DESERPIDINE

US Previously Marketed

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 Search

SMILES

CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C(NC5=C4C=CC=C5)[C@H]3C[C@@H]2[C@@H]1C(=O)OC)OC(=O)C6=CC(OC)=C(OC)C(OC)=C6

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
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 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.drugbank.ca/drugs/DB01089	Primary		Approved 8583	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 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	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13817998	Sources: https://pubmed.ncbi.nlm.nih.gov/13817998

Sourcing

Vendor/Aggregator	ID	URL
Achemtek	0104-012320	http://www.achemtek.com/131-01-1
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
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
eNovation Chemicals	D673943	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673943
Hairui	HR130666	http://www.hairuichem.com/en/product/131-01-1.html
Lab Network	LN00191104	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00191104
LGC Standards	LGCFOR1654.00	https://www.lgcstandards.com/US/en/p/LGCFOR1654.00
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

PubMed

Title	Date	PubMed
Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response.	2010-09-13	20936178
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.	2010-07	20378717
Beta-escin has potent anti-allergic efficacy and reduces allergic airway inflammation.	2010-05-21	20487574
KMUP-1 ameliorates monocrotaline-induced pulmonary arterial hypertension through the modulation of Ca2+ sensitization and K+-channel.	2010-05-08	20303989
Calcium sensitization induced by sodium fluoride in permeabilized rat mesenteric arteries.	2010-02	20221280
Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1).	2010	20721355
Liquid chromatography/tandem mass spectrometry method for the quantification of deserpidine in human plasma: Application to a pharmacokinetic study.	2009-10-01	19620026
Beta-escin, a natural triterpenoid saponin from Chinese horse chestnut seeds, depresses HL-60 human leukaemia cell proliferation and induces apoptosis.	2008-09	18718126
Dynamic modulation of intracellular glucose imaged in single cells using a FRET-based glucose nanosensor.	2008-05	18071748
Intracellular calcium stores in beta-escin skinned rat and guinea-pig bladders.	2007-07-02	17475242
Acylation with diangeloyl groups at C21-22 positions in triterpenoid saponins is essential for cytotoxicity towards tumor cells.	2007-02-01	17092489
The shikonin derivatives and pyrrolizidine alkaloids in hairy root cultures of Lithospermum canescens (Michx.) Lehm.	2006-10	16670900
Beta-escin inhibits colonic aberrant crypt foci formation in rats and regulates the cell cycle growth by inducing p21(waf1/cip1) in colon cancer cells.	2006-06	16818504
Involvement of Rho kinase and protein kinase C in carbachol-induced calcium sensitization in beta-escin skinned rat and guinea-pig bladders.	2006-06	16565731
Ranolazine improves abnormal repolarization and contraction in left ventricular myocytes of dogs with heart failure by inhibiting late sodium current.	2006-05	16686675
Synthesis of deserpidine from reserpine.	2005-11	16309312
Decrypting the biochemical function of an essential gene from Streptococcus pneumoniae using ThermoFluor technology.	2005-03-25	15634672
Ca2+-independent hypoxic vasorelaxation in porcine coronary artery.	2005-02-01	15564284
Inhibition by cytoplasmic nucleotides of a new cation channel in freshly isolated human and rat type II pneumocytes.	2004-12	15321785
Beta-escin diminishes voltage-gated calcium current rundown in perforated patch-clamp recordings from rat primary afferent neurons.	2004-10-15	15351522
Nitric oxide relaxes rat tail artery smooth muscle by cyclic GMP-independent decrease in calcium sensitivity of myofilaments.	2004-08	15193864
Perforated patch recording of L-type calcium current with beta-escin in guinea pig ventricular myocytes.	2003-11	14627491
Dependence of Ca2+-induced contraction on ATP in alpha-toxin-permeabilized preparations of rat femoral artery.	2003-10	14578585
Lowdenic acid: a new antifungal polyketide-derived metabolite from a new fungicolous Verticillium sp.	2003-09	14510612
Characterization of alpha-soluble N-ethylmaleimide-sensitive fusion attachment protein in alveolar type II cells: implications in lung surfactant secretion.	2003-09	12663329
Antithetic regulation by beta-adrenergic receptors of Gq receptor signaling via phospholipase C underlies the airway beta-agonist paradox.	2003-08	12925702
Troponin I inhibitory peptide suppresses the force generation in smooth muscle by directly interfering with cross-bridge formation.	2003-07-25	12859945
Measurement of the dissociation constant of Fluo-3 for Ca2+ in isolated rabbit cardiomyocytes using Ca2+ wave characteristics.	2003-07	12767887
Pyrrolizidine alkaloids from Lithospermum canescens Lehm.	2003-04-25	12710723
CaM kinase IIalpha mediates norepinephrine-induced translocation of cytosolic phospholipase A2 to the nuclear envelope.	2003-01-15	12482921
[Effect of inhibiting protein kinase C on calcium sensitivity of contractile apparatus of vascular smooth muscle during vasospasms of different origins].	2003	14965035
Extensive skinning of cell membrane diminishes the force-inhibiting effect of okadaic acid on smooth muscles of Guinea pig hepatic portal vein.	2002-04	12139772
Xestospongin C, a novel blocker of IP3 receptor, attenuates the increase in cytosolic calcium level and degranulation that is induced by antigen in RBL-2H3 mast cells.	2002-04	11959799
Muscarinic excitation-contraction coupling mechanisms in tracheal and bronchial smooth muscles.	2001-09	11509509
Synexin and GTP increase surfactant secretion in permeabilized alveolar type II cells.	2001-05	11290524
Inhibition of capacitative calcium entry is not obligatory for relaxation of the mouse anococcygeus by the NO/cyclic GMP signalling pathway.	2001-02	11181421
Protein kinase C suppresses spontaneous, transient, outwards K+ currents through modulation of the Na/Ca exchanger in guinea-pig gastric myocytes.	2001-01	11214600
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991-01-01	1710653

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 `Mon Mar 31 17:50:50 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:50 GMT 2025`
Record UNII	9016E3VB47
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HALMONYL

Preferred Name

English

DESERPIDINE

Official Name

English

deserpidine [INN]

Common Name

English

ORETICYL FORTE COMPONENT DESERPIDINE

Common 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 [MART.]

Common Name

English

HARMONYL

Brand Name

English

DESERPIDINE [ORANGE BOOK]

Common Name

English

DESERPIDINE, (-)-

Common Name

English

Methyl 18?-hydroxy-17?-methoxy-3?,20?-yohimban-16?-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