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Identification
NameMetaraminol
Accession NumberDB00610  (APRD00555)
TypeSmall Molecule
GroupsApproved, 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
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
AcetaminophenThe risk or severity of adverse effects can be increased when Metaraminol is combined with Acetaminophen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Metaraminol is combined with Acetylsalicylic acid.
AminophyllineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Aminophylline.
AmphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Metaraminol is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Metaraminol.
BenzphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Benzphetamine.
ButalbitalThe risk or severity of adverse effects can be increased when Metaraminol is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Caffeine.
CocaineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Cocaine.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Metaraminol is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dipivefrin.
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.
DoxapramThe risk or severity of adverse effects can be increased when Metaraminol is combined with Doxapram.
DronabinolDronabinol may increase the tachycardic activities of Metaraminol.
DyphyllineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Dyphylline.
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 Metaraminol is combined with Epinephrine.
FenoterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Fenoterol.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Metaraminol is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Formoterol.
IndacaterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Metaraminol.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Metaraminol is combined with Ipratropium bromide.
IsomethepteneThe risk or severity of adverse effects can be increased when Metaraminol is combined with Isometheptene.
LevonordefrinThe risk or severity of adverse effects can be increased when Metaraminol is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Metaraminol.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Lisdexamfetamine.
MepivacaineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Mepivacaine.
MethamphetamineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Midodrine.
ModafinilThe risk or severity of adverse effects can be increased when Metaraminol is combined with Modafinil.
NabiloneNabilone may increase the tachycardic activities of Metaraminol.
NaphazolineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Naphazoline.
NorepinephrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Norepinephrine.
OlodaterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Olodaterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Oxymetazoline.
PhendimetrazineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Phendimetrazine.
PheniramineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Pheniramine.
PhentermineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Phenylephrine.
PirbuterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Pirbuterol.
PropylhexedrineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Propylhexedrine.
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.
SalbutamolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Salmeterol.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Metaraminol.
TerbutalineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Terbutaline.
TheophyllineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Theophylline.
TriprolidineThe risk or severity of adverse effects can be increased when Metaraminol is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Vilanterol.
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