DESERPIDINE HYDROCHLORIDE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H38N2O8.ClH
Molecular Weight	615.114
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[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=YCNOGQOHKRDAHJ-UZXCFUCJSA-N

InChI=1S/C32H38N2O8.ClH/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;1H/t18-,21+,23-,26-,27+,30+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: https://www.drugbank.ca/drugs/DB01089

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

Targets

Primary Target	Pharmacology	Condition	Potency
Synaptic vesicular amine transporter 57 Target ID: CHEMBL1893 Sources: https://www.drugbank.ca/drugs/DB01089	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.drugbank.ca/drugs/DB01089	Primary		Approved 8429	HARMONYL Approved Use For the treatment of hypertension. Launch Date 1957

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Inhibition of capacitative calcium entry is not obligatory for relaxation of the mouse anococcygeus by the NO/cyclic GMP signalling pathway.	2001 Feb	11181421
Extensive skinning of cell membrane diminishes the force-inhibiting effect of okadaic acid on smooth muscles of Guinea pig hepatic portal vein.	2002 Apr	12139772
CaM kinase IIalpha mediates norepinephrine-induced translocation of cytosolic phospholipase A2 to the nuclear envelope.	2003 Jan 15	12482921
Dependence of Ca2+-induced contraction on ATP in alpha-toxin-permeabilized preparations of rat femoral artery.	2003 Oct	14578585
Inhibition by cytoplasmic nucleotides of a new cation channel in freshly isolated human and rat type II pneumocytes.	2004 Dec	15321785
Ranolazine improves abnormal repolarization and contraction in left ventricular myocytes of dogs with heart failure by inhibiting late sodium current.	2006 May	16686675
Acylation with diangeloyl groups at C21-22 positions in triterpenoid saponins is essential for cytotoxicity towards tumor cells.	2007 Feb 1	17092489
Intracellular calcium stores in beta-escin skinned rat and guinea-pig bladders.	2007 Jul 2	17475242
Dynamic modulation of intracellular glucose imaged in single cells using a FRET-based glucose nanosensor.	2008 May	18071748
Beta-escin, a natural triterpenoid saponin from Chinese horse chestnut seeds, depresses HL-60 human leukaemia cell proliferation and induces apoptosis.	2008 Sep	18718126
Liquid chromatography/tandem mass spectrometry method for the quantification of deserpidine in human plasma: Application to a pharmacokinetic study.	2009 Oct 1	19620026
Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1).	2010	20721355
Calcium sensitization induced by sodium fluoride in permeabilized rat mesenteric arteries.	2010 Feb	20221280
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	20378717
Beta-escin has potent anti-allergic efficacy and reduces allergic airway inflammation.	2010 May 21	20487574
KMUP-1 ameliorates monocrotaline-induced pulmonary arterial hypertension through the modulation of Ca2+ sensitization and K+-channel.	2010 May 8	20303989
Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response.	2010 Sep 13	20936178

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:06:41 GMT 2023` Edited by `admin` on `Sat Dec 16 10:06:41 GMT 2023`
Record UNII	6LPC48045D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DESERPIDINE HYDROCHLORIDE

Common Name

English

CANESCINE HYDROCHLORIDE

Common Name

English

YOHIMBAN-16-CARBOXYLIC ACID, 17-METHOXY-18-((3,4,5-TRIMETHOXYBENZOYL)OXY)-, METHYL ESTER, MONOHYDROCHLORIDE, (3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-

Systematic Name

English

DESERPIDINE HYDROCHLORIDE, (-)-

Common Name

English

DESERPIDINE HYDROCHLORIDE [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

73425400