Identification

Name
Metaraminol
Accession Number
DB00610  (APRD00555)
Type
Small Molecule
Groups
Approved, Investigational
Description

An adrenergic agonist that acts predominantly at alpha adrenergic receptors and also stimulates the release of norepinephrine. It has been used primarily as a vasoconstrictor in the treatment of hypotension. [PubChem]

Structure
Thumb
Synonyms
  • (-)-Erythro-metaraminol
  • 1-(m-Hydroxyphenyl)-2-amino-1-propanol
  • 1-Metaraminol
  • 2-Amino-1-(m-hydroxyphenyl)-1-propanol
  • 3-Hydroxyphenylisopropanolamine
  • alpha-(1-Aminoethyl)-3-hydroxybenzenemethanol
  • alpha-(m-Hydroxyphenyl)-beta-aminopropanol
  • Hydroxynorephedrine
  • L-Metaraminol
  • m-Hydroxy norephedrine
  • m-Hydroxyphenylpropanolamine
  • m-Hydroxypropadrine
  • Metaraminol
  • Métaraminol
  • Metaraminolum
Product Ingredients
IngredientUNIICASInChI Key
Metaraminol BitartrateZC4202M9P333402-03-8VENXSELNXQXCNT-IJYXXVHRSA-N
Metaraminol TartrateNot AvailableNot AvailableNot applicable
International/Other Brands
Aramine (Merck) / Metaramin / Pressonex
Categories
UNII
818U2PZ2EH
CAS number
54-49-9
Weight
Average: 167.205
Monoisotopic: 167.094628665
Chemical Formula
C9H13NO2
InChI Key
WXFIGDLSSYIKKV-RCOVLWMOSA-N
InChI
InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1
IUPAC Name
3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
SMILES
C[C@H](N)[C@H](O)C1=CC(O)=CC=C1

Pharmacology

Indication

For the treatment and prevention of hypotension due to hemorrhage, spinal anesthesia, and shock associated with brain damage

Pharmacodynamics

Metaraminol is a potent sympathomimetic amine that increases both systolic and diastolic blood pressure. Metaraminol is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor. Metaraminol acts on both α1-adrenergic receptors but appears to have no effect on β-adrenergic receptors. It acts by increasing the force of the heart's pumping action as well as constricting peripheral blood vessels.

Mechanism of action

Metaraminol acts through peripheral vasoconstriction by acting as a pure alpha-1 adrenergic receptor agonist, consequently increasing systemic blood pressure (both systolic & diastolic). Its effect is thought to be associated with the inhibition of adenyl cyclase which leads to an inhibition of the production of cAMP. Another effect of Metaraminol is that it releases norepinephrine from its storage sites indirectly.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Human
Absorption

The effect starts 1-2 min after IV injection, 10 min after IM injection, 5-20 min after subcutaneous injection.

Volume of distribution
Not Available
Protein binding

Approximately 45%

Metabolism

Hepatic

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

LD50=240 mg/kg (rat, oral); LD50=99 mg/kg (mouse, oral)

