Identification
- Summary
Methoxamine is an alpha adrenergic agonist used to treat hypotension.
- Generic Name
- Methoxamine
- DrugBank Accession Number
- DB00723
- Background
An alpha-adrenergic agonist that causes prolonged peripheral vasoconstriction. It has little if any direct effect on the central nervous system.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Methoxamine (DB00723)
- Weight
- Average: 211.2576
Monoisotopic: 211.120843415 - Chemical Formula
- C11H17NO3
- Synonyms
- Méthoxamédrine
- Methoxamin
- Méthoxamine
- Methoxamine
- Methoxaminum
- Metossamina
- Metoxamina
- Pseudomethoxamine
- External IDs
- NRL-001
- NRL001
Pharmacology
- Indication
Indicated for the treatment and management of hypotension.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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).
Target Actions Organism AAlpha-1A adrenergic receptor agonistHumans UAlpha-1D adrenergic receptor binderHumans UAlpha-1B adrenergic receptor agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Low
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Methoxamine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Methoxamine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Methoxamine is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Methoxamine is combined with Acetylsalicylic acid. Aclidinium The risk or severity of Tachycardia can be increased when Methoxamine is combined with Aclidinium. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Methoxamine hydrochloride 8MB4MJ9R7L 61-16-5 YGRFXPCHZBRUKP-UHFFFAOYSA-N - International/Other Brands
- Mexan (Nippon Shinyaku) / Vasoxine / Vasoxyl
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vasoxyl Inj 20mg/ml Liquid 20 mg / mL Intramuscular; Intravenous Glaxo Wellcome 1950-12-31 2001-01-25 Canada 
Categories
- ATC Codes
- C01CA10 — Methoxamine
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-Agonists
- Adrenergic and Dopaminergic Agents
- Agents producing tachycardia
- Agents that produce hypertension
- Alcohols
- Amines
- Amino Alcohols
- Autonomic Agents
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Cardiovascular Agents
- Ethylamines
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Phenethylamines
- Propanolamines
- Propanols
- Sympathomimetics
- Vasoconstrictor Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Methoxybenzenes
- Direct Parent
- Dimethoxybenzenes
- Alternative Parents
- Phenylpropanes / Phenoxy compounds / Anisoles / Aralkylamines / Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives show 1 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Dimethoxybenzene / Ether show 13 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- amphetamines (CHEBI:6839)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- HUQ1KC1YLI
- CAS number
- 390-28-3
- InChI Key
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014861
- KEGG Drug
- D08201
- KEGG Compound
- C07513
- PubChem Compound
- 6082
- PubChem Substance
- 46506264
- ChemSpider
- 5857
- BindingDB
- 50026777
- 6853
- ChEBI
- 6839
- ChEMBL
- CHEMBL524
- Therapeutic Targets Database
- DAP000796
- PharmGKB
- PA450431
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Methoxamine
- MSDS
- Download (24.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Active Not Recruiting Treatment Anaplastic Ependymoma / Cellular Ependymoma / Clear Cell Ependymoma / Ependymoma / Papillary Ependymoma 1 3 Active Not Recruiting Treatment Medulloblastomas 1 3 Recruiting Treatment B Acute Lymphoblastic Leukemia With t(9;22)(q34.1;q11.2); BCR-ABL1 1 2 Completed Treatment Fecal Incontinence 1 2 Recruiting Treatment Central Nervous System Nongerminomatous Germ Cell Tumor / Choriocarcinoma / Embryonal Carcinoma / Immature Teratoma / Malignant Teratoma / Mixed Germ Cell Tumor / Pineal Germ Cell Tumor / Pineal Region Immature Teratoma / Pineal Region Yolk Sac Tumor / Suprasellar Germ Cell Tumor 1
Pharmacoeconomics
- Manufacturers
- Glaxosmithkline
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Intramuscular; Intravenous 20 mg / mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble (185 g/L) Not Available logP 0.8 Not Available - Predicted Properties
Property Value Source Water Solubility 9.21 mg/mL ALOGPS logP 0.41 ALOGPS logP 0.57 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 13.61 Chemaxon pKa (Strongest Basic) 9.28 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 64.71 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 57.84 m3·mol-1 Chemaxon Polarizability 22.81 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9751 Blood Brain Barrier - 0.8857 Caco-2 permeable + 0.5637 P-glycoprotein substrate Non-substrate 0.6457 P-glycoprotein inhibitor I Non-inhibitor 0.9698 P-glycoprotein inhibitor II Non-inhibitor 0.9823 Renal organic cation transporter Non-inhibitor 0.9217 CYP450 2C9 substrate Non-substrate 0.8341 CYP450 2D6 substrate Non-substrate 0.6858 CYP450 3A4 substrate Non-substrate 0.6635 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9506 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8328 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8476 Ames test Non AMES toxic 0.637 Carcinogenicity Non-carcinogens 0.8754 Biodegradation Not ready biodegradable 0.9117 Rat acute toxicity 2.0534 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.951 hERG inhibition (predictor II) Non-inhibitor 0.9331
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 158.3719484 predictedDarkChem Lite v0.1.0 [M-H]- 148.02757 predictedDeepCCS 1.0 (2019) [M+H]+ 159.3108484 predictedDarkChem Lite v0.1.0 [M+H]+ 150.38557 predictedDeepCCS 1.0 (2019) [M+Na]+ 158.4337484 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.539 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- 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) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Alpha-1D adrenergic receptor
- Molecular Weight
- 60462.205 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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) prot...
- Gene Name
- ADRA1B
- Uniprot ID
- P35368
- Uniprot Name
- Alpha-1B adrenergic receptor
- Molecular Weight
- 56835.375 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:59