U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C32H38N2O8
Molecular Weight 578.6527
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESERPIDINE

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@@]4([H])N(CCC5=C4NC6=C5C=CC=C6)C2

InChI

InChIKey=CVBMAZKKCSYWQR-WCGOZPBSSA-N
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

HIDE SMILES / InChI
Molecular Formula C32H38N2O8
Molecular Weight 578.6527
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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. 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. 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.

CNS Activity

Originator

Approval Year

1957
114
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
HARMONYL

Approved Use

For the treatment of hypertension.

Launch Date

-4.00896E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
172 pg/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S1570023209004073
0.25 mg single, oral
dose: 0.25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESERPIDINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4193 pg × h/mL
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S1570023209004073
0.25 mg single, oral
dose: 0.25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESERPIDINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
42.9 h
EXPERIMENT
https://www.sciencedirect.com/science/article/pii/S1570023209004073
0.25 mg single, oral
dose: 0.25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESERPIDINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
6 mg 3 times / day multiple, oral (max)
Highest studied dose
Dose: 6 mg, 3 times / day
Route: oral
Route: multiple
Dose: 6 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13817998
Page: p.1115
unhealthy
n = 13
Health Status: unhealthy
Condition: Schizophrenia
Sex: M
Population Size: 13
Sources:
https://pubmed.ncbi.nlm.nih.gov/13817998
Page: p.1115
Sources:
https://pubmed.ncbi.nlm.nih.gov/13817998
Page: p.1115
Sourcing

Sourcing

Vendor/AggregatorIDURL
AHH Chemical co.,ltd
MT-00050
http://www.ahhchemical.com/product/MT-00050.html
AK Scientific, Inc. (AKSCI)
71845
http://www.aksci.com/item_detail.php?cat=71845
Achemtek
0104-012320
http://www.achemtek.com/131-01-1
Ambinter
Amb10974932
http://www.ambinter.com/reference/10974932
Aurora Fine Chemicals LLC
A13.107.779
http://online.aurorafinechemicals.com/info?ID=A13.107.779
AvaChem Scientific
3055
http://www.avachem.com/productSearch.asp?3055
BioSynth
J-005923
https://www.biosynth.com/en/products/all-products/products/J-005923.html
Chem Scene
CS-0028177
http://www.chemscene.com/131-01-1.html
ChemMol
49426650
http://www.chemmol.com/chemmol/49426650.html
Chemspace
CSSB00000054260
https://chem-space.com/CSSB00000054260
Hairui
HR130666
http://www.hairuichem.com/en/product/131-01-1.html
LGC Standards
LGCFOR1654.00
https://www.lgcstandards.com/US/en/p/LGCFOR1654.00
Lab Network
LN00191104
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00191104
Matrix Scientific
94177
https://www.matrixscientific.com/094177.html
MedChem Express
HY-107339
https://www.medchemexpress.com/deserpidine.html
MuseChem
R023620
https://www.musechem.com/product/R023620.html
OChem
4570
http://www.ocheminc.com/index.php?act=psearch&pid=131D011
Sigma-Aldrich
PH006815_ALDRICH
https://www.sigmaaldrich.com/catalog/product/aldrich/ph006815
eNovation Chemicals
D673943
https://www.enovationchem.com/ProductDetails.asp?ProductID=D673943
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Protein kinase C suppresses spontaneous, transient, outwards K+ currents through modulation of the Na/Ca exchanger in guinea-pig gastric myocytes.
2001 Jan
Muscarinic excitation-contraction coupling mechanisms in tracheal and bronchial smooth muscles.
2001 Sep
Extensive skinning of cell membrane diminishes the force-inhibiting effect of okadaic acid on smooth muscles of Guinea pig hepatic portal vein.
2002 Apr
Dependence of Ca2+-induced contraction on ATP in alpha-toxin-permeabilized preparations of rat femoral artery.
2003 Oct
Nitric oxide relaxes rat tail artery smooth muscle by cyclic GMP-independent decrease in calcium sensitivity of myofilaments.
2004 Aug
Inhibition by cytoplasmic nucleotides of a new cation channel in freshly isolated human and rat type II pneumocytes.
2004 Dec
Ca2+-independent hypoxic vasorelaxation in porcine coronary artery.
2005 Feb 1
Synthesis of deserpidine from reserpine.
2005 Nov
Involvement of Rho kinase and protein kinase C in carbachol-induced calcium sensitization in beta-escin skinned rat and guinea-pig bladders.
2006 Jun
Intracellular calcium stores in beta-escin skinned rat and guinea-pig bladders.
2007 Jul 2
Dynamic modulation of intracellular glucose imaged in single cells using a FRET-based glucose nanosensor.
2008 May
Beta-escin, a natural triterpenoid saponin from Chinese horse chestnut seeds, depresses HL-60 human leukaemia cell proliferation and induces apoptosis.
2008 Sep
Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1).
2010
Calcium sensitization induced by sodium fluoride in permeabilized rat mesenteric arteries.
2010 Feb
Identification of beta-escin as a novel inhibitor of signal transducer and activator of transcription 3/Janus-activated kinase 2 signaling pathway that suppresses proliferation and induces apoptosis in human hepatocellular carcinoma cells.
2010 Jul
Beta-escin has potent anti-allergic efficacy and reduces allergic airway inflammation.
2010 May 21
KMUP-1 ameliorates monocrotaline-induced pulmonary arterial hypertension through the modulation of Ca2+ sensitization and K+-channel.
2010 May 8
Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response.
2010 Sep 13
Patents

