Details of the Drug

General Information of Drug (ID: DM264B3)

Drug Name

Dimenhydrinate

Synonyms

Gravamin (TN); Gravol (TN); Vertirosan (TN); Dimenhydrinate (JP15/USP/INN); 2-(diphenylmethoxy)-N,N-dimethylethanaminium 8-chloro-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ide; 2-benzhydryloxyethyl(dimethyl)azanium; 8-chloro-1,3-dimethyl-2-oxopurin-6-olate; 8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione-2-(diphenylmethoxy)-N,N-dimethylethanamine (1:1)

Indication

Disease Entry	ICD 11	Status	REF
Nausea	MD90	Approved	[1]

Therapeutic Class

Antiemetics

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

470

Topological Polar Surface Area

Not Available

Rotatable Bond Count

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 72.6 mcg/L [2]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2.7 h [2]
Elimination: 1-3% of the dissociated diphenhydramine is eliminated in the urine unchanged, while 64% of diphenhydramine is eliminated in the urine as metabolites [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 - 8 hours [2]
Metabolism: The drug is metabolized via UGTs to diphenhydramine N-glucuronide or N-demethylated by CYP2D6, CYP1A2, CYP2C9, and CYP2C19 to N-desmethyldiphenhydramine [3]
Vd: The volume of distribution (Vd) of drug is 3-4 L/kg [2]

Chemical Identifiers

Formula: C24H28ClN5O3
IUPAC Name: 2-benzhydryloxy-N,N-dimethylethanamine;8-chloro-1,3-dimethyl-7H-purine-2,6-dione
Canonical SMILES: CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Cl.CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
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)
InChIKey: NFLLKCVHYJRNRH-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 10660
ChEBI ID: CHEBI:94848
CAS Number: 523-87-5
DrugBank ID: DB00985
TTD ID: D0U8UV
ACDINA ID: D00201

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Histamine H1 receptor (H1R)	TTTIBOJ	HRH1_HUMAN	Antagonist	[4], [5]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Nausea

ICD Disease Classification

MD90

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Histamine H1 receptor (H1R)	DTT	HRH1	6.74E-01	0.13	0.43

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Dimenhydrinate

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Promethazine	DM6I5GR	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Promethazine.	Nausea/vomiting [MD90]	[14]
Cyclizine	DM9G7BS	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Cyclizine.	Nausea/vomiting [MD90]	[14]
Metoclopramide	DMFA5MY	Moderate	Antagonize the effect of Dimenhydrinate when combined with Metoclopramide.	Nausea/vomiting [MD90]	[15]
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Coadministration of a Drug Treating the Disease Different from Dimenhydrinate (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Bethanechol	DMCLHO0	Moderate	Antagonize the effect of Dimenhydrinate when combined with Bethanechol.	Abnormal micturition [MF50]	[16]
Mepyramine	DMB4SFH	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Mepyramine.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[17]
Phenyltoloxamine	DMKAEQW	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Phenyltoloxamine.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[17]
Memantine	DMD9WSC	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Memantine.	Alzheimer disease [8A20]	[14]
Rivastigmine	DMG629M	Moderate	Antagonize the effect of Dimenhydrinate when combined with Rivastigmine.	Alzheimer disease [8A20]	[18]
Dronedarone	DMA8FS5	Moderate	Increased risk of prolong QT interval by the combination of Dimenhydrinate and Dronedarone.	Angina pectoris [BA40]	[19]
Desipramine	DMT2FDC	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Desipramine.	Attention deficit hyperactivity disorder [6A05]	[14]
Cariprazine	DMJYDVK	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Cariprazine.	Bipolar disorder [6A60]	[14]
Acetylcholine	DMDF79Z	Moderate	Antagonize the effect of Dimenhydrinate when combined with Acetylcholine.	Cataract [9B10]	[20]
Tiotropium	DMFDC0Q	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Tiotropium.	Chronic obstructive pulmonary disease [CA22]	[21]
Revefenacin	DMMP5SI	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Revefenacin.	Chronic obstructive pulmonary disease [CA22]	[21]
Isocarboxazid	DMAF1NB	Minor	Additive anticholinergic effects by the combination of Dimenhydrinate and Isocarboxazid.	Depression [6A70-6A7Z]	[14]
OPC-34712	DMHG57U	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and OPC-34712.	Depression [6A70-6A7Z]	[14]
Clomipramine	DMINRKW	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Clomipramine.	Depression [6A70-6A7Z]	[14]
Doxepin	DMPI98T	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Doxepin.	Depression [6A70-6A7Z]	[14]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Dimenhydrinate and Esketamine.	Depression [6A70-6A7Z]	[19]
Mepenzolate	DM8YU2F	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Mepenzolate.	Digestive system disease [DE2Z]	[14]
Oxybutynine	DMJPBAX	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Oxybutynine.	Discovery agent [N.A.]	[14]
Diphenhydramine	DMKQTBA	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Diphenhydramine.	Episodic vestibular syndrome [AB31]	[14]
Solifenacin	DMG592Q	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Solifenacin.	Functional bladder disorder [GC50]	[14]
Tolterodine	DMSHPW8	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Tolterodine.	Functional bladder disorder [GC50]	[14]
Pilocarpine	DMV9ADG	Moderate	Antagonize the effect of Dimenhydrinate when combined with Pilocarpine.	Glaucoma [9C61]	[16]
Belladonna	DM2RBWK	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Belladonna.	Infectious gastroenteritis/colitis [1A40]	[14]
ITI-007	DMUQ1DO	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and ITI-007.	Insomnia [7A00-7A0Z]	[14]
R0-93877	DMM4U9G	Moderate	Antagonize the effect of Dimenhydrinate when combined with R0-93877.	Irritable bowel syndrome [DD91]	[22]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Dimenhydrinate and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[23]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Dimenhydrinate and Lasmiditan.	Migraine [8A80]	[24]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Dimenhydrinate and Flibanserin.	Mood disorder [6A60-6E23]	[25]
Phenindamine	DMDTC7R	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Phenindamine.	Nasopharyngitis [CA00]	[14]
Flavoxate	DMKV4NL	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Flavoxate.	Pain [MG30-MG3Z]	[14]
Orphenadrine	DMW542E	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Orphenadrine.	Parkinsonism [8A00]	[14]
Methylscopolamine	DM5VWOB	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Methylscopolamine.	Peptic ulcer [DA61]	[14]
Levomepromazine	DMIKFEL	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Levomepromazine.	Psychotic disorder [6A20-6A25]	[14]
Quetiapine	DM1N62C	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Quetiapine.	Schizophrenia [6A20]	[14]
Aripiprazole	DM3NUMH	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Aripiprazole.	Schizophrenia [6A20]	[14]
Iloperidone	DM6AUFY	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Iloperidone.	Schizophrenia [6A20]	[14]
Paliperidone	DM7NPJS	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Paliperidone.	Schizophrenia [6A20]	[14]
