Human Metabolome Database Version 3.5

Showing metabocard for Phenylephrine (HMDB02182)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:40 -0600
Update Date 2013-02-08 17:11:31 -0700
HMDB ID HMDB02182
Secondary Accession Numbers None
Metabolite Identification
Common Name Phenylephrine
Description Phenylephrine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H13NO2
Average Molecular Weight 167.205
Monoisotopic Molecular Weight 167.094628665
IUPAC Name 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
Traditional IUPAC Name phenylephrine
CAS Registry Number 59-42-7
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 Key SONNWYBIRXJNDC-VIFPVBQESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenethylamines
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • phenylethanolamines(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Benzyl Alcohol Derivative
  • Phenol
  • Phenol Derivative
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Phenethylamines
Ontology
Status Detected and Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -0.31 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 22 g/L ALOGPS
LogP -0.69 ALOGPS
LogP -0.07 ChemAxon
LogS -0.88 ALOGPS
pKa (strongest acidic) 9.07 ChemAxon
pKa (strongest basic) 9.69 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 52.49 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 47.25 ChemAxon
Polarizability 18.2 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Muscle
  • Bladder
  • Kidney
  • Brain
  • Prostate
  • Adipose Tissue
  • Nerve Cells
  • Spleen
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
2.3 (0.029-3.0) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0019 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022891
KNApSAcK ID Not Available
Chemspider ID 5818 Link_out
KEGG Compound ID C07441 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Phenylephrine Link_out
NuGOwