Synephrine
Identification
- Generic Name
- Synephrine
- DrugBank Accession Number
- DB09203
- Background
Synephrine, also referred to as, p-synephrine, is naturally occurring alkaloid. It is present in approved drug products as neo-synephrine, its m-substituted analog. p-synephrine and m-synephrine are known for their longer acting adrenergic effects compared to norepinephrine.
The similarity of naming between m-synephrine and the unsubstituted form, synephrine, is a source of some confusion however m-synephrine refers to a related drug more commonly known as phenylephrine. While the compounds share some chemical and pharmacological similarities, they are in fact distinct chemical entities.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 167.205
Monoisotopic: 167.094628665 - Chemical Formula
- C9H13NO2
- Synonyms
- (±)-Synephrine
- Oxedrine
- p-synephrine
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAlpha-1 adrenergic receptors Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- 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 Synephrine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Synephrine. Acemetacin The risk or severity of hypertension can be increased when Synephrine is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Synephrine. Aclidinium The risk or severity of Tachycardia can be increased when Aclidinium is combined with Synephrine. - 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 Synephrine tartrate 9I99I5995J 16589-24-5 KZZBAIXGUQOHKI-CEAXSRTFSA-N - International/Other Brands
- Sympatol
Categories
- ATC Codes
- S01GA06 — Oxedrine
- S01GA — Sympathomimetics used as decongestants
- S01G — DECONGESTANTS AND ANTIALLERGICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- S01GA — Sympathomimetics used as decongestants
- S01G — DECONGESTANTS AND ANTIALLERGICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-Agonists
- Adrenergic and Dopaminergic Agents
- Agents producing tachycardia
- Agents that produce hypertension
- Alcohols
- Amines
- Amino Alcohols
- Autonomic Agents
- Biogenic Amines
- Biogenic Monoamines
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Cardiovascular Agents
- Decongestants and Antiallergics
- Ethanolamines
- Nasal Decongestants
- Neurotransmitter Agents
- Ophthalmologicals
- Peripheral Nervous System Agents
- Respiratory System Agents
- Sensory Organs
- Sympathomimetics
- Sympathomimetics Used as Decongestants
- Vasoconstrictor Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- 1-hydroxy-2-unsubstituted benzenoids
- Direct Parent
- 1-hydroxy-2-unsubstituted benzenoids
- Alternative Parents
- Aralkylamines / Benzene and substituted derivatives / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- phenols, ethanolamines, phenethylamine alkaloid (CHEBI:29081)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- PEG5DP7434
- CAS number
- 94-07-5
- InChI Key
- YRCWQPVGYLYSOX-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3
- IUPAC Name
- 4-[1-hydroxy-2-(methylamino)ethyl]phenol
- SMILES
- CNCC(O)C1=CC=C(O)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0004826
- KEGG Drug
- D07148
- KEGG Compound
- C04548
- PubChem Compound
- 7172
- PubChem Substance
- 310265111
- ChemSpider
- 6904
- BindingDB
- 50102660
- 10288
- ChEBI
- 29081
- ChEMBL
- CHEMBL33720
- Wikipedia
- Synephrine
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 4 Completed Prevention Anesthesia therapy / Hypotension 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 18.6 mg/mL ALOGPS logP -0.62 ALOGPS logP -0.071 Chemaxon logS -0.95 ALOGPS pKa (Strongest Acidic) 9.76 Chemaxon pKa (Strongest Basic) 9.15 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 52.49 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 47.25 m3·mol-1 Chemaxon Polarizability 18.23 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 141.5277449 predictedDarkChem Lite v0.1.0 [M-H]- 141.8749449 predictedDarkChem Lite v0.1.0 [M-H]- 134.34602 predictedDeepCCS 1.0 (2019) [M+H]+ 142.5919449 predictedDarkChem Lite v0.1.0 [M+H]+ 142.8487449 predictedDarkChem Lite v0.1.0 [M+H]+ 138.17403 predictedDeepCCS 1.0 (2019) [M+Na]+ 141.6264449 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.3162449 predictedDarkChem Lite v0.1.0 [M+Na]+ 147.51509 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- 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...
Components:
Name | UniProt ID |
---|---|
Alpha-1A adrenergic receptor | P35348 |
Alpha-1B adrenergic receptor | P35368 |
Alpha-1D adrenergic receptor | P25100 |
References
- Huang YT, Lin HC, Chang YY, Yang YY, Lee SD, Hong CY: Hemodynamic effects of synephrine treatment in portal hypertensive rats. Jpn J Pharmacol. 2001 Feb;85(2):183-8. [Article]
Drug created at October 19, 2015 18:45 / Updated at December 06, 2020 04:50