Identification

Name
Deserpidine
Accession Number
DB01089  (APRD00906)
Type
Small Molecule
Groups
Approved
Description

Deserpidine is an ester alkaloid drug isolated from Rauwolfia canescens (family Apocynaceae) with antipsychotic and antihypertensive properties that has been used for the control of high blood pressure and for the relief of psychotic behavior.

Structure
Thumb
Synonyms
  • (3beta,16beta,17alpha,18beta,20alpha)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
  • 11-demethoxyreserpine
  • 11-desmethoxyreserpine
  • Canescine
  • Deserpidina
  • Deserpidine
  • Deserpidinum
  • Raunormine
  • Recanescine
Product Ingredients
IngredientUNIICASInChI Key
Deserpidine hydrochloride6LPC48045D6033-69-8YCNOGQOHKRDAHJ-UZXCFUCJSA-N
International/Other Brands
Harmonyl (Abbott)
Categories
UNII
9016E3VB47
CAS number
131-01-1
Weight
Average: 578.6527
Monoisotopic: 578.262816202
Chemical Formula
C32H38N2O8
InChI Key
CVBMAZKKCSYWQR-WCGOZPBSSA-N
InChI
InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
IUPAC Name
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate
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@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2

Pharmacology

Indication

For the treatment of hypertension.

Pharmacodynamics

Deserpidine, an alkaloid of Rauwolfia canescens, is used as an antihypertensive. Rauwolfia alkaloids work by controlling nerve impulses along certain nerve pathways. As a result, they act on the heart and blood vessels to lower blood pressure.

Mechanism of action

Deserpidine's mechanism of action is through inhibition of the ATP/Mg2+ pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase (MAO) causing a reduction in catecholamines.

