Details of the Drug

General Information of Drug (ID: DM6VM38)

Drug Name
Reserpine
Synonyms
Abesta; Abicol; Adelfan; Adelphin; Alkarau; Alkaserp; Alserin; Apoplon; Apsical; Ascoserp; Ascoserpina; Austrapine; Banasil; Banisil; Benazyl; Bioserpine; Brinderdin; Briserine; Broserpine; Cardioserpin; Carditivo; Carpacil; Carrserp; Darebon; Deserpine; Dralserp; Eberpine; Eberspine; Ebserpine; Elfanex; Elserpine; Enipresser; Escaspere; Eserpine; Eskaserp; Eskaserpine; Gammaserpine; Gilucard; Helfoserpin; Hexaplin; Hiposerpil; Hiserpia; Hydropine; Hydroserp; Hypersil; Hypersine; Hypertensan; Idoserp; Idsoserp; Interpina; Kitine; Klimanosid; Lemiserp; Loweserp; Mallopress; Maviserpin; Mayserpine; Mephaserpin; Modenol; Naquival; Nembuserpin; Neoserfin; Neoserp; Neoslowten; Orthoserpina; Perskleran; Pressimedin; Purserpine; Quiescin; Raucap; Raudiford; Raudixin; Raudixoid; Raugal; Raulen; Rauloydin; Raumorine; Raunervil; Raunorine; Raunova; Raupasil; Raupoid; Raurine; Rausan; Rausedan; Rausedil; Rausedyl; Rauserpin; Rauserpine; Rauserpol; Rausingle; Rautrin; Rauvlid; Rauwasedin; Rauwilid; Rauwiloid; Rauwipur; Rauwita; Rauwoleaf; Rawilid; Recipin; Regroton; Resaltex; Resedrex; Resedril; Reserbal; Resercaps; Resercen; Reserfia; Reserjen; Reserlor; Reserp; Reserpal; Reserpamed; Reserpanca; Reserpene; Reserpex; Reserpidefe; Reserpil; Reserpin; Reserpina; Reserpinum; Reserpka; Reserpoid; Reserpur; Reserutin; Resiatric; Residin; Residine; Resine; Resocalm; Resperin; Resperine; Respital; Restran; Rezerpin; Riserpa; Rivased; Rivasin; Rolserp; Roxel; Roxinoid; Roxynoid; Ryser; Salupres; Sandril; Sandron; Sedaraupin; Sedaraupina; Sederaupin; Sedserp; Seominal; Serfin; Serfolia; Serolfia; Serpalan; Serpaloid; Serpaneurona; Serpanray; Serpasil; Serpasol; Serpate; Serpazil; Serpazol; Serpedin; Serpen; Serpena; Serpentil; Serpentin; Serpentina; Serpicon; Serpil; Serpiloid; Serpilum; Serpine; Serpipur; Serpivate; Serpivite; Serpogen; Serpoid; Serpone; Serpyrit; Sertabs; Sertens; Sertensin; Sertina; Supergan; Tefaserpina; Temposerpine; Tensanyl; Tenserpinie; Tensional; Tensionorme; Tepserpine; Terbolan; Transerpin; Triserpin; Tylandril; Unilord; Unipres; VIXO; Esc aspere; Hydromox R; Hypercal B; Loweser p; Neose rfin; Rau sedyl; Renese R; Rese rpamed; Se rpate; V Serp; VI XO; Diupres 250; Diupres 500; ENT 50146; H 520; Hydropres 25; Hydropres 50; Hydrosine 25; R 0875; Apoplon (TN); Diupres-250; Diupres-500; Diurese-R; Diutensen-R; HYDRO-RESERP; Hydrap-ES; Hydromox-R; Key-serpine; L-Carpserp; Neo-serp; Rau-Sed; Renese-R; Rese-lar; Reser-ar; SK-Reserpine; T-Serp; Usaf cb-27; V-Serp; Vio-Serpine; Cam-Ap-Es; L"-Carpserp; R-e-s; Ser-A-Gen; 3P Reserp
Indication
Disease Entry ICD 11 Status REF
Hypertension BA00-BA04 Approved [1]
Malignant essential hypertension BA00 Approved [2]
Psychotic disorder 6A20-6A25 Approved [2]
Therapeutic Class
Antihypertensive Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 608.7
Logarithm of the Partition Coefficient (xlogp) 4
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 10
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Elimination
1% of drug is excreted from urine in the unchanged form [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.1408 micromolar/kg/day [4]
Water Solubility
The ability of drug to dissolve in water is measured as 0.01 mg/mL [3]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Cytology abnormal Not Available SLC18A1 OT01OALS [5]
Flushing Not Available NPY OT4ICV3P [5]
Flushing Not Available ATP1A1 OTCJ458Q [5]
Flushing Not Available ADCY1 OTSLLFZO [5]
Metabolic disorder Not Available CHGB OT7SAQT2 [5]
Metabolic disorder Not Available PAM OTX8HV5B [5]
