Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C33H40N2O9.H3O4P |
| Molecular Weight | 706.6739 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(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=CC(OC)=CC=C56)C2
InChI
InChIKey=DDFUAKBZKZESMV-BQTSRIDJSA-N
InChI=1S/C33H40N2O9.H3O4P/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;(H3,1,2,3,4)/t18-,22+,24-,27-,28+,31+;/m1./s1
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1838 |
160.0 nM [IC50] | ||
Target ID: CHEMBL1893 |
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 Date1955 |
|||
| 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 Date1955 |
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 |
|---|---|---|
| The effect of 5-hydroxytrytamine synthesis inhibitors on neuroleptic-induced catalepsy in rats. | 1975 |
|
| Pharmacological analysis of a new anorexic substance: 5-hydroxy-5(4'-chlorophenyl)-2, 3-dihydro-5H-imidazo-(2, 1-a) isoindole (Mazindol). | 1975 Apr |
|
| Effects of aminergic drugs and glutamic acid on audiogenic seizures induced by early exposure to ethanol. | 1975 Mar |
|
| [Behavior pharmacology of maprotiline, a new antidepressant]. | 1975 Nov |
|
| Transient global amnesia associated with cardiac arrhythmia and digitalis intoxication. | 1975 Sep-Oct |
|
| Determination of PAH in food samples by HPLC with fluorimetric detection following sonication extraction without sample clean-up. | 2001 Aug |
|
| [Characterization and recognition key components in Astragalus membranaceus]. | 2001 Jul |
|
| [Determination of intestinal trefoil factor in burned rats by reversed-phase high performance liquid chromatography]. | 2001 Jul |
|
| [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 |
|
| [Determination of acyclovir in mouse plasma and tissues by reversed-phase high performance liquid chromatography]. | 2001 Nov |
|
| A simple, isocratic high-performance liquid chromatography assay for linezolid in human serum. | 2001 Nov |
|
| 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 |
|
| Reversed-phase liquid chromatographic method for estrogen determination in equine biological samples. | 2001 Sep |
|
| Studies on the cardiotoxicity of noradrenaline in isolated rabbit hearts. | 2002 |
|
| Behavioral effects of MK-801 on reserpine-treated mice. | 2002 Apr |
|
| Augmentation of immune cell activity against tumor cells by Rauwolfia radix. | 2002 Aug |
|
| High-performance liquid chromatographic, capillary electrophoretic and capillary electrophoretic-electrospray ionisation mass spectrometric analysis of selected alkaloid groups. | 2002 Aug 16 |
|
| [Determination of ofloxacin in human fallopian tube, uterus and serum by high performance liquid chromatography]. | 2002 Feb |
|
| [Application of fingerprint chromatogram in quality control of Shen-Mai injection]. | 2002 Jul |
|
| Determination of L-sesamin and L-asarinin in Zanthoxylum(Roxb.) DC. by high performance liquid chromatography. | 2002 Jul |
|
| Increase of free cysteine and citric acid in plant cells exposed to cobalt ions. | 2002 Jul |
|
| Determination of terbutaline sulfate and its degradation products in pharmaceutical formulations using LC. | 2002 Jul 31 |
|
| Validated HPLC method for determination of sennosides A and B in senna tablets. | 2002 Jul 31 |
|
| Development and optimization of a reversed-phase high-performance liquid chromatographic method for the determination of piperacillin and tazobactam in tazocin injectable powder. | 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 |
|
| Simultaneous determination of N-oxides and free bases of pyrrolizidine alkaloids by cation-exchange solid-phase extraction and ion-pair high-performance liquid chromatography. | 2002 Mar 8 |
|
| Validation of a simple liquid chromatographic method for determination and quantitation of residual ivermectin and doramectin in pig liver. | 2002 Mar-Apr |
|
| [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 |
|
| [Determination of aspirin and free salicylic acid in lysinipirine injection by high performance liquid chromatography]. | 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 |
|
| A modified HPLC method for the determination of ochratoxin A by fluorescence detection. | 2002 Oct |
|
| Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. | 2002 Oct |
|
| Development and substantiation of a liquid chromatographic method for monitoring organic reactions involved in synthesis of 4-methoxyphenylacetic acid. | 2002 Oct 4 |
|
| The physiology of overwintering in a turtle that occupies multiple habitats, the common snapping turtle (Chelydra serpentina). | 2002 Sep-Oct |
|
| Effects of CB1 cannabinoid receptor modulating compounds on the hyperkinesia induced by high-dose levodopa in the reserpine-treated rat model of Parkinson's disease. | 2003 Feb |
|
| 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 |
|
| Antitumour 2-(4-aminophenyl)benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo. | 2003 Feb 10 |
|
| 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 |
|
| Optimization and validation of conventional and micellar LC methods for the analysis of methyltestosterone in sugar-coated pills. | 2003 Feb 5 |
|
| 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 |
|
| Rat stomach ECL cells: mode of activation of histidine decarboxylase. | 2003 Jun 15 |
|
| Assessment of a controlled release hydrophilic matrix formulation for metoclopramide HCl. | 2003 May |
|
| 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
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DTXSID80925500
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N17XZO8L8G
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121434
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1263-94-1
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SUBSTANCE RECORD
