reserpina

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

composto químico

In the Vinony graph

Vinony's link graph records 1,404 inbound references to reserpina, and connects out to fluphenazine, zuclopenthixol and pipotiazine.

It sits within the topics Alkaloids found in Rauvolfia, Antihypertensive agents and Benzoate esters.

Vinony links it to 34 Wikipedia language editions.

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Withdrawn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

Show 13 more facts

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)

via Wikidata · CC0

Article · Português

A reserpina (em latim reserpinum) é um alcalóide proveniente do arbusto Rauwolfia serpentina, da família das Apocynaceae, nativo da Índia. Primeiro fármaco a atuar no sistema nervoso simpático dos humanos. A forma das raízes, às vezes tortuosas, levaram os hindus a darem à planta um nome relacionado às serpentes.

Abstract from DBpedia / Wikipedia · CC BY-SA