| Revision as of 13:44, 22 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 461776820 of page Icariin for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 20:26, 23 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenol ethers; added Category:4-Methoxyphenyl compounds using HotCat |
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{{distinguish|Icaridin}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Chembox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 461775344 |
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| verifiedrevid = 461936642 |
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<!-- Images --> |
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| IUPAC_name = 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7- |
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| ImageFile = Icariin.svg |
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oxy-3- |
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| ImageSize = 200px |
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oxychromen-4-one |
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| ImageAlt = |
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| image = Icariin.svg |
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<!-- Names --> |
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| width = 280 |
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| IUPACName = 7-(β-<small>D</small>-Glucopyranosyloxy)-5-hydroxy-4′-methoxy-8-(3-methylbut-2-en-1-yl)-3-(α-<small>L</small>-rhamnopyranosyloxy)flavone |
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| SystematicName = 5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{oxy}-3-{oxy}-4''H''-1-benzopyran-4-one |
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<!--Clinical data--> |
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| tradename = |
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| OtherNames = |
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<!-- Sections --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| Section1 = {{Chembox Identifiers |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| CASNo = 489-32-7 |
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| pregnancy_category = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| UNII = VNM47R2QSQ |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| SMILES = O=C3C(\O1O((O)(O)1O)C)=C(/Oc4c(c(O2O(CO)(O)(O)2O)cc(O)c34)C\C=C(/C)C)c5ccc(OC)cc5 |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| InChI = 1/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 |
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| legal_status = Legal |
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| InChIKey = TZJALUIVHRYQQB-XLRXWWTNBA |
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| routes_of_administration = Oral |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 |
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<!--Pharmacokinetic data--> |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| bioavailability = |
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| StdInChIKey = TZJALUIVHRYQQB-XLRXWWTNSA-N |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 489-32-7 --> |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 553204 |
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| ChEMBL = 553204 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 78420 |
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| PubChem = 5318997 |
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| PubChem = 5318997 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4477421 |
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| ChemSpiderID = 4477421 |
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}} |
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| Section2 = {{Chembox Properties |
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<!--Chemical data--> |
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| C=33 | H=40 | O=15 |
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| C=33 | H=40 | O=15 |
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| Appearance = |
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| molecular_weight = 676.662 g/mol |
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| Density = |
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| smiles = O=C3C(\O1O((O)(O)1O)C)=C(/Oc4c(c(O2O(CO)(O)(O)2O)cc(O)c34)C\C=C(/C)C)c5ccc(OC)cc5 |
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| MeltingPt = |
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| InChI = 1/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 |
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| BoilingPt = |
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| InChIKey = TZJALUIVHRYQQB-XLRXWWTNBA |
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| Solubility = |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| StdInChI = 1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 |
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| Section3 = {{Chembox Hazards |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| MainHazards = |
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| StdInChIKey = TZJALUIVHRYQQB-XLRXWWTNSA-N |
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| FlashPt = |
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| AutoignitionPt = |
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}} |
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}} |
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}} |
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'''Icariin''' is a ] classified as a ] ] ], a type of ]. It is the 8-prenyl derivative of ] 3,7-''O''-di]. The compound has been isolated from several species of plant belonging to the genus '']'' which are commonly known as horny goat weed, Yin Yang Huo,<ref>{{cite journal |vauthors=Liu JJ, Li SP, Wang YT |title=Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design |journal=] |volume=1103 |issue=2 |pages=344–349 |year=2006 |pmid=16337210 |doi=10.1016/j.chroma.2005.11.036 }}</ref> and ''Herba epimedii''.<ref name="pmid22216122">{{cite journal |vauthors=Cai WJ, Huang JH, Zhang SQ, Wu B, Kapahi P, Zhang XM, Shen ZY| title=Icariin and its derivative icariside II extend healthspan via insulin/IGF-1 pathway in C. elegans | journal=PLOS ONE | volume=6 | issue=12 | year=2011 | page=e28835 | pmid=22216122 | pmc = 3244416 | doi-access=free | doi=10.1371/journal.pone.0028835 | veditors=Blagosklonny MV | bibcode=2011PLoSO...628835C }}</ref> Extracts from these plants produce ] effects, and are used in ] to enhance erectile function.<ref>{{cite journal |vauthors=Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP |title=Effect of lipid-based suspension of ''Epimedium koreanum Nakai'' extract on sexual behavior in rats |journal=] |volume=114 |issue=3 |pages=412–416 |year=2007 |pmid=17890032 |doi=10.1016/j.jep.2007.08.021 }}</ref> However, clinical trial data are lacking to support these claims.<ref>{{cite web|url=https://www.drugs.com/npp/horny-goat-weed.html|title=Horny Goat Weed|date=August 5, 2019|access-date=November 7, 2019|website=Drugs.com}}</ref><ref>{{Cite journal |last1=Fang |first1=Jian |last2=Zhang |first2=Yongjun |date=2017-10-12 |title=Icariin, an Anti-atherosclerotic Drug from Chinese Medicinal Herb Horny Goat Weed |journal=Frontiers in Pharmacology |volume=8 |pages=734 |doi=10.3389/fphar.2017.00734 |doi-access=free |issn=1663-9812 |pmc=5644024 |pmid=29075193}}</ref> |
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== References == |
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{{reflist|2}} |
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{{Phosphodiesterase inhibitors}} |
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{{Flavonol}} |
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] |
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] |
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] |
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] |
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] |