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
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
DescriptionSources: https://www.drugbank.ca/drugs/DB01089
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 |
---|---|---|---|
Target ID: CHEMBL1893 Sources: https://www.drugbank.ca/drugs/DB01089 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.drugbank.ca/drugs/DB01089 |
Primary | HARMONYL Approved UseFor the treatment of hypertension. Launch Date-4.00896E11 |
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 |
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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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CaM kinase IIalpha mediates norepinephrine-induced translocation of cytosolic phospholipase A2 to the nuclear envelope. | 2003 Jan 15 |
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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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Characterization of alpha-soluble N-ethylmaleimide-sensitive fusion attachment protein in alveolar type II cells: implications in lung surfactant secretion. | 2003 Sep |
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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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Liquid chromatography/tandem mass spectrometry method for the quantification of deserpidine in human plasma: Application to a pharmacokinetic study. | 2009 Oct 1 |
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Calcium sensitization induced by sodium fluoride in permeabilized rat mesenteric arteries. | 2010 Feb |
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KMUP-1 ameliorates monocrotaline-induced pulmonary arterial hypertension through the modulation of Ca2+ sensitization and K+-channel. | 2010 May 8 |
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Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response. | 2010 Sep 13 |
Patents
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C270
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WHO-ATC |
C02LA03
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NDF-RT |
N0000175650
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WHO-VATC |
QC02AA05
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NDF-RT |
N0000175640
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WHO-VATC |
QC02LA03
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LIVERTOX |
281
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WHO-ATC |
C02AA05
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Code System | Code | Type | Description | ||
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DTXSID8020383
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DB01089
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100000083187
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7064
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205-004-8
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810
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C100104
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m4189
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C61699
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656
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131-01-1
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9016E3VB47
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CHEMBL1200515
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72138
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8550
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DESERPIDINE
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62174
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SUB06992MIG
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27478
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ACTIVE MOIETY