TargetActionsOrganism
ASynaptic vesicular amine transporter
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Symptoms of overdose include dizziness or drowsiness (severe), flushing of skin, pinpoint pupils of eyes and slowed pulse.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Deserpidine.Experimental
AcebutololAcebutolol may increase the hypotensive activities of Deserpidine.Approved, Investigational
AcemetacinThe therapeutic efficacy of Deserpidine can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
AlfuzosinAlfuzosin may increase the hypotensive activities of Deserpidine.Approved, Investigational
AliskirenAliskiren may increase the hypotensive activities of Deserpidine.Approved, Investigational
AlprenololAlprenolol may increase the hypotensive activities of Deserpidine.Approved, Withdrawn
AmbrisentanDeserpidine may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineDeserpidine may increase the hypotensive activities of Amifostine.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Deserpidine.Approved
AmphetamineAmphetamine may increase the hypotensive activities of Deserpidine.Approved, Illicit, Investigational
AtenololAtenolol may increase the hypotensive activities of Deserpidine.Approved
AvanafilAvanafil may increase the antihypertensive activities of Deserpidine.Approved
BarnidipineDeserpidine may increase the antihypertensive activities of Barnidipine.Approved
BenazeprilBenazepril may increase the hypotensive activities of Deserpidine.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Deserpidine.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Deserpidine.Withdrawn
BepridilBepridil may increase the hypotensive activities of Deserpidine.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Deserpidine.Approved, Investigational
BethanidineBethanidine may increase the hypotensive activities of Deserpidine.Approved
BietaserpineBietaserpine may increase the hypotensive activities of Deserpidine.Experimental
BimatoprostBimatoprost may increase the hypotensive activities of Deserpidine.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Deserpidine.Approved
BosentanBosentan may increase the hypotensive activities of Deserpidine.Approved, Investigational
BQ-123BQ-123 may increase the hypotensive activities of Deserpidine.Investigational
BretyliumBretylium may increase the hypotensive activities of Deserpidine.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Deserpidine.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Deserpidine.Experimental
BupranololBupranolol may increase the hypotensive activities of Deserpidine.Approved
CadralazineCadralazine may increase the hypotensive activities of Deserpidine.Experimental
CafedrineCafedrine may increase the hypotensive activities of Deserpidine.Investigational
CandesartanCandesartan may increase the hypotensive activities of Deserpidine.Experimental
Candesartan cilexetilCandesartan cilexetil may increase the hypotensive activities of Deserpidine.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Deserpidine.Experimental
CaptoprilCaptopril may increase the hypotensive activities of Deserpidine.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Deserpidine.Withdrawn
CarteololCarteolol may increase the hypotensive activities of Deserpidine.Approved
CarvedilolCarvedilol may increase the hypotensive activities of Deserpidine.Approved, Investigational
CeliprololCeliprolol may increase the hypotensive activities of Deserpidine.Approved, Investigational
ChlorothiazideChlorothiazide may increase the hypotensive activities of Deserpidine.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Deserpidine.Approved
CicletanineCicletanine may increase the hypotensive activities of Deserpidine.Investigational
CilazaprilCilazapril may increase the hypotensive activities of Deserpidine.Approved
ClonidineClonidine may increase the hypotensive activities of Deserpidine.Approved
CloranololCloranolol may increase the hypotensive activities of Deserpidine.Experimental
CryptenamineCryptenamine may increase the hypotensive activities of Deserpidine.Approved
CyclopenthiazideCyclopenthiazide may increase the hypotensive activities of Deserpidine.Experimental
CyclothiazideCyclothiazide may increase the hypotensive activities of Deserpidine.Approved
DebrisoquinDebrisoquin may increase the hypotensive activities of Deserpidine.Approved, Investigational
DelaprilDelapril may increase the hypotensive activities of Deserpidine.Experimental
DiazoxideDiazoxide may increase the hypotensive activities of Deserpidine.Approved
DiethylnorspermineDiethylnorspermine may increase the hypotensive activities of Deserpidine.Investigational
DihydralazineDihydralazine may increase the hypotensive activities of Deserpidine.Approved, Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Deserpidine.Approved, Investigational
DipyridamoleDipyridamole may increase the antihypertensive activities of Deserpidine.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Deserpidine.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Deserpidine.Approved
EfonidipineEfonidipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
EnalaprilEnalapril may increase the hypotensive activities of Deserpidine.Approved, Vet Approved
EnalaprilatEnalaprilat may increase the hypotensive activities of Deserpidine.Approved
EndralazineEndralazine may increase the hypotensive activities of Deserpidine.Experimental
EpanololEpanolol may increase the hypotensive activities of Deserpidine.Experimental
EpoprostenolEpoprostenol may increase the hypotensive activities of Deserpidine.Approved
EprosartanEprosartan may increase the hypotensive activities of Deserpidine.Approved
FelodipineFelodipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Deserpidine.Approved
Ferulic acidFerulic acid may increase the hypotensive activities of Deserpidine.Experimental
FosinoprilFosinopril may increase the hypotensive activities of Deserpidine.Approved
FostamatinibFostamatinib may increase the antihypertensive activities of Deserpidine.Approved, Investigational
FurazolidoneFurazolidone may increase the hypotensive activities of Deserpidine.Approved, Investigational, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Deserpidine.Approved, Investigational
GuanadrelGuanadrel may increase the hypotensive activities of Deserpidine.Approved
GuanazodineDeserpidine may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineGuanethidine may increase the hypotensive activities of Deserpidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Deserpidine.Approved, Investigational
GuanoclorDeserpidine may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzDeserpidine may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanDeserpidine may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Deserpidine.Experimental
HexamethoniumHexamethonium may increase the hypotensive activities of Deserpidine.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Deserpidine.Experimental
HydralazineHydralazine may increase the hypotensive activities of Deserpidine.Approved
HydrochlorothiazideHydrochlorothiazide may increase the hypotensive activities of Deserpidine.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Deserpidine.Approved, Investigational
IloprostIloprost may increase the hypotensive activities of Deserpidine.Approved, Investigational
ImidaprilImidapril may increase the hypotensive activities of Deserpidine.Investigational
IndapamideIndapamide may increase the hypotensive activities of Deserpidine.Approved
IndenololIndenolol may increase the hypotensive activities of Deserpidine.Withdrawn
IndoraminIndoramin may increase the hypotensive activities of Deserpidine.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Deserpidine.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Deserpidine.Withdrawn
IrbesartanIrbesartan may increase the hypotensive activities of Deserpidine.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Deserpidine.Approved
IsradipineIsradipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
KetanserinKetanserin may increase the hypotensive activities of Deserpidine.Investigational
LabetalolLabetalol may increase the hypotensive activities of Deserpidine.Approved
LacidipineLacidipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
LatanoprostLatanoprost may increase the hypotensive activities of Deserpidine.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
LinsidomineLinsidomine may increase the hypotensive activities of Deserpidine.Experimental
LisinoprilLisinopril may increase the hypotensive activities of Deserpidine.Approved, Investigational
LofexidineLofexidine may increase the hypotensive activities of Deserpidine.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Deserpidine.Approved
MacitentanDeserpidine may increase the hypotensive activities of Macitentan.Approved
ManidipineManidipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
MebanazineMebanazine may increase the hypotensive activities of Deserpidine.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Deserpidine.Approved, Investigational
MethoserpidineDeserpidine may increase the hypotensive activities of Methoserpidine.Experimental
MethyldopaMethyldopa may increase the hypotensive activities of Deserpidine.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Deserpidine.Approved, Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Deserpidine.Approved, Investigational
MetipranololMetipranolol may increase the hypotensive activities of Deserpidine.Approved
MetolazoneMetolazone may increase the hypotensive activities of Deserpidine.Approved
MetoprololMetoprolol may increase the hypotensive activities of Deserpidine.Approved, Investigational
MetyrosineMetyrosine may increase the hypotensive activities of Deserpidine.Approved
MibefradilMibefradil may increase the hypotensive activities of Deserpidine.Investigational, Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Deserpidine.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Deserpidine.Approved, Investigational
MirodenafilMirodenafil may increase the antihypertensive activities of Deserpidine.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Deserpidine.Approved, Investigational
MoexiprilMoexipril may increase the hypotensive activities of Deserpidine.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Deserpidine.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Deserpidine.Approved, Investigational
MuzolimineMuzolimine may increase the hypotensive activities of Deserpidine.Experimental
NadololNadolol may increase the hypotensive activities of Deserpidine.Approved
NaftopidilNaftopidil may increase the hypotensive activities of Deserpidine.Investigational
NebivololNebivolol may increase the hypotensive activities of Deserpidine.Approved, Investigational
NialamideNialamide may increase the hypotensive activities of Deserpidine.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
NicorandilNicorandil may increase the hypotensive activities of Deserpidine.Approved, Investigational
NiguldipineNiguldipine may increase the hypotensive activities of Deserpidine.Experimental
NilvadipineNilvadipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
NimodipineNimodipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
NisoldipineNisoldipine may increase the hypotensive activities of Deserpidine.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Deserpidine.Approved, Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Deserpidine.Approved, Investigational
ObinutuzumabDeserpidine may increase the hypotensive activities of Obinutuzumab.Approved, Investigational
OctamoxinOctamoxin may increase the hypotensive activities of Deserpidine.Withdrawn
OlmesartanOlmesartan may increase the hypotensive activities of Deserpidine.Approved, Investigational
OmapatrilatOmapatrilat may increase the hypotensive activities of Deserpidine.Investigational
OxprenololOxprenolol may increase the hypotensive activities of Deserpidine.Approved
PargylinePargyline may increase the hypotensive activities of Deserpidine.Approved
PenbutololPenbutolol may increase the hypotensive activities of Deserpidine.Approved, Investigational