Metabolic disorder Not Available CPE OTXNTV79 [5]
Metabolic disorder Not Available SCG2 OTXWUQQL [5]
Systemic lupus erythematosus Not Available NAA20 OTJB0VA6 [5]
⏷ Show the Full List of 9 ADR Information of This Drug
Chemical Identifiers
Formula
C33H40N2O9
IUPAC Name
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Canonical SMILES
CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
InChI
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
InChIKey
QEVHRUUCFGRFIF-MDEJGZGSSA-N
Cross-matching ID
PubChem CID
5770
ChEBI ID
CHEBI:28487
CAS Number
50-55-5
DrugBank ID
DB00206
TTD ID
D0J4JM
VARIDT ID
DR00636
INTEDE ID
DR2310
ACDINA ID
D00588
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Synaptic vesicle amine transporter (SLC18A2) TTNZRI3 VMAT2_HUMAN Blocker [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [7]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [8]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Adenylate cyclase type 1 (ADCY1) OTSLLFZO ADCY1_HUMAN Drug Response [5]
Aldo-keto reductase family 1 member B10 (AKR1B10) OTOA4HTH AK1BA_HUMAN Gene/Protein Processing [9]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [10]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Protein Interaction/Cellular Processes [11]
Beta-1,3-galactosyl-O-glycosyl-glycoprotein beta-1,6-N-acetylglucosaminyltransferase 3 (GCNT3) OTQ9ALTR GCNT3_HUMAN Gene/Protein Processing [9]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [12]
Carboxypeptidase E (CPE) OTXNTV79 CBPE_HUMAN Drug Response [5]
Chromaffin granule amine transporter (SLC18A1) OT01OALS VMAT1_HUMAN Drug Response [5]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [13]
Cytochrome P450 3A5 (CYP3A5) OTSXFBXB CP3A5_HUMAN Gene/Protein Processing [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Hypertension
ICD Disease Classification BA00-BA04
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Synaptic vesicle amine transporter (SLC18A2) DTT SLC18A2 2.69E-02 -0.04 -0.11
P-glycoprotein 1 (ABCB1) DTP P-GP 9.39E-02 1.07E-01 2.80E-01
Breast cancer resistance protein (ABCG2) DTP BCRP 9.45E-01 -5.34E-02 -9.01E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Reserpine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Methylene blue DMJAPE7 Moderate Additive hypertensive effects by the combination of Reserpine and Methylene blue. Acquired methaemoglobinaemia [3A93] [15]
Promazine DMZAL7W Moderate Additive hypotensive effects by the combination of Reserpine and Promazine. Appearance/behaviour symptom [MB23] [16]
Linezolid DMGFPU2 Moderate Additive hypertensive effects by the combination of Reserpine and Linezolid. Bacterial infection [1A00-1C4Z] [15]
Cariprazine DMJYDVK Moderate Additive hypotensive effects by the combination of Reserpine and Cariprazine. Bipolar disorder [6A60] [16]
Talazoparib DM1KS78 Moderate Decreased clearance of Reserpine due to the transporter inhibition by Talazoparib. Breast cancer [2C60-2C6Y] [17]
Selegiline DM6034S Moderate Additive hypertensive effects by the combination of Reserpine and Selegiline. Depression [6A70-6A7Z] [15]
Isocarboxazid DMAF1NB Moderate Additive hypertensive effects by the combination of Reserpine and Isocarboxazid. Depression [6A70-6A7Z] [15]
Tranylcypromine DMGB5RE Moderate Additive hypertensive effects by the combination of Reserpine and Tranylcypromine. Depression [6A70-6A7Z] [15]
OPC-34712 DMHG57U Moderate Additive hypotensive effects by the combination of Reserpine and OPC-34712. Depression [6A70-6A7Z] [16]
Phenelzine DMHIDUE Moderate Additive hypertensive effects by the combination of Reserpine and Phenelzine. Depression [6A70-6A7Z] [15]
