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Revision as of 10:18, 13 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'DrugBank_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox val...← Previous edit Latest revision as of 20:07, 23 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenol ethers; added Category:4-Methoxyphenyl compounds using HotCat 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 455348077 | verifiedrevid = 455349170
| IUPAC_name = 1-- 3-(4-methoxybenzyl)quinoxalin- 2(1''H'')-one | IUPAC_name = 1-- 3-(4-methoxybenzyl)quinoxalin- 2(1''H'')-one
| image = Caroverine.png | image = Caroverine.png
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 23465-76-1 | CAS_number = 23465-76-1
| ATC_prefix = A03 | ATC_prefix = A03
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| StdInChIKey = MSPRUJDUTKRMLM-UHFFFAOYSA-N | StdInChIKey = MSPRUJDUTKRMLM-UHFFFAOYSA-N
| PubChem = 65709 | PubChem = 65709
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1729803
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 59135 | ChemSpiderID = 59135
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<!--Chemical data--> <!--Chemical data-->
| C=22 | H=27 | N=3 | O=2 | C=22 | H=27 | N=3 | O=2
| molecular_weight = 365.47 g/mol
| smiles = O=C/1N(c3c(\N=C\1Cc2ccc(OC)cc2)cccc3)CCN(CC)CC | smiles = O=C/1N(c3c(\N=C\1Cc2ccc(OC)cc2)cccc3)CCN(CC)CC
| InChI = 1/C22H27N3O2/c1-4-24(5-2)14-15-25-21-9-7-6-8-19(21)23-20(22(25)26)16-17-10-12-18(27-3)13-11-17/h6-13H,4-5,14-16H2,1-3H3
| InChIKey = MSPRUJDUTKRMLM-UHFFFAOYAM
}} }}


'''Caroverine''' ('''Spasmium''', '''Tinnitin''', '''Tinnex''') is a ] used in Austria and Switzerland to relieve ]s in ]s (which include intestines, arteries, and other organs), and the use in those countries was extended to aid with ]s there, and eventually to treat ].<ref name=Martindale36/> It is also used to treat tinnitus in India.
'''Caroverine''' ('''Spasmium''', '''Spadon''') is a ] used as a ] and ''otoneuroprotective'' (] ]) agent in some countries.<ref name=pmid12473379>{{cite journal |author=Udilova N, Kozlov AV, Bieberschulte W, Frei K, Ehrenberger K, Nohl H |title=The antioxidant activity of caroverine |journal=Biochemical Pharmacology |volume=65 |issue=1 |pages=59–65 |year=2003 |month=January |pmid=12473379 |doi=10.1016/S0006-2952(02)01452-1}}</ref> It acts as an ] ], ] ] ], and ] ] ].<ref name=pmid12473379/> It also has potent ] effects.<ref name=pmid12473379/><ref name=pmid14757980>{{cite journal |author=Nohl H, Bieberschulte W, Dietrich B, Udilova N, Kozlov AV |title=Caroverine, a multifunctional drug with antioxidant functions |journal=BioFactors |volume=19 |issue=1–2 |pages=79–85 |year=2003 |pmid=14757980 |doi=10.1002/biof.5520190110}}</ref>


Chemically, it is a quinoxalineone<ref>{{cite book | vauthors = Bungardt E, Mutschler E |chapter=Spasmolytics |title=Ullmann's Encyclopedia of Industrial Chemistry |date=15 June 2000 |doi=10.1002/14356007.a24_515 |publisher=Wiley|page=11|isbn=978-3527306732 }}</ref> and is available in both a base and ] forms.<ref name=Martindale36>{{cite book | veditors = Sweetman SC |title=Martindale |date=2009 |publisher=Pharmaceutical Press |isbn=9780853698401 |page=2277 |edition= 36th}}</ref>
⚫ == References ==
⚫ {{Reflist|2}}


Pharmacologically, it has been described as a nonspecific ] and as an antagonist of both non-] and NMDA ]s.<ref name=Dobie1999/><ref name=Langguth2009/>

It was discovered in Austria in the 1950s<ref name=Dobie1999/> and was ] by Austrian company Phafag AG.<ref name=Dobie1999/>

Its INN name, caroverine, was proposed in 1972.<ref>{{cite journal |title=Proposed INNs List 28 |journal=WHO Chronicle |date=1972 |volume=26 |issue=9 |url=https://www.who.int/medicines/publications/druginformation/innlists/PL28.pdf}}</ref>

An intravenous formulation was tested in a single-blinded study in tinnitus that published in 1997 and had positive results; an effort to replicate those results failed to show any effect,<ref name=Langguth2009>{{cite journal | vauthors = Langguth B, Salvi R, Elgoyhen AB | title = Emerging pharmacotherapy of tinnitus | journal = Expert Opinion on Emerging Drugs | volume = 14 | issue = 4 | pages = 687–702 | date = December 2009 | pmid = 19712015 | pmc = 2832848 | doi = 10.1517/14728210903206975 }}</ref> and more people had their condition worsen than experienced benefit.<ref name=Dobie1999>{{cite journal | vauthors = Dobie RA | title = A review of randomized clinical trials in tinnitus | journal = The Laryngoscope | volume = 109 | issue = 8 | pages = 1202–1211 | date = August 1999 | pmid = 10443820 | doi = 10.1097/00005537-199908000-00004 | s2cid = 21409406 }}</ref> Pilot studies using a spray formulation for tinnitus published in 2005.<ref>{{cite book | vauthors = Darlington CL, Smith PF | title = Tinnitus: Pathophysiology and Treatment | chapter = Drug treatments for tinnitus | series = Progress in Brain Research | volume = 166 | pages = 249–262 | date = 2007 | pmid = 17956789 | doi = 10.1016/S0079-6123(07)66023-3 | isbn = 9780444531674 }}</ref>

In 2010 Phafag licensed rights to caroverine to the Indian company, Lincoln Pharmaceuticals, to develop the drug for tinnitus in India.<ref>{{cite news |title=Press release: Lincoln Pharma ties up with Swiss Phafag for Tinnitin injections |url=https://www.business-standard.com/article/companies/lincoln-pharma-ties-up-with-swiss-phafag-for-tinnitin-injections-110111700044_1.html |work=Lincoln via Business Standard India |date=17 November 2010}}</ref> Lincoln first marketed it for that purpose in India in 2011.<ref>{{cite news |title=Press Release: Lincoln Pharma launches Tinnex Injection |url=https://www.business-standard.com/article/press-releases/lincoln-pharma-launches-tinnex-injection-111041400145_1.html |work=Lincoln via Business Standard India |date=14 April 2011}}</ref>

As of 2016 it had been studied in a small clinical trial in people with ].<ref>{{cite journal | vauthors = Harless L, Liang J | title = Pharmacologic treatment for postviral olfactory dysfunction: a systematic review | journal = International Forum of Allergy & Rhinology | volume = 6 | issue = 7 | pages = 760–767 | date = July 2016 | pmid = 26879592 | doi = 10.1002/alr.21727 | s2cid = 29620152 }}</ref>

As of 2018 it was marketed under the brand names Spasmium and Tinnitin in Austria, and under the brand Tinnex in India.<ref>{{cite web |title=Caroverine International Brands |url=https://www.drugs.com/international/caroverine.html |publisher=Drugs.com |access-date=14 July 2018}}</ref>

⚫ == References ==
⚫ {{Reflist}}


{{Muscle relaxants}} {{Muscle relaxants}}
{{Calcium channel blockers}} {{Ion channel modulators}}
{{Ionotropic glutamate receptor modulators}}
{{Glutamatergics}}


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