Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Metaraminol
- DrugBank Accession Number
- DB00610
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Metaraminol (DB00610)
- Weight
- Average: 167.205
Monoisotopic: 167.094628665 - Chemical Formula
- C9H13NO2
- 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
Pharmacology
- Indication
For the treatment and prevention of hypotension due to hemorrhage, spinal anesthesia, and shock associated with brain damage
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
Metaraminol 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 action
Metaraminol 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.
Target Actions Organism AD(2) dopamine receptor agonistHumans AAlpha-1A adrenergic receptor agonistHumans - Absorption
The effect starts 1-2 min after IV injection, 10 min after IM injection, 5-20 min after subcutaneous injection.
- Volume of distribution
Not Available
- Protein binding
Approximately 45%
- Metabolism
Hepatic
- 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
LD50=240 mg/kg (rat, oral); LD50=99 mg/kg (mouse, oral)
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 Metaraminol can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Metaraminol is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Metaraminol is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Metaraminol is combined with Acetylsalicylic acid. Aclidinium The risk or severity of Tachycardia can be increased when Metaraminol 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 Metaraminol bitartrate ZC4202M9P3 33402-03-8 VENXSELNXQXCNT-IJYXXVHRSA-N - International/Other Brands
- Aramine (Merck) / Metaramin / Pressonex
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Metaraminol Bitartrate Injection 10 mg/1mL Intramuscular; Intravenous Azurity Pharmaceuticals, Inc. 2024-07-01 Not applicable US 
Categories
- ATC Codes
- C01CA09 — Metaraminol
- 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
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Propanolamines
- Propanols
- Sympathomimetics
- Vasoconstrictor Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylpropanes
- Direct Parent
- Phenylpropanes
- Alternative Parents
- Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenylethanolamines (CHEBI:6794)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 818U2PZ2EH
- CAS number
- 54-49-9
- InChI Key
- 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[C@H](N)[C@H](O)C1=CC(O)=CC=C1
References
- General References
- 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. [Article]
- Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014748
- KEGG Compound
- C07146
- PubChem Compound
- 5906
- PubChem Substance
- 46505593
- ChemSpider
- 5695
- BindingDB
- 50239972
- 6805
- ChEBI
- 6794
- ChEMBL
- CHEMBL1201319
- ZINC
- ZINC000000001695
- Therapeutic Targets Database
- DAP000225
- PharmGKB
- PA164748761
- RxList
- RxList Drug Page
- Wikipedia
- Metaraminol
- MSDS
- Download (52.4 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Unknown Status Diagnostic Pre-Eclampsia 1 somestatus stop reason just information to hide 4 Completed Prevention Complications; Cesarean Section 2 somestatus stop reason just information to hide 4 Recruiting Treatment Acute Respiratory Distress Syndrome (ARDS) 1 somestatus stop reason just information to hide 3 Withdrawn Treatment Pre-Eclampsia / Pregnancy Toxemias 1 somestatus stop reason just information to hide 2 Completed Treatment Hypotension 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Merck and co inc
- Abraxis pharmaceutical products
- App pharmaceuticals llc
- Elkins sinn div ah robins co inc
- Gd searle llc
- Packagers
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Solution / drops Injection Intramuscular; Intravenous 10 mg/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 107.5 °C PhysProp boiling point (°C) 218 °C PhysProp water solubility 1000 g/L Not Available logP -0.27 HANSCH,C ET AL. (1995); ion-corrected pKa 8.79 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 12.8 mg/mL ALOGPS logP -0.59 ALOGPS logP -0.045 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 9.03 Chemaxon pKa (Strongest Basic) 9.68 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 66.48 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 46.89 m3·mol-1 Chemaxon Polarizability 17.84 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 + 0.9922 Blood Brain Barrier - 0.8926 Caco-2 permeable + 0.6112 P-glycoprotein substrate Non-substrate 0.721 P-glycoprotein inhibitor I Non-inhibitor 0.9907 P-glycoprotein inhibitor II Non-inhibitor 0.9961 Renal organic cation transporter Non-inhibitor 0.9152 CYP450 2C9 substrate Non-substrate 0.7922 CYP450 2D6 substrate Non-substrate 0.6311 CYP450 3A4 substrate Non-substrate 0.7459 CYP450 1A2 substrate Non-inhibitor 0.899 CYP450 2C9 inhibitor Non-inhibitor 0.9538 CYP450 2D6 inhibitor Non-inhibitor 0.9724 CYP450 2C19 inhibitor Non-inhibitor 0.9255 CYP450 3A4 inhibitor Non-inhibitor 0.8264 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9205 Ames test Non AMES toxic 0.8102 Carcinogenicity Non-carcinogens 0.837 Biodegradation Not ready biodegradable 0.6456 Rat acute toxicity 2.7863 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9126 hERG inhibition (predictor II) Non-inhibitor 0.9492
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.7500449 predictedDarkChem Lite v0.1.0 [M-H]- 140.23839 predictedDeepCCS 1.0 (2019) [M+H]+ 141.3801449 predictedDarkChem Lite v0.1.0 [M+H]+ 142.63396 predictedDeepCCS 1.0 (2019) [M+Na]+ 141.0317449 predictedDarkChem Lite v0.1.0 [M+Na]+ 148.54648 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
- Specific Function
- dopamine binding
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General 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
- Specific Function
- alpha1-adrenergic receptor activity
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 13, 2024 04:00