reserpine Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
derivatives of Rauwolfia alkaloids 2370 50-55-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • reserpine
  • deserpine
  • elserpine
  • rauwasedin
  • rivasin
  • serpine
An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.
  • Molecular weight: 608.69
  • Formula: C33H40N2O9
  • CLOGP: 3.86
  • LIPINSKI: 2
  • HAC: 11
  • HDO: 1
  • TPSA: 117.78
  • ALOGS: -4.73
  • ROTB: 10

Drug dosage:

DoseUnitRoute
0.50 mg O
0.50 mg P

Approvals:

DateAgencyCompanyOrphan
Oct. 12, 1955 FDA LANNETT

FDA Adverse Event Reporting System

None

Pharmacologic Action:

SourceCodeDescription
ATC C02AA02 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, CENTRALLY ACTING
Rauwolfia alkaloids
ATC C02AA52 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, CENTRALLY ACTING
Rauwolfia alkaloids
ATC C02LA01 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
Rauwolfia alkaloids and diuretics in combination
ATC C02LA51 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
Rauwolfia alkaloids and diuretics in combination
ATC C02LA71 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
Rauwolfia alkaloids and diuretics in combination
FDA EPC N0000175640 Catecholamine-depleting Sympatholytic
FDA PE N0000175650 Decreased Sympathetic Activity
MeSH PA D018663 Adrenergic Agents
MeSH PA D018759 Adrenergic Uptake Inhibitors
MeSH PA D000959 Antihypertensive Agents
MeSH PA D014150 Antipsychotic Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
CHEBI has role CHEBI:65190 first generation antipsychotic
CHEBI has role CHEBI:35640 adrenergic uptake inhibitor
CHEBI has role CHEBI:35674 antihypertensive agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Psychotic disorder indication 69322001
Fluid volume disorder contraindication 1860003
Anuria contraindication 2472002 DOID:2983
Suicidal thoughts contraindication 6471006
Peptic ulcer contraindication 13200003 DOID:750
Hypercholesterolemia contraindication 13644009
Chronic disease of respiratory system contraindication 17097001
Cirrhosis of liver contraindication 19943007 DOID:5082
Secondary angle-closure glaucoma contraindication 21571006
Electroconvulsive therapy contraindication 23835007
Hypovolemia contraindication 28560003
Dehydration contraindication 34095006
Depressive disorder contraindication 35489007 DOID:2848
Hyperuricemia contraindication 35885006 DOID:1920
Hypokalemia contraindication 43339004
Diabetes mellitus type 2 contraindication 44054006 DOID:9352
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Diabetes mellitus type 1 contraindication 46635009 DOID:9744
Chronic heart failure contraindication 48447003
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Sympathectomy contraindication 57071006
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Hypercalcemia contraindication 66931009 DOID:12678
Hyperparathyroidism contraindication 66999008 DOID:13543
Benign intracranial hypertension contraindication 68267002 DOID:11459
Hypochloremic alkalosis contraindication 70134007
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Oliguria contraindication 83128009
Epilepsy contraindication 84757009 DOID:1826
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:2527
Hypomagnesemia contraindication 190855004
Acute pancreatitis contraindication 197456007 DOID:2913
Impaired renal function disorder contraindication 197663003
Cerebrovascular accident contraindication 230690007 DOID:6713
Disease of liver contraindication 235856003 DOID:409
Lupus erythematosus and erythema multiforme-like syndrome contraindication 238926009
Calculus in biliary tract contraindication 266474003
Neonatal hyperbilirubinemia contraindication 281610001
Hypertriglyceridemia contraindication 302870006
Disorder of coronary artery contraindication 414024009
Myocardial infarction in recovery phase contraindication 418044006
Slow acetylator due to N-acetyltransferase enzyme variant contraindication 425079005
Azotemia contraindication 445009001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.2 acidic
pKa2 6.78 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Synaptic vesicular amine transporter Transporter INHIBITOR Ki 7.90 IUPHAR CHEMBL
Mu-type opioid receptor GPCR Ki 5.77 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.22 WOMBAT-PK
D(2) dopamine receptor GPCR Ki 6.23 WOMBAT-PK
Chromaffin granule amine transporter Transporter INHIBITOR Ki 7.45 IUPHAR
5-hydroxytryptamine receptor 1A GPCR Ki 5.74 PDSP
D(1A) dopamine receptor GPCR Ki 5.41 PDSP
Multidrug resistance protein 1 Transporter Ki 7 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.80 CHEMBL
ATP-binding cassette sub-family G member 2 Transporter IC50 4.58 CHEMBL
Sodium-dependent serotonin transporter Transporter Kd 5.84 SCIENTIFIC LITERATURE
Quinolone resistance protein NorA Transporter IC50 5.15 CHEMBL
Synaptic vesicular amine transporter Transporter Ki 9 CHEMBL

External reference:

IDSource
DB00206 DRUGBANK_ID
4823 IUPHAR_LIGAND_ID
4017506 VUID
N0000145891 NUI
C0035179 UMLSCUI
D00197 KEGG_DRUG
CHEMBL772 ChEMBL_ID
4017506 VANDF
1013 MMSL
9260 RXNORM
387447004 SNOMEDCT_US
78379001 SNOMEDCT_US
5417 MMSL
d00367 MMSL
N0000145891 NDFRT
N0000006632 NDFRT
000640 NDDF
8B1QWR724A UNII
282 INN_ID
D012110 MESH_DESCRIPTOR_UI
5770 PUBCHEM_CID
CHEBI:28487 CHEBI

Pharmaceutical products:

None