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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H40N2O9.H2O4S
Molecular Weight 706.7596
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RESERPINE SULFATE

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.OS(=O)(=O)O

InChI

InChIKey=FAXJAGWYPFUKMP-BQTSRIDJSA-N
InChI=1S/C33H40N2O9.H2O4S/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;1-5(2,3)4/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3;(H2,1,2,3,4)/t18-,22+,24-,27-,28+,31+;/m1./s1

HIDE SMILES / InChI

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

Molecular Formula H2O4S
Molecular Weight 98.0796
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: Later Ciba-Geigy and now Novartis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
160.0 nM [IC50]
350.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RESERPINE

Approved Use

Mild 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 Use

Mild 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

Cmax

ValueDoseCo-administeredAnalytePopulation
0.2 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
4.8 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
23.6 h
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

Doses

DosePopulationAdverse 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)
Light headedness (light, 1 patient)
Sources:
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)
Postural hypotension (1 patient)
Electrocardiogram abnormal (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
The effect of 5-hydroxytrytamine synthesis inhibitors on neuroleptic-induced catalepsy in rats.
1975
The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved?
1999
Reserpine modulates serotonin transporter mRNA levels in the rat brain.
1999
Effects of ropinirole on various parkinsonian models in mice, rats, and cynomolgus monkeys.
2000 Mar
Role of prolactin in chloro-S-triazine rat mammary tumorigenesis.
2000 Nov
SCH 58261, an A(2A) adenosine receptor antagonist, counteracts parkinsonian-like muscle rigidity in rats.
2001 Aug
Trends in antihypertensive drug use among orally treated diabetic patients, in France between 1981 and 1992. Impact of guidelines and new drugs.
2001 Dec
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
Determination of vitamin B(6) in cooked sausages.
2001 Jan
Separation of the insecticidal pyrethrin esters by capillary electrochromatography.
2001 Jan 5
Liquid chromatographic method with electrochemical detection for determination of cisapride in serum.
2001 Jan-Feb
Analysis of phenolic constituents of biological interest in red wines by high-performance liquid chromatography.
2001 Jul 13
Striatal cannabinoid CB1 receptor mRNA expression is decreased in the reserpine-treated rat model of Parkinson's disease.
2001 Jun
[Recognition and quantitative contrast characteristic components for root of Chinese angelica].
2001 Mar
[Determination of bifonazole in cream by high performance liquid chromatography].
2001 May
[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 nitidine in different parts of Zanthoxylum nitidum].
2001 Sep
Identification of mammary carcinogens in rodent bioassays.
2002
Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids.
2002 Apr
Temperature effect on peak width and column efficiency in subcritical water chromatography.
2002 Feb
Simultaneous determination of cloricromene and its active metabolite in rabbit aqueous humor by high-performance liquid chromatography.
2002 Feb 5
Development and validation of a reversed-phase high-performance liquid chromatographic method for the determination of ethyl-3-(N-n-butyl-N-acetyl)aminopropionate in an insect repellent semi-solid formulation.
2002 Feb 8
[Application of fingerprint chromatogram in quality control of Shen-Mai injection].
2002 Jul
Increase of free cysteine and citric acid in plant cells exposed to cobalt ions.
2002 Jul
Validated HPLC method for determination of sennosides A and B in senna tablets.
2002 Jul 31
Rapid high-performance liquid chromatographic assay of dorzolamide in rabbit aqueous humor.
2002 Jun
Determination of ethylenediamine tetraacetic acid in injection forms by ion-pair chromatography.
2002 Jun 15
[The effect of shourong compound formula on levels of dopamine and its metabolites in brain of Parkinson's disease mice induced by reserpine].
2002 May
LC-MS/MS determination of a farnesyl transferase inhibitor in human plasma and urine.
2002 Nov 7
Determination of undecylenic and sorbic acids in cosmetic preparations by high performance liquid chromatography with electrochemical detection.
2002 Nov 7
The physiology of overwintering in a turtle that occupies multiple habitats, the common snapping turtle (Chelydra serpentina).
2002 Sep-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
Analysis of flecainide and two metabolites in biological specimens by HPLC: application to a fatal intoxication.
2003 Jan-Feb
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:45:34 UTC 2021
Edited
by admin
on Sat Jun 26 13:45:34 UTC 2021
Record UNII
KM25ND9T2H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RESERPINE SULFATE
Common Name English
YOHIMBAN-16-CARBOXYLIC ACID, 11,17-DIMETHOXY-18-((3,4,5-TRIMETHOXYBENZOYL)OXY)-, METHYL ESTER, (3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-, SULFATE (1:1)
Systematic Name English
3.BETA.,20.ALPHA.-YOHIMBAN-16.BETA.-CARBOXYLIC ACID, 18.BETA.-HYDROXY-11,17.ALPHA.-DIMETHOXY-, METHYL ESTER, 3,4,5-TRIMETHOXYBENZOATE (ESTER), SULFATE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
KM25ND9T2H
Created by admin on Sat Jun 26 13:45:35 UTC 2021 , Edited by admin on Sat Jun 26 13:45:35 UTC 2021
PRIMARY
CAS
6105-95-9
Created by admin on Sat Jun 26 13:45:35 UTC 2021 , Edited by admin on Sat Jun 26 13:45:35 UTC 2021
PRIMARY
PUBCHEM
133082397
Created by admin on Sat Jun 26 13:45:35 UTC 2021 , Edited by admin on Sat Jun 26 13:45:35 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE