利血平

Also known as Serpalan®, (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester, Apoplon, Serpalan, Reserpin, 3,4,5-trimethoxybenzoyl methyl reserpate, (-)-reserpine, Reserpine

Reserpine is a drug that is used for the treatment of high blood pressure, usually in combination with a thiazide diuretic or vasodilator. Large clinical trials have shown that combined treatment with reserpine plus a thiazide diuretic reduces mortality of people with hypertension. Although the use of reserpine as a solo drug has declined since it was first approved by the FDA in 1955, the combined use of reserpine and a thiazide diuretic or vasodilator is still recommended in patients who do not achieve adequate lowering of blood pressure with first-line drug treatment alone. The reserpine-hy

Key facts

Drug.width: 250px
Drug.Watchedfields: changed
Drug.verifiedrevid: 460779417
Drug.IUPAC_name: methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
Drug.image: Reserpine.svg
Drug.image_class: skin-invert-image
Drug.image2: Reserpine structure.png
Drug.image_class2: bg-transparent
Drug.width2: 250px
Drug.tradename: Serpasil, others
Drug.MedlinePlus: a601107
Drug.licence_US: Reserpine
Drug.pregnancy_category: C
Drug.legal_status: Rx-only (banned/discontinued in some countries)
Drug.routes_of_administration: Oral
Drug.bioavailability: 50%
Drug.metabolism: gut/liver
Drug.elimination_half life: phase 1 = 4.5h, phase 2 = 271h, average = 33h

via Wikipedia infobox

Chemical data

Formula: C33H40N2O9
Molecular weight: 608.7 g/mol
IUPAC name: methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
SMILES: CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
InChIKey: QEVHRUUCFGRFIF-MDEJGZGSSA-N
XLogP: 4
Polar surface area: 118 Å²
H-bond donors: 1
H-bond acceptors: 10
Formal charge: 0

via PubChem

Drug data · ChEMBL

Withdrawn

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1960
Admin. routes: oral, parenteral
Indications: hypertension, pulmonary arterial hypertension, cocaine dependence, cerebrovascular disorder

via ChEMBL · EBI

Research

19,071 papers

The effects of reserpine on depression: A systematic review.Journal of psychopharmacology (Oxford, England) · 2023
[Reserpine-diuretic combinations in therapy of arterial hypertension. Current considerations].Medizinische Klinik (Munich, Germany : 1983) · 1998
Tetrahydrocannabinol potentiates reserpine-induced hypokinesia.Pharmacology, biochemistry, and behavior · 1981
Pelargonidin ameliorates reserpine-induced neuronal mitochondrial dysfunction and apoptotic cascade: a comparative in vivo study.Drug and chemical toxicology · 2023
Reserpine-induced reduction in norepinephrine transporter function requires catecholamine storage vesicles.Neurochemistry international · 2010

via PubMed

Wikidata facts

Has part: carbon
Mass: 608.273381
Has use: medication

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chemical formula: C₃₃H₄₀N₂O₉
Commons gallery: Reserpine
World Health Organisation international non-proprietary name: reserpine
medical condition treated: arterial hypertension
melting point: 265
isomeric SMILES: CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
canonical SMILES: COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
different from: deserpidine
subject has role: carcinogen
physically interacts with: Solute carrier family 18 member A2
found in taxon: Rauvolfia afra
Commons category: Reserpine
defined daily dose: 0.5

Sources (9)

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Article · 中文

利血平（英語：Reserpine），或作利舍平，蛇根碱，是一种用于治疗高血压及精神病的吲哚类生物碱药物，最初是在萝芙木属植物蛇根木中提煉而成。如今由于副作用较多并且更优的新药上市，利血平已不再是治疗的首选药物。儿茶酚胺类（属于单胺类神经递质）在对心率、心肌收缩力和外周阻力的调控上有著极大作用，利血平的降压作用是透過消耗外周交感神经末梢的儿茶酚胺而发挥药效。

Abstract from DBpedia / Wikipedia · CC BY-SA

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利血平