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

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

Pharmacology

Indication

For the treatment of hypertension.

Reduce drug development failure rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

See how

Build, train, & validate predictive machine-learning models with structured datasets.

See how

Contraindications & Blackbox Warnings

Avoid life-threatening adverse drug events

Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Learn more

Avoid life-threatening adverse drug events & improve clinical decision support.

Learn more

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.

Target	Actions	Organism
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

Improve decision support & research outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.

Learn more

Improve decision support & research outcomes with our structured adverse effects data.

Learn more

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

Not Available

Interactions

Drug Interactions

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.

Drug	Interaction
Integrate drug-drug interactions in your software
Abaloparatide	Abaloparatide may increase the hypotensive activities of Deserpidine.
Acebutolol	Deserpidine may increase the hypotensive activities of Acebutolol.
Aceclofenac	The therapeutic efficacy of Deserpidine can be decreased when used in combination with Aceclofenac.
Acemetacin	The therapeutic efficacy of Deserpidine can be decreased when used in combination with Acemetacin.
Acetylsalicylic acid	Acetylsalicylic acid may decrease the antihypertensive activities of Deserpidine.
Alclofenac	The therapeutic efficacy of Deserpidine can be decreased when used in combination with Alclofenac.
Aldesleukin	Aldesleukin may increase the hypotensive activities of Deserpidine.
Alfentanil	Alfentanil may decrease the antihypertensive activities of Deserpidine.
Alfuzosin	Alfuzosin may increase the hypotensive activities of Deserpidine.
Aliskiren	Deserpidine may increase the hypotensive activities of Aliskiren.

Identify potential medication risks

Easily compare up to 40 drugs with our drug interaction checker.

Get severity rating, description, and management advice.

Learn more

Food Interactions

Not Available

Products

Drug product information from 10+ global regions

Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.

Access now

Access drug product information from over 10 global regions.

Access now

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Deserpidine hydrochloride	6LPC48045D	6033-69-8	YCNOGQOHKRDAHJ-UZXCFUCJSA-N

International/Other Brands

Halmonyl / Harmonyl (Abbott)

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Enduronyl	Deserpidine (0.25 mg/1) + Methyclothiazide (5 mg/1)	Tablet	Oral	Physicians Total Care, Inc.	1961-08-01	2006-12-31
Enduronyl	Deserpidine (0.25 mg/1) + Methyclothiazide (5 mg/1)	Tablet	Oral	Abbvie	1961-08-01	2002-04-30
Enduronyl Forte	Deserpidine (0.5 mg/1) + Methyclothiazide (5 mg/1)	Tablet	Oral	Abbvie	1961-08-01	2001-04-30

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

External Links

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

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	228-232	Ulshafer, P.R.; US. Patent 2,982,769; May 2, 1961; assigned to Ciba Pharmaceutical.
logP	3.3	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0111 mg/mL	ALOGPS
logP	4.25	ALOGPS
logP	3.69	Chemaxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.37	Chemaxon
pKa (Strongest Basic)	7.4	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	7	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	108.55 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	154.96 m³·mol^-1	Chemaxon
Polarizability	62.6 Å³	Chemaxon
Number of Rings	6	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9353
Blood Brain Barrier	+	0.9496
Caco-2 permeable	+	0.6582
P-glycoprotein substrate	Substrate	0.8178
P-glycoprotein inhibitor I	Inhibitor	0.8302
P-glycoprotein inhibitor II	Non-inhibitor	0.8096
Renal organic cation transporter	Inhibitor	0.5326
CYP450 2C9 substrate	Non-substrate	0.894
CYP450 2D6 substrate	Non-substrate	0.8761
CYP450 3A4 substrate	Substrate	0.7198
CYP450 1A2 substrate	Inhibitor	0.8392
CYP450 2C9 inhibitor	Non-inhibitor	0.8701
CYP450 2D6 inhibitor	Non-inhibitor	0.9064
CYP450 2C19 inhibitor	Non-inhibitor	0.8954
CYP450 3A4 inhibitor	Non-inhibitor	0.8353
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7081
Ames test	Non AMES toxic	0.9234
Carcinogenicity	Non-carcinogens	0.9484
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	3.0921 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7952
hERG inhibition (predictor II)	Non-inhibitor	0.6277

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-014i-7967010000-b3758c647fba3c682e47
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Learn more

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Learn more

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

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]
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]
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]
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]
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]
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

Deserpidine

Identification

Structure for Deserpidine (DB01089)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References