Identification

Name
Debrisoquin
Accession Number
DB04840
Type
Small Molecule
Groups
Approved, Investigational
Description

An adrenergic neuron-blocking drug similar in effects to guanethidine. It is also noteworthy in being a substrate for a polymorphic cytochrome P-450 enzyme. Persons with certain isoforms of this enzyme are unable to properly metabolize this and many other clinically important drugs. They are commonly referred to as having a debrisoquin 4-hydroxylase polymorphism. [PubChem]

Structure
Thumb
Synonyms
  • Debrisochinum
  • Debrisoquin
  • Debrisoquina
  • Debrisoquine
  • Debrisoquinum
  • Isocaramidine
Product Ingredients
IngredientUNIICASInChI Key
Debrisoquin sulfateQ94064N9NW581-88-4CAYGYVYWRIHZCQ-UHFFFAOYSA-N
International/Other Brands
Bonipress (lkapharm) / Declinax (Roche) / Tendor (Chinoin)
Categories
UNII
X31CDK040E
CAS number
1131-64-2
Weight
Average: 175.2303
Monoisotopic: 175.110947431
Chemical Formula
C10H13N3
InChI Key
JWPGJSVJDAJRLW-UHFFFAOYSA-N
InChI
InChI=1S/C10H13N3/c11-10(12)13-6-5-8-3-1-2-4-9(8)7-13/h1-4H,5-7H2,(H3,11,12)
IUPAC Name
1,2,3,4-tetrahydroisoquinoline-2-carboximidamide
SMILES
NC(=N)N1CCC2=CC=CC=C2C1

Pharmacology

Indication

For the treatment of moderate and severe hypertension, either alone or as an adjunct, and for the treatment of renal hypertension.

Structured Indications
Not Available
Pharmacodynamics

Debrisoquin is an adrenergic neuron-blocking drug similar in effects to guanethidine. It is a substrate for a polymorphic cytochrome P-450 enzyme. Persons with certain isoforms of this enzyme are unable to properly metabolize this and many other clinically important drugs. They are commonly referred to as having a debrisoquin 4-hydroxylase polymorphism.

Mechanism of action

Debrisoquin acts at the sympathetic neuroeffector junction by inhibiting or interfering with the release and/or distribution of norepinephrine, rather than acting at the effector cell by inhibiting the association of norepinephrine with its receptors. It is taken up by norepinephrine transporters. It becomes concentrated in NE transmitter vesicles, replacing NE in these vesicles. This leads to a gradual depletion of NE stores in the nerve endings. Once inside the terminal it blocks the release of noradrenaline in response to arrival of an action potential. In contrast to ganglionic blocking agents, debrisoquin suppresses equally the responses mediated by alpha-and beta-adrenergic receptors but does not produce parasympathetic blockade. Since sympathetic blockade results in modest decreases in peripheral resistance and cardiac output, debrisoquin lowers blood pressure in the supine position. It further reduces blood pressure by decreasing the degree of vasoconstriction that normally results from reflex sympathetic nervous activity upon assumption of the upright posture, thus reducing venous return and cardiac output more.

