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Identification
NameMetaraminol
Accession NumberDB00610  (APRD00555)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionAn 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AramineMerck
MetaraminNot Available
PressonexNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Metaraminol Bitartrate
ThumbNot applicableDBSALT001017
Metaraminol Tartrate
ThumbNot applicableDBSALT001016
Categories
UNII818U2PZ2EH
CAS number54-49-9
WeightAverage: 167.205
Monoisotopic: 167.094628665
Chemical FormulaC9H13NO2
InChI KeyWXFIGDLSSYIKKV-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[[email protected]](N)[[email protected]](O)C1=CC(O)=CC=C1
Pharmacology
IndicationFor the treatment and prevention of hypotension due to hemorrhage, spinal anesthesia, and shock associated with brain damage
Structured Indications Not Available
PharmacodynamicsMetaraminol 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 actionMetaraminol 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-1A adrenergic receptorProteinyes
agonist
HumanP35348 details
Related Articles
AbsorptionThe effect starts 1-2 min after IV injection, 10 min after IM injection, 5-20 min after subcutaneous injection.
Volume of distributionNot Available
Protein bindingApproximately 45%
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=240 mg/kg (rat, oral); LD50=99 mg/kg (mouse, oral)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
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
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Metaraminol.Approved, Illicit
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
BromocriptineBromocriptine may increase the hypertensive activities of Metaraminol.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Metaraminol.Investigational
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
ClenbuterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Clenbuterol.Approved, Vet Approved
ClomipramineClomipramine may increase the vasopressor activities of Metaraminol.Approved, Vet Approved
CyclobenzaprineCyclobenzaprine may increase the vasopressor activities of Metaraminol.Approved
DesipramineDesipramine may increase the vasopressor activities of Metaraminol.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Metaraminol.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Metaraminol.Approved
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
DoxofyllineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Metaraminol.Approved, Illicit
DuloxetineDuloxetine may increase the tachycardic activities of Metaraminol.Approved
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 activities of Metaraminol.Approved
ErgonovineErgonovine may increase the hypertensive activities of Metaraminol.Approved
ErgotamineErgotamine may increase the hypertensive activities of Metaraminol.Approved
EsmirtazapineEsmirtazapine may increase the vasopressor activities of Metaraminol.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
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Metaraminol.Approved, Illicit, Investigational, Vet Approved
FurazolidoneFurazolidone may increase the hypertensive activities of Metaraminol.Approved, Vet Approved
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Metaraminol.Approved, Investigational
HydracarbazineHydracarbazine may increase the hypertensive activities of Metaraminol.Approved
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Metaraminol is combined with Hydroxyamphetamine hydrobromide.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
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
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
LinezolidLinezolid may increase the hypertensive activities of Metaraminol.Approved, Investigational
MebanazineMebanazine may increase the hypertensive activities of Metaraminol.Withdrawn
MephentermineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Mephentermine.Approved
MethamphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methamphetamine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methoxamine.Approved
Methylene blueMethylene blue may increase the hypertensive activities of Metaraminol.Investigational
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
MinaprineMinaprine may increase the hypertensive activities of Metaraminol.Approved
MirtazapineMirtazapine may increase the vasopressor activities of Metaraminol.Approved
MoclobemideMoclobemide may increase the hypertensive activities of Metaraminol.Approved
NabiloneNabilone may increase the tachycardic activities of Metaraminol.Approved, Investigational
NialamideNialamide may increase the hypertensive activities of Metaraminol.Withdrawn
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
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
PargylinePargyline may increase the hypertensive activities of Metaraminol.Approved
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
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
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
PrazosinPrazosin may decrease the vasoconstricting activities of Metaraminol.Approved
ProcaterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Procaterol.Approved
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
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
RitodrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ritodrine.Approved
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
TetryzolineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Tetryzoline.Approved
TianeptineTianeptine may increase the vasopressor activities of Metaraminol.Approved
ToloxatoneToloxatone may increase the hypertensive activities of Metaraminol.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Metaraminol.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Metaraminol.Approved
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
VenlafaxineVenlafaxine may increase the tachycardic activities of Metaraminol.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesC01CA09
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (52.4 KB)
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Merck and co inc
  • Abraxis pharmaceutical products
  • App pharmaceuticals llc
  • Elkins sinn div ah robins co inc
  • Gd searle llc
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point107.5 °CPhysProp
boiling point218 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Aralkylamine
  • Phenol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23