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targets (2)
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Identification
Name Methoxamine
Accession Number DB00723 (APRD00062)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Methoxamedrine
  • Methoxamin
  • Methoxaminum [INN-Latin]
  • Metossamina [DCIT]
  • Metoxamina [INN-Spanish]
  • Pseudomethoxamine
  • Vasoxine
  • Vasoxyl
Brand name mixtures Not Available
Categories
  • Vasoconstrictor Agents
  • Sympathomimetics
  • Adrenergic alpha-Agonists
CAS number 390-28-3
Weight Average: 211.2576
Monoisotopic: 211.120843415
Chemical Formula C11H17NO3
InChI Key InChIKey=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
Plain Text
IUPAC Name
2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
SMILES
COC1=CC(C(O)C(C)N)=C(OC)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Amphetamines
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Phenols and Derivatives
  • Aliphatic and Aryl Amines
  • Ethers
  • Benzene and Derivatives
  • Hydroquinones
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Anisoles
  • Alcohols and Polyols
  • Phenyl Esters
  • Amphetamines
Pharmacology
Indication Indicated for the treatment and management of hypotension.
Pharmacodynamics Methoxamine 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 action Methoxamine acts through peripheral vasoconstriction by acting as a pure alpha-1 adrenergic receptor agonist, consequently increasing systemic blood pressure (both systolic and diastolic).
Absorption Not Available
Volume of distribution Not Available
Protein binding Low
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility Soluble (185 g/L) PhysProp
logP 0.8 PhysProp
Predicted Properties
Property Value Source
water solubility 9.21e+00 g/l ALOGPS
logP 0.41 ALOGPS
logP 0.57 ChemAxon Molconvert
logS -1.36 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 64.71 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 57.84 ChemAxon Molconvert
polarizability 22.79 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07513 Link_out
PubChem Compound 6082 Link_out
PubChem Substance 46506264 Link_out
ChemSpider 5857 Link_out
BindingDB 50026777 Link_out
Therapeutic Targets Database DAP000796 Link_out
PharmGKB PA450431 Link_out
Drug Product Database 4480 Link_out
Wikipedia http://en.wikipedia.org/wiki/Methoxamine Link_out
ATC Codes
  • C01CA10
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (24.5 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Alpha-1A adrenergic receptor

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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
  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

2. Alpha-1B adrenergic receptor

Pharmacological action: unknown
Actions: agonist

This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system

Organism class: human
UniProt ID: P35368 Link_out
Gene: ADRA1B Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:42

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