PentoliniumPentolinium may increase the hypotensive activities of Deserpidine.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Deserpidine.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Deserpidine.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Deserpidine.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Deserpidine.Withdrawn
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Deserpidine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Deserpidine.Withdrawn
PhentolaminePhentolamine may increase the hypotensive activities of Deserpidine.Approved
PinacidilPinacidil may increase the hypotensive activities of Deserpidine.Approved
PindololPindolol may increase the hypotensive activities of Deserpidine.Approved, Investigational
PirlindolePirlindole may increase the hypotensive activities of Deserpidine.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Deserpidine.Withdrawn
Platelet Activating FactorPlatelet Activating Factor may increase the hypotensive activities of Deserpidine.Experimental
PolythiazidePolythiazide may increase the hypotensive activities of Deserpidine.Approved
PrazosinPrazosin may increase the hypotensive activities of Deserpidine.Approved
ProcaineProcaine may increase the hypotensive activities of Deserpidine.Approved, Investigational, Vet Approved
ProcarbazineProcarbazine may increase the hypotensive activities of Deserpidine.Approved, Investigational
PropranololPropranolol may increase the hypotensive activities of Deserpidine.Approved, Investigational
QuinaprilQuinapril may increase the hypotensive activities of Deserpidine.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Deserpidine.Approved
RamiprilRamipril may increase the hypotensive activities of Deserpidine.Approved
RasagilineRasagiline may increase the hypotensive activities of Deserpidine.Approved
RemikirenRemikiren may increase the hypotensive activities of Deserpidine.Approved
RescinnamineDeserpidine may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Deserpidine.Approved, Investigational
RilmenidineRilmenidine may increase the hypotensive activities of Deserpidine.Approved, Investigational
RiociguatDeserpidine may increase the hypotensive activities of Riociguat.Approved
RituximabDeserpidine may increase the hypotensive activities of Rituximab.Approved
SafrazineSafrazine may increase the hypotensive activities of Deserpidine.Withdrawn
SaprisartanSaprisartan may increase the hypotensive activities of Deserpidine.Experimental
SelegilineSelegiline may increase the hypotensive activities of Deserpidine.Approved, Investigational, Vet Approved
SelexipagSelexipag may increase the hypotensive activities of Deserpidine.Approved
SildenafilSildenafil may increase the antihypertensive activities of Deserpidine.Approved, Investigational
SitaxentanDeserpidine may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilSpirapril may increase the hypotensive activities of Deserpidine.Approved
TadalafilTadalafil may increase the antihypertensive activities of Deserpidine.Approved, Investigational
TalinololTalinolol may increase the hypotensive activities of Deserpidine.Investigational
TelmisartanTelmisartan may increase the hypotensive activities of Deserpidine.Approved, Investigational
TemocaprilTemocapril may increase the hypotensive activities of Deserpidine.Experimental, Investigational
TerlipressinTerlipressin may increase the hypotensive activities of Deserpidine.Approved, Investigational
TetrahydropalmatineTetrahydropalmatine may increase the hypotensive activities of Deserpidine.Investigational
TheodrenalineTheodrenaline may increase the hypotensive activities of Deserpidine.Investigational
TheophyllineTheophylline may increase the antihypertensive activities of Deserpidine.Approved
TiboloneTibolone may increase the hypotensive activities of Deserpidine.Approved, Investigational
TicrynafenTicrynafen may increase the hypotensive activities of Deserpidine.Withdrawn
TimololTimolol may increase the hypotensive activities of Deserpidine.Approved
TolazolineTolazoline may increase the hypotensive activities of Deserpidine.Approved, Vet Approved
TolonidineDeserpidine may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Deserpidine.Approved
TorasemideTorasemide may increase the hypotensive activities of Deserpidine.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Deserpidine.Approved
TranylcypromineTranylcypromine may increase the hypotensive activities of Deserpidine.Approved, Investigational
TravoprostTravoprost may increase the hypotensive activities of Deserpidine.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Deserpidine.Approved, Investigational
TrichlormethiazideTrichlormethiazide may increase the hypotensive activities of Deserpidine.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Deserpidine.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Deserpidine.Approved, Investigational
UdenafilUdenafil may increase the antihypertensive activities of Deserpidine.Approved, Investigational
UnoprostoneUnoprostone may increase the hypotensive activities of Deserpidine.Approved, Investigational
UrapidilUrapidil may increase the hypotensive activities of Deserpidine.Investigational
ValsartanValsartan may increase the hypotensive activities of Deserpidine.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Deserpidine.Approved
VincamineVincamine may increase the hypotensive activities of Deserpidine.Experimental
VinpocetineVinpocetine may increase the hypotensive activities of Deserpidine.Investigational
XipamideXipamide may increase the hypotensive activities of Deserpidine.Experimental
XylometazolineXylometazoline may increase the hypotensive activities of Deserpidine.Approved, Investigational
YohimbineYohimbine may decrease the antihypertensive activities of Deserpidine.Approved, Investigational, Vet Approved
ZofenoprilZofenopril may increase the hypotensive activities of Deserpidine.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Gabriele Fontana, Ezio Bombardelli, Cristian Samori, Eleonora Baldelli, Andrea Guerrini, Arturo Battaglia, Bruno Danieli, "Process for the Semisynthesis of Deserpidine." U.S. Patent US20080242864, issued October 02, 2008.

