Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H40N2O9 |
Molecular Weight | 608.6787 |
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(OC)=C6)C2
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
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 |
---|---|---|
Pharmacological analysis of a new anorexic substance: 5-hydroxy-5(4'-chlorophenyl)-2, 3-dihydro-5H-imidazo-(2, 1-a) isoindole (Mazindol). | 1975 Apr |
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Antagonistic effect of cyproheptadine on neuroleptic-induced catalepsy. | 1975 Jan-Feb |
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[Behavior pharmacology of maprotiline, a new antidepressant]. | 1975 Nov |
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Transient global amnesia associated with cardiac arrhythmia and digitalis intoxication. | 1975 Sep-Oct |
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On the anticataleptic action of cyproheptadine. | 1976 Aug |
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Antidepressant effect of an ethanolic extract of the leaves of Cissampelos sympodialis in rats and mice. | 1998 Dec |
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Reserpine modulates serotonin transporter mRNA levels in the rat brain. | 1999 |
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The adrenergic receptor agonist, clonidine, potentiates the anti-parkinsonian action of the selective kappa-opioid receptor agonist, enadoline, in the monoamine-depleted rat. | 1999 Dec |
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The role of the sympathetic nervous system in the regulation of leptin synthesis in C57BL/6 mice. | 1999 Feb 12 |
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Modulation of gastrin processing by vesicular monoamine transporter type 1 (VMAT1) in rat gastrin cells. | 1999 Jun 1 |
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The group II metabotropic glutamate receptor agonist, DCG-IV, alleviates akinesia following intranigral or intraventricular administration in the reserpine-treated rat. | 2000 Feb |
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Brain alpha(2)-adrenoceptors in monoamine-depleted rats: increased receptor density, G coupling proteins, receptor turnover and receptor mRNA. | 2001 Apr |
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Blood pressure-independent effect of angiotensin AT1 receptor blockade on renal endothelin-1 production in hypertensive uremic rats. | 2001 Aug |
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A sensitive method for the determination of gemfibrozil in human plasma samples by RP-LC. | 2001 Aug |
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Simultaneous determination of olanzapine, clozapine and demethylated metabolites in serum by on-line column-switching high-performance liquid chromatography. | 2001 Aug 5 |
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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 |
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Determination of vitamin B(6) in cooked sausages. | 2001 Jan |
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Separation of the insecticidal pyrethrin esters by capillary electrochromatography. | 2001 Jan 5 |
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Liquid chromatographic method with electrochemical detection for determination of cisapride in serum. | 2001 Jan-Feb |
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Determination of famotidine in low-volume human plasma by normal-phase liquid chromatography/tandem mass spectrometry. | 2001 Jul |
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Analysis of phenolic constituents of biological interest in red wines by high-performance liquid chromatography. | 2001 Jul 13 |
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Direct analysis of urinary trans,trans-muconic acid by coupled column liquid chromatography and spectrophotometric ultraviolet detection: method applicability to human urine. | 2001 Jul 15 |
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Application of conventional UV, photodiode array (PDA) and fluorescence (FL) detection to analysis of phenolic acids in plant material and pharmaceutical preparations. | 2001 Mar |
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Quantitation of itraconazole in rat heparinized plasma by liquid chromatography-mass spectrometry. | 2001 Mar 5 |
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Peroxisome proliferator-activated receptor-gamma agonist troglitazone protects against nondiabetic glomerulosclerosis in rats. | 2001 May |
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Determination of 3'-azido-2',3'-dideoxyuridine in maternal plasma, amniotic fluid, fetal and placental tissues by high-performance liquid chromatography. | 2001 May 5 |
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Determination of aliphatic amines in water by liquid chromatography using solid-phase extraction cartridges for preconcentration and derivatization. | 2001 Oct |
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Rapid high-performance liquid chromatographic method for the separation of hydroxylated testosterone metabolites. | 2001 Sep 5 |
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Behavioral effects of MK-801 on reserpine-treated mice. | 2002 Apr |
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Temperature effect on peak width and column efficiency in subcritical water chromatography. | 2002 Feb |
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Direct-injection HPLC assay for the determination of a new carbapenem antibiotic in human plasma and urine. | 2002 Feb 1 |
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Simultaneous determination of cloricromene and its active metabolite in rabbit aqueous humor by high-performance liquid chromatography. | 2002 Feb 5 |
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Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice. | 2002 Jan-Feb |
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Determination of L-sesamin and L-asarinin in Zanthoxylum(Roxb.) DC. by high performance liquid chromatography. | 2002 Jul |
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Determination of terbutaline sulfate and its degradation products in pharmaceutical formulations using LC. | 2002 Jul 31 |
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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 |
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[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 |
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LC-MS/MS determination of a farnesyl transferase inhibitor in human plasma and urine. | 2002 Nov 7 |
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Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. | 2002 Oct |
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Development and substantiation of a liquid chromatographic method for monitoring organic reactions involved in synthesis of 4-methoxyphenylacetic acid. | 2002 Oct 4 |
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The physiology of overwintering in a turtle that occupies multiple habitats, the common snapping turtle (Chelydra serpentina). | 2002 Sep-Oct |
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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 |
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Antitumour 2-(4-aminophenyl)benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo. | 2003 Feb 10 |
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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 |
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Analysis of flecainide and two metabolites in biological specimens by HPLC: application to a fatal intoxication. | 2003 Jan-Feb |
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Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition. | 2003 Jun |
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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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 |
NBK548348
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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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8B1QWR724A
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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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4823
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50-55-5
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1601000
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RESERPINE
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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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DTXSID7021237
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200-047-9
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SUB10286MIG
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213
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237659
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CHEMBL772
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28487
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9260
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PRIMARY | RxNorm | ||
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RESERPINE
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59272
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D012110
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Reserpine
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)