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.[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=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
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 |
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: Page: p.1115 |
unhealthy n = 13 Health Status: unhealthy Condition: Schizophrenia Sex: M Population Size: 13 Sources: Page: p.1115 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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| Inhibition of capacitative calcium entry is not obligatory for relaxation of the mouse anococcygeus by the NO/cyclic GMP signalling pathway. | 2001 Feb |
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| Protein kinase C suppresses spontaneous, transient, outwards K+ currents through modulation of the Na/Ca exchanger in guinea-pig gastric myocytes. | 2001 Jan |
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| Synexin and GTP increase surfactant secretion in permeabilized alveolar type II cells. | 2001 May |
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| Muscarinic excitation-contraction coupling mechanisms in tracheal and bronchial smooth muscles. | 2001 Sep |
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| Extensive skinning of cell membrane diminishes the force-inhibiting effect of okadaic acid on smooth muscles of Guinea pig hepatic portal vein. | 2002 Apr |
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| 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 Apr |
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| [Effect of inhibiting protein kinase C on calcium sensitivity of contractile apparatus of vascular smooth muscle during vasospasms of different origins]. | 2003 |
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| Antithetic regulation by beta-adrenergic receptors of Gq receptor signaling via phospholipase C underlies the airway beta-agonist paradox. | 2003 Aug |
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| CaM kinase IIalpha mediates norepinephrine-induced translocation of cytosolic phospholipase A2 to the nuclear envelope. | 2003 Jan 15 |
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| Measurement of the dissociation constant of Fluo-3 for Ca2+ in isolated rabbit cardiomyocytes using Ca2+ wave characteristics. | 2003 Jul |
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| Troponin I inhibitory peptide suppresses the force generation in smooth muscle by directly interfering with cross-bridge formation. | 2003 Jul 25 |
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| Pyrrolizidine alkaloids from Lithospermum canescens Lehm. | 2003 Mar-Apr |
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| Perforated patch recording of L-type calcium current with beta-escin in guinea pig ventricular myocytes. | 2003 Nov |
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| Dependence of Ca2+-induced contraction on ATP in alpha-toxin-permeabilized preparations of rat femoral artery. | 2003 Oct |
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| Lowdenic acid: a new antifungal polyketide-derived metabolite from a new fungicolous Verticillium sp. | 2003 Sep |
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| Characterization of alpha-soluble N-ethylmaleimide-sensitive fusion attachment protein in alveolar type II cells: implications in lung surfactant secretion. | 2003 Sep |
|
| Nitric oxide relaxes rat tail artery smooth muscle by cyclic GMP-independent decrease in calcium sensitivity of myofilaments. | 2004 Aug |
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| Inhibition by cytoplasmic nucleotides of a new cation channel in freshly isolated human and rat type II pneumocytes. | 2004 Dec |
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| Beta-escin diminishes voltage-gated calcium current rundown in perforated patch-clamp recordings from rat primary afferent neurons. | 2004 Oct 15 |
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| Ca2+-independent hypoxic vasorelaxation in porcine coronary artery. | 2005 Feb 1 |
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| Decrypting the biochemical function of an essential gene from Streptococcus pneumoniae using ThermoFluor technology. | 2005 Mar 25 |
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| Synthesis of deserpidine from reserpine. | 2005 Nov |
|
| 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 Jun |
|
| Involvement of Rho kinase and protein kinase C in carbachol-induced calcium sensitization in beta-escin skinned rat and guinea-pig bladders. | 2006 Jun |
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| Ranolazine improves abnormal repolarization and contraction in left ventricular myocytes of dogs with heart failure by inhibiting late sodium current. | 2006 May |
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| The shikonin derivatives and pyrrolizidine alkaloids in hairy root cultures of Lithospermum canescens (Michx.) Lehm. | 2006 Oct |
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| Acylation with diangeloyl groups at C21-22 positions in triterpenoid saponins is essential for cytotoxicity towards tumor cells. | 2007 Feb 1 |
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| Intracellular calcium stores in beta-escin skinned rat and guinea-pig bladders. | 2007 Jul 2 |
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| 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 |
|
| Liquid chromatography/tandem mass spectrometry method for the quantification of deserpidine in human plasma: Application to a pharmacokinetic study. | 2009 Oct 1 |
|
| Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1). | 2010 |
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| 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 |
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| Beta-escin has potent anti-allergic efficacy and reduces allergic airway inflammation. | 2010 May 21 |
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| 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
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m4189
Created by
admin on Sat Dec 16 10:58:41 GMT 2023 , Edited by admin on Sat Dec 16 10:58:41 GMT 2023
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PRIMARY | Merck Index | ||
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9X2GS858BC
Created by
admin on Sat Dec 16 10:58:41 GMT 2023 , Edited by admin on Sat Dec 16 10:58:41 GMT 2023
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119506-01-3
Created by
admin on Sat Dec 16 10:58:41 GMT 2023 , Edited by admin on Sat Dec 16 10:58:41 GMT 2023
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70501720
Created by
admin on Sat Dec 16 10:58:41 GMT 2023 , Edited by admin on Sat Dec 16 10:58:41 GMT 2023
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
