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Saving copy of the {{drugbox}} taken from revid 456667820 of page Rescinnamine for the Chem/Drugbox validation project (updated: 'DrugBank').
 
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{{short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Rescinnamine|oldid=456667820}} 456667820] of page [[Rescinnamine]] with values updated to verified values.}}
{{Drugbox
{{Drugbox
| verifiedrevid = 464380960
| Verifiedfields = changed
| IUPAC_name = methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-<nowiki/>{[(2''E'')-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}yohimban-16-carboxylate
| verifiedrevid = 408987920
| IUPAC_name = methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-{[(2''E'')-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}yohimban-16-carboxylate
| image = Rescinnamine.svg
| image = Rescinnamine.svg
| image2 = [[File:Rescinnamine.png|frameless|rescinnamine 3D BS]]

| width = 300
<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename = Moderil, Cinnasil, Anaprel
| pregnancy_category =
| pregnancy_category =
| legal_status = Rx-only
| legal_status = Rx-only
| routes_of_administration = oral
| routes_of_administration = [[Oral administration|By mouth]]

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =

<!--Identifiers-->
<!--Identifiers-->
| IUPHAR_ligand = 7098
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 24815-24-5
| CAS_number = 24815-24-5
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444446
| ChemSpiderID = 4444446
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Q6W1F7DJ2D
| UNII = Q6W1F7DJ2D
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00198
| KEGG = D00198
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28572
| ChEBI = 28572
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1668
| ChEMBL = 1668

<!--Chemical data-->
<!--Chemical data-->
| C=35 | H=42 | N=2 | O=9
| C=35 | H=42 | N=2 | O=9
| smiles = [H][C@]26C[C@@H](OC(=O)/C=C/c1cc(OC)c(OC)c(OC)c1)[C@H](OC)[C@@H](C(=O)OC)[C@@]2([H])C[C@]5([H])c4[nH]c3cc(OC)ccc3c4CCN5C6
| molecular_weight = 634.716 g/mol
| smiles = O=C(OC)[C@H]6[C@H]4C[C@@H]3c2nc1cc(OC)ccc1c2CCN3C[C@H]4C[C@@H](OC(=O)\C=C\c5cc(OC)c(OC)c(OC)c5)[C@@H]6OC
| InChI = 1/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1
| InChIKey = SZLZWPPUNLXJEA-QEGASFHIBN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1
| StdInChI = 1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SZLZWPPUNLXJEA-QEGASFHISA-N
| StdInChIKey = SZLZWPPUNLXJEA-QEGASFHISA-N
| synonyms = <small>methyl (1''R'',15''S'',17''R'',18''R'',19''S'',20''S'')-6,18-dimethoxy-17-{[(2''E'')-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0<sup>2,10</sup>.0<sup>4,9</sup>.0<sup>15,20</sup>]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate</small>
| synonyms = <small>methyl (1''R'',15''S'',17''R'',18''R'',19''S'',20''S'')-6,18-dimethoxy-17-<nowiki/>{[(2''E'')-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0<sup>2,10</sup>.0<sup>4,9</sup>.0<sup>15,20</sup>]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate</small>
}}
}}

'''Rescinnamine''', known by the brand names '''''Moderil''''', '''''Cinnasil''''', and '''''Anaprel''''', is an [[ACE inhibitor|angiotensin-converting enzyme inhibitor]] used as an [[antihypertensive]] [[medication|drug]].

It is an indoloquinolizine [[alkaloid]] similar to [[reserpine]], obtained from ''[[Rauvolfia serpentina]]''<ref name="pmid13699407">{{cite journal |vauthors=FIFE R, MACLAURIN JC, WRIGHT JH |title=Rescinnamine in treatment of hypertension in hospital clinic and in general practice |journal=British Medical Journal |volume=2 |issue=5216 |pages=1848–50 |date=December 1960 |pmid=13699407 |pmc=2098607 |doi= 10.1136/bmj.2.5216.1848}}</ref> and other [[species]] of ''[[Rauvolfia]]''.<ref>{{cite journal |journal = Planta Med. |year = 1982 |volume = 44 |issue = 2 |pages = 91–3 |title = Alkaloids of Vinca major cv. Variegata. |vauthors = Balsevich J, Constabel F, Kurz WG |pmid = 17402086 |doi=10.1055/s-2007-971409}}</ref>

== References ==
{{reflist}}

{{ACE inhibitors}}
{{Angiotensin receptor modulators}}
{{Tryptamines}}

[[Category:Indoloquinolizines]]
[[Category:Tryptamine alkaloids]]
[[Category:Isoquinoline alkaloids]]
[[Category:ACE inhibitors]]
[[Category:Antihypertensive agents]]
[[Category:Alkaloids found in Rauvolfia]]
[[Category:Pyrogallol ethers]]
[[Category:Cinnamate esters]]
[[Category:Indole ethers at the benzene ring]]
[[Category:Heterocyclic compounds with 5 rings]]
[[Category:Methoxy compounds]]
[[Category:Methyl esters]]

{{Antihypertensive-stub}}