Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H40N2O9 |
Molecular Weight | 608.68 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COc1ccc2c3CCN4C[C@@]5([H])C[C@]([H])([C@@]([H])([C@]([H])([C@@]5([H])C[C@]4([H])c3[nH]c2c1)C(=O)OC)OC)OC(=O)c6cc(c(c(c6)OC)OC)OC
InChI
InChIKey=QEVHRUUCFGRFIF-MDEJGZGSSA-N
InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
Molecular Formula | C33H40N2O9 |
Molecular Weight | 608.68 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Reserpine is an alkaloid, isolated from the Rauwolfia serpentina plant and developed by Ciba pharma. Reserpine was approved by FDA for the treatment of hypertension and psychotic disorders. The drug exerts its effect by blocking two vesicular monoamine transporters, VMAT1 and VMAT2. The blockade results in vesicles that lose their ability to store neurotransmitter molecules. Neurotransmitters, thus retained in cytosol, are then neutralized by MAO.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15529229
Curator's Comment:: Later Ciba-Geigy and now Novartis.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1838 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23831411 |
160.0 nM [IC50] | ||
Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23831411 |
350.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | RESERPINE Approved UseMild essential hypertension; also useful as adjunctive therapy with other antihypertensive agents in the more severe forms of hypertension; relief of symptoms in agitated psychotic states (e.g., schizophrenia), primarily in those individuals unable to tolerate phenothiazine derivatives or in those who also require antihypertensive medication. Launch Date-4.66300797E11 |
|||
Palliative | RESERPINE Approved UseMild essential hypertension; also useful as adjunctive therapy with other antihypertensive agents in the more severe forms of hypertension; relief of symptoms in agitated psychotic states (e.g., schizophrenia), primarily in those individuals unable to tolerate phenothiazine derivatives or in those who also require antihypertensive medication. Launch Date-4.66300797E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30465727 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
RESERPINE plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.8 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30465727 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
RESERPINE plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30465727 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
RESERPINE plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
Dose | Population | Adverse events |
---|---|---|
0.25 mg 2 times / day multiple, oral Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, 41.2 years n = 60 Health Status: unhealthy Condition: cocaine dependence Age Group: 41.2 years Sex: M+F Population Size: 60 Sources: |
Disc. AE: Drowsiness, Light headedness... AEs leading to discontinuation/dose reduction: Drowsiness (1 patient) Sources: Light headedness (light, 1 patient) |
0.25 mg 2 times / day multiple, oral Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, 41.2 years n = 60 Health Status: unhealthy Condition: cocaine dependence Age Group: 41.2 years Sex: M+F Population Size: 60 Sources: |
Disc. AE: Upper abdominal pain, Postural hypotension... AEs leading to discontinuation/dose reduction: Upper abdominal pain (1 patient) Sources: Postural hypotension (1 patient) Electrocardiogram abnormal (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Drowsiness | 1 patient Disc. AE |
0.25 mg 2 times / day multiple, oral Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, 41.2 years n = 60 Health Status: unhealthy Condition: cocaine dependence Age Group: 41.2 years Sex: M+F Population Size: 60 Sources: |
Light headedness | light, 1 patient Disc. AE |
0.25 mg 2 times / day multiple, oral Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, 41.2 years n = 60 Health Status: unhealthy Condition: cocaine dependence Age Group: 41.2 years Sex: M+F Population Size: 60 Sources: |
Electrocardiogram abnormal | 1 patient Disc. AE |
0.25 mg 2 times / day multiple, oral Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, 41.2 years n = 60 Health Status: unhealthy Condition: cocaine dependence Age Group: 41.2 years Sex: M+F Population Size: 60 Sources: |
Postural hypotension | 1 patient Disc. AE |
0.25 mg 2 times / day multiple, oral Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, 41.2 years n = 60 Health Status: unhealthy Condition: cocaine dependence Age Group: 41.2 years Sex: M+F Population Size: 60 Sources: |
Upper abdominal pain | 1 patient Disc. AE |
0.25 mg 2 times / day multiple, oral Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, 41.2 years n = 60 Health Status: unhealthy Condition: cocaine dependence Age Group: 41.2 years Sex: M+F Population Size: 60 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [Activation >3.9811 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no | ||||
no | ||||
unlikely [Inhibition 20 uM] | ||||
weak [IC50 133 uM] | ||||
weak [IC50 133 uM] | ||||
weak [IC50 58 uM] | ||||
yes [IC50 2.8 uM] | ||||
yes [IC50 20.4 uM] | ||||
yes [IC50 26.3 uM] | ||||
yes [IC50 <0.03 uM] | ||||
yes [IC50 <0.2 uM] | ||||
yes [Inhibition 20 uM] | ||||
yes [Inhibition 20 uM] | ||||
yes [Ki 1.38 uM] | ||||
yes [Ki 295 uM] | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Transient global amnesia associated with cardiac arrhythmia and digitalis intoxication. | 1975 Sep-Oct |
|
The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved? | 1999 |
|
Reserpine modulates serotonin transporter mRNA levels in the rat brain. | 1999 |
|
The role of the sympathetic nervous system in the regulation of leptin synthesis in C57BL/6 mice. | 1999 Feb 12 |
|
The group II metabotropic glutamate receptor agonist, DCG-IV, alleviates akinesia following intranigral or intraventricular administration in the reserpine-treated rat. | 2000 Feb |
|
Effects of ropinirole on various parkinsonian models in mice, rats, and cynomolgus monkeys. | 2000 Mar |
|
Determination of PAH in food samples by HPLC with fluorimetric detection following sonication extraction without sample clean-up. | 2001 Aug |
|
Blood pressure-independent effect of angiotensin AT1 receptor blockade on renal endothelin-1 production in hypertensive uremic rats. | 2001 Aug |
|
Simultaneous determination of olanzapine, clozapine and demethylated metabolites in serum by on-line column-switching high-performance liquid chromatography. | 2001 Aug 5 |
|
The role of the D(2) dopamine receptor (D(2)R) in A(2A) adenosine receptor (A(2A)R)-mediated behavioral and cellular responses as revealed by A(2A) and D(2) receptor knockout mice. | 2001 Feb 13 |
|
Spectrophotometric, septrofluorimetric and LC determination of lisinopril. | 2001 Jul |
|
Striatal cannabinoid CB1 receptor mRNA expression is decreased in the reserpine-treated rat model of Parkinson's disease. | 2001 Jun |
|
Application of conventional UV, photodiode array (PDA) and fluorescence (FL) detection to analysis of phenolic acids in plant material and pharmaceutical preparations. | 2001 Mar |
|
[Study of diphacinone in biological samples by high performance liquid chromatography/diode array detector]. | 2001 May |
|
Peroxisome proliferator-activated receptor-gamma agonist troglitazone protects against nondiabetic glomerulosclerosis in rats. | 2001 May |
|
Determination of aliphatic amines in water by liquid chromatography using solid-phase extraction cartridges for preconcentration and derivatization. | 2001 Oct |
|
[Determination of nitidine in different parts of Zanthoxylum nitidum]. | 2001 Sep |
|
[Determination of ofloxacin in human fallopian tube, uterus and serum by high performance liquid chromatography]. | 2002 Feb |
|
Increase of free cysteine and citric acid in plant cells exposed to cobalt ions. | 2002 Jul |
|
A modified HPLC method for the determination of ochratoxin A by fluorescence detection. | 2002 Oct |
|
Determination of peptides and amino acids from wool and beer with sensitive fluorescent reagent 2-(9-carbazole)-ethyl chloroformate by reverse phase high-performance liquid chromotography and liquid chromotography mass spectrometry. | 2003 Feb 1 |
|
DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells. | 2003 Feb 24 |
|
Analysis of selected withanolides in plant extract by capillary electrochromatography and microemulsion electrokinetic chromatography. | 2003 Jan |
|
Growth-inhibitory effects of the chemopreventive agent indole-3-carbinol are increased in combination with the polyamine putrescine in the SW480 colon tumour cell line. | 2003 Jan 14 |
|
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition. | 2003 Jun |
|
The Seventh Report of the Joint National Committee on Prevention, Detection, Evaluation, and Treatment of High Blood Pressure: the JNC 7 report. | 2003 May 21 |
Patents
Sample Use Guides
Hypertension: In the average patient not receiving other antihypertensive agents, the usual initial dosage is 0.5 mg daily for 1 or 2 weeks. For maintenance, reduce to 0.1-0.25 mg daily. Psychiatric Disorders: the usual initial dosage is 0.5 mg daily, but may range from 0.1 mg to 1.0 mg. Adjust dosage upward or downward according to the patient's response.
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 20:57:12 UTC 2021
by
admin
on
Fri Jun 25 20:57:12 UTC 2021
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Record UNII |
8B1QWR724A
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
C02LA71
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NCI_THESAURUS |
C1744
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WHO-ATC |
C02AA52
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NDF-RT |
N0000175650
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WHO-ATC |
C02LA01
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NCI_THESAURUS |
C29747
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WHO-ATC |
C02LA51
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WHO-VATC |
QC02LA51
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WHO-ATC |
C02AA02
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NDF-RT |
N0000175640
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EPA PESTICIDE CODE |
123101
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WHO-VATC |
QC02AA02
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WHO-VATC |
QC02LA01
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WHO-VATC |
QC02AA52
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WHO-VATC |
QC02LA71
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LIVERTOX |
841
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IARC | Reserpine |
Code System | Code | Type | Description | ||
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M9535
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PRIMARY | Merck Index | ||
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282
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PRIMARY | |||
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2370
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PRIMARY | |||
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DB00206
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PRIMARY | |||
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5770
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PRIMARY | |||
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C803
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PRIMARY | |||
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4823
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PRIMARY | |||
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50-55-5
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PRIMARY | |||
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1601000
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PRIMARY | USP-RS | ||
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RESERPINE
Created by
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PRIMARY | Description: Small, white to pale beige crystals or a white to pale beige, crystalline powder; odourless. Solubility: Practically insoluble in water; soluble in 90 parts of acetone R; very slightly soluble in methanol R, ethanol (~750 g/l) TS, and ether R. Category: Neuroleptic; hypotensive. Storage: Reserpine should be kept in a well-closed container, protected from light.Additional information: Reserpine darkens slowly on exposure to light, but more rapidly in solution. Definition: Reserpine contains not less than 98.0% and not more than 102.0% of C33H40N2O9, calculated with reference to thedried substance. | ||
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8B1QWR724A
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PRIMARY | |||
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50-55-5
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PRIMARY | |||
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200-047-9
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PRIMARY | |||
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SUB10286MIG
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PRIMARY | |||
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213
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PRIMARY | |||
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CHEMBL772
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PRIMARY | |||
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9260
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PRIMARY | RxNorm | ||
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RESERPINE
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PRIMARY | |||
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D012110
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PRIMARY | |||
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Reserpine
Created by
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PRIMARY |
Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |