Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C32H38N2O8.C2H2O4 |
| Molecular Weight | 668.6876 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C(O)=O.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=DUKYLQQMCIZGHM-UZXCFUCJSA-N
InChI=1S/C32H38N2O8.C2H2O4/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;3-1(4)2(5)6/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3;(H,3,4)(H,5,6)/t18-,21+,23-,26-,27+,30+;/m1./s1
| 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 |
| Molecular Formula | C2H2O4 |
| Molecular Weight | 90.0349 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
172 pg/mL |
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 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
42.9 h |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response. | 2010-09-13 |
|
| 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 |
|
| Beta-escin has potent anti-allergic efficacy and reduces allergic airway inflammation. | 2010-05-21 |
|
| KMUP-1 ameliorates monocrotaline-induced pulmonary arterial hypertension through the modulation of Ca2+ sensitization and K+-channel. | 2010-05-08 |
|
| Calcium sensitization induced by sodium fluoride in permeabilized rat mesenteric arteries. | 2010-02 |
|
| Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1). | 2010 |
|
| Liquid chromatography/tandem mass spectrometry method for the quantification of deserpidine in human plasma: Application to a pharmacokinetic study. | 2009-10-01 |
|
| Beta-escin, a natural triterpenoid saponin from Chinese horse chestnut seeds, depresses HL-60 human leukaemia cell proliferation and induces apoptosis. | 2008-09 |
|
| Dynamic modulation of intracellular glucose imaged in single cells using a FRET-based glucose nanosensor. | 2008-05 |
|
| Intracellular calcium stores in beta-escin skinned rat and guinea-pig bladders. | 2007-07-02 |
|
| Acylation with diangeloyl groups at C21-22 positions in triterpenoid saponins is essential for cytotoxicity towards tumor cells. | 2007-02-01 |
|
| The shikonin derivatives and pyrrolizidine alkaloids in hairy root cultures of Lithospermum canescens (Michx.) Lehm. | 2006-10 |
|
| 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 |
|
| Involvement of Rho kinase and protein kinase C in carbachol-induced calcium sensitization in beta-escin skinned rat and guinea-pig bladders. | 2006-06 |
|
| Ranolazine improves abnormal repolarization and contraction in left ventricular myocytes of dogs with heart failure by inhibiting late sodium current. | 2006-05 |
|
| Synthesis of deserpidine from reserpine. | 2005-11 |
|
| Decrypting the biochemical function of an essential gene from Streptococcus pneumoniae using ThermoFluor technology. | 2005-03-25 |
|
| Ca2+-independent hypoxic vasorelaxation in porcine coronary artery. | 2005-02-01 |
|
| Inhibition by cytoplasmic nucleotides of a new cation channel in freshly isolated human and rat type II pneumocytes. | 2004-12 |
|
| Beta-escin diminishes voltage-gated calcium current rundown in perforated patch-clamp recordings from rat primary afferent neurons. | 2004-10-15 |
|
| Nitric oxide relaxes rat tail artery smooth muscle by cyclic GMP-independent decrease in calcium sensitivity of myofilaments. | 2004-08 |
|
| Perforated patch recording of L-type calcium current with beta-escin in guinea pig ventricular myocytes. | 2003-11 |
|
| Dependence of Ca2+-induced contraction on ATP in alpha-toxin-permeabilized preparations of rat femoral artery. | 2003-10 |
|
| Lowdenic acid: a new antifungal polyketide-derived metabolite from a new fungicolous Verticillium sp. | 2003-09 |
|
| Characterization of alpha-soluble N-ethylmaleimide-sensitive fusion attachment protein in alveolar type II cells: implications in lung surfactant secretion. | 2003-09 |
|
| Antithetic regulation by beta-adrenergic receptors of Gq receptor signaling via phospholipase C underlies the airway beta-agonist paradox. | 2003-08 |
|
| Troponin I inhibitory peptide suppresses the force generation in smooth muscle by directly interfering with cross-bridge formation. | 2003-07-25 |
|
| Measurement of the dissociation constant of Fluo-3 for Ca2+ in isolated rabbit cardiomyocytes using Ca2+ wave characteristics. | 2003-07 |
|
| Pyrrolizidine alkaloids from Lithospermum canescens Lehm. | 2003-04-25 |
|
| CaM kinase IIalpha mediates norepinephrine-induced translocation of cytosolic phospholipase A2 to the nuclear envelope. | 2003-01-15 |
|
| [Effect of inhibiting protein kinase C on calcium sensitivity of contractile apparatus of vascular smooth muscle during vasospasms of different origins]. | 2003 |
|
| Extensive skinning of cell membrane diminishes the force-inhibiting effect of okadaic acid on smooth muscles of Guinea pig hepatic portal vein. | 2002-04 |
|
| 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 |
|
| Muscarinic excitation-contraction coupling mechanisms in tracheal and bronchial smooth muscles. | 2001-09 |
|
| Synexin and GTP increase surfactant secretion in permeabilized alveolar type II cells. | 2001-05 |
|
| Inhibition of capacitative calcium entry is not obligatory for relaxation of the mouse anococcygeus by the NO/cyclic GMP signalling pathway. | 2001-02 |
|
| Protein kinase C suppresses spontaneous, transient, outwards K+ currents through modulation of the Na/Ca exchanger in guinea-pig gastric myocytes. | 2001-01 |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991-01-01 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:33:00 GMT 2025
by
admin
on
Mon Mar 31 23:33:00 GMT 2025
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| Record UNII |
9X2GS858BC
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| Record Status |
Validated (UNII)
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| Record Version |
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m4189
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PRIMARY | Merck Index | ||
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9X2GS858BC
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119506-01-3
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70501720
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