TargetActionsOrganism
ASodium-dependent noradrenaline transporter
inducer
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
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 Debrisoquin.Experimental
AbirateroneThe serum concentration of Debrisoquin can be increased when it is combined with Abiraterone.Approved
AcebutololDebrisoquin may increase the hypotensive activities of Acebutolol.Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Debrisoquin.Approved, Investigational
AliskirenDebrisoquin may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololDebrisoquin may increase the hypotensive activities of Alprenolol.Approved, Withdrawn
AmbrisentanDebrisoquin may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineDebrisoquin may increase the hypotensive activities of Amifostine.Approved, Investigational
AmiodaroneThe metabolism of Debrisoquin can be decreased when combined with Amiodarone.Approved, Investigational
ArtemetherThe metabolism of Debrisoquin can be decreased when combined with Artemether.Approved
AtomoxetineThe metabolism of Debrisoquin can be decreased when combined with Atomoxetine.Approved
BenazeprilDebrisoquin may increase the hypotensive activities of Benazepril.Approved, Investigational
BendroflumethiazideDebrisoquin may increase the hypotensive activities of Bendroflumethiazide.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Debrisoquin.Withdrawn
BetaxololThe metabolism of Debrisoquin can be decreased when combined with Betaxolol.Approved
BethanidineBethanidine may increase the hypotensive activities of Debrisoquin.Approved
BietaserpineDebrisoquin may increase the hypotensive activities of Bietaserpine.Experimental
BimatoprostDebrisoquin may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BisoprololDebrisoquin may increase the hypotensive activities of Bisoprolol.Approved
BosentanBosentan may increase the hypotensive activities of Debrisoquin.Approved, Investigational
BQ-123Debrisoquin may increase the hypotensive activities of BQ-123.Investigational
BretyliumDebrisoquin may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Debrisoquin.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Debrisoquin.Experimental
BupranololDebrisoquin may increase the hypotensive activities of Bupranolol.Approved
BupropionThe metabolism of Debrisoquin can be decreased when combined with Bupropion.Approved
CadralazineDebrisoquin may increase the hypotensive activities of Cadralazine.Experimental
CafedrineDebrisoquin may increase the hypotensive activities of Cafedrine.Investigational
CandoxatrilDebrisoquin may increase the hypotensive activities of Candoxatril.Experimental
CaroxazoneCaroxazone may increase the hypotensive activities of Debrisoquin.Withdrawn
CarteololDebrisoquin may increase the hypotensive activities of Carteolol.Approved
CelecoxibThe metabolism of Debrisoquin can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololDebrisoquin may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChlorothiazideDebrisoquin may increase the hypotensive activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneDebrisoquin may increase the hypotensive activities of Chlorthalidone.Approved
CholecalciferolThe metabolism of Debrisoquin can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CicletanineDebrisoquin may increase the hypotensive activities of Cicletanine.Investigational
CinacalcetThe metabolism of Debrisoquin can be decreased when combined with Cinacalcet.Approved
ClemastineThe metabolism of Debrisoquin can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Debrisoquin can be decreased when combined with Clobazam.Approved, Illicit
ClonidineClonidine may increase the hypotensive activities of Debrisoquin.Approved
CloranololDebrisoquin may increase the hypotensive activities of Cloranolol.Experimental
ClozapineThe metabolism of Debrisoquin can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Debrisoquin can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Debrisoquin can be decreased when combined with Cocaine.Approved, Illicit
CryptenamineDebrisoquin may increase the hypotensive activities of Cryptenamine.Approved
CyclopenthiazideDebrisoquin may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclothiazideDebrisoquin may increase the hypotensive activities of Cyclothiazide.Approved
DarifenacinThe metabolism of Debrisoquin can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Debrisoquin can be increased when it is combined with Darunavir.Approved
DelaprilDebrisoquin may increase the hypotensive activities of Delapril.Experimental
DelavirdineThe metabolism of Debrisoquin can be decreased when combined with Delavirdine.Approved
DeserpidineDebrisoquin may increase the hypotensive activities of Deserpidine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Debrisoquin.Approved
diethylnorspermineDebrisoquin may increase the hypotensive activities of diethylnorspermine.Investigational
DihydralazineDebrisoquin may increase the hypotensive activities of Dihydralazine.Investigational
DiphenhydramineThe metabolism of Debrisoquin can be decreased when combined with Diphenhydramine.Approved
DorzolamideDebrisoquin may increase the hypotensive activities of Dorzolamide.Approved
DosulepinThe metabolism of Debrisoquin can be decreased when combined with Dosulepin.Approved
DuloxetineThe metabolism of Debrisoquin can be decreased when combined with Duloxetine.Approved
EfonidipineDebrisoquin may increase the hypotensive activities of Efonidipine.Approved
EliglustatThe metabolism of Debrisoquin can be decreased when combined with Eliglustat.Approved
EnalaprilatDebrisoquin may increase the hypotensive activities of Enalaprilat.Approved
EndralazineDebrisoquin may increase the hypotensive activities of Endralazine.Experimental
EpanololDebrisoquin may increase the hypotensive activities of Epanolol.Experimental
EpoprostenolDebrisoquin may increase the hypotensive activities of Epoprostenol.Approved
EprosartanDebrisoquin may increase the hypotensive activities of Eprosartan.Approved
FenoldopamDebrisoquin may increase the hypotensive activities of Fenoldopam.Approved
Ferulic acidDebrisoquin may increase the hypotensive activities of Ferulic acid.Experimental
FluoxetineThe metabolism of Debrisoquin can be decreased when combined with Fluoxetine.Approved, Vet Approved
FosinoprilDebrisoquin may increase the hypotensive activities of Fosinopril.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Debrisoquin.Approved, Investigational, Vet Approved
GuanabenzDebrisoquin may increase the hypotensive activities of Guanabenz.Approved, Investigational
GuanadrelDebrisoquin may increase the hypotensive activities of Guanadrel.Approved
GuanazodineDebrisoquin may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineGuanethidine may increase the hypotensive activities of Debrisoquin.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Debrisoquin.Approved, Investigational
GuanoclorDebrisoquin may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzDebrisoquin may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanDebrisoquin may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Debrisoquin.Experimental
HexamethoniumDebrisoquin may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Debrisoquin.Experimental
HydralazineHydralazine may increase the hypotensive activities of Debrisoquin.Approved
HydrochlorothiazideDebrisoquin may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideDebrisoquin may increase the hypotensive activities of Hydroflumethiazide.Approved, Investigational
IloprostIloprost may increase the hypotensive activities of Debrisoquin.Approved, Investigational
ImidaprilDebrisoquin may increase the hypotensive activities of Imidapril.Investigational
IndapamideDebrisoquin may increase the hypotensive activities of Indapamide.Approved
IndenololDebrisoquin may increase the hypotensive activities of Indenolol.Withdrawn
IndoraminDebrisoquin may increase the hypotensive activities of Indoramin.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Debrisoquin.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Debrisoquin.Withdrawn
IrbesartanDebrisoquin may increase the hypotensive activities of Irbesartan.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Debrisoquin.Approved
IsoniazidThe metabolism of Debrisoquin can be decreased when combined with Isoniazid.Approved
IsradipineDebrisoquin may increase the hypotensive activities of Isradipine.Approved
KetanserinDebrisoquin may increase the hypotensive activities of Ketanserin.Investigational
LabetalolDebrisoquin may increase the hypotensive activities of Labetalol.Approved
LacidipineDebrisoquin may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostDebrisoquin may increase the hypotensive activities of Latanoprost.Approved, Investigational
LercanidipineDebrisoquin may increase the hypotensive activities of Lercanidipine.Approved, Investigational
LinsidomineDebrisoquin may increase the hypotensive activities of Linsidomine.Experimental
LofexidineDebrisoquin may increase the hypotensive activities of Lofexidine.Approved, Investigational
LopinavirThe metabolism of Debrisoquin can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Debrisoquin can be decreased when combined with Lorcaserin.Approved
LumacaftorThe serum concentration of Debrisoquin can be decreased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Debrisoquin can be decreased when combined with Lumefantrine.Approved
MacitentanDebrisoquin may increase the hypotensive activities of Macitentan.Approved
ManidipineDebrisoquin may increase the hypotensive activities of Manidipine.Approved, Investigational
MebanazineMebanazine may increase the hypotensive activities of Debrisoquin.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Debrisoquin.Approved
MethoserpidineDebrisoquin may increase the hypotensive activities of Methoserpidine.Experimental
MethotrimeprazineThe metabolism of Debrisoquin can be decreased when combined with Methotrimeprazine.Approved
MethyldopaDebrisoquin may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Debrisoquin.Approved, Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Debrisoquin.Approved, Investigational
MetipranololDebrisoquin may increase the hypotensive activities of Metipranolol.Approved
MetolazoneDebrisoquin may increase the hypotensive activities of Metolazone.Approved
MetyrosineDebrisoquin may increase the hypotensive activities of Metyrosine.Approved
MidostaurinThe metabolism of Debrisoquin can be decreased when combined with Midostaurin.Approved
MinaprineMinaprine may increase the hypotensive activities of Debrisoquin.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Debrisoquin.Approved
MirabegronThe metabolism of Debrisoquin can be decreased when combined with Mirabegron.Approved
MirodenafilMirodenafil may increase the antihypertensive activities of Debrisoquin.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Debrisoquin.Approved
MoexiprilDebrisoquin may increase the hypotensive activities of Moexipril.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Debrisoquin.Approved, Investigational
MoxonidineDebrisoquin may increase the hypotensive activities of Moxonidine.Approved, Investigational
MuzolimineDebrisoquin may increase the hypotensive activities of Muzolimine.Experimental
NadololDebrisoquin may increase the hypotensive activities of Nadolol.Approved
NaftopidilDebrisoquin may increase the hypotensive activities of Naftopidil.Investigational
NebivololDebrisoquin may increase the hypotensive activities of Nebivolol.Approved, Investigational
NevirapineThe metabolism of Debrisoquin can be decreased when combined with Nevirapine.Approved
NialamideNialamide may increase the hypotensive activities of Debrisoquin.Withdrawn
NicorandilDebrisoquin may increase the hypotensive activities of Nicorandil.Approved, Investigational
NiguldipineDebrisoquin may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineDebrisoquin may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimodipineDebrisoquin may increase the hypotensive activities of Nimodipine.Approved
NitroprussideNitroprusside may increase the hypotensive activities of Debrisoquin.Approved
ObinutuzumabDebrisoquin may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Debrisoquin.Withdrawn
OlmesartanDebrisoquin may increase the hypotensive activities of Olmesartan.Approved, Investigational
OmapatrilatDebrisoquin may increase the hypotensive activities of Omapatrilat.Investigational
OxprenololDebrisoquin may increase the hypotensive activities of Oxprenolol.Approved
PanobinostatThe serum concentration of Debrisoquin can be increased when it is combined with Panobinostat.Approved, Investigational
PargylinePargyline may increase the hypotensive activities of Debrisoquin.Approved
ParoxetineThe metabolism of Debrisoquin can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Debrisoquin can be decreased when it is combined with Peginterferon alfa-2b.Approved
PenbutololDebrisoquin may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentoliniumDebrisoquin may increase the hypotensive activities of Pentolinium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Debrisoquin.Approved, Investigational
PhenelzinePhenelzine may increase the hypotensive activities of Debrisoquin.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Debrisoquin.Withdrawn
PhenoxybenzamineDebrisoquin may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Debrisoquin.Withdrawn
PhentolamineDebrisoquin may increase the hypotensive activities of Phentolamine.Approved
PinacidilDebrisoquin may increase the hypotensive activities of Pinacidil.Withdrawn
PindololDebrisoquin may increase the hypotensive activities of Pindolol.Approved
PirlindolePirlindole may increase the hypotensive activities of Debrisoquin.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Debrisoquin.Withdrawn
PolythiazideDebrisoquin may increase the hypotensive activities of Polythiazide.Approved
PromazineThe metabolism of Debrisoquin can be decreased when combined with Promazine.Approved, Vet Approved
QuinaprilDebrisoquin may increase the hypotensive activities of Quinapril.Approved, Investigational
QuinidineThe metabolism of Debrisoquin can be decreased when combined with Quinidine.Approved
QuinineQuinine may increase the hypotensive activities of Debrisoquin.Approved
RamiprilDebrisoquin may increase the hypotensive activities of Ramipril.Approved
RanolazineThe serum concentration of Debrisoquin can be increased when it is combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the hypotensive activities of Debrisoquin.Approved
RemikirenDebrisoquin may increase the hypotensive activities of Remikiren.Approved
RescinnamineDebrisoquin may increase the hypotensive activities of Rescinnamine.Approved
RilmenidineDebrisoquin may increase the hypotensive activities of Rilmenidine.Investigational
RiociguatDebrisoquin may increase the hypotensive activities of Riociguat.Approved
RitonavirThe metabolism of Debrisoquin can be decreased when combined with Ritonavir.Approved, Investigational
RituximabDebrisoquin may increase the hypotensive activities of Rituximab.Approved
RopiniroleThe metabolism of Debrisoquin can be decreased when combined with Ropinirole.Approved, Investigational
SafrazineSafrazine may increase the hypotensive activities of Debrisoquin.Withdrawn
SaprisartanDebrisoquin may increase the hypotensive activities of Saprisartan.Experimental
SelexipagDebrisoquin may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Debrisoquin.Approved, Investigational
SitaxentanDebrisoquin may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilDebrisoquin may increase the hypotensive activities of Spirapril.Approved
StiripentolThe metabolism of Debrisoquin can be decreased when combined with Stiripentol.Approved
TadalafilTadalafil may increase the antihypertensive activities of Debrisoquin.Approved, Investigational
TalinololDebrisoquin may increase the hypotensive activities of Talinolol.Investigational
TemocaprilDebrisoquin may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerbinafineThe metabolism of Debrisoquin can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerlipressinDebrisoquin may increase the hypotensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatineDebrisoquin may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TheodrenalineDebrisoquin may increase the hypotensive activities of Theodrenaline.Investigational
ThioridazineThe metabolism of Debrisoquin can be decreased when combined with Thioridazine.Approved, Withdrawn
TiboloneDebrisoquin may increase the hypotensive activities of Tibolone.Approved, Investigational
TiclopidineThe metabolism of Debrisoquin can be decreased when combined with Ticlopidine.Approved
TicrynafenDebrisoquin may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololDebrisoquin may increase the hypotensive activities of Timolol.Approved
TipranavirThe metabolism of Debrisoquin can be decreased when combined with Tipranavir.Approved, Investigational
TolazolineDebrisoquin may increase the hypotensive activities of Tolazoline.Approved, Vet Approved
TolonidineDebrisoquin may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Debrisoquin.Approved
TorasemideDebrisoquin may increase the hypotensive activities of Torasemide.Approved
TrandolaprilDebrisoquin may increase the hypotensive activities of Trandolapril.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Debrisoquin.Experimental
TranylcypromineThe metabolism of Debrisoquin can be decreased when combined with Tranylcypromine.Approved
TravoprostDebrisoquin may increase the hypotensive activities of Travoprost.Approved
TreprostinilDebrisoquin may increase the hypotensive activities of Treprostinil.Approved, Investigational
TrichlormethiazideDebrisoquin may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinDebrisoquin may increase the hypotensive activities of Trimazosin.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Debrisoquin.Approved, Investigational
UdenafilUdenafil may increase the antihypertensive activities of Debrisoquin.Approved, Investigational
UnoprostoneDebrisoquin may increase the hypotensive activities of Unoprostone.Approved
UrapidilDebrisoquin may increase the hypotensive activities of Urapidil.Investigational
ValsartanDebrisoquin may increase the hypotensive activities of Valsartan.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Debrisoquin.Approved
VincamineDebrisoquin may increase the hypotensive activities of Vincamine.Experimental
VinpocetineDebrisoquin may increase the hypotensive activities of Vinpocetine.Investigational
XipamideDebrisoquin may increase the hypotensive activities of Xipamide.Experimental
XylometazolineDebrisoquin may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Debrisoquin.Approved, Vet Approved
ZiprasidoneThe metabolism of Debrisoquin can be decreased when combined with Ziprasidone.Approved
ZofenoprilDebrisoquin may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Wenner,W.; U.S. Patent 3,157,573; November 17,1964; assigned to Hoffmann-LaRoche, Inc.

