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Category:Alkaloids found in Rauvolfia |
Capitalised brand names, as is common (after seeing a bottle of Moderil on eBay). Also italicised them (makes them look a little bit better than simply bold). |
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{{short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| verifiedrevid = 464380960 |
| verifiedrevid = 464380960 |
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| 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 |
| 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 |
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| image = Rescinnamine.svg |
| image = Rescinnamine.svg |
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| image2 = [[File:Rescinnamine.png|frameless|rescinnamine 3D BS]] |
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| width = 300 |
| width = 300 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = Moderil, Cinnasil, Anaprel |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_status = Rx-only |
| legal_status = Rx-only |
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| routes_of_administration = |
| routes_of_administration = [[Oral administration|By mouth]] |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| IUPHAR_ligand = 7098 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 24815-24-5 |
| CAS_number = 24815-24-5 |
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| PubChem = 5280954 |
| PubChem = 5280954 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01180 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4444446 |
| ChemSpiderID = 4444446 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1668 |
| ChEMBL = 1668 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=35 | H=42 | N=2 | O=9 |
| C=35 | H=42 | N=2 | O=9 |
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| 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 |
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| molecular_weight = 634.716 g/mol |
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| 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 |
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| 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 |
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| InChIKey = SZLZWPPUNLXJEA-QEGASFHIBN |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SZLZWPPUNLXJEA-QEGASFHISA-N |
| StdInChIKey = SZLZWPPUNLXJEA-QEGASFHISA-N |
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| 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> |
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}} |
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⚫ | |||
⚫ | It is |
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⚫ | It is a [[vinca alkaloid]] 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> |
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== Brand names == |
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'''Moderil''', '''Cinnasil''', '''Anaprel''' |
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== References == |
== References == |
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{{reflist}} |
{{reflist}} |
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{{ACE inhibitors}} |
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{{Antihypertensives and diuretics}} |
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{{Angiotensin receptor modulators}} |
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[[Category:Indoloquinolizines]] |
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[[Category:Tryptamine alkaloids]] |
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[[Category:Isoquinoline alkaloids]] |
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[[Category:ACE inhibitors]] |
[[Category:ACE inhibitors]] |
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[[Category:Antihypertensive agents]] |
[[Category:Antihypertensive agents]] |
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[[Category:Alkaloids found in Rauvolfia]] |
[[Category:Alkaloids found in Rauvolfia]] |
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[[Category: |
[[Category:Pyrogallol ethers]] |
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[[Category: |
[[Category:Cinnamate esters]] |
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[[Category:Indole ethers at the benzene ring]] |
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[[Category:Heterocyclic compounds with 5 rings]] |
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[[Category:Methoxy compounds]] |
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[[Category:Methyl esters]] |
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{{Antihypertensive-stub}} |
{{Antihypertensive-stub}} |
Revision as of 21:18, 30 July 2023
Clinical data | |
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Trade names | Moderil, Cinnasil, Anaprel |
Other names | methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate |
Routes of administration | By mouth |
ATC code | |
Legal status | |
Legal status |
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Identifiers | |
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CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.042.232 |
Chemical and physical data | |
Formula | C35H42N2O9 |
Molar mass | 634.726 g·mol−1 |
3D model (JSmol) | |
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(verify) |
Rescinnamine, known by the brand names Moderil, Cinnasil, and Anaprel, is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.
It is a vinca alkaloid obtained from Rauvolfia serpentina[1] and other species of Rauvolfia.[2]
References
- ^ FIFE R, MACLAURIN JC, WRIGHT JH (December 1960). "Rescinnamine in treatment of hypertension in hospital clinic and in general practice". British Medical Journal. 2 (5216): 1848–50. doi:10.1136/bmj.2.5216.1848. PMC 2098607. PMID 13699407.
- ^ Balsevich J, Constabel F, Kurz WG (1982). "Alkaloids of Vinca major cv. Variegata". Planta Med. 44 (2): 91–3. doi:10.1055/s-2007-971409. PMID 17402086.