydryl-β-dimethylaminoethylether 8-chlorotheophylline
Dimenhidrinato
Dimenhydrinate
Dimenhydrinatum
diphenhydramine 8-chlorotheophyllinate
diphenhydramine 8-chlorotheophylline
Diphenhydramine theoclate
N,N-dimethyl-2-diphenylmethoxyethylamine 8-chlorotheophyllinate
O-benzhydryldimethylaminoethanol 8-chlorotheophyllinate
β-dimethylaminoethyl benzhydryl ether 1,3-dimethyl-8-chloroxanthine

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Pharmacology

Indication

Dimenhydrinate is indicated for the prevention and treatment of nausea, vomiting, or vertigo of motion sickness.^9,10

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level
Used in combination for symptomatic treatment of	Dizziness	Combination Product in combination with: Pyridoxine (DB00165)	••••••••••••
Symptomatic treatment of	Labyrinthine disorder		••••••••••••
Symptomatic treatment of	Meniere's disease		••••••••••••
Used in combination to treat	Morning sickness	Combination Product in combination with: Pyridoxine (DB00165)	••••••••••••
Prophylaxis of	Motion sickness		••• •••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Dimenhydrinate is indicated for the prevention and treatment of nausea, vomiting, or vertigo of motion sickness.^9,10 It has a short duration of action of 4-8 hours.⁴ Patients should be counselled regarding pronounced drowsiness, avoiding alcohol and other sedatives, and exercising caution when operating a motor vehicle or heavy machinery.⁹

Mechanism of action

Dimenhydrinate is a theoclate salt that separates into diphenhydramine and 8-chlorotheophylline.^10,13 While the exact mechanism of action is unknown, diphenhydramine is theorized to reduce disturbances to equilibrium through antimuscarinic effects or histamine H1 antagonism.⁷ 8-chlorotheophylline may produce excitation through blocking adenosine receptors, reducing the drowsiness produced by diphenhydramine.¹³

Target	Actions	Organism
AHistamine H1 receptor	antagonist	Humans

Absorption

A 50 mg oral film coated tablet reaches a C_max of 72.6 ng/mL with a T_max of 2.7 hours.¹² A 100 mg suppository reaches a C_max of 112.2 ng/mL with a T_max of 5.3 hours.¹³

Volume of distribution

The volume of distribution of dimenhydrinate is 3-4 L/kg.¹²

Protein binding

Dimenhydrinate is 70-85% protein bound in plasma.¹²

Metabolism

Dimenhydrinate is a theoclate salt that separates into diphenhydramine and 8-chlorotheophylline.¹⁰ diphenhydramine can either be N-glucuronidated by UGTs to diphenhydramine N-glucuronide or N-demethylated by CYP2D6, CYP1A2, CYP2C9, and CYP2C19 to N-desmethyldiphenhydramine.⁶ N-desmethyldiphenhydramine can be N-demethylated again by the same enzymes to N,N-didesmethyldiphenhydramine, which undergoes oxidative deamination to form diphenylmethoxyacetic acid.⁶

Hover over products below to view reaction partners

Dimenhydrinate
- 8-chlorotheophylline + Diphenhydramine
  - N-Desmethyldiphenhydramine
    - N,N-Didesmethyldiphenhydramine
      - Diphenylmethoxyacetic acid
  - Diphenhydramine N-glucuronide

Route of elimination

Dimenhydrinate is predominantly eliminated in the urine.¹² 1-3% of the dissociated diphenhydramine is eliminated in the urine unchanged, while 64% of diphenhydramine is eliminated in the urine as metabolites.¹³ The elimination of dimenhydrinate has not been fully studied.¹³

Half-life

The plasma elimination half life of dimenhydrinate is 5-8 hours.¹²

Clearance

Not Available

Adverse Effects

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Toxicity

Infants and children experiencing an overdose may lead to hallucinations, convulsions, or death.¹⁰ Adults experiencing an overdose may present with drowsiness, convulsions, coma, or respiratory depression.¹⁰ Treat overdoses with symptomatic and supportive measures including mechanically assisted ventilation.¹⁰

In mice the oral LD₅₀ is 203 mg/kg, while in rats it is 1320 mg/kg.¹⁰ The intraperitoneal LD₅₀ in mice is 149 mg/kg.¹⁰

Pathways

Not Available

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of CNS depression can be increased when Dimenhydrinate is combined with 1,2-Benzodiazepine.
Acetazolamide	The risk or severity of CNS depression can be increased when Acetazolamide is combined with Dimenhydrinate.
Acetophenazine	The risk or severity of CNS depression can be increased when Dimenhydrinate is combined with Acetophenazine.
Acrivastine	The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Dimenhydrinate.
Adenosine	The risk or severity of QTc prolongation can be increased when Adenosine is combined with Dimenhydrinate.