General References
Not Available
External Links
Human Metabolome Database
HMDB06543
KEGG Compound
C13650
PubChem Compound
2966
PubChem Substance
46507664
ChemSpider
2860
BindingDB
50122613
ChEBI
34665
ChEMBL
CHEMBL169901
Therapeutic Targets Database
DAP000125
PharmGKB
PA452616
ATC Codes
C02CC04 — Debrisoquine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableRecruitingOtherHealthy Volunteers1

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)278-280 °CPhysProp
logP0.75SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.842 mg/mLALOGPS
logP0.58ALOGPS
logP1.07ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)12.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.11 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity63.85 m3·mol-1ChemAxon
Polarizability19.48 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9714
Blood Brain Barrier+0.9106
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.8427
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterInhibitor0.8817
CYP450 2C9 substrateNon-substrate0.8429
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.7101
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9549
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9532
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9462
Ames testNon AMES toxic0.7018
CarcinogenicityNon-carcinogens0.976
BiodegradationNot ready biodegradable0.9422
Rat acute toxicity2.7479 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6904
hERG inhibition (predictor II)Inhibitor0.5928
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
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 tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Tetrahydroisoquinolines
Sub Class
Not Available
Direct Parent
Tetrahydroisoquinolines
Alternative Parents
Benzenoids / Guanidines / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Imines / Hydrocarbon derivatives
Substituents
Tetrahydroisoquinoline / Benzenoid / Guanidine / Azacycle / Carboximidamide / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Imine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carboxamidine, isoquinolines (CHEBI:34665)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Joyce PI, Rizzi D, Calo G, Rowbotham DJ, Lambert DG: The effect of guanethidine and local anesthetics on the electrically stimulated mouse vas deferens. Anesth Analg. 2002 Nov;95(5):1339-43, table of contents. [PubMed:12401623]
  2. Bryan-Lluka LJ, Seers H, Sharpe I: Amezinium and debrisoquine are substrates of uptake1 and potent inhibitors of monoamine oxidase in perfused lungs of rats. Naunyn Schmiedebergs Arch Pharmacol. 1996 Apr;353(5):536-44. [PubMed:8740147]
  3. Mitchell JR, Cavanaugh JH, Arias L, Oates JA: Guanethidine and related agents. 3. Antagonism by drugs which inhibit the norepinephrine pump in man. J Clin Invest. 1970 Aug;49(8):1596-604. [PubMed:5431666]
  4. Yi E, Love JA: Alpha-adrenergic modulation of synaptic transmission in rabbit pancreatic ganglia. Auton Neurosci. 2005 Oct 30;122(1-2):45-57. Epub 2005 Aug 25. [PubMed:16126010]
  5. Galli A, Blakely RD, DeFelice LJ: Norepinephrine transporters have channel modes of conduction. Proc Natl Acad Sci U S A. 1996 Aug 6;93(16):8671-6. [PubMed:8710929]

Enzymes

Details
1. Cytochrome P450 2D6
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372]

Drug created on September 26, 2007 09:28 / Updated on November 09, 2017 03:48