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Revision as of 12:12, 7 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 19:03, 8 October 2023 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,518 edits CONSistent citation formatting
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			{{Short description|Medication used for hyperthyroidism}}
	{{drugbox
			{{Drugbox
	| verifiedrevid = 414048579
			| Watchedfields = changed
	| IUPAC_name = ethyl 3-methyl-2-sulfanylidene-imidazole-1-carboxylate
			| verifiedrevid=443497878
	| image = Carbimazole.svg
			| IUPAC_name=ethyl 3-methyl-2-sulfanylidene-imidazole-1-carboxylate
	| width = 120
			| image=Carbimazole.svg
	| CASNo_Ref = {{cascite|correct|CAS}}
			| width=200
			<!--Clinical data-->
			| tradename=Neo-Mercazole, Anti-Thyrox, etc.
			| Drugs.com={{drugs.com|international|carbimazole}}
			| pregnancy_AU=D
			| pregnancy_AU_comment = <ref>{{cite web | title=Updates to the Prescribing Medicines in Pregnancy database | website=Therapeutic Goods Administration (TGA) | date=12 May 2022 | url=https://www.tga.gov.au/resources/resource/guidance/updates-prescribing-medicines-pregnancy-database | access-date=13 May 2022}}</ref>
			| pregnancy_category=
			| legal_status=Rx-only
			| routes_of_administration=]
			<!--Pharmacokinetic data-->
			| bioavailability=
			| protein_bound=85%
			| metabolism=
			| elimination_half-life=5.3h
			| excretion =] >90%
			<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|??}}
			| CAS_number=22232-54-8
			| ATC_prefix=H03
			| ATC_suffix=BB01
			| ATC_supplemental=
			| PubChem=31072
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank=DB00389
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 28829		| ChemSpiderID=28829
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 8KQ660G60G		| UNII=8KQ660G60G
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D07616		| KEGG=D07616
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| InChI = 1/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3
			| ChEBI=617099
	| smiles = S=C1N(\C=C/N1C(=O)OCC)C
	| InChIKey = CFOYWRHIYXMDOT-UHFFFAOYAV
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 508102		| ChEMBL=508102
			<!--Chemical data-->
			| C=7 | H=10 | N=2 | O=2 | S=1
			| smiles=S=C1N(\C=C/N1C(=O)OCC)C
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3		| StdInChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = CFOYWRHIYXMDOT-UHFFFAOYSA-N		| StdInChIKey=CFOYWRHIYXMDOT-UHFFFAOYSA-N
			| melting_point = 122
	| CAS_number = 22232-54-8
	| ATC_prefix = H03		| melting_high = 125
	| ATC_suffix = BB01
	| ATC_supplemental =
	| ChEBI = 617099
	| PubChem = 31072
	| DrugBank = APRD00503
	| C = 7 | H = 10 | N = 2 | O = 2 | S = 1
	| molecular_weight = 186.233 g/mol
	| bioavailability =
	| protein_bound = 85%
	| metabolism =
	| elimination_half-life =
	| pregnancy_AU =
	| pregnancy_US =
	| pregnancy_category =
	| legal_status = Rx-only
	| routes_of_administration = oral
	}}		}}
	{{Unreferenced|date=October 2008}}		{{More citations needed|date=October 2008}}
	'''Carbimazole''' is used to treat ]. Carbimazole is a ] as after absorption it is converted to the active form, ]. Methimazole prevents the ] enzyme from coupling and iodinating the tyrosine residues on ], hence reducing the production of the thyroid hormones T3 and T4 (]).		'''Carbimazole''' (brand names Neo-Mercazole, Anti-Thyrox, etc.) is used to treat ]. Carbimazole is a ] as after absorption it is converted to the active form, ]. Methimazole prevents ] enzyme from iodinating and coupling the ] residues on ], hence reducing the production of the thyroid hormones ] and T<sub>4</sub> (]).
			It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref>
	==Clinical use==
	Therapy for hyperthyroidism generally starts at a high daily dose of 15 - 40mg continued until the patient has normal ], and then reduced to a maintenance dose of 5 - 15mg. Treatment is usually given for 12 - 18 months followed by a trial withdraw.
			==Medical uses==
	The onset of anti-thyroid effect is rapid but the onset of clinical effects on thyroid hormone levels in the blood is much slower. This is because the large store of pre-formed T3 and T4 in the thyroid gland and bound to ] (99% bound) has to be depleted before any beneficial clinical effect occurs.
			Medical therapy for hyperthyroidism typically involves either titrating the dose of carbimazole until the patient becomes euthyroid or maintaining a high dose of carbimazole to suppress endogenous thyroid production, and then replacing thyroid hormone with levothyroxine ("block and replace"). Treatment is usually given for 18–24 months followed by a trial withdraw.<ref>{{cite journal | vauthors = Lawrence N, Cheetham T, Elder C | title = How do paediatricians use and monitor antithyroid drugs in the UK? A clinician survey | journal = Clinical Endocrinology | volume = 91 | issue = 3 | pages = 417–423 | date = September 2019 | pmid = 31179554 | doi = 10.1111/cen.14046 | name-list-style = vanc | s2cid = 182948575 | url = https://eprints.whiterose.ac.uk/148158/1/2019-05-17%20Clinical%20Endocrinology%20resubmission.pdf }}</ref>
			The onset of anti-thyroid effect is rapid but the onset of clinical effects on thyroid hormone levels in the blood is much slower. This is because the large store of pre-formed T<sub>3</sub> and T<sub>4</sub> in the thyroid gland and bound to ] (99% bound) has to be depleted before any beneficial clinical effect occurs.
