関: trimethobenzamide hydrochloride

同: Tigan

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/05/09 21:16:15」(JST)

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Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting. It is often prescribed for patients with gastroenteritis, medication-induced nausea, and other illnesses. Trimethobenzamide is generally considered the most potent antiemetic that does not have effects on the serotonergic, dopaminergic, or histaminergic systems, so it has a lower likelihood of causing undesired side effects. In the United States, it requires a prescription.

Mechanism of action

Trimethobenzamide is an antagonist of the D₂ receptor.^[1] It is believed to affect the chemoreceptor trigger zone (CTZ) of the medulla oblongata to suppress nausea and vomiting.

Side effects

Possible side effects include drowsiness, dizziness, headache, diarrhea, muscle cramps, and blurred vision. More serious adverse effects include skin rash, tremors, parkinsonism, and jaundice.

Formulations

Trimethobenzamide is marketed under the brand names Tebamide and Tigan, manufactured by GlaxoSmithKline and King Pharmaceuticals, respectively. It is available as oral capsules and injectable formulations.

Trimethobenzamide was also available as a rectal suppository, but such formulations were banned by the U.S. Food and Drug Administration on April 6, 2007 due to unproven efficacy.^[2]

Synthesis

Trimethobenzamide synthesis: Hoffmann La Roche, U.S. Patent 2,879,293 (1959).

Alkylation of the sodium salt of p-hydroxybenzaldehyde (1) with 2-dimethylaminoethyl chloride affords the ether (2). Reductive amination of the aldehyde in the presence of ammonia gives diamine (3). Acylation of that product with 3,4,5-trimethoxybenzoyl chloride affords trimethobenzamide (4).

References

^ Smith HS, Cox LR, Smith BR (2012). "Dopamine receptor antagonists". Ann Palliat Med. 1 (2): 137–42. doi:10.3978/j.issn.2224-5820.2012.07.09. PMID 25841474.
^ Waknine, Yael (April 6, 2007). "FDA Bans Suppositories With Trimethobenzamide". Medscape. Retrieved 2007-04-06. ^{[dead link]}

External links

Tebamide
Tigan (manufacturer's website)^{[dead link]}

UpToDate Contents

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English Journal

Apomorphine Subcutaneous Injection for the Management of Morning Akinesia in Parkinson's Disease.

Isaacson S1, Lew M2, Ondo W3, Hubble J4, Clinch T4, Pagan F5.
Movement disorders clinical practice.Mov Disord Clin Pract.2017 Jan-Feb;4(1):78-83. doi: 10.1002/mdc3.12350. Epub 2016 May 25.
PMID 28239615

Sublingual apomorphine (APL-130277) for the acute conversion of OFF to ON in Parkinson's disease.

Hauser RA1, Olanow CW2, Dzyngel B3, Bilbault T3, Shill H4, Isaacson S5, Dubow J3, Agro A3.
Movement disorders : official journal of the Movement Disorder Society.Mov Disord.2016 Sep;31(9):1366-72. doi: 10.1002/mds.26697. Epub 2016 Jul 19.
PMID 27430123

Canadian Headache Society systematic review and recommendations on the treatment of migraine pain in emergency settings.

Orr SL1, Aubé M2, Becker WJ3, Davenport WJ4, Dilli E5, Dodick D6, Giammarco R7, Gladstone J8, Leroux E9, Pim H9, Dickinson G10, Christie SN10.
Cephalalgia : an international journal of headache.Cephalalgia.2015 Mar;35(3):271-84. doi: 10.1177/0333102414535997. Epub 2014 May 29.
PMID 24875925

Japanese Journal

Effect of Theophylline and Trimethobenzamide When Given During Kainate-Induced Status Epilepticus: An Improved Histopathologic Rat Model of Human Hippocampal Sclerosis

KATZIR Hilli,MENDOZA Delia,MATHERN Gary W.
Epilepsia : journal of the International League against Epilepsy 41(11), 1390-1399, 2000-11-01
NAID 10010907702

Effect of theophylline and trimethobenzamide when given during kainate-induced status epilepticus: an improved histopathologic rat model of human hippocampal sclerosis

KATZIR H.
Epilepsia 41, 1390-1399, 2000
NAID 30014394242

「トリメトベンズアミド」

Trimethobenzamide
Clinical data
Trade names	Tigan, Tebamide
AHFS/Drugs.com	Monograph
MedlinePlus	a682693
Pregnancy; category	US: C (Risk not ruled out); ;
Routes of; administration	Oral, rectal, intramuscular
ATC code	R06AA10 (WHO);
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	60-100%
Biological half-life	7 to 9 hours (mean)
Excretion	urine (30-50%), faeces
Identifiers
	IUPAC name N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}-; 3,4,5-trimethoxy-benzamide;
CAS Number	138-56-7 ;
PubChem CID	5577;
IUPHAR/BPS	7614;
DrugBank	DB00662 ;
ChemSpider	5375 ;
UNII	W2X096QY97;
ChEBI	CHEBI:27796 ;
ChEMBL	CHEMBL1201256 ;
ECHA InfoCard	100.004.848
Chemical and physical data
Formula	C21H28N2O5
Molar mass	388.458 g/mol
3D model (Jmol)	Interactive image;
	SMILES O=C(c1cc(OC)c(OC)c(OC)c1)NCc2ccc(OCCN(C)C)cc2 ;
	InChI InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24) ; Key:FEZBIKUBAYAZIU-UHFFFAOYSA-N ;
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英: trimethobenzamide、trimethobenzamide hydrochloride
関: 塩酸トリメトベンズアミド

[Smith2012-1] Smith HS, Cox LR, Smith BR (2012). "Dopamine receptor antagonists". Ann Palliat Med. 1 (2): 137–42. doi:10.3978/j.issn.2224-5820.2012.07.09. PMID 25841474.

[2] Waknine, Yael (April 6, 2007). "FDA Bans Suppositories With Trimethobenzamide". Medscape. Retrieved 2007-04-06. ^{[dead link]}

v t e Antiemetics (A04)

5-HT₃ serotonin ion channel antagonists	Alosetron Azasetron Bemesetron Cilansetron Clozapine Dazopride Dolasetron Granisetron Lerisetron Metoclopramide Mianserin Mirtazapine Olanzapine Ondansetron Palonosetron (+netupitant) Quetiapine Ramosetron Ricasetron Tropisetron Zatosetron

5-HT serotonin G-protein receptor antagonists	Clozapine Cyproheptadine Hydroxyzine Olanzapine Risperidone Ziprasidone

CB₁ agonists (cannabinoids)	Dronabinol Nabilone Tetrahydrocannabinol (cannabis)

D₂/D₃ antagonists	Alizapride Bromopride Chlorpromazine Clebopride Domperidone Haloperidol Hydroxyzine Itopride Metoclopramide Metopimazine Prochlorperazine Thiethylperazine Trimethobenzamide

H₁ antagonists (antihistamines)	Cyclizine Dimenhydrinate Diphenhydramine Hydroxyzine Meclizine Promethazine

mACh antagonists (anticholinergics)	Atropine Diphenhydramine Hydroxyzine (very mild) Hyoscyamine Scopolamine

NK₁ antagonists	Aprepitant Casopitant Ezlopitant Fosaprepitant Maropitant Netupitant Rolapitant Vestipitant

Others	Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol

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trimethobenzamide