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
| 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 |
| 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 |
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 |
|
| Protein kinase C suppresses spontaneous, transient, outwards K+ currents through modulation of the Na/Ca exchanger in guinea-pig gastric myocytes. | 2001 Jan |
|
| Synexin and GTP increase surfactant secretion in permeabilized alveolar type II cells. | 2001 May |
|
| Muscarinic excitation-contraction coupling mechanisms in tracheal and bronchial smooth muscles. | 2001 Sep |
|
| [Effect of inhibiting protein kinase C on calcium sensitivity of contractile apparatus of vascular smooth muscle during vasospasms of different origins]. | 2003 |
|
| Antithetic regulation by beta-adrenergic receptors of Gq receptor signaling via phospholipase C underlies the airway beta-agonist paradox. | 2003 Aug |
|
| CaM kinase IIalpha mediates norepinephrine-induced translocation of cytosolic phospholipase A2 to the nuclear envelope. | 2003 Jan 15 |
|
| Dependence of Ca2+-induced contraction on ATP in alpha-toxin-permeabilized preparations of rat femoral artery. | 2003 Oct |
|
| Inhibition by cytoplasmic nucleotides of a new cation channel in freshly isolated human and rat type II pneumocytes. | 2004 Dec |
|
| Involvement of Rho kinase and protein kinase C in carbachol-induced calcium sensitization in beta-escin skinned rat and guinea-pig bladders. | 2006 Jun |
|
| The shikonin derivatives and pyrrolizidine alkaloids in hairy root cultures of Lithospermum canescens (Michx.) Lehm. | 2006 Oct |
|
| Acylation with diangeloyl groups at C21-22 positions in triterpenoid saponins is essential for cytotoxicity towards tumor cells. | 2007 Feb 1 |
|
| Brain Activation by Peptide Pro-Leu-Gly-NH(2) (MIF-1). | 2010 |
|
| Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response. | 2010 Sep 13 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:58:41 GMT 2023
by
admin
on
Sat Dec 16 10:58:41 GMT 2023
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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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9X2GS858BC
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70501720
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