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 Date1957 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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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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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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[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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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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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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Nitric oxide relaxes rat tail artery smooth muscle by cyclic GMP-independent decrease in calcium sensitivity of myofilaments. | 2004 Aug |
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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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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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Beta-escin, a natural triterpenoid saponin from Chinese horse chestnut seeds, depresses HL-60 human leukaemia cell proliferation and induces apoptosis. | 2008 Sep |
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Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1). | 2010 |
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Beta-escin has potent anti-allergic efficacy and reduces allergic airway inflammation. | 2010 May 21 |
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Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response. | 2010 Sep 13 |
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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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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