Deserpidine
Identification
- Name
- Deserpidine
- Accession Number
- DB01089
- Description
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
Structure for Deserpidine (DB01089)
- 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.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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 inhibitorHumans - 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Symptoms of overdose include dizziness or drowsiness (severe), flushing of skin, pinpoint pupils of eyes and slowed pulse.
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAcebutolol 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 Aliskiren may increase the hypotensive activities of Deserpidine. Almotriptan Almotriptan may decrease the antihypertensive activities of Deserpidine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- 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 Region Image Enduronyl Deserpidine (0.25 mg/1) + Methyclothiazide (5 mg/1) Tablet Oral Abbvie 1961-08-01 2002-04-30 US 
Enduronyl Deserpidine (0.25 mg/1) + Methyclothiazide (5 mg/1) Tablet Oral Physicians Total Care, Inc. 1961-08-01 2006-12-31 US Enduronyl Forte Deserpidine (0.5 mg/1) + Methyclothiazide (5 mg/1) Tablet Oral Abbvie 1961-08-01 2001-04-30 US
Categories
- ATC Codes
- C02LA03 — Deserpidine and diuretics
- C02LA — Rauwolfia alkaloids and diuretics in combination
- C02L — ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
- C02 — ANTIHYPERTENSIVES
- C — CARDIOVASCULAR SYSTEM
- 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)
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[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate
- SMILES
- [H][[email protected]]12C[[email protected]@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[[email protected]](OC)[[email protected]@H](C(=O)OC)[[email protected]@]1([H])C[[email protected]@]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
- 62174
- ChEBI
- 27478
- ChEMBL
- CHEMBL1200515
- ZINC
- ZINC000004097186
- Therapeutic Targets Database
- DAP000909
- PharmGKB
- PA164742966
- Wikipedia
- Deserpidine
Clinical Trials
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) 7.57 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 62.59 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
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
- 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. [PubMed:17559790]
- 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. [PubMed:8525459]
- 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. [PubMed:1438304]
- 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. [PubMed:20176067]
- 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. [PubMed:11134]
- 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. [PubMed:574544]
Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51
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