Food Interactions

Avoid alcohol.

Products

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Active Moieties

Name	Kind	UNII	CAS	InChI Key
Diphenhydramine	salt	8GTS82S83M	58-73-1	ZZVUWRFHKOJYTH-UHFFFAOYSA-N
8-chlorotheophylline	salt	GE2UA340FM	85-18-7	RYIGNEOBDRVTHA-UHFFFAOYSA-N

Product Images

International/Other Brands

Gravol (Church & Dwight) / Vertirosan (Astellas) / Vomex A (Astellas) / Xamamina (Adilna)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Dimenhydrinate Inj 10mg/ml	Liquid	10 mg / mL	Intravenous	Astra Pharma Inc.	1986-12-31	1999-07-29
Dimenhydrinate Injection 50mg/ml	Solution	50 mg / mL	Intramuscular; Intravenous	Astra Zeneca	1986-12-31	2005-05-31
Dimenhydrinate Injection USP	Solution	10 mg / mL	Intravenous	Sandoz Canada Incorporated	1973-12-31	Not applicable
Dimenhydrinate Injection USP	Solution	50 mg / mL	Intramuscular; Intravenous	Sandoz Canada Incorporated	Not applicable	Not applicable
Dimenhydrinate Injection USP	Solution	50 mg / mL	Intramuscular; Intravenous	Sandoz Canada Incorporated	1973-12-31	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Dimenhydrinate	Injection, solution	50 mg/1mL	Intramuscular; Intravenous	Fresenius Kabi USA, LLC	2004-11-29	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ag-dimenhydrinate	Tablet	50 mg	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Airmit Ace	Tablet	25 mg/1	Oral	Sato Pharmaceutical Co., Ltd.	2005-03-11	Not applicable
Anti-nauseant	Tablet	50 mg	Oral	Pharmascience Inc	2002-08-23	Not applicable
Anti-nauseant	Tablet	50 mg	Oral	Apotex Corporation	2013-07-02	Not applicable
Anti-nauseant	Tablet	50 mg	Oral	Vita Health Products Inc	2000-05-01	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Arlevert 20 mg/40 mg Tabletten	Dimenhydrinate (40 mg) + Cinnarizine (20 mg)	Tablet	Oral	Hennig Arzneimittel Gmb H & Co Kg	2007-09-06	Not applicable
Gravergol Capsules	Dimenhydrinate (50 mg) + Caffeine (100 mg) + Ergotamine tartrate (1 mg)	Capsule	Oral	Can Med Pharma Inc.	1957-12-31	2011-12-07
Neo - Emedyl - Dragees	Dimenhydrinate (50 mg) + Caffeine (50 mg)	Tablet, sugar coated	Oral	Pharmazeutische Fabrik Montavit Gmb H	1965-05-20	Not applicable
Vertirosan Vitamin B6 - Manteldragees	Dimenhydrinate (50 mg) + Pyridoxine hydrochloride (25 mg)	Tablet, coated	Oral	Sigmapharm Arzneimittel Gmb H	1962-03-29	Not applicable
Vertirosan Vitamin B6 - Zäpfchen	Dimenhydrinate (50 mg) + Pyridoxine hydrochloride (50 mg)	Suppository	Rectal	Umip Limited	1962-03-29	Not applicable

Chemical Identifiers

UNII: JB937PER5C
CAS number: 523-87-5
InChI Key: NFLLKCVHYJRNRH-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)
IUPAC Name: 8-chloro-1,3-dimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione; [2-(diphenylmethoxy)ethyl]dimethylamine
SMILES: CN1C2=C(N=C(Cl)N2)C(=O)N(C)C1=O.CN(C)CCOC(C1=CC=CC=C1)C1=CC=CC=C1

References

Synthesis Reference

Cusic, J.W.; U.S. Patent 2,499,058; February 28,1950; assigned to G.D. Searle & Co. Cusic, J.W.; U.S. Patent 2,534,813; December 19,1950; assigned to G.D. Searle & Co.

