Trimethobenzamide: Difference between revisions

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Revision as of 08:21, 23 October 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified and watched fields - updated 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit		Latest revision as of 08:04, 11 August 2024 edit undo2a00:23c6:19a8:f401:d1e2:e98f:2b02:7f18 (talk) Fixed typo, this is an antiemetic not an antisemeticTags: Mobile edit Mobile web edit
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			{{Short description\|Antiemetic medication}}
	{{Drugbox		{{Drugbox
	\| Verifiedfields = changed		\| Verifiedfields = changed
	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = ~~402698677~~		\| verifiedrevid = 470615098
	\| IUPAC_name = ''N''-{methyl}-<br>3,4,5-trimethoxy-benzamide		\| IUPAC_name = ''N''-{methyl}-<br>3,4,5-trimethoxy-benzamide
	\| image = ~~Trimethobenzamide~~.svg		\| image = Trimethobenzamide2DACS.svg
			\| image2 = Trimethobenzamidefinal.png
	\| width = 250px		\| width = 250px

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename = Tigan		\| tradename = Tigan, Tebamide
	\| Drugs.com = {{drugs.com\|monograph\|trimethobenzamide-hydrochloride}}		\| Drugs.com = {{drugs.com\|monograph\|trimethobenzamide-hydrochloride}}
	\| MedlinePlus = a682693		\| MedlinePlus = a682693
	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->		\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	\| pregnancy_US = ~~<!-- A / B /~~ C ~~/ D / X -->~~		\| pregnancy_US = C
	\| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->		\| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
	\| legal_UK = <!-- GSL / P / POM / CD -->		\| legal_UK = <!-- GSL / P / POM / CD -->
	\| legal_US = Rx-only		\| legal_US = Rx-only
	\| routes_of_administration = Oral, rectal, ]		\| routes_of_administration = Oral, rectal, ]

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
			\| bioavailability = 60-100%
	\| elimination_half-life = 7 to 9 hours (mean)		\| elimination_half-life = 7 to 9 hours (mean)
			\| excretion = urine (30-50%), faeces

	<!--Identifiers-->		<!--Identifiers-->
			\| IUPHAR_ligand = 7614
	\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CAS_number_Ref = {{cascite\|correct\|??}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 138-56-7		\| CAS_number = 138-56-7
	\| ATC_prefix = ~~none~~		\| ATC_prefix = R06
			\| ATC_suffix = AA10
	\| PubChem = 5577		\| PubChem = 5577
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = ~~APRD01277~~		\| DrugBank = DB00662
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 5375		\| ChemSpiderID = 5375
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = W2X096QY97		\| UNII = W2X096QY97
	\| ChEBI_Ref = {{ebicite\|~~changed~~\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 27796		\| ChEBI = 27796
	\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}		\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
	\| ChEMBL = 1201256		\| ChEMBL = 1201256

	<!--Chemical data-->		<!--Chemical data-->
	\| C=21 \| H=28 \| N=2 \| O=5		\| C=21 \| H=28 \| N=2 \| O=5
	\| molecular_weight = 388.458 g/mol
	\| smiles = O=C(c1cc(OC)c(OC)c(OC)c1)NCc2ccc(OCCN(C)C)cc2		\| smiles = O=C(c1cc(OC)c(OC)c(OC)c1)NCc2ccc(OCCN(C)C)cc2
	\| InChI = 1/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)
	\| InChIKey = FEZBIKUBAYAZIU-UHFFFAOYAO
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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)		\| StdInChI = 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)
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	}}		}}

	'''Trimethobenzamide''' ('''Tebamide''', '''Tigan''') is an ] used to prevent ] and ]. It is often prescribed for patients with ], 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.		'''Trimethobenzamide''' (trade names '''Tebamide''', '''Tigan''') is an ] used to prevent ] and ].

	== Mechanism of action ==		== Mechanism of action ==
			Trimethobenzamide is an ] of the ].<ref name="Smith2012">{{cite journal \| vauthors = Smith HS, Cox LR, Smith BR \| title = Dopamine receptor antagonists \| journal = Ann Palliat Med \| volume = 1 \| issue = 2 \| pages = 137–42 \| year = 2012 \| pmid = 25841474 \| doi = 10.3978/j.issn.2224-5820.2012.07.09 }}</ref> It is believed to affect the ] (CTZ) of the ] to suppress ] and ].

	Although the specific mechanism through which trimethobenzamide functions is unknown, it is believed to affect the ] (CTZ) of the ].

	== Side effects ==		== Side effects ==

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

	== Formulations ==		== Formulations ==

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

	Trimethobenzamide was also available as a rectal ], but such formulations were banned by the U.S. ] on April 6, 2007 due to unproven efficacy.<ref>{{cite web \| url = http://www.medscape.com/viewarticle/554812 \| title = FDA Bans Suppositories With Trimethobenzamide \| last = Waknine \| first = Yael \| date = April 6, 2007 \| ~~accessdate~~ = 2007-04-06 \| publisher = ]\| ~~archiveurl~~ = ~~http://web.archive.org/web/20070416054940/http://www.medscape.com/viewarticle/554812~~\| ~~archivedate~~ = ~~April 16, 2007~~}}</ref>		Trimethobenzamide was also available as a rectal ], but such formulations were banned by the U.S. ] on April 6, 2007, due to unproven efficacy.<ref>{{cite web \| url = http://www.medscape.com/viewarticle/554812 \| title = FDA Bans Suppositories With Trimethobenzamide \| last = Waknine \| first = Yael \| date = April 6, 2007 \| access-date = 2007-04-06 \| publisher = ]}}{{dead link\|date=September 2016\|bot=medic}}{{cbignore\|bot=medic}}</ref>

			==Synthesis==
			], {{US patent\|2879293}} (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).

	== See also ==		== See also ==
	* ]		* ]
			* ]

	== References ==		== References ==
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	== External links ==		== External links ==
	* ~~(manufacturer's website) {{Dead link\|date=July 2009}}~~		*
	* (manufacturer's website) ~~{{Dead link\|date=July 2009}}~~		* (manufacturer's website)


	{{Antiemetics}}		{{Antiemetics}}
			{{Dopaminergics}}

	]		]
	]		]
			]
	]		]

Latest revision as of 08:04, 11 August 2024

Antiemetic medication Pharmaceutical compound

Trimethobenzamide
Clinical data


Trade names	Tigan, Tebamide
AHFS/Drugs.com	Monograph
MedlinePlus	a682693
Routes of administration	Oral, rectal, intramuscular
ATC code	R06AA10 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	60-100%
Elimination half-life	7 to 9 hours (mean)
Excretion	urine (30-50%), faeces
Identifiers
IUPAC name N-{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
CompTox Dashboard (EPA)	DTXSID8023711
ECHA InfoCard	100.004.848
Chemical and physical data
Formula	C₂₁H₂₈N₂O₅
Molar mass	388.464 g·mol
3D model (JSmol)	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
(what is this?) (verify)

Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting.

Mechanism of action

Trimethobenzamide is an antagonist of the D₂ receptor. 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, 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.

Synthesis

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.

External links

Tebamide
Tigan (manufacturer's website)

v t e Antiemetics (A04)
5-HT₃ serotonin ion channel antagonists	Alosetron Azasetron Bemesetron Cilansetron Clozapine Dazopride Dolasetron Granisetron Lerisetron 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	Chlorpromazine Haloperidol Hydroxyzine 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 Fosaprepitant Maropitant Netupitant Rolapitant
Others	Amisulpride Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol