NAV

Deserpidine

Identification

Summary

Deserpidine is an alkaloid that has been used to manage hypertension.

Generic Name
Deserpidine
DrugBank Accession Number
DB01089
Background

Deserpidine is an ester alkaloid drug isolated from Rauwolfia canescens (family Apocynaceae) with antipsychotic and antihypertensive properties that has been used for the control of high blood pressure and for the relief of psychotic behavior.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 578.6527
Monoisotopic: 578.262816202
Chemical Formula
C32H38N2O8
Synonyms
  • (3β,16β,17α,18β,20α)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
  • 11-demethoxyreserpine
  • 11-desmethoxyreserpine
  • Canescine
  • Deserpidina
  • Deserpidine
  • Deserpidinum
  • Raunormine
  • Recanescine
External IDs
  • A-11025
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Pharmacology

Indication

For the treatment of hypertension.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Deserpidine, an alkaloid of Rauwolfia canescens, is used as an antihypertensive. Rauwolfia alkaloids work by controlling nerve impulses along certain nerve pathways. As a result, they act on the heart and blood vessels to lower blood pressure.

Mechanism of action

Deserpidine's mechanism of action is through inhibition of the ATP/Mg2+ pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase (MAO) causing a reduction in catecholamines.

TargetActionsOrganism
ASynaptic vesicular amine transporter
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include dizziness or drowsiness (severe), flushing of skin, pinpoint pupils of eyes and slowed pulse.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbaloparatideAbaloparatide may increase the hypotensive activities of Deserpidine.
AcebutololDeserpidine may increase the hypotensive activities of Acebutolol.
AceclofenacThe therapeutic efficacy of Deserpidine can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Deserpidine can be decreased when used in combination with Acemetacin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Deserpidine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Deserpidine hydrochloride6LPC48045D6033-69-8YCNOGQOHKRDAHJ-UZXCFUCJSA-N
International/Other Brands
Halmonyl / Harmonyl (Abbott)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EnduronylDeserpidine (0.25 mg/1) + Methyclothiazide (5 mg/1)TabletOralPhysicians Total Care, Inc.1961-08-012006-12-31US flag
EnduronylDeserpidine (0.25 mg/1) + Methyclothiazide (5 mg/1)TabletOralAbbvie1961-08-012002-04-30US flag
Enduronyl ForteDeserpidine (0.5 mg/1) + Methyclothiazide (5 mg/1)TabletOralAbbvie1961-08-012001-04-30US flag

Categories

ATC Codes
C02LA03 — Deserpidine and diureticsC02AA05 — Deserpidine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Yohimbine alkaloids
Sub Class
Not Available
Direct Parent
Yohimbine alkaloids
Alternative Parents
Corynanthean-type alkaloids / Beta carbolines / Gallic acid and derivatives / M-methoxybenzoic acids and derivatives / P-methoxybenzoic acids and derivatives / 3-alkylindoles / Benzoic acid esters / Anisoles / Methoxybenzenes / Phenoxy compounds
show 16 more
Substituents
3-alkylindole / Alkyl aryl ether / Amine / Amino acid or derivatives / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoate ester
show 36 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound, methyl ester, benzoate ester, alkaloid ester, yohimban alkaloid (CHEBI:27478) / Indole alkaloids (C06541)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
9016E3VB47
CAS number
131-01-1
InChI Key
CVBMAZKKCSYWQR-WCGOZPBSSA-N
InChI
InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
IUPAC Name
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
SMILES
[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2

References

Synthesis Reference

Gabriele Fontana, Ezio Bombardelli, Cristian Samori, Eleonora Baldelli, Andrea Guerrini, Arturo Battaglia, Bruno Danieli, "Process for the Semisynthesis of Deserpidine." U.S. Patent US20080242864, issued October 02, 2008.

US20080242864
General References
Not Available
Human Metabolome Database
HMDB0015221
KEGG Drug
D08194
KEGG Compound
C06541
PubChem Compound
8550
PubChem Substance
46505311
ChemSpider
8232
RxNav
62174
ChEBI
27478
ChEMBL
CHEMBL1200515
ZINC
ZINC000004097186
Therapeutic Targets Database
DAP000909
PharmGKB
PA164742966
Wikipedia
Deserpidine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)228-232Ulshafer, P.R.; US. Patent 2,982,769; May 2, 1961; assigned to Ciba Pharmaceutical.
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0111 mg/mLALOGPS
logP4.25ALOGPS
logP3.69Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)16.37Chemaxon
pKa (Strongest Basic)7.4Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area108.55 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity154.96 m3·mol-1Chemaxon
Polarizability62.6 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9353
Blood Brain Barrier+0.9496
Caco-2 permeable+0.6582
P-glycoprotein substrateSubstrate0.8178
P-glycoprotein inhibitor IInhibitor0.8302
P-glycoprotein inhibitor IINon-inhibitor0.8096
Renal organic cation transporterInhibitor0.5326
CYP450 2C9 substrateNon-substrate0.894
CYP450 2D6 substrateNon-substrate0.8761
CYP450 3A4 substrateSubstrate0.7198
CYP450 1A2 substrateInhibitor0.8392
CYP450 2C9 inhibitorNon-inhibitor0.8701
CYP450 2D6 inhibitorNon-inhibitor0.9064
CYP450 2C19 inhibitorNon-inhibitor0.8954
CYP450 3A4 inhibitorNon-inhibitor0.8353
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7081
Ames testNon AMES toxic0.9234
CarcinogenicityNon-carcinogens0.9484
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.0921 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7952
hERG inhibition (predictor II)Non-inhibitor0.6277
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-014j-0849160000-31b897a373d9e518c58c
GC-MS Spectrum - EI-BGC-MSsplash10-014i-7967010000-b3758c647fba3c682e47
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0000090000-477f48178c34aee2cea9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0001090000-c6b263d1862e27d58102
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0001090000-6443c006bdcf04cadb5d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02ej-0000190000-5ec038d7d1c3da5b8f95
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002r-0612190000-b7221c8eba3907c5356e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-1311970000-953a5430bef8e62d9f49
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-244.3555696
predicted
DarkChem Lite v0.1.0
[M-H]-271.6895696
predicted
DarkChem Lite v0.1.0
[M-H]-260.9601696
predicted
DarkChem Lite v0.1.0
[M-H]-221.3059
predicted
DeepCCS 1.0 (2019)
[M+H]+246.0508696
predicted
DarkChem Lite v0.1.0
[M+H]+272.4805696
predicted
DarkChem Lite v0.1.0
[M+H]+261.1650696
predicted
DarkChem Lite v0.1.0
[M+H]+223.13078
predicted
DeepCCS 1.0 (2019)
[M+Na]+244.8399696
predicted
DarkChem Lite v0.1.0
[M+Na]+272.0995696
predicted
DarkChem Lite v0.1.0
[M+Na]+228.73662
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Synaptic vesicular amine transporter
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. Sievert MK, Hajipour AR, Ruoho AE: Specific derivatization of the vesicle monoamine transporter with novel carrier-free radioiodinated reserpine and tetrabenazine photoaffinity labels. Anal Biochem. 2007 Aug 1;367(1):68-78. Epub 2007 May 3. [Article]
  2. Naudon L, Leroux-Nicollet I, Raisman-Vozari R, Botton D, Costentin J: Time-course of modifications elicited by reserpine on the density and mRNA synthesis of the vesicular monoamine transporter, and on the density of the membrane dopamine uptake complex. Synapse. 1995 Sep;21(1):29-36. [Article]
  3. Erickson JD, Eiden LE, Hoffman BJ: Expression cloning of a reserpine-sensitive vesicular monoamine transporter. Proc Natl Acad Sci U S A. 1992 Nov 15;89(22):10993-7. [Article]
  4. Mandela P, Chandley M, Xu YY, Zhu MY, Ordway GA: Reserpine-induced reduction in norepinephrine transporter function requires catecholamine storage vesicles. Neurochem Int. 2010 May-Jun;56(6-7):760-7. doi: 10.1016/j.neuint.2010.02.011. Epub 2010 Feb 20. [Article]
  5. Fulton SC, Healy MD: Comparison of the effectiveness of deserpidine, reserpine, and alpha-methyltyrosine on brain biogenic amines. Fed Proc. 1976 Dec;35(14):2558-62. [Article]
  6. Loeffler LJ, Schran HF: Antibody specificity studies for reserpine, its metabolites, and synthetic reserpine congeners: radioimmunoassay. J Pharm Sci. 1979 Nov;68(11):1433-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:22