| Revision as of 17:37, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit |
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{{Short description|Chemical compound}} |
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{{drugbox |
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{{distinguish|doravirine}} |
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{{Drugbox |
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| Verifiedfields = changed |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| Watchedfields = changed |
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| verifiedrevid = 443713917 |
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| UNII = 98QS4N58TW |
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| IUPAC_name = (''Z'')-1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline |
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| verifiedrevid = 414437117 |
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| image = Drotaverine.svg |
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| IUPAC_name = (''Z'')-1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline |
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| image = Drotaverine.svg |
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| image2= Drotaverine ball-and-stick.png |
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<!--Clinical data--> |
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| tradename = No-Spa, Doverin |
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| Drugs.com = {{drugs.com|international|drotaverine}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_status = OTC (tablets), Rx-only (solution for injection) <small>(])</small><ref name="PI">{{cite web|title=Инструкция по применению препарата Но-шпа // No-Spa (tablets) Full Prescribing Information|url=http://grls.rosminzdrav.ru/InstrImgMZ.aspx?isNew=1&idReg=6198&page=4&isOld=1&t=|website=National Register of Drugs|publisher=Chinoin Pharmaceutical and Chemical Works|pages=3–8|language=ru}}</ref> |
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| routes_of_administration = Oral, ], ] |
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<!--Pharmacokinetic data--> |
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| bioavailability = Highly variable (~65%), peak at 45–60 min |
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| protein_bound = 95–98% |
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| metabolism = ] |
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| elimination_half-life = 7–16 hours |
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| excretion = >50% in urine and ~30% in bile<ref name=PI /> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|CAS}} |
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| CAS_number = 14009-24-6 |
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| ATC_prefix = A03 |
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| ATC_suffix = AD02 |
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| PubChem = 1712095 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB06751 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 1361582 |
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| ChemSpiderID = 1361582 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C24H31NO4/c1-5-26-21-10-9-17(14-22(21)27-6-2)13-20-19-16-24(29-8-4)23(28-7-3)15-18(19)11-12-25-20/h9-10,13-16,25H,5-8,11-12H2,1-4H3/b20-13- |
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| UNII = 98QS4N58TW |
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| InChIKey = OMFNSKIUKYOYRG-MOSHPQCFBI |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| smiles = O(c1ccc(cc1OCC)\C=C3\c2c(cc(OCC)c(OCC)c2)CCN3)CC |
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| KEGG = D07879 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 551978 |
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| ChEMBL = 551978 |
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<!--Chemical data--> |
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| C=24 | H=31 | N=1 | O=4 |
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| smiles = O(c1ccc(cc1OCC)\C=C3\c2c(cc(OCC)c(OCC)c2)CCN3)CC |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C24H31NO4/c1-5-26-21-10-9-17(14-22(21)27-6-2)13-20-19-16-24(29-8-4)23(28-7-3)15-18(19)11-12-25-20/h9-10,13-16,25H,5-8,11-12H2,1-4H3/b20-13- |
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| StdInChI = 1S/C24H31NO4/c1-5-26-21-10-9-17(14-22(21)27-6-2)13-20-19-16-24(29-8-4)23(28-7-3)15-18(19)11-12-25-20/h9-10,13-16,25H,5-8,11-12H2,1-4H3/b20-13- |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = OMFNSKIUKYOYRG-MOSHPQCFSA-N |
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| StdInChIKey = OMFNSKIUKYOYRG-MOSHPQCFSA-N |
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| CAS_number = 985-12-6 |
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| ATC_prefix = A03 |
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| ATC_suffix = AD02 |
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| PubChem = 1712095 |
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| DrugBank = DB06751 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07879 |
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| C=24|H=31|N=1|O=4 |
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| molecular_weight = 397.507 g/mol |
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| bioavailability = Highly variable |
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| protein_bound = 80 to 95% |
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| metabolism = ] |
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| elimination_half-life = 7 to 12 hours |
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| excretion = Fecal and ] |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = Oral, ] |
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}} |
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}} |
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'''Drotaverine''' (], also known as '''drotaverin''') is an ] drug, structurally related to ]. Drotaverine is a ], and has no ] effects.{{Citation needed|date=May 2010}} Drotaverine has been shown to possess dose-dependant analgesic effects in animal models.<ref>{{cite journal |author=Stepaniuk AG, Stepaniuk NG, Stoliarchuk AA, Stepaniuk GI, Chernobrovyĭ VN |title= |language=Russian |journal=Eksperimental'naia I Klinicheskaia Farmakologiia |volume=61 |issue=4 |pages=17–9 |year=1998 |pmid=9783101}}</ref> One small study has shown drotaverine to be eliminated mainly non-renally.<ref>{{cite journal |doi=10.1007/BF03189716 |author=Bolaji OO, Onyeji CO, Ogundaini AO, Olugbade TA, Ogunbona FA |title=Pharmacokinetics and bioavailability of drotaverine in humans |journal=European Journal of Drug Metabolism and Pharmacokinetics |volume=21 |issue=3 |pages=217–21 |year=1996 |pmid=8980918}}</ref> |
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'''Drotaverine''' (], also known as '''drotaverin''') is an ] drug, used to enhance ] during ] and to relieve ] ] in the ], ], and ].<ref>{{cite book |title=Title Textbook of Obstetrics |vauthors=Padubidri V, Anand E |date=2006 |publisher=BI Publications Pvt Ltd |isbn=9788172252236 |pages=283}}</ref><ref name="pmid14698825">{{cite journal | vauthors = Singh KC, Jain P, Goel N, Saxena A | title = Drotaverine hydrochloride for augmentation of labor | journal = International Journal of Gynaecology and Obstetrics | volume = 84 | issue = 1 | pages = 17–22 | date = January 2004 | pmid = 14698825 | doi = 10.1016/s0020-7292(03)00276-5 | s2cid = 43824027 | url = }}</ref><ref>{{Cite web |title=DROTAVERINE: Uses, Side Effects and Medicines {{!}} Apollo Pharmacy |url=https://www.apollopharmacy.in/salt/DROTAVERINE |access-date=2022-05-24 |website=www.apollopharmacy.in}}</ref><ref name=":0" /> |
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A few small 2003 studies found drotaverine to be nearly 80% effective in treating ].<ref>{{cite journal |author=Romics I, Molnár DL, Timberg G, ''et al.'' |title=The effect of drotaverine hydrochloride in acute colicky pain caused by renal and ureteric stones |journal=BJU International |volume=92 |issue=1 |pages=92–6 |year=2003 |month=July |pmid=12823389 |doi=10.1046/j.1464-410X.2003.04262.x}}</ref><ref>{{cite journal |author=Garmish OS, Zabashnyĭ SI, Smirnova EV, Kobeliatskiĭ IuIu |title= |language=Russian |journal=Klinichna Khirurhiia |volume= |issue=2 |pages=47–50 |year=2003 |month=February |pmid=12784437}}</ref> It has also been studied in accelerating ] by speeding up cervical dilation, but the results have been conflicting.