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Identification
NameMethoxamine
Accession NumberDB00723  (APRD00062)
TypeSmall Molecule
GroupsApproved
DescriptionAn 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
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vasoxyl Inj 20mg/mlLiquid20 mgIntramuscular; IntravenousGlaxo Wellcome Inc.1950-12-312001-01-25Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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 KeyWJAJPNHVVFWKKL-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
Pharmacology
IndicationIndicated for the treatment and management of hypotension.
Structured Indications Not Available
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).
TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-1A adrenergic receptorProteinyes
agonist
HumanP35348 details
Alpha-1B adrenergic receptorProteinunknown
agonist
HumanP35368 details
Alpha-1D adrenergic receptorProteinunknown
binder
HumanP25100 details
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
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 Methoxamine.Experimental
AcebutololThe risk or severity of adverse effects can be increased when Methoxamine is combined with Acebutolol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Methoxamine.Approved, Investigational
AmineptineAmineptine may increase the vasopressor activities of Methoxamine.Illicit, Withdrawn
AmitriptylineAmitriptyline may increase the vasopressor activities of Methoxamine.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Methoxamine.Approved, Illicit
AtomoxetineAtomoxetine may increase the hypertensive activities of Methoxamine.Approved
BenmoxinBenmoxin may increase the hypertensive activities of Methoxamine.Withdrawn
BenzphetamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysineMethoxamine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Methoxamine.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Methoxamine.Investigational
CabergolineCabergoline may increase the hypertensive activities of Methoxamine.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of Methoxamine.Withdrawn
CarvedilolCarvedilol may decrease the vasoconstricting activities of Methoxamine.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Methoxamine is combined with Celiprolol.Approved, Investigational
ChlorphentermineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Chlorphentermine.Illicit, Withdrawn
ClenbuterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Clenbuterol.Approved, Vet Approved
ClomipramineClomipramine may increase the vasopressor activities of Methoxamine.Approved, Vet Approved
CyclobenzaprineCyclobenzaprine may increase the vasopressor activities of Methoxamine.Approved
DesipramineDesipramine may increase the vasopressor activities of Methoxamine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Methoxamine.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Methoxamine.Approved
DobutamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dobutamine.Approved
DopamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Dopamine.Approved
DosulepinDosulepin may increase the vasopressor activities of Methoxamine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Methoxamine.Approved
DoxepinDoxepin may increase the vasopressor activities of Methoxamine.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Methoxamine.Approved, Illicit
DuloxetineDuloxetine may increase the tachycardic activities of Methoxamine.Approved
EphedrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Ephedrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Methoxamine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Methoxamine.Approved
ErgonovineErgonovine may increase the hypertensive activities of Methoxamine.Approved
ErgotamineErgotamine may increase the hypertensive activities of Methoxamine.Approved
EsmirtazapineEsmirtazapine may increase the vasopressor activities of Methoxamine.Investigational
EtilefrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Etilefrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Fenoterol.Approved
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Methoxamine.Approved, Illicit, Investigational, Vet Approved
FurazolidoneFurazolidone may increase the hypertensive activities of Methoxamine.Approved, Vet Approved
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Methoxamine.Approved, Investigational
HydracarbazineHydracarbazine may increase the hypertensive activities of Methoxamine.Approved
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Methoxamine is combined with Hydroxyamphetamine hydrobromide.Approved
ImipramineImipramine may increase the vasopressor activities of Methoxamine.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Methoxamine.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Methoxamine.Approved
IproclozideIproclozide may increase the hypertensive activities of Methoxamine.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Methoxamine.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Methoxamine.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Isoprenaline.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Isoxsuprine.Approved, Withdrawn
LabetalolLabetalol may decrease the vasoconstricting activities of Methoxamine.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Methoxamine.Approved
LinezolidLinezolid may increase the hypertensive activities of Methoxamine.Approved, Investigational
MebanazineMebanazine may increase the hypertensive activities of Methoxamine.Withdrawn
MephentermineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Mephentermine.Approved
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Methoxamine.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Methamphetamine.Approved, Illicit
Methylene blueMethylene blue may increase the hypertensive activities of Methoxamine.Investigational
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Methoxamine.Approved
MilnacipranMilnacipran may increase the tachycardic activities of Methoxamine.Approved
MinaprineMinaprine may increase the hypertensive activities of Methoxamine.Approved
MirtazapineMirtazapine may increase the vasopressor activities of Methoxamine.Approved
MoclobemideMoclobemide may increase the hypertensive activities of Methoxamine.Approved
NabiloneNabilone may increase the tachycardic activities of Methoxamine.Approved, Investigational
NialamideNialamide may increase the hypertensive activities of Methoxamine.Withdrawn
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Methoxamine.Approved
NortriptylineNortriptyline may increase the vasopressor activities of Methoxamine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Methoxamine is combined with Nylidrin.Approved
OctamoxinOctamoxin may increase the hypertensive activities of Methoxamine.Withdrawn
OpipramolOpipramol may increase the vasopressor activities of Methoxamine.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Orciprenaline.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Oxymetazoline.Approved
PargylinePargyline may increase the hypertensive activities of Methoxamine.Approved
PhenelzinePhenelzine may increase the hypertensive activities of Methoxamine.Approved
PheniprazinePheniprazine may increase the hypertensive activities of Methoxamine.Withdrawn
PhenmetrazineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Phenmetrazine.Approved, Illicit
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Methoxamine.Withdrawn
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Methoxamine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Methoxamine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Methoxamine.Approved, Vet Approved, Withdrawn
PirlindolePirlindole may increase the hypertensive activities of Methoxamine.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of Methoxamine.Withdrawn
PrazosinPrazosin may decrease the vasoconstricting activities of Methoxamine.Approved
ProcaterolThe risk or severity of adverse effects can be increased when Methoxamine is combined with Procaterol.Approved
ProtriptylineProtriptyline may increase the vasopressor activities of Methoxamine.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Pseudoephedrine.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Racepinephrine.Approved
RasagilineRasagiline may increase the hypertensive activities of Methoxamine.Approved
RitodrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Ritodrine.Approved
SafrazineSafrazine may increase the hypertensive activities of Methoxamine.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of Methoxamine.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Methoxamine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Methoxamine.Approved
SynephrineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Synephrine.Experimental
TamsulosinTamsulosin may decrease the vasoconstricting activities of Methoxamine.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Methoxamine.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Methoxamine.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Terbutaline.Approved
TetryzolineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Tetryzoline.Approved
TianeptineTianeptine may increase the vasopressor activities of Methoxamine.Approved
ToloxatoneToloxatone may increase the hypertensive activities of Methoxamine.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Methoxamine.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Methoxamine.Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Methoxamine.Experimental
TrimipramineTrimipramine may increase the vasopressor activities of Methoxamine.Approved
TyramineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Tyramine.Investigational, Nutraceutical
VenlafaxineVenlafaxine may increase the tachycardic activities of Methoxamine.Approved
Food InteractionsNot 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)
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
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 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

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 August 17, 2016 12:23