General References

Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [Article]
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. [Article]
Spealman RD: Psychomotor stimulant effects of methylxanthines in squirrel monkeys: relation to adenosine antagonism. Psychopharmacology (Berl). 1988;95(1):19-24. [Article]
Koch A, Cascorbi I, Westhofen M, Dafotakis M, Klapa S, Kuhtz-Buschbeck JP: The Neurophysiology and Treatment of Motion Sickness. Dtsch Arztebl Int. 2018 Oct 12;115(41):687-696. doi: 10.3238/arztebl.2018.0687. [Article]
FLEMING JF: New drug effective in motion sickness. Hosp Top. 1949 Mar;27(3):26. [Article]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
FERMIN H, van DEINSE JB, HAMMELBURG E: The effect of dimenhydrinate upon the labyrinth; (an experimental study). Acta Otolaryngol. 1950 Dec;38(6):543-9. doi: 10.3109/00016485009118417. [Article]
FDA Approved Drug Products: Dimenhydrinate Oral Liquid (Discontinued) [Link]
Dailymed: Dimenhydrinate Oral Tablet [Link]
Dailymed: Dimenhydrinate Intramuscular and Intravenous Injection [Link]
US Patent: US2499058A [Link]
Sandoz Canada: Dimenhydrinate Intramuscular and Intravenous Injection [Link]
Heads of Medicines Agencies Public Assessment Report: Dimenhydrinate Oral Lozenge [Link]

External Links

Human Metabolome Database: HMDB0015120
KEGG Drug: D00520
PubChem Compound: 441281
PubChem Substance: 46504881
ChemSpider: 10210
RxNav: 3444
ChEBI: 94848
ChEMBL: CHEMBL1200406
Therapeutic Targets Database: DAP000333
PharmGKB: PA449338
Drugs.com: Drugs.com Drug Page
Wikipedia: Dimenhydrinate

MSDS

Download (72 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Prevention	Post Operative Nausea and Vomiting (PONV)	1
4	Completed	Treatment	Gastroenteritis	1
4	Completed	Treatment	Nausea / Vertigo / Vomiting	1
4	Completed	Treatment	Pain / Postoperative pain	1
4	Completed	Treatment	Vertigo, Peripheral	1

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

APP Pharmaceuticals
C.O. Truxton Inc.
Consolidated Midland Corp.
Dispensing Solutions
Hospira Inc.
Ivax Pharmaceuticals
Major Pharmaceuticals
Martin Surgical Supply
Medisca Inc.
Nexgen Pharma Inc.
Pfizer Inc.
Pharmacia Inc.
Prescript Pharmaceuticals
Southwood Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet	Oral	25 mg/1
Suspension
Tablet, coated	Oral	50 mg
Solution	Oral	15 mg / 5 mL
Suppository	Rectal	50 mg
Syrup	Oral	250.000 mg
Injection, solution	Intramuscular; Intravenous	50 mg/1mL
Tablet	Oral
Tablet	Oral	50 mg/1
Tablet, film coated	Oral	50 mg/1
Liquid	Intravenous	10 mg / mL
Solution	Intramuscular; Intravenous	250 mg / 5 mL
Solution	Intramuscular; Intravenous	50 mg / mL
Solution	Intravenous	10 mg / mL
Liquid	Oral	15 mg / 5 mL
Capsule	Oral	50.0 mg
Tablet	Oral	50.0 mg
Tablet, chewable	Oral	50 mg/1
Tablet, chewable	Oral	25 mg/1
Tablet	Oral
Syrup	Oral	12.5 MG/5ML
Capsule	Oral
Capsule, liquid filled	Oral	50 mg/1
Capsule, extended release	Oral	75 mg
Tablet, chewable	Oral	50 mg
Tablet	Oral	15 mg
Solution	Intramuscular	50 mg / mL
Tablet, multilayer	Oral	100 mg
Capsule	Oral	50 mg
Tablet, extended release	Oral	75 mg
Suppository	Rectal	100 mg
Tablet	Oral	25 mg
Capsule	Oral	50.0000 mg
Tablet, chewable	Oral	15 mg
Syrup	Oral	15 mg / 5 mL
Suppository	Rectal	25 mg
Tablet	Oral	0.05 g
Syrup	Oral	25 mg/5ml
Syrup	Oral
Tablet, coated	Oral	50 mg/1
Solution	Oral	0.25 g
Syrup	Oral	3 mg / mL
Suppository	Rectal
Gum, chewing	Oral
Gum, chewing	Oral	20 MG
Tablet, sugar coated	Oral	20 mg
Tablet, coated	Oral	100 MG
Tablet, coated	Oral	25 MG
Injection, solution	Intramuscular; Intravenous	150 mg/ml
Injection, solution	Intramuscular; Intravenous	50 mg/ml
Solution / drops	Oral	92.5 mg/ml
Tablet, coated	Oral
Suppository	Rectal
Tablet	Oral	5000000 mg
Suppository	Rectal	150 MG
Suppository	Rectal	70 MG
Suppository	Rectal	40 MG
Tablet, orally disintegrating	Sublingual	50 MG
Solution	Oral	25.000 mg
Solution	Parenteral	50.000 mg
Tablet	Oral	50.000 mg
Injection	Intramuscular; Intravenous	50 mg/ml
Injection	Intramuscular; Intravenous
Tablet, film coated	Oral	50 mg
Tablet
Capsule
Tablet, sugar coated	Oral
Solution		50 mg/1ml
Tablet	Oral	50 mg
Tablet, sugar coated	Oral	50 mg
Syrup	Oral	15 mg/5ml