<ref>{{cite journal |author=Singh KC, Jain P, Goel N, Saxena A |title=Drotaverine hydrochloride for augmentation of labor |journal=International Journal of Gynaecology and Obstetrics |volume=84 |issue=1 |pages=17–22 |year=2004 |month=January |pmid=14698825 |doi=10.1016/S0020-7292(03)00276-5}}</ref><ref>{{cite journal |author=Madhu C, Mahavarkar S, Bhave S |title=A randomised controlled study comparing Drotaverine hydrochloride and Valethamate bromide in the augmentation of labour |journal=Archives of Gynecology and Obstetrics |volume= 282|issue= 1|pages= 11–5|year=2009 |month=July |pmid=19644697 |doi=10.1007/s00404-009-1188-8}}</ref><ref>{{cite journal |author=Gupta B, Nellore V, Mittal S |title=Drotaverine hydrochloride versus hyoscine-N-butylbromide in augmentation of labor |journal=International Journal of Gynaecology and Obstetrics |volume=100 |issue=3 |pages=244–7 |year=2008 |month=March |pmid=18031745 |doi=10.1016/j.ijgo.2007.08.020}}</ref> Drotaverine has been shown to be effective in ] in managing pain during hysteroscopy and endometrial biopsy when administered together with ].<ref>{{cite journal |author=Sharma JB, Aruna J, Kumar P, Roy KK, Malhotra N, Kumar S |title=Comparison of efficacy of oral drotaverine plus mefenamic acid with paracervical block and with intravenous sedation for pain relief during hysteroscopy and endometrial biopsy |journal=Indian Journal of Medical Sciences |volume=63 |issue=6 |pages=244–52 |year=2009 |month=June |pmid=19602758 |doi=10.4103/0019-5359.53394}}</ref> ] patients presenting with predominant ] are more likely to benefit from ].<ref>{{cite journal |author=Khalif IL, Quigley EM, Makarchuk PA, Golovenko OV, Podmarenkova LF, Dzhanayev YA |title=Interactions between symptoms and motor and visceral sensory responses of irritable bowel syndrome patients to spasmolytics (antispasmodics) |journal=Journal of Gastrointestinal and Liver Diseases |volume=18 |issue=1 |pages=17–22 |year=2009 |month=March |pmid=19337628 |url=http://www.jgld.ro/12009/12009_2.html}}</ref> Drotaverin has also been tested in combination with ] for antiviral activity against A and B type ].<ref>{{cite journal |author=Zhilinskaya IN, Konovalova NI, Kiselev OI, Ashmarin IP |title=No-Spa and Remantadin are the novel complex preparations that inhibit effectively reproduction of the avian influenza viruses |journal=Doklady Biological Sciences |volume=414 |issue= 1|pages=249–50 |year=2007 |pmid=17668635 |doi=10.1134/S0012496607030234}}</ref> Drotaverin has an adverse effects frequency of 0.9%, side effects being relatively uncommon.<ref>{{cite journal |author=Tar A, Singer J |title= |language=Hungarian |journal=Orvosi Hetilap |volume=143 |issue=11 |pages=559–62 |year=2002 |month=March |pmid=12583325}}</ref> |
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It is structurally related to ], and is a selective ], and has no ] effects.<ref name="drugbank">{{cite web|title=The DrugBank database: Drotaverine|url=http://www.drugbank.ca/drugs/DB06751|website=DrugBank Version 4.1|publisher=The Metabolomics Innovation Centre|access-date=9 August 2014}}</ref> |
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Drotaverine in sold under brand name No-Spa (Chinoin Pharmaceutical and Chemical Works, Hungary, a member of the ]).{{Citation needed|date=May 2010}} |
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It is available in ],{{Specify |reason=Which jurisdictions? |date=October 2019}} ] (Poland,<ref>{{Cite web |title=No-Spa, 40 mg, tabletki, 20 szt. |url=https://www.doz.pl/apteka/p6349-No-Spa_40_mg_tabletki_20_szt. |access-date=2023-01-09 |website=doz.pl |language=pl}}</ref> Hungary,<ref>{{Cite web |title=DROTAVERIN-CHINOIN 40 mg tabletta 24 db - PATIKA24 Gyógyszer |url=https://www.patika24.hu/drotaverin-chinoin-40-mg-tabletta-24-db.html |access-date=2023-01-09 |website=www.patika24.hu |language=hu}}</ref> Estonia,<ref>{{Cite web |title=NO-SPA ÕHUKE POLÜMEERKATTEGA TBL 40MG N24 {{!}} BENU Veebiap |url=https://www.benu.ee:443/products-by-categories/hygiene-ee/no-spa-kaetud-tbl-40mg-n24 |access-date=2023-01-09 |website=www.benu.ee |language=ee}}</ref> Latvia,<ref>{{Cite web |title=NO-SPA 40 mg tabletes, 24 gab. - Piegāde visā Latvijā {{!}} Mēness aptieka |url=https://www.e-menessaptieka.lv/no-spa-40-mg-tabletes-24-gab-1142207 |access-date=2023-01-09 |website=www.e-menessaptieka.lv |language=lv}}</ref> Lithuania<ref>{{Cite web |title=Drotaverine - Vaistai.lt |url=https://vaistai.lt/grupe/drotaverine.html |access-date=2023-01-09 |website=vaistai.lt}}</ref>) under several brand names.<ref>Drotaverine - Drugs.com Page accessed June 28, 2015</ref> A popular brand is ''No-Spa,'' owned by ]). It is distributed by Sanofi as ''Но-Шпа'' (No-shpa) in Russia.<ref>{{Cite web |title=Но-шпа — инструкция по применению, дозы, побочные действия, отзывы о препарате: таблетки, покрытые пленочной оболочкой,таблетки,раствор для внутривенного и внутримышечного введения, 20 мг/мл, 40 мг, 40 мг |url=https://www.rlsnet.ru/drugs/no-spa-2216 |access-date=2023-10-26 |website=РЛС® |language=ru}}</ref> |
