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Record Information
Version3.6
Creation Date2006-05-22 14:17:40 UTC
Update Date2013-02-09 00:11:31 UTC
HMDB IDHMDB02182
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenylephrine
DescriptionPhenylephrine is an alpha-adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent (PubChem). Phenylephrine is used as a decongestant, available as an oral medicine or as a nasal spray. Phenylephrine is not the most common over-the-counter (OTC) decongestant (wikipedia).
Structure
Thumb
Synonyms
  1. Adrianol
  2. Ak-Dilate
  3. Ak-Nefrin
  4. Alcon efrin
  5. Alconefrin Nasal Drops 12
  6. Alconefrin Nasal Drops 25
  7. Alconefrin Nasal Drops 50
  8. Alconefrin Nasal Spray 25
  9. Biomydrin
  10. Dilatair
  11. Dionephrine
  12. Doktors
  13. Duration
  14. Fenilefrina
  15. I-Phrine
  16. Isophrim
  17. Isophrin
  18. Isopto Frin
  19. m-Methylaminoethanolphenol
  20. m-Oxedrine
  21. m-Sympathol
  22. m-Sympatol
  23. m-Synephrine
  24. Mesaton
  25. Mesatone
  26. Mesatonum
  27. Metaoxedrin
  28. Metaoxedrine
  29. Metaoxedrinum
  30. Metasympatol
  31. Metasynephrine
  32. Mezaton
  33. Minims Phenylephrine
  34. Mydfrin
  35. Neo-Synephrine
  36. Neo-Synephrine Nasal Drops
  37. Neo-Synephrine Nasal Jelly
  38. Neo-Synephrine Nasal Spray
  39. Neo-Synephrine Pediatric Nasal Drops
  40. Neofrin
  41. Neophryn
  42. Neosynephrine
  43. Nostril
  44. Nostril Spray Pump
  45. Nostril Spray Pump Mild
  46. Ocu-Phrin Sterile Eye Drops
  47. Ocu-Phrin Sterile Ophthalmic Solution
  48. Ocugestrin
  49. Phenoptic
  50. Phenylephrinum
  51. Prefrin
  52. Prefrin Liquifilm
  53. Pyracort D
  54. R(-)-Mezaton
  55. R(-)-Phenylephrine
  56. Relief Eye Drops for Red Eyes
  57. Rhinall
  58. Spersaphrine
  59. Vicks Sinex
  60. Visadron
Chemical FormulaC9H13NO2
Average Molecular Weight167.205
Monoisotopic Molecular Weight167.094628665
IUPAC Name3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
Traditional Namephenylephrine
CAS Registry Number59-42-7
SMILES
CNC[C@H](O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1
InChI KeySONNWYBIRXJNDC-VIFPVBQESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenethylamines
Sub ClassN/A
Other Descriptors
  • Organic Compounds
  • phenylethanolamines(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct ParentPhenethylamines
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.31HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility22 g/LALOGPS
logP-0.69ALOGPS
logP-0.07ChemAxon
logS-0.88ALOGPS
pKa (Strongest Acidic)9.07ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.25ChemAxon
Polarizability18.2ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adipose Tissue
  • Bladder
  • Brain
  • Kidney
  • Muscle
  • Nerve Cells
  • Prostate
  • Spleen
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.3 (0.029-3.0) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0019 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022891
KNApSAcK IDNot Available
Chemspider ID5818
KEGG Compound IDC07441
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylephrine
NuGOwiki LinkHMDB02182
Metagene LinkHMDB02182
METLIN ID699
PubChem Compound6041
PDB IDNot Available
ChEBI ID8093
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kamiya A, Kawada T, Yamamoto K, Michikami D, Ariumi H, Miyamoto T, Uemura K, Sugimachi M, Sunagawa K: Muscle sympathetic nerve activity averaged over 1 minute parallels renal and cardiac sympathetic nerve activity in response to a forced baroreceptor pressure change. Circulation. 2005 Jul 19;112(3):384-6. Epub 2005 Jul 5. Pubmed: 15998668
  2. Thebault S, Zholos A, Enfissi A, Slomianny C, Dewailly E, Roudbaraki M, Parys J, Prevarskaya N: Receptor-operated Ca2+ entry mediated by TRPC3/TRPC6 proteins in rat prostate smooth muscle (PS1) cell line. J Cell Physiol. 2005 Jul;204(1):320-8. Pubmed: 15672411
  3. Rios JD, Horikawa Y, Chen LL, Kublin CL, Hodges RR, Dartt DA, Zoukhri D: Age-dependent alterations in mouse exorbital lacrimal gland structure, innervation and secretory response. Exp Eye Res. 2005 Apr;80(4):477-91. Pubmed: 15781275
  4. Gao YJ, Zeng ZH, Teoh K, Sharma AM, Abouzahr L, Cybulsky I, Lamy A, Semelhago L, Lee RM: Perivascular adipose tissue modulates vascular function in the human internal thoracic artery. J Thorac Cardiovasc Surg. 2005 Oct;130(4):1130-6. Pubmed: 16214530
  5. Gonzalez-Cadavid NF, Ryndin I, Vernet D, Magee TR, Rajfer J: Presence of NMDA receptor subunits in the male lower urogenital tract. J Androl. 2000 Jul-Aug;21(4):566-78. Pubmed: 10901443
  6. Grassi G, Dell'Oro R, Facchini A, Quarti Trevano F, Bolla GB, Mancia G: Effect of central and peripheral body fat distribution on sympathetic and baroreflex function in obese normotensives. J Hypertens. 2004 Dec;22(12):2363-9. Pubmed: 15614031
  7. Bouchelouche K, Andersen L, Alvarez S, Nordling J, Bouchelouche P: Increased contractile response to phenylephrine in detrusor of patients with bladder outlet obstruction: effect of the alpha1A and alpha1D-adrenergic receptor antagonist tamsulosin. J Urol. 2005 Feb;173(2):657-61. Pubmed: 15643283
  8. Boschmann M, Krupp G, Luft FC, Klaus S, Jordan J: In vivo response to alpha(1)-adrenoreceptor stimulation in human white adipose tissue. Obes Res. 2002 Jun;10(6):555-8. Pubmed: 12055332
  9. Chueh SC, Chern JW, Choong CM, Guh JH, Teng CM: Characterization of some novel alpha 1-adrenoceptor antagonists in human hyperplastic prostate. Eur J Pharmacol. 2002 Jun 7;445(1-2):125-31. Pubmed: 12065203
  10. Wang SY, Song Y, Xu M, Hao TP, Han QD, Zhang YY: [Redistribution of three alpha1-adrenergic receptor subtypes in the stably transfected HEK 293A cells upon agonist stimulation.] Sheng Li Xue Bao. 2005 Aug 25;57(4):480-5. Pubmed: 16094496
  11. Guh JH, Hsieh CH, Teng CM: Investigation of the effects of some alkaloidal alpha1-adrenoceptor antagonists on human hyperplastic prostate. Eur J Pharmacol. 1999 Jun 25;374(3):503-10. Pubmed: 10422796
  12. Nomiya M, Yamaguchi O: A quantitative analysis of mRNA expression of alpha 1 and beta-adrenoceptor subtypes and their functional roles in human normal and obstructed bladders. J Urol. 2003 Aug;170(2 Pt 1):649-53. Pubmed: 12853849
  13. Lam KY, Yuen AP: Cancer of the larynx in Hong Kong: a clinico-pathological study. Eur J Surg Oncol. 1996 Apr;22(2):166-70. Pubmed: 8608835

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
General function:
Involved in G-protein coupled receptor protein signaling pathway
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) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
General function:
Involved in nucleotide binding
Specific function:
May be a regulated effector of stress granule assembly. Phosphorylation-dependent sequence-specific endoribonuclease in vitro. Cleaves exclusively between cytosine and adenine and cleaves MYC mRNA preferentially at the 3'-UTR. ATP- and magnesium-dependent helicase. Unwinds preferentially partial DNA and RNA duplexes having a 17 bp annealed portion and either a hanging 3' tail or hanging tails at both 5'- and 3'-ends. Unwinds DNA/DNA, RNA/DNA, and RNA/RNA substrates with comparable efficiency. Acts unidirectionally by moving in the 5' to 3' direction along the bound single-stranded DNA.
Gene Name:
G3BP1
Uniprot ID:
Q13283
Molecular weight:
52164.045