Molindone	DMAH70G	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Molindone.	Schizophrenia [6A20]	[14]
Thiothixene	DMDINC4	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Thiothixene.	Schizophrenia [6A20]	[14]
Asenapine	DMSQZE2	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Asenapine.	Schizophrenia [6A20]	[14]
Pimozide	DMW83TP	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Pimozide.	Schizophrenia [6A20]	[14]
Chlorpheniramine	DM5URA2	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Chlorpheniramine.	Vasomotor/allergic rhinitis [CA08]	[14]
Trimeprazine	DMEMV9D	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[17]
Acrivastine	DMTIGA0	Moderate	Additive anticholinergic effects by the combination of Dimenhydrinate and Acrivastine.	Vasomotor/allergic rhinitis [CA08]	[14]
Bretylium	DM1FX74	Moderate	Increased risk of prolong QT interval by the combination of Dimenhydrinate and Bretylium.	Ventricular tachyarrhythmia [BC71]	[19]
Procainamide	DMNMXR8	Moderate	Increased risk of prolong QT interval by the combination of Dimenhydrinate and Procainamide.	Ventricular tachyarrhythmia [BC71]	[19]
Amiodarone	DMUTEX3	Moderate	Increased risk of prolong QT interval by the combination of Dimenhydrinate and Amiodarone.	Ventricular tachyarrhythmia [BC71]	[19]
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⏷ Show the Full List of 47 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Aspartame	E00402	134601	Flavoring agent
Kyselina citronova	E00014	311	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Brushite	E00392	104805	Diluent
Calcium hydrogenphosphate	E00294	24441	Diluent
Carmellose sodium	E00625	Not Available	Disintegrant
Citric acid monohydrate	E00271	22230	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Dextrin	E00359	62698	Binding agent; Diluent; Microencapsulating agent; Stiffening agent; Suspending agent; Viscosity-controlling agent
Hexahydric alcohol	E00083	5780	Diluent; Flavoring agent; Humectant; Plasticizing agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
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⏷ Show the Full List of 17 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Dimenhydrinate 50 mg tablet	50 mg	Chewable Tablet	Oral
Dimenhydrinate 50 mg tablet	50 mg	Oral Tablet	Oral
Dimenhydrinate 25 mg tablet	25 mg	Oral Tablet	Oral
Dimenhydrinate 25 mg tablet	25 mg	Chewable Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040519.
2	Sandoz Canada: Dimenhydrinate Intramuscular and Intravenous Injection
3	Dailymed: Dimenhydrinate Intramuscular and Intravenous Injection
4	Histamine 1 receptor antagonist in symptomatic treatment of renal colic accompanied by nausea: two birds with one stone Urology. 2009 Jan;73(1):32-6.
5	Mechanisms and abuse liability of the anti-histamine dimenhydrinate. Neurosci Biobehav Rev. 2002 Jan;26(1):61-7.
6	Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow. Mol Pharmacol. 2001 Mar;59(3):420-6.
7	Clinical research of Ibudilast on treating the steroid resistant allergic rhinitis. Lin Chung Er Bi Yan Hou Tou Jing Wai Ke Za Zhi. 2009 Jan;23(2):63-6.
8	Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization. J Pharmacol Sci. 2008 May;107(1):66-79.
9	Update on prescription and over-the-counter histamine inverse agonists in rhinitis therapy. Curr Allergy Asthma Rep. 2009 Mar;9(2):140-8.
10	Central effects of cinnarizine: restricted use in aircrew. Aviat Space Environ Med. 2002 Jun;73(6):570-4.
11	Novel therapeutic usage of low-dose doxepin hydrochloride. Expert Opin Investig Drugs. 2007 Aug;16(8):1295-305.
12	Influence of epinastine hydrochloride, an H1-receptor antagonist, on the function of mite allergen-pulsed murine bone marrow-derived dendritic cell... Mediators Inflamm. 2009;2009:738038.
13	Examining the tolerability of the non-sedating antihistamine desloratadine: a prescription-event monitoring study in England. Drug Saf. 2009;32(2):169-79.
14	Cohen MA, Alfonso CA, Mosquera M. Development of urinary retention during treatment with clozapine and meclizine [published correction appears in Am J Psychiatry 1994 Jun;151(6):952]. Am J Psychiatry. 1994;151(4):619-620. [PMID: 8147469]
15	Product Information. Motilium (domperidone). Janssen-Ortho Inc, Toronto, ON.
16	Benjamin KW "Toxicity of ocular medications." Int Ophthalmol Clin 19 (1979): 199-255. [PMID: 376469]
17	Kulik AV, Wilbur R "Delirium and stereotypy from anticholinergic antiparkinson drugs." Prog Neuropsychopharmacol Biol Psychiatry 6 (1982): 75-82. [PMID: 7202232]
18	Beers MH, Ouslander JG, Rollingher I, Reuben DB, Brooks J, Beck JC "Explicit criteria for determining inappropriate medication use in nursing home residents." Arch Intern Med 151 (1991): 1825-32. [PMID: 1888249]
19	Cerner Multum, Inc. "Australian Product Information.".
20	Multum Information Services, Inc. Expert Review Panel.
21	Cole JM, Sheehan AH, Jordan JK "Concomitant use of ipratropium and tiotropium in chronic obstructive plmonary disease." Ann Pharmacother 46 (2012): 1717-21. [PMID: 23170031]
22	EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
23	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
24	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
25	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.