Patents

JP2007530467A
3
US20080242864
3
US2982769
3

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:33 UTC 2023
Edited
by admin
on Fri Dec 15 15:13:33 UTC 2023
Record UNII
9016E3VB47
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESERPIDINE
INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
DESERPIDINE COMPONENT OF ENDURONYL
Common Name English
deserpidine [INN]
Common Name English
ORETICYL FORTE COMPONENT DESERPIDINE
Common Name English
HALMONYL
Brand Name English
DESERPIDINE [MI]
Common Name English
METHYL 17.ALPHA.-METHOXY-18.BETA.-((3,4,5-TRIMETHOXYBENZOYL)OXY)-3.BETA.,20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLATE
Common Name English
NSC-72138
Code English
DESERPIDINE COMPONENT OF ORETICYL FORTE
Common Name English
DESERPIDINE [MART.]
Common Name English
HARMONYL
Brand Name English
DESERPIDINE [ORANGE BOOK]
Common Name English
DESERPIDINE, (-)-
Common Name English
Methyl 18β-hydroxy-17α-methoxy-3β,20α-yohimban-16β-carboxylate, 3,4,5-trimethoxybenzoate (ester)
Common Name English
Deserpidine [WHO-DD]
Common Name English
ENDURONYL COMPONENT DESERPIDINE
Common Name English
DESERPIDINE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C270
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
WHO-ATC C02LA03
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
NDF-RT N0000175650
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
WHO-VATC QC02AA05
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
NDF-RT N0000175640
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
WHO-VATC QC02LA03
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
LIVERTOX 281
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
WHO-ATC C02AA05
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID8020383
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
PRIMARY
DRUG BANK
DB01089
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PRIMARY
SMS_ID
100000083187
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PRIMARY
IUPHAR
7064
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PRIMARY
ECHA (EC/EINECS)
205-004-8
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PRIMARY
DRUG CENTRAL
810
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PRIMARY
MESH
C100104
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PRIMARY
MERCK INDEX
m4189
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PRIMARY Merck Index
NCI_THESAURUS
C61699
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PRIMARY
INN
656
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PRIMARY
CAS
131-01-1
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
PRIMARY
FDA UNII
9016E3VB47
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200515
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PRIMARY
NSC
72138
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PRIMARY
PUBCHEM
8550
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
PRIMARY
WIKIPEDIA
DESERPIDINE
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
PRIMARY
RXCUI
62174
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
PRIMARY RxNorm
EVMPD
SUB06992MIG
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
PRIMARY
CHEBI
27478
Created by admin on Fri Dec 15 15:13:33 UTC 2023 , Edited by admin on Fri Dec 15 15:13:33 UTC 2023
PRIMARY
Related Record Type Details
Structure of DESERPIDINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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