Structure via PubChem · Public domain (PubChem)
Reserpina
Sign in to saveAlso 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
farmaco
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 Ų
- H-bond donors
- 1
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
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 · Italiano
La reserpina è un alcaloide indolico con attività antipertensiva e antipsicotica. È stata ampiamente utilizzata nella terapia farmacologica dell'ipertensione e di alcune psicosi, anche se la messa a punto di composti più efficaci con effetti indesiderati considerevolmente più contenuti la rende un farmaco obsoleto, ritirato dal commercio in diversi paesi. L'effetto antipertensivo della reserpina è dovuto alla sua capacità di esaurire nei terminali nervosi simpatici periferici le riserve di catecolamine, neurotrasmettitori normalmente coinvolti nel controllo della frequenza cardiaca e delle resistenze periferiche. Per questo motivo nella farmacopea inglese viene classificata come amine depletor. La deplezione di a livello sinaptico operata dalla reserpina viene spesso citata come prova della teoria monoaminergica della patogenesi della depressione (Everett & Tolman, 1959), che può difatti costituire un effetto indesiderato della terapia con reserpina.
Abstract from DBpedia / Wikipedia · CC BY-SA