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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/03/24 08:10:08」(JST)
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Rescinnamine
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Systematic (IUPAC) name |
methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}yohimban-16-carboxylate |
Clinical data |
Legal status
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Routes of
administration
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oral |
Identifiers |
CAS Registry Number
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24815-24-5 Y |
ATC code
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C02AA01 |
PubChem |
CID 5280954 |
DrugBank |
DB01180 Y |
ChemSpider |
4444446 Y |
UNII |
Q6W1F7DJ2D Y |
KEGG |
D00198 Y |
ChEBI |
CHEBI:28572 Y |
ChEMBL |
CHEMBL1668 Y |
Synonyms |
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 |
Chemical data |
Formula |
C35H42N2O9 |
Molecular mass
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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
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InChI
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InChI=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 Y
Key:SZLZWPPUNLXJEA-QEGASFHISA-N Y
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Y (what is this?) (verify) |
Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.
It is an vinca alkaloid obtained from Rauwolfia serpentina[1] and other species of Rauwolfia.[2]
Brand names
Moderil, Cinnasil, Anaprel
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.
Sympatholytic (and closely related) antihypertensives (C02)
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Sympatholytics
(antagonize α-adrenergic
vasoconstriction) |
Central
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α2 agonist
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- Clonidine
- Guanabenz
- Guanfacine
- Methyldopa#
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Adrenergic release inhibitors
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- Bethanidine
- Bretylium
- Debrisoquine
- Guanadrel
- Guanazodine
- Guanethidine
- Guanoclor
- Guanazodine
- Guanoxabenz
- Guanoxan
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|
Imidazoline receptor agonist
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|
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Ganglion-blocking/nicotinic antagonist
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- Mecamylamine
- Pentolinium
- Trimethaphan
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Peripheral
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Indirect
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MAOI
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Adrenergic uptake inhibitor
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- Bietaserpine
- Deserpidine
- Methoserpidine
- Rescinnamine
- Reserpine
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Tyrosine hydroxylase inhibitor
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Direct
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α1 blockers
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- Prazosin
- Indoramin
- Trimazosin
- Doxazosin
- Urapidil
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Non-selective α blocker
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Other antagonists |
Serotonin antagonist
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|
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Endothelin antagonist (for PH)
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- dual (Bosentan, Macitentan)
- selective (Ambrisentan, Sitaxentan)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of the circulatory system
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|
Description |
- Anatomy
- Arteries
- head and neck
- arms
- chest
- abdomen
- legs
- Veins
- head and neck
- arms
- chest
- abdomen and pelvis
- legs
- Development
- Cells
- Physiology
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|
Disease |
- Congenital
- Neoplasms and cancer
- Lymphatic vessels
- Injury
- Vasculitis
- Other
- Symptoms and signs
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|
Treatment |
- Procedures
- Drugs
- beta blockers
- channel blockers
- diuretics
- nonsympatholytic vasodilatory antihypertensives
- peripheral vasodilators
- renin–angiotensin system
- sympatholytic antihypertensives
- vasoprotectives
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English Journal
- Simultaneous determination of reserpine, rescinnamine, and yohimbine in human plasma by ultraperformance liquid chromatography tandem mass spectrometry.
- Iqbal M1, Alam A2, Wani TA3, Khalil NY3.
- Journal of analytical methods in chemistry.J Anal Methods Chem.2013;2013:940861. doi: 10.1155/2013/940861. Epub 2013 Dec 5.
- A sensitive and selective UPLC-MS/MS method was developed and validated for the determination of three indolic alkaloids (reserpine, rescinnamine, and yohimbine) in human plasma using papaverine as internal standard (IS). After a one step protein precipitation with acetonitrile, separation was carri
- PMID 24383039
- Computational and synthetic studies towards improving rescinnamine as an inducer of MSH2-dependent apoptosis in cancer treatment.
- AbdelHafez EM1, Diamanduros A2, Negureanu L3, Luy Y3, Bean JH2, Zielke K2, Crowe B2, Vasilyeva A4, Clodfelter JE5, Aly OM6, Abuo-Rahma GE6, Scarpinato KD2, Salsbury FR Jr3, King SB1.
- Molecular cancer biology.Mol Cancer Biol.2013;1(1). pii: 44.
- We, and others, have previously shown that mismatch repair proteins, in addition to their repair function, contribute to cell death initiation. In response to some drugs, this cell death activity is independent of the repair function of the proteins. Rescinnamine, a derivative of the indole alkaloid
- PMID 25485184
- Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response.
- Vasilyeva A1, Clodfelter JE, Gorczynski MJ, Gerardi AR, King SB, Salsbury F, Scarpinato KD.
- Journal of nucleic acids.J Nucleic Acids.2010 Sep 13;2010. pii: 162018. doi: 10.4061/2010/162018.
- Mismatch repair proteins modulate the cytotoxicity of several chemotherapeutic agents. We have recently proposed a "death conformation" of the MutS homologous proteins that is distinguishable from their "repair conformation." This conformation can be induced by a small molecule, reserpine, leading t
- PMID 20936178
Japanese Journal
- Rauwolfia Alkaloidsによるビンブラスチン増感作用について
- 宮本 謙一 [他],涌沢 伸哉,柳岡 利一,越浦 良三
- 藥學雜誌 104(12), 1295-1300, 1984-12-25
- … When cells were treated with VBL and each alkaloid for 30 min, reserpine, rescinnamine, syrosingopine, and ajmaline markedly potentiated the effect of VBL, but dimethylaminoethylreserplinate hydrochloride (DMAR) and yohimbine did not influence. …
- NAID 110003650598
- Methyl o‐(4‐hydroxy‐3‐methoxycinnamoyl)reserpate(CD‐3400)の射精におよぼす影響について
- 米沢 章彦 [他],只野 武,浦野 慎一,木皿 憲佐,木村 行雄
- 日本薬理学雑誌 80(3), 239-249, 1982
- … 薬を目的に開発された新しいrauwolfia alkaloids誘導体 Methyl <I>o</I>-(4-hydroxy-3-methoxycinnamoyl) reserpate (CD-3400)の勃起,射精および脳内モノアミンに及ぼす影響を,雄性雑種成犬を使用し,reserpine(RES)およびrescinnamine(RCN)と比較検討した.1) 各薬物を1回経口投与(0.032mg/kg~0.5mg/kg)すると,勃起はほぼ完全勃起に近い状態を維持していたが,射精は用量依存的に抑制され,CD-3400(0.5mg/kg)では投与24時間後に,RES,RCN(0.125mg/kg)で …
- NAID 130000751825
- 新ラウオルフィア・アルカロイド誘導体 Methyl 0-(4-hydroxy-3-methoxycinnamoyl) reserpate (CD-3400) の健康人に対する作用
Related Links
- Rescinnamine. From Wikipedia, the free encyclopedia. Jump to: navigation, search ... Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and ...
- Structure, classification, information, physical and chemical properties for Rescinnamin, Moderil, Apoterin, Cinnaloid, Rescisan, Resealoid, Reserpinine, Scinnamina, Anaprel.
Related Pictures