Tetrabenazine DMYWQ0O Major Additive antidopaminergic effects by the combination of Reserpine and Tetrabenazine. Dissociative neurological symptom disorder [6B60] [18]
Deutetrabenazine DMUPFLI Major Additive antidopaminergic effects by the combination of Reserpine and Deutetrabenazine. Dystonic disorder [8A02] [18]
Ripretinib DM958QB Moderate Decreased clearance of Reserpine due to the transporter inhibition by Ripretinib. Gastrointestinal stromal tumour [2B5B] [19]
Procarbazine DMIK367 Moderate Additive hypertensive effects by the combination of Reserpine and Procarbazine. Hodgkin lymphoma [2B30] [15]
Propiomazine DMKY8V1 Moderate Additive hypotensive effects by the combination of Reserpine and Propiomazine. Insomnia [7A00-7A0Z] [16]
ITI-007 DMUQ1DO Moderate Additive hypotensive effects by the combination of Reserpine and ITI-007. Insomnia [7A00-7A0Z] [16]
Cladribine DM3JDRP Moderate Decreased clearance of Reserpine due to the transporter inhibition by Cladribine. Mature B-cell leukaemia [2A82] [19]
Arry-162 DM1P6FR Moderate Decreased clearance of Reserpine due to the transporter inhibition by Arry-162. Melanoma [2C30] [19]
Thalidomide DM70BU5 Moderate Additive CNS depression effects by the combination of Reserpine and Thalidomide. Multiple myeloma [2A83] [20]
Ozanimod DMT6AM2 Moderate Additive hypertensive effects by the combination of Reserpine and Ozanimod. Multiple sclerosis [8A40] [15]
Prochlorperazine DM53SRA Moderate Additive hypotensive effects by the combination of Reserpine and Prochlorperazine. Nausea/vomiting [MD90] [16]
Promethazine DM6I5GR Moderate Additive hypotensive effects by the combination of Reserpine and Promethazine. Nausea/vomiting [MD90] [16]
Levomepromazine DMIKFEL Moderate Additive hypotensive effects by the combination of Reserpine and Levomepromazine. Psychotic disorder [6A20-6A25] [16]
Fluphenazine DMIT8LX Moderate Additive hypotensive effects by the combination of Reserpine and Fluphenazine. Psychotic disorder [6A20-6A25] [16]
Triflupromazine DMKFQJP Moderate Additive hypotensive effects by the combination of Reserpine and Triflupromazine. Psychotic disorder [6A20-6A25] [16]
Quetiapine DM1N62C Moderate Additive hypotensive effects by the combination of Reserpine and Quetiapine. Schizophrenia [6A20] [16]
Mesoridazine DM2ZGAN Moderate Additive hypotensive effects by the combination of Reserpine and Mesoridazine. Schizophrenia [6A20] [16]
Thioridazine DM35M8J Moderate Additive hypotensive effects by the combination of Reserpine and Thioridazine. Schizophrenia [6A20] [16]
Aripiprazole DM3NUMH Moderate Additive hypotensive effects by the combination of Reserpine and Aripiprazole. Schizophrenia [6A20] [16]
Iloperidone DM6AUFY Moderate Additive hypotensive effects by the combination of Reserpine and Iloperidone. Schizophrenia [6A20] [16]
Paliperidone DM7NPJS Moderate Additive hypotensive effects by the combination of Reserpine and Paliperidone. Schizophrenia [6A20] [16]
Loxapine DM8AI9U Moderate Additive hypotensive effects by the combination of Reserpine and Loxapine. Schizophrenia [6A20] [16]
Molindone DMAH70G Moderate Additive hypotensive effects by the combination of Reserpine and Molindone. Schizophrenia [6A20] [16]
Chlorpromazine DMBGZI3 Moderate Additive hypotensive effects by the combination of Reserpine and Chlorpromazine. Schizophrenia [6A20] [16]
Thiothixene DMDINC4 Moderate Additive hypotensive effects by the combination of Reserpine and Thiothixene. Schizophrenia [6A20] [16]
Clozapine DMFC71L Moderate Additive hypotensive effects by the combination of Reserpine and Clozapine. Schizophrenia [6A20] [16]
Trifluoperazine DMKBYWI Moderate Additive hypotensive effects by the combination of Reserpine and Trifluoperazine. Schizophrenia [6A20] [16]