Prices

Unit description	Cost	Unit
Dimenhydrinate 50 mg/ml vial	5.7USD	ml
Dimenhydrinate I.M. 50 mg/ml	1.17USD	ml
Meclizine 12.5 mg tablet	0.62USD	tablet
Dramamine less drowsy tablet	0.42USD	tablet
Dimenhydrinate I.V. 10 mg/ml	0.32USD	ml
Dramamine 50 mg tablet	0.28USD	tablet
Novamine 15% iv solution	0.09USD	ml
Dimenhydrinate 100% powder	0.07USD	g
Driminate 50 mg tablet	0.05USD	tablet
Dimenhydrinate 50 mg tablet	0.03USD	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 (°C)	103-104	Cusic, J.W.; U.S. Patent 2,499,058; February 28,1950; assigned to G.D. Searle & Co. Cusic, J.W.; U.S. Patent 2,534,813; December 19,1950; assigned to G.D. Searle & Co.
water solubility	3000 mg/L	MERCK INDEX (1996); approx.

Predicted Properties

Property	Value	Source
Water Solubility	9.86 mg/mL	ALOGPS
logP	0.44	ALOGPS
logP	3.65	Chemaxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	8.87	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	12.47 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	79.93 m³·mol^-1	Chemaxon
Polarizability	30.02 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9975
Blood Brain Barrier	+	0.8551
Caco-2 permeable	+	0.5198
P-glycoprotein substrate	Substrate	0.7863
P-glycoprotein inhibitor I	Non-inhibitor	0.6923
P-glycoprotein inhibitor II	Inhibitor	0.6502
Renal organic cation transporter	Non-inhibitor	0.6507
CYP450 2C9 substrate	Non-substrate	0.7536
CYP450 2D6 substrate	Non-substrate	0.8181
CYP450 3A4 substrate	Substrate	0.7086
CYP450 1A2 substrate	Inhibitor	0.5287
CYP450 2C9 inhibitor	Non-inhibitor	0.6308
CYP450 2D6 inhibitor	Non-inhibitor	0.8589
CYP450 2C19 inhibitor	Non-inhibitor	0.5817
CYP450 3A4 inhibitor	Non-inhibitor	0.9028
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5738
Ames test	Non AMES toxic	0.5629
Carcinogenicity	Non-carcinogens	0.7548
Biodegradation	Not ready biodegradable	0.8211
Rat acute toxicity	2.4087 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.5364
hERG inhibition (predictor II)	Inhibitor	0.5405

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. Histamine H1 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Histamine receptor activity
Specific Function: 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 catecholamin...
Gene Name: HRH1
Uniprot ID: P35367
Uniprot Name: Histamine H1 receptor
Molecular Weight: 55783.61 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Halpert AG, Olmstead MC, Beninger RJ: Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Dimenhydrinate

Identification

Structure for Dimenhydrinate (DB00985)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References