	==Precautions==
	Some people are allergic to ](s).
			==Adverse effects==
	Some azole drugs have adverse ]s.
			Whilst ]es and ] are common, these can often be treated with ]s without stopping the carbimazole. For those patients where sensitivity reactions cannot be controlled, ] may be used as an alternative; cross-sensitivity between these drugs is rare.
			Its most serious rare side effect is ] causing ] and ]. This may occur at any stage during treatment and without warning; monitoring of white cell count is not useful. Patients are advised to immediately report symptoms of infection, such as ] or fever, so that a ] test may be arranged. If this confirms a low neutrophil count, discontinuation of the drug leads to recovery. However failure to report suggestive symptoms or delays in considering the possibility of immunosuppression and its testing, can lead to fatalities.
	Some azole drugs may disrupt ] production in ], affecting pregnancy outcome.
	==Side Effects==		===Precautions===
			Some people are allergic to ](s). Some azole drugs have adverse ]s. Some azole drugs may disrupt ] production in ], affecting pregnancy outcome.{{R|"Informa1"}}{{Verify source|date=October 2012}}
	Whilst ]es and ] are common, these can often be treated with ]s without stopping the carbimazole. For those patients where sensitivity reactions can not be controlled, ] may be used as an alternative.
			Carbimazole should be used judiciously in pregnancy as it crosses the placenta. It has (rarely) been associated with congenital defects, including ] of the neonate but is not contra-indicated. However, it more predictably may cause fetal ] so (in minimal doses) it can be used in order to control maternal ]. There are reported cases of goiter and ] in fetus.<ref>{{cite book | vauthors = Brunton L, Chabner BA, Knollman B |title=Goodman & Gilman's pharmacological basis of therapeutics. |date=2011 |publisher=McGraw-Hill |isbn=978-0-07-162442-8 |edition=12th}}</ref> Furthermore, breast feeding is possible but only if lowest effective dose is used and neonatal development is closely monitored.
	Its most serious rare side effect is ] causing ] and ]. This may occur at any stage during treatment and without warning. Patients are advised to immediately report symptoms of infection, especially ], so that a ] test may be arranged. If this confirms a low neutrophil count then the drug must be discontinued immediately, allowing for usually a prompt recovery. However failure to report suggestive symptoms or delays in considering the possibility of immunosuppression and its testing, can lead to fatalities.
	Should be used with caution in pregnancy as crosses the placenta barrier.
			For the above reasons, it is preferable to use ] in pregnancy, especially in the first trimester, with the possibility of changing to carbimazole for the second and third trimesters.<ref name="pmid19583480">{{cite journal | vauthors = Bahn RS, Burch HS, Cooper DS, Garber JR, Greenlee CM, Klein IL, Laurberg P, McDougall IR, Rivkees SA, Ross D, Sosa JA, Stan MN | display-authors = 6 | title = The Role of Propylthiouracil in the Management of Graves' Disease in Adults: report of a meeting jointly sponsored by the American Thyroid Association and the Food and Drug Administration | journal = Thyroid | volume = 19 | issue = 7 | pages = 673–674 | date = July 2009 | pmid = 19583480 | doi = 10.1089/thy.2009.0169 }}</ref>
	==Brand names==		==Brand names==
			* Neo-mercazole<ref>{{cite web | title = Neo-Mercazole Carbimazole | url = http://www.nicholas.co.id/product/?module=detailberita&id=128&act=neo-mercazole.html/ | publisher = Nicholas Laboratories Indonesia | access-date = 2021-06-22 | archive-date = 2016-03-04 | archive-url = https://web.archive.org/web/20160304104900/http://www.nicholas.co.id/product/?module=detailberita&id=128&act=neo-mercazole.html%2F | url-status = dead }}</ref>
	* Neomercazole
	* Vidalta		* Vidalta
			* Thyrocab
	* Camazol
			* Neomerdin
	==See also==		== References ==
			{{Reflist|refs=
	* ]
			<ref name="Informa1">{{cite journal | vauthors = Kragie L, Turner SD, Patten CJ, Crespi CL, Stresser DM | title = Assessing pregnancy risks of azole antifungals using a high throughput aromatase inhibition assay | journal = Endocrine Research | volume = 28 | issue = 3 | pages = 129–140 | date = August 2002 | pmid = 12489563 | doi = 10.1081/ERC-120015045 | s2cid = 8282678 }}</ref>
	* ]
			}}
			== Further reading ==
	==References==
			{{refbegin}}
	* ] '''45''' March 2003
			* {{cite book | title = British National Formulary | isbn = 978-0-85369-555-4 | volume = 45 | date = March 2003 | title-link = British National Formulary | vauthors = Mehta DK }}
			{{refend}}
	{{Thyroid therapy}}		{{Thyroid therapy}}
			{{Thyroid hormone receptor modulators}}
	]		]
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	]		]
	]		]
	{{systemic-hormonal-drug-stub}}
	]
	]
	]
	]