Ziprasidone DMM58JY Moderate Additive hypotensive effects by the combination of Reserpine and Ziprasidone. Schizophrenia [6A20] [16]
Risperidone DMN6DXL Moderate Additive hypotensive effects by the combination of Reserpine and Risperidone. Schizophrenia [6A20] [16]
Olanzapine DMPFN6Y Moderate Additive hypotensive effects by the combination of Reserpine and Olanzapine. Schizophrenia [6A20] [16]
Amisulpride DMSJVAM Moderate Additive hypotensive effects by the combination of Reserpine and Amisulpride. Schizophrenia [6A20] [16]
Asenapine DMSQZE2 Moderate Additive hypotensive effects by the combination of Reserpine and Asenapine. Schizophrenia [6A20] [16]
Lusutrombopag DMH6IKO Moderate Decreased clearance of Reserpine due to the transporter inhibition by Lusutrombopag. Thrombocytopenia [3B64] [21]
Methdilazine DMAUHQX Moderate Additive hypotensive effects by the combination of Reserpine and Methdilazine. Vasomotor/allergic rhinitis [CA08] [16]
Trimeprazine DMEMV9D Moderate Additive hypotensive effects by the combination of Reserpine and Trimeprazine. Vasomotor/allergic rhinitis [CA08] [22]
Betrixaban DM2C4RF Moderate Decreased clearance of Reserpine due to the transporter inhibition by Betrixaban. Venous thromboembolism [BD72] [23]
⏷ Show the Full List of 46 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Saccharose E00091 5988 Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Reserpine 0.25 mg tablet 0.25 mg Oral Tablet Oral
Reserpine 0.1 mg tablet 0.1 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4823).
2 Reserpine FDA Label
3 BDDCS applied to over 900 drugs
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
6 Dopamine signaling is required for depolarization-induced slow current in cerebellar Purkinje cells. J Neurosci. 2009 Jul 1;29(26):8530-8.
7 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
8 Improving the prediction of the brain disposition for orally administered drugs using BDDCS. Adv Drug Deliv Rev. 2012 Jan;64(1):95-109.
9 Oxidative stress mechanisms do not discriminate between genotoxic and nongenotoxic liver carcinogens. Chem Res Toxicol. 2015 Aug 17;28(8):1636-46.
10 A structure-function relationship among reserpine and yohimbine analogues in their ability to increase expression of mdr1 and P-glycoprotein in a human colon carcinoma cell line. Mol Pharmacol. 1995 Oct;48(4):682-9.
11 Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry. J Mass Spectrom. 2008 Mar;43(3):327-35. doi: 10.1002/jms.1320.
12 Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
13 Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction. Drug Metab Dispos. 2006 Oct;34(10):1742-8.
14 Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8.
15 De Vita VT, Hahn MA, Oliverio VT "Monoamine oxidase inhibition by a new carcinostatic agent, n-isopropyl-a-(2-methylhydrazino)-p-toluamide (MIH). (30590)." Proc Soc Exp Biol Med 120 (1965): 561-5. [PMID: 4379192]
16 Aronowitz JS, Chakos MH, Safferman AZ, Lieberman JA "Syncope associated with the combination of clozapine and enalapril." J Clin Psychopharmacol 14 (1994): 429-30. [PMID: 7884028]
17 Product Information. Talzenna (talazoparib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
18 Product Information. Xenazine (tetrabenazine). Prestwick Pharmaceuticals Inc, Washington DC, VA.
19 Cerner Multum, Inc. "Australian Product Information.".
20 Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ.
21 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
22 Product Information. Clozaril (clozapine). Novartis Pharmaceuticals, East Hanover, NJ.
23 Product Information. Bevyxxa (betrixaban). Portola Pharmaceuticals, South San Francisco, CA.