US20080242864
General References
Not Available
External Links
Human Metabolome Database
HMDB0015221
KEGG Compound
C06541
PubChem Compound
8550
PubChem Substance
46505311
ChemSpider
8232
ChEBI
27478
ChEMBL
CHEMBL1200515
Therapeutic Targets Database
DAP000909
PharmGKB
PA164742966
Wikipedia
Deserpidine
ATC Codes
C02AA05 — DeserpidineC02LA03 — Deserpidine and diuretics

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)228-232Ulshafer, P.R.; US. Patent 2,982,769; May 2, 1961; assigned to Ciba Pharmaceutical.
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0111 mg/mLALOGPS
logP4.25ALOGPS
logP3.69ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)16.37ChemAxon
pKa (Strongest Basic)7.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area108.55 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity154.96 m3·mol-1ChemAxon
Polarizability62.59 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9353
Blood Brain Barrier+0.9496
Caco-2 permeable+0.6582
P-glycoprotein substrateSubstrate0.8178
P-glycoprotein inhibitor IInhibitor0.8302
P-glycoprotein inhibitor IINon-inhibitor0.8096
Renal organic cation transporterInhibitor0.5326
CYP450 2C9 substrateNon-substrate0.894
CYP450 2D6 substrateNon-substrate0.8761
CYP450 3A4 substrateSubstrate0.7198
CYP450 1A2 substrateInhibitor0.8392
CYP450 2C9 inhibitorNon-inhibitor0.8701
CYP450 2D6 inhibitorNon-inhibitor0.9064
CYP450 2C19 inhibitorNon-inhibitor0.8954
CYP450 3A4 inhibitorNon-inhibitor0.8353
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7081
Ames testNon AMES toxic0.9234
CarcinogenicityNon-carcinogens0.9484
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.0921 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7952
hERG inhibition (predictor II)Non-inhibitor0.6277
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-014i-7967010000-b3758c647fba3c682e47
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Yohimbine alkaloids
Sub Class
Not Available
Direct Parent
Yohimbine alkaloids
Alternative Parents
Corynanthean-type alkaloids / Beta carbolines / Gallic acid and derivatives / M-methoxybenzoic acids and derivatives / P-methoxybenzoic acids and derivatives / 3-alkylindoles / Benzoic acid esters / Anisoles / Methoxybenzenes / Phenoxy compounds
show 16 more
Substituents
Yohimbine / Corynanthean skeleton / Yohimbine alkaloid / Pyridoindole / Beta-carboline / Gallic acid or derivatives / P-methoxybenzoic acid or derivatives / M-methoxybenzoic acid or derivatives / Benzoate ester / 3-alkylindole
show 36 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound, methyl ester, benzoate ester, alkaloid ester, yohimban alkaloid (CHEBI:27478) / Indole alkaloids (C06541)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. Sievert MK, Hajipour AR, Ruoho AE: Specific derivatization of the vesicle monoamine transporter with novel carrier-free radioiodinated reserpine and tetrabenazine photoaffinity labels. Anal Biochem. 2007 Aug 1;367(1):68-78. Epub 2007 May 3. [PubMed:17559790]
  2. Naudon L, Leroux-Nicollet I, Raisman-Vozari R, Botton D, Costentin J: Time-course of modifications elicited by reserpine on the density and mRNA synthesis of the vesicular monoamine transporter, and on the density of the membrane dopamine uptake complex. Synapse. 1995 Sep;21(1):29-36. [PubMed:8525459]
  3. Erickson JD, Eiden LE, Hoffman BJ: Expression cloning of a reserpine-sensitive vesicular monoamine transporter. Proc Natl Acad Sci U S A. 1992 Nov 15;89(22):10993-7. [PubMed:1438304]
  4. Mandela P, Chandley M, Xu YY, Zhu MY, Ordway GA: Reserpine-induced reduction in norepinephrine transporter function requires catecholamine storage vesicles. Neurochem Int. 2010 May-Jun;56(6-7):760-7. doi: 10.1016/j.neuint.2010.02.011. Epub 2010 Feb 20. [PubMed:20176067]
  5. Fulton SC, Healy MD: Comparison of the effectiveness of deserpidine, reserpine, and alpha-methyltyrosine on brain biogenic amines. Fed Proc. 1976 Dec;35(14):2558-62. [PubMed:11134]
  6. Loeffler LJ, Schran HF: Antibody specificity studies for reserpine, its metabolites, and synthetic reserpine congeners: radioimmunoassay. J Pharm Sci. 1979 Nov;68(11):1433-5. [PubMed:574544]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 09:48