reserpine

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

Drug data · ChEMBL

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

• 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

via Wikidata · CC0