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 hypertensive activities of Metaraminol.Experimental
AcebutololThe risk or severity of adverse effects can be increased when Metaraminol is combined with Acebutolol.Approved, Investigational
AcepromazineAcepromazine may decrease the vasoconstricting activities of Metaraminol.Approved, Vet Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
AmineptineAmineptine may increase the vasopressor activities of Metaraminol.Illicit, Withdrawn
AmitriptylineAmitriptyline may increase the vasopressor activities of Metaraminol.Approved
AmitriptylinoxideAmitriptylinoxide may increase the vasopressor activities of Metaraminol.Approved, Investigational
AmoxapineAmoxapine may increase the vasopressor activities of Metaraminol.Approved
AmphetamineAmphetamine may increase the hypertensive activities of Metaraminol.Approved, Illicit, Investigational
AripiprazoleAripiprazole may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
AsenapineAsenapine may decrease the vasoconstricting activities of Metaraminol.Approved
AtomoxetineAtomoxetine may increase the hypertensive activities of Metaraminol.Approved
BenmoxinBenmoxin may increase the hypertensive activities of Metaraminol.Withdrawn
BenzphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysineMetaraminol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BevantololBevantolol may decrease the vasoconstricting activities of Metaraminol.Approved
BrexpiprazoleBrexpiprazole may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
BrofaromineBrofaromine may increase the hypertensive activities of Metaraminol.Experimental
BromocriptineBromocriptine may increase the hypertensive activities of Metaraminol.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Metaraminol.Investigational
BunazosinBunazosin may decrease the vasoconstricting activities of Metaraminol.Investigational
ButriptylineButriptyline may increase the vasopressor activities of Metaraminol.Approved
CabergolineCabergoline may increase the hypertensive activities of Metaraminol.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of Metaraminol.Withdrawn
CarvedilolCarvedilol may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Metaraminol is combined with Celiprolol.Approved, Investigational
ChlorphentermineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Chlorphentermine.Illicit, Withdrawn
ChlorpromazineChlorpromazine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational, Vet Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Clenbuterol.Approved, Investigational, Vet Approved
ClomipramineClomipramine may increase the vasopressor activities of Metaraminol.Approved, Investigational, Vet Approved
ClozapineClozapine may decrease the vasoconstricting activities of Metaraminol.Approved
DapiprazoleDapiprazole may decrease the vasoconstricting activities of Metaraminol.Approved
DesipramineDesipramine may increase the vasopressor activities of Metaraminol.Approved, Investigational
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Metaraminol.Approved, Investigational
DextroamphetamineDextroamphetamine may decrease the vasoconstricting activities of Metaraminol.Approved, Illicit
DibenzepinDibenzepin may increase the vasopressor activities of Metaraminol.Experimental
DihydroergocornineDihydroergocornine may increase the hypertensive activities of Metaraminol.Approved
DihydroergocristineDihydroergocristine may increase the hypertensive activities of Metaraminol.Approved, Experimental
DihydroergocryptineDihydroergocryptine may increase the hypertensive activities of Metaraminol.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Metaraminol.Approved, Investigational
DimetacrineDimetacrine may increase the vasopressor activities of Metaraminol.Approved, Withdrawn
DobutamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dobutamine.Approved
DopamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dopamine.Approved
DosulepinDosulepin may increase the vasopressor activities of Metaraminol.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Metaraminol.Approved
DoxepinDoxepin may increase the vasopressor activities of Metaraminol.Approved, Investigational
DoxofyllineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Doxofylline.Approved, Investigational
DronabinolDronabinol may increase the tachycardic activities of Metaraminol.Approved, Illicit
DronedaroneDronedarone may decrease the vasoconstricting activities of Metaraminol.Approved
DroperidolDroperidol may decrease the vasoconstricting activities of Metaraminol.Approved, Vet Approved
DuloxetineDuloxetine may increase the tachycardic activities of Metaraminol.Approved
EpanololThe risk or severity of adverse effects can be increased when Metaraminol is combined with Epanolol.Experimental
EphedrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ephedrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Epinephrine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive and vasoconstricting activities of Metaraminol.Approved
ErgonovineErgonovine may increase the hypertensive activities of Metaraminol.Approved
ErgotamineErgotamine may increase the hypertensive activities of Metaraminol.Approved
EscitalopramEscitalopram may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
EtilefrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Etilefrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Fenoterol.Approved, Investigational
FenozoloneThe risk or severity of adverse effects can be increased when Metaraminol is combined with Fenozolone.Experimental
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Metaraminol.Approved, Illicit, Investigational, Vet Approved
FlupentixolFlupentixol may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational, Withdrawn
FurazolidoneFurazolidone may increase the hypertensive activities of Metaraminol.Approved, Investigational, Vet Approved
HarmalineHarmaline may increase the hypertensive activities of Metaraminol.Experimental
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Metaraminol.Approved, Investigational
HydracarbazineHydracarbazine may increase the hypertensive activities of Metaraminol.Experimental
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Hydroxyamphetamine.Approved
IloperidoneIloperidone may decrease the vasoconstricting activities of Metaraminol.Approved
ImipramineImipramine may increase the vasopressor activities of Metaraminol.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Metaraminol.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Metaraminol.Approved, Investigational
IprindoleIprindole may increase the vasopressor activities of Metaraminol.Experimental
IproclozideIproclozide may increase the hypertensive activities of Metaraminol.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Metaraminol.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Metaraminol.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Isoprenaline.Approved, Investigational
IsoxsuprineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Isoxsuprine.Approved, Withdrawn
LabetalolLabetalol may decrease the vasoconstricting activities of Metaraminol.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Metaraminol.Approved, Investigational
LinezolidLinezolid may increase the hypertensive activities of Metaraminol.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
LisurideLisuride may increase the hypertensive activities of Metaraminol.Approved, Investigational
LofepramineLofepramine may increase the vasopressor activities of Metaraminol.Experimental
Lysergic Acid DiethylamideLysergic Acid Diethylamide may increase the hypertensive activities of Metaraminol.Illicit, Investigational, Withdrawn
MebanazineMebanazine may increase the hypertensive activities of Metaraminol.Withdrawn
MefenorexThe risk or severity of adverse effects can be increased when Metaraminol is combined with Mefenorex.Experimental
MelitracenMelitracen may increase the vasopressor activities of Metaraminol.Experimental, Investigational
MephentermineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Mephentermine.Approved
MetergolineMetergoline may increase the hypertensive activities of Metaraminol.Experimental
MethamphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methamphetamine.Approved, Illicit
MethotrimeprazineMethotrimeprazine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
MethoxamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methoxamine.Approved, Investigational
Methylene blueMethylene blue may increase the hypertensive activities of Metaraminol.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive and vasoconstricting activities of Metaraminol.Approved
MethysergideMethysergide may increase the hypertensive activities of Metaraminol.Approved
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Metaraminol.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Metaraminol.Approved, Investigational
MinaprineMinaprine may increase the hypertensive activities of Metaraminol.Approved
MoclobemideMoclobemide may increase the hypertensive activities of Metaraminol.Approved, Investigational
NabiloneNabilone may increase the tachycardic activities of Metaraminol.Approved, Investigational
NefazodoneNefazodone may decrease the vasoconstricting activities of Metaraminol.Approved, Withdrawn
NialamideNialamide may increase the hypertensive activities of Metaraminol.Withdrawn
NicardipineNicardipine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
NicergolineNicergoline may increase the hypertensive activities of Metaraminol.Approved, Investigational
NiguldipineNiguldipine may decrease the vasoconstricting activities of Metaraminol.Experimental
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Metaraminol.Approved
NortriptylineNortriptyline may increase the vasopressor activities of Metaraminol.Approved
NylidrinThe risk or severity of adverse effects can be increased when Metaraminol is combined with Nylidrin.Approved
OctamoxinOctamoxin may increase the hypertensive activities of Metaraminol.Withdrawn
OlanzapineOlanzapine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
OpipramolOpipramol may increase the vasopressor activities of Metaraminol.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Orciprenaline.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Oxymetazoline.Approved, Investigational
PaliperidonePaliperidone may decrease the vasoconstricting activities of Metaraminol.Approved
PargylinePargyline may increase the hypertensive activities of Metaraminol.Approved
Patent BlueThe therapeutic efficacy of Metaraminol can be decreased when used in combination with Patent Blue.Approved
PergolidePergolide may increase the hypertensive activities of Metaraminol.Approved, Investigational, Vet Approved, Withdrawn
PhenelzinePhenelzine may increase the hypertensive activities of Metaraminol.Approved
PheniprazinePheniprazine may increase the hypertensive activities of Metaraminol.Withdrawn
PhenmetrazineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Phenmetrazine.Approved, Illicit
PhenoxybenzaminePhenoxybenzamine may decrease the vasoconstricting activities of Metaraminol.Approved
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Metaraminol.Withdrawn
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Metaraminol.Approved, Illicit
PhentolaminePhentolamine may decrease the vasoconstricting activities of Metaraminol.Approved
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Metaraminol.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Metaraminol.Approved, Vet Approved, Withdrawn
PirlindolePirlindole may increase the hypertensive activities of Metaraminol.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of Metaraminol.Withdrawn
PizotifenPizotifen may decrease the vasoconstricting activities of Metaraminol.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Metaraminol.Approved
PrenalterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Prenalterol.Experimental
ProcaineProcaine may increase the hypertensive activities of Metaraminol.Approved, Investigational, Vet Approved
ProcarbazineProcarbazine may increase the hypertensive activities of Metaraminol.Approved, Investigational
ProcaterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Procaterol.Approved, Investigational
PromazinePromazine may decrease the vasoconstricting activities of Metaraminol.Approved, Vet Approved
PropericiazinePropericiazine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
PropiomazinePropiomazine may decrease the vasoconstricting activities of Metaraminol.Approved
PropiverinePropiverine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
ProtriptylineProtriptyline may increase the vasopressor activities of Metaraminol.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Pseudoephedrine.Approved
QuetiapineQuetiapine may decrease the vasoconstricting activities of Metaraminol.Approved
QuinidineQuinidine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
RacepinephrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Racepinephrine.Approved
RasagilineRasagiline may increase the hypertensive activities of Metaraminol.Approved
RisperidoneRisperidone may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
RitodrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ritodrine.Approved, Investigational
SafrazineSafrazine may increase the hypertensive activities of Metaraminol.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of Metaraminol.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Metaraminol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Metaraminol.Approved
SynephrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Synephrine.Experimental
TamsulosinTamsulosin may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Metaraminol.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Metaraminol.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Terbutaline.Approved
TergurideTerguride may increase the hypertensive activities of Metaraminol.Experimental
TetryzolineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Tetryzoline.Approved
ThioproperazineThioproperazine may decrease the vasoconstricting activities of Metaraminol.Approved
ThioridazineThioridazine may decrease the vasoconstricting activities of Metaraminol.Approved, Withdrawn
TianeptineTianeptine may increase the vasopressor activities of Metaraminol.Approved, Investigational
TolazolineTolazoline may decrease the vasoconstricting activities of Metaraminol.Approved, Vet Approved
ToloxatoneToloxatone may increase the hypertensive activities of Metaraminol.Approved
TramazolineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Tramazoline.Investigational
TranylcypromineTranylcypromine may increase the hypertensive activities of Metaraminol.Approved, Investigational
TrazodoneTrazodone may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
TretoquinolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Tretoquinol.Experimental
TrifluoperazineTrifluoperazine may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
TrimazosinTrimazosin may decrease the vasoconstricting activities of Metaraminol.Experimental
TrimipramineTrimipramine may increase the vasopressor activities of Metaraminol.Approved
TyramineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Tyramine.Investigational, Nutraceutical
UrapidilUrapidil may decrease the vasoconstricting activities of Metaraminol.Investigational
VenlafaxineVenlafaxine may increase the tachycardic activities of Metaraminol.Approved
VerapamilVerapamil may decrease the vasoconstricting activities of Metaraminol.Approved
ZiprasidoneZiprasidone may decrease the vasoconstricting activities of Metaraminol.Approved
ZuclopenthixolZuclopenthixol may decrease the vasoconstricting activities of Metaraminol.Approved, Investigational
Food Interactions
Not Available

References

General References
  1. McDonald M, Santucci RA: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. Int Braz J Urol. 2004 Mar-Apr;30(2):121-2. [PubMed:15703094]
  2. Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. [PubMed:2258979]
  3. Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism]. Urologe A. 1988 Jul;27(4):225-9. [PubMed:3140463]
External Links
Human Metabolome Database
HMDB0014748
KEGG Compound
C07146
PubChem Compound
5906
PubChem Substance
46505593
ChemSpider
5695
ChEBI
6794
ChEMBL
CHEMBL1201319
Therapeutic Targets Database
DAP000225
PharmGKB
PA164748761
RxList
RxList Drug Page
Wikipedia
Metaraminol
ATC Codes
C01CA09 — Metaraminol
MSDS
Download (52.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentArterial Hypotension1
3WithdrawnTreatmentPreeclampsia / Pregnancy Toxemias1
Not AvailableUnknown StatusDiagnosticPreeclampsia1

Pharmacoeconomics

Manufacturers
  • Merck and co inc
  • Abraxis pharmaceutical products
  • App pharmaceuticals llc
  • Elkins sinn div ah robins co inc
  • Gd searle llc
Packagers
  • Physicians Total Care Inc.
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)107.5 °CPhysProp
boiling point (°C)218 °CPhysProp
water solubility1000 g/LNot Available
logP-0.27HANSCH,C ET AL. (1995); ion-corrected
pKa8.79SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility12.8 mg/mLALOGPS
logP-0.59ALOGPS
logP-0.045ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.03ChemAxon
pKa (Strongest Basic)9.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.89 m3·mol-1ChemAxon
Polarizability17.84 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9922
Blood Brain Barrier-0.8926
Caco-2 permeable+0.6112
P-glycoprotein substrateNon-substrate0.721
P-glycoprotein inhibitor INon-inhibitor0.9907
P-glycoprotein inhibitor IINon-inhibitor0.9961
Renal organic cation transporterNon-inhibitor0.9152
CYP450 2C9 substrateNon-substrate0.7922
CYP450 2D6 substrateNon-substrate0.6311
CYP450 3A4 substrateNon-substrate0.7459
CYP450 1A2 substrateNon-inhibitor0.899
CYP450 2C9 inhibitorNon-inhibitor0.9538
CYP450 2D6 inhibitorNon-inhibitor0.9724
CYP450 2C19 inhibitorNon-inhibitor0.9255
CYP450 3A4 inhibitorNon-inhibitor0.8264
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9205
Ames testNon AMES toxic0.8102
CarcinogenicityNon-carcinogens0.837
BiodegradationNot ready biodegradable0.6456
Rat acute toxicity2.7863 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9126
hERG inhibition (predictor II)Non-inhibitor0.9492
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
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0uxr-0900000000-54fdef7fb806e9618517
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-1900000000-53aa60f30061472008e2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-3900000000-03da43641cb5f6da239a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-056r-9700000000-bb18dd53ad6ac9a58e4f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-9300000000-3d3ebdc9e7c553d5122c

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Phenylpropane / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Organic nitrogen compound / Aromatic alcohol / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenylethanolamines (CHEBI:6794)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Tatsuta M, Iishi H, Baba M, Yano H, Sakai N, Uehara H, Hirasawa R, Nakaizumi A: Alpha1-adrenoceptor stimulation enhances experimental gastric carcinogenesis induced by N-methyl-N'-nitro-N-nitrosoguanidine in Wistar rats. Int J Cancer. 1998 Jul 29;77(3):467-9. [PubMed:9663612]

Drug created on June 13, 2005 07:24 / Updated on July 02, 2018 20:40