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Identification
NameMethoxamine
Accession NumberDB00723  (APRD00062)
TypeSmall Molecule
GroupsApproved
Description

An alpha-adrenergic agonist that causes prolonged peripheral vasoconstriction. It has little if any direct effect on the central nervous system. [PubChem]

Structure
Thumb
Synonyms
Méthoxamédrine
Methoxamin
Méthoxamine
Methoxaminum
Metossamina
Metoxamina
Pseudomethoxamine
Vasoxyl
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vasoxyl Inj 20mg/mlliquid20 mgintramuscular; intravenousGlaxo Wellcome Inc.1950-12-312001-01-25Canada
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
MexanNippon Shinyaku
VasoxineNot Available
VasoxylNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Methoxamine Hydrochloride
ThumbNot applicableDBSALT000971
Categories
UNIIHUQ1KC1YLI
CAS number390-28-3
WeightAverage: 211.2576
Monoisotopic: 211.120843415
Chemical FormulaC11H17NO3
InChI KeyInChIKey=WJAJPNHVVFWKKL-UHFFFAOYSA-N
InChI
InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3
IUPAC Name
2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
SMILES
COC1=CC(C(O)C(C)N)=C(OC)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • P-dimethoxybenzene
  • Dimethoxybenzene
  • Phenylpropane
  • Phenol ether
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Ether
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationIndicated for the treatment and management of hypotension.
PharmacodynamicsMethoxamine is a potent sympathomimetic amine that increases both systolic and diastolic blood pressure. Methoxamine 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. Methoxamine 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 actionMethoxamine acts through peripheral vasoconstriction by acting as a pure alpha-1 adrenergic receptor agonist, consequently increasing systemic blood pressure (both systolic and diastolic).
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingLow
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
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+0.9751
Blood Brain Barrier-0.8857
Caco-2 permeable+0.5637
P-glycoprotein substrateNon-substrate0.6457
P-glycoprotein inhibitor INon-inhibitor0.9698
P-glycoprotein inhibitor IINon-inhibitor0.9823
Renal organic cation transporterNon-inhibitor0.9217
CYP450 2C9 substrateNon-substrate0.8341
CYP450 2D6 substrateNon-substrate0.6858
CYP450 3A4 substrateNon-substrate0.6635
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9506
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8328
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8476
Ames testNon AMES toxic0.637
CarcinogenicityNon-carcinogens0.8754
BiodegradationNot ready biodegradable0.9117
Rat acute toxicity2.0534 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.951
hERG inhibition (predictor II)Non-inhibitor0.9331
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
PackagersNot Available
Dosage forms
FormRouteStrength
Liquidintramuscular; intravenous20 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySoluble (185 g/L)Not Available
logP0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility9.21 mg/mLALOGPS
logP0.41ALOGPS
logP0.57ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)9.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.71 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.84 m3·mol-1ChemAxon
Polarizability22.79 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC01CA10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (24.5 KB)
Interactions
Drug Interactions
Drug
AcetaminophenThe risk or severity of adverse effects can be increased when Methoxamine is combined with Acetaminophen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Methoxamine is combined with Acetylsalicylic acid.
AminophyllineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Aminophylline.
AmphetamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Methoxamine is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Methoxamine.
BenzphetamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Benzphetamine.
ButalbitalThe risk or severity of adverse effects can be increased when Methoxamine is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Caffeine.
CocaineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Cocaine.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Methoxamine is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dopamine.
DoxapramThe risk or severity of adverse effects can be increased when Methoxamine is combined with Doxapram.
DronabinolDronabinol may increase the tachycardic activities of Methoxamine.
DyphyllineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Epinephrine.
FenoterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Fenoterol.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Methoxamine is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Formoterol.
IndacaterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Methoxamine.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Methoxamine is combined with Ipratropium bromide.
IsomethepteneThe risk or severity of adverse effects can be increased when Methoxamine is combined with Isometheptene.
LevonordefrinThe risk or severity of adverse effects can be increased when Methoxamine is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Methoxamine.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Lisdexamfetamine.
MepivacaineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Mepivacaine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Methoxamine is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Midodrine.
ModafinilThe risk or severity of adverse effects can be increased when Methoxamine is combined with Modafinil.
NabiloneNabilone may increase the tachycardic activities of Methoxamine.
NaphazolineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Naphazoline.
NorepinephrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Norepinephrine.
OlodaterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Olodaterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Oxymetazoline.
PhendimetrazineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Phendimetrazine.
PheniramineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Pheniramine.
PhentermineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Phenylephrine.
PirbuterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Pirbuterol.
PropylhexedrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Propylhexedrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Racepinephrine.
SalbutamolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Salmeterol.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Methoxamine.
TerbutalineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Terbutaline.
TheophyllineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Theophylline.
TriprolidineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Methoxamine 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. Satoh M, Kojima C, Kokubu N, Takayanagi I: Alpha 1-adrenoceptor subtypes mediating the regulation and modulation of Ca2+ sensitization in rabbit thoracic aorta. Eur J Pharmacol. 1994 Nov 24;265(3):133-9. [PubMed:7875228 ]
  2. Suzuki E, Tsujimoto G, Tamura K, Hashimoto K: Two pharmacologically distinct alpha 1-adrenoceptor subtypes in the contraction of rabbit aorta: each subtype couples with a different Ca2+ signalling mechanism and plays a different physiological role. Mol Pharmacol. 1990 Nov;38(5):725-36. [PubMed:1978244 ]
  3. Piascik MT, Sparks MS, Pruitt TA, Soltis EE: Evidence for a complex interaction between the subtypes of the alpha 1-adrenoceptor. Eur J Pharmacol. 1991 Jul 9;199(3):279-89. [PubMed:1680715 ]
  4. Sattar MA, Johns EJ: Evidence for an alpha 1-adrenoceptor subtype mediating adrenergic vasoconstriction in Wistar normotensive and stroke-prone spontaneously hypertensive rat kidney. J Cardiovasc Pharmacol. 1994 Feb;23(2):232-9. [PubMed:7511752 ]
  5. Hoang TV, Choe EU, Burgess RS, Cork RC, Flint LM, Ferrara JJ: Characterization of alpha-adrenoceptor activity in the preterm piglet mesentery. J Pediatr Surg. 1996 Dec;31(12):1659-62. [PubMed:8986981 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
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:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Tsujimoto G, Tsujimoto A, Suzuki E, Hashimoto K: Glycogen phosphorylase activation by two different alpha 1-adrenergic receptor subtypes: methoxamine selectively stimulates a putative alpha 1-adrenergic receptor subtype (alpha 1a) that couples with Ca2+ influx. Mol Pharmacol. 1989 Jul;36(1):166-76. [PubMed:2546049 ]
  2. Simpson P: Stimulation of hypertrophy of cultured neonatal rat heart cells through an alpha 1-adrenergic receptor and induction of beating through an alpha 1- and beta 1-adrenergic receptor interaction. Evidence for independent regulation of growth and beating. Circ Res. 1985 Jun;56(6):884-94. [PubMed:2988814 ]
  3. Oleksa LM, Hool LC, Harvey RD: Alpha 1-adrenergic inhibition of the beta-adrenergically activated Cl- current in guinea pig ventricular myocytes. Circ Res. 1996 Jun;78(6):1090-9. [PubMed:8635240 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  5. Waugh DJ, Gaivin RJ, Zuscik MJ, Gonzalez-Cabrera P, Ross SA, Yun J, Perez DM: Phe-308 and Phe-312 in transmembrane domain 7 are major sites of alpha 1-adrenergic receptor antagonist binding. Imidazoline agonists bind like antagonists. J Biol Chem. 2001 Jul 6;276(27):25366-71. Epub 2001 Apr 30. [PubMed:11331292 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Alpha1-adrenergic receptor activity
Specific Function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular Weight:
60462.205 Da
References
  1. Zeng A, Yuan B, Wang C, Yang G, He L: Frontal analysis of cell-membrane chromatography for determination of drug-alpha(1D) adrenergic receptor affinity. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jul 1;877(20-21):1833-7. doi: 10.1016/j.jchromb.2009.05.021. Epub 2009 May 18. [PubMed:19493707 ]
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Drug created on June 13, 2005 07:24 / Updated on January 15, 2016 17:38