Synephrine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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
Thumb
Weight
Average: 167.205
Monoisotopic: 167.094628665
Chemical Formula
C9H13NO2
Synonyms
  • (±)-Synephrine
  • Oxedrine
  • p-synephrine

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAlpha-1 adrenergic receptorsNot AvailableHumans
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
Medicalerrors
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Toxicity

Not Available

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.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Synephrine is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Synephrine can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Synephrine.
AcemetacinThe risk or severity of hypertension can be increased when Synephrine is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Synephrine.
AclidiniumThe risk or severity of Tachycardia can be increased when Aclidinium is combined with Synephrine.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Synephrine.
AlclofenacThe risk or severity of hypertension can be increased when Synephrine is combined with Alclofenac.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Synephrine.
AlfuzosinThe therapeutic efficacy of Synephrine can be decreased when used in combination with Alfuzosin.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Synephrine tartrate9I99I5995J16589-24-5KZZBAIXGUQOHKI-CEAXSRTFSA-N
International/Other Brands
Sympatol

Categories

ATC Codes
S01GA06 — OxedrineS01GA56 — Oxedrine, combinationsC01CA08 — Oxedrine
Drug Categories
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
Human Metabolome Database
HMDB0004826
KEGG Drug
D07148
KEGG Compound
C04548
PubChem Compound
7172
PubChem Substance
310265111
ChemSpider
6904
BindingDB
50102660
RxNav
10288
ChEBI
29081
ChEMBL
CHEMBL33720
Wikipedia
Synephrine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility18.6 mg/mLALOGPS
logP-0.62ALOGPS
logP-0.071ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)9.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.25 m3·mol-1ChemAxon
Polarizability18.23 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-014i-0900000000-e033087fd86dbd769b28
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-0900000000-e033087fd86dbd769b28
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0900000000-c295e3a3035d15a699ee
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-2790000000-3975fb57a4851efa17dd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1890000000-ddb8778ef0aef4591f0d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-0900000000-a8d55f47d1721c88e142
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-0900000000-eb318fdbbcefb5c0f42b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01c3-8900000000-750750ed3b7c777f8966
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-73b64b38d378f6d409bc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014j-2900000000-a2fc7c196d4cb2205cd2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-b3081d3e77cf948c0bab
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-0900000000-87218af459df32d035bb
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-0900000000-dd62606af13291e0de32
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-279ae142a098a2d8cfbb
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-35c196c82d47f666eb5b

Targets

Drugtargets
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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:
References
  1. 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. [PubMed:11286401]

Drug created on October 19, 2015 18:45 / Updated on December 06, 2020 04:50