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== Pharmacodynamics == |
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Drotaverine hydrochloride has a ], myotropic, ], ] action.<ref name=":0">{{Cite web |title=RUE Belmedpreparaty - pharmaceutical enterprise in the Republic of Belarus - DROTAVERINE HYDROCHLORIDE |url=https://www.belmedpreparaty.com/product/anot.php?anat_id=395&lang_id=2 |url-status=live |archive-url=https://archive.today/20220817130104/https://www.belmedpreparaty.com/product/anot.php?anat_id=395&lang_id=2 |archive-date=2022-08-17 |access-date=2022-05-24 |website=RUE Belmedpreparaty - pharmaceutical enterprise in the Republic of Belarus |language=en}}</ref> |
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Drotaverine decreases active ionized calcium supply binding to smooth muscle cells due to inhibition of ] and intracellular accumulation of ]. It has an apparent and prolonged action on smooth muscles of internal organs and blood vessels and it moderately decreases ], increases ] (minute volume of heart), and has some ] potential.<ref name=":0" /> |
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Drotaverine decreases ] of ] and increases blood-filling. Practically, Drotaverine does not influence the ] and does not penetrate into the ].<ref name=":0" /> |
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== Side effects == |
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Possible side effects include: heating sensation, dizziness, headache (rarely), insomnia. May be observed: arrhythmia (rarely), hypotension, tachycardia, sweating, nausea.<ref name=":0" /> |
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Overdose of Drotaverine potentially can cause ], ], paralysis of respiratory system.<ref name=":0" /> |
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==Counterfeits== |
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In ] the product is known under the brand name "No-Spa" by the general public<ref name="study">, Israeli patent and trade mark office, 11 July 2007</ref> which did not receive a permit to be distributed by the ],<ref name="smuggler"> ''NRG'', 11 March 2009</ref> however due to high demand local medical counterfeiters have managed to smuggle No-Spa tablets over the years.<ref name="smuggler"/> |
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In 2008, the Israeli health organization warned consumers against counterfeit No-Spa pills after a smuggler had been arrested at the ] with several thousand pills.<ref>{{Cite news |last=ניב |first=שי |date=2008-02-11 |title=חשש כי תרופה מזויפת בשם NO-SPA הוברחה לישראל ועשויה לגרום לסכנה בריאותית |language=he |trans-title=It is feared that a fake drug called NO-SPA has been smuggled into Israel and may cause a health hazard |work=Globes |url=https://www.globes.co.il/news/article.aspx?did=1000308494 |access-date=}}</ref><ref>{{Cite web |last=Bader |first=H |date=11 February 2008 |title=משרד הבריאות מזהיר משימוש בתרופה לא מאושרת בשם: No-Spa |trans-title=The Ministry of Health warns against the use of an unapproved medicine called: No-Spa |url=https://www.inn.co.il/flashes/209104 |url-status=live |archive-url=https://web.archive.org/web/20220310114639/https://www.inn.co.il/flashes/209104 |archive-date=10 March 2022 |website=Israel National News |language=he}}</ref> |
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In 2011, the Israeli patent and trademark office declined the use of No-SPA.<ref name="study"/> |
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== Risks == |
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An article from 2013 described the effects from overdose (in a 19-year-old female) as including vomiting, seizures and fatal cardiac toxicity.<ref>{{cite journal | url=https://link.springer.com/article/10.1007/s40278-013-7608-3 | doi=10.1007/s40278-013-7608-3 | title=Drotaverine overdose | journal=Reactions Weekly | date=2013 | volume=1481 | page=17 }}</ref> |
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In 2016, the young Russian chess player ] died of a massive overdose (or poisoning) of the drug, which was initially thought to be a stroke; the dose detected in his blood was 17 mg/kg.<ref> {{Webarchive|url=https://web.archive.org/web/20161218132653/http://chess-news.ru/node/21958 |date=2016-12-18 }} (Russian, Chess-News)</ref> |
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==References== |
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==References== |
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{{gastrointestinal-drug-stub}} |
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