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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 KeyInChIKey=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[[email protected]](N)[[email protected]](O)C1=CC(O)=CC=C1
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
Pharmacology
IndicationFor the treatment and prevention of hypotension due to hemorrhage, spinal anesthesia, and shock associated with brain damage
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.
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
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
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)
Interactions
Drug Interactions
Drug
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of Metaraminol.
AcebutololThe risk or severity of adverse effects can be increased when Metaraminol is combined with Acebutolol.
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Metaraminol.
AmineptineAmineptine may increase the vasopressor activities of Metaraminol.
AmitriptylineAmitriptyline may increase the vasopressor activities of Metaraminol.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Metaraminol.
AtomoxetineAtomoxetine may increase the hypertensive activities of Metaraminol.
BenmoxinBenmoxin may increase the hypertensive activities of Metaraminol.
BenzphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Benzphetamine.
Benzylpenicilloyl PolylysineMetaraminol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
BromocriptineBromocriptine may increase the hypertensive activities of Metaraminol.
CabergolineCabergoline may increase the hypertensive activities of Metaraminol.
CaroxazoneCaroxazone may increase the hypertensive activities of Metaraminol.
CarvedilolCarvedilol may decrease the vasoconstricting activities of Metaraminol.
CeliprololThe risk or severity of adverse effects can be increased when Metaraminol is combined with Celiprolol.
ChlorphentermineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Chlorphentermine.
ClenbuterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Clenbuterol.
ClomipramineClomipramine may increase the vasopressor activities of Metaraminol.
CyclobenzaprineCyclobenzaprine may increase the vasopressor activities of Metaraminol.
DesipramineDesipramine may increase the vasopressor activities of Metaraminol.
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Metaraminol.
DobutamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dopamine.
DosulepinDosulepin may increase the vasopressor activities of Metaraminol.
DoxazosinDoxazosin may decrease the vasoconstricting activities of Metaraminol.
DoxepinDoxepin may increase the vasopressor activities of Metaraminol.
DoxofyllineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Metaraminol.
EphedrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Metaraminol.
ErgonovineErgonovine may increase the hypertensive activities of Metaraminol.
ErgotamineErgotamine may increase the hypertensive activities of Metaraminol.
EsmirtazapineEsmirtazapine may increase the vasopressor activities of Metaraminol.
EtilefrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Etilefrine.
FenoterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Fenoterol.
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Metaraminol.
FurazolidoneFurazolidone may increase the hypertensive activities of Metaraminol.
HydracarbazineHydracarbazine may increase the hypertensive activities of Metaraminol.
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Metaraminol is combined with Hydroxyamphetamine hydrobromide.
ImipramineImipramine may increase the vasopressor activities of Metaraminol.
IndoraminIndoramin may decrease the vasoconstricting activities of Metaraminol.
IproclozideIproclozide may increase the hypertensive activities of Metaraminol.
IproniazidIproniazid may increase the hypertensive activities of Metaraminol.
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Metaraminol.
IsoprenalineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Isoprenaline.
IsoxsuprineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Isoxsuprine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Metaraminol.
LinezolidLinezolid may increase the hypertensive activities of Metaraminol.
MebanazineMebanazine may increase the hypertensive activities of Metaraminol.
MephentermineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Mephentermine.
MethamphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methamphetamine.
MethoxamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methoxamine.
Methylene blueMethylene blue may increase the hypertensive activities of Metaraminol.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Metaraminol.
MinaprineMinaprine may increase the hypertensive activities of Metaraminol.
MirtazapineMirtazapine may increase the vasopressor activities of Metaraminol.
MoclobemideMoclobemide may increase the hypertensive activities of Metaraminol.
NabiloneNabilone may increase the tachycardic activities of Metaraminol.
NialamideNialamide may increase the hypertensive activities of Metaraminol.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Metaraminol.
NortriptylineNortriptyline may increase the vasopressor activities of Metaraminol.
NylidrinThe risk or severity of adverse effects can be increased when Metaraminol is combined with Nylidrin.
OctamoxinOctamoxin may increase the hypertensive activities of Metaraminol.
OrciprenalineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Orciprenaline.
OxymetazolineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Oxymetazoline.
PargylinePargyline may increase the hypertensive activities of Metaraminol.
PhenelzinePhenelzine may increase the hypertensive activities of Metaraminol.
PheniprazinePheniprazine may increase the hypertensive activities of Metaraminol.
PhenmetrazineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Phenmetrazine.
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Metaraminol.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Metaraminol.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Metaraminol.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Metaraminol.
PirlindolePirlindole may increase the hypertensive activities of Metaraminol.
PivhydrazinePivhydrazine may increase the hypertensive activities of Metaraminol.
PrazosinPrazosin may decrease the vasoconstricting activities of Metaraminol.
ProcaterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Procaterol.
ProtriptylineProtriptyline may increase the vasopressor activities of Metaraminol.
PseudoephedrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Racepinephrine.
RasagilineRasagiline may increase the hypertensive activities of Metaraminol.
RitodrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ritodrine.
SafrazineSafrazine may increase the hypertensive activities of Metaraminol.
SelegilineSelegiline may increase the hypertensive activities of Metaraminol.
SilodosinSilodosin may decrease the vasoconstricting activities of Metaraminol.
SynephrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Synephrine.
TamsulosinTamsulosin may decrease the vasoconstricting activities of Metaraminol.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Metaraminol.
TerazosinTerazosin may decrease the vasoconstricting activities of Metaraminol.
TerbutalineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Terbutaline.
TetryzolineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Tetryzoline.
TianeptineTianeptine may increase the vasopressor activities of Metaraminol.
ToloxatoneToloxatone may increase the hypertensive activities of Metaraminol.
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Metaraminol.
TranylcypromineTranylcypromine may increase the hypertensive activities of Metaraminol.
TrimazosinTrimazosin may decrease the vasoconstricting activities of Metaraminol.
TrimipramineTrimipramine may increase the vasopressor activities of Metaraminol.
TyramineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Tyramine.
Food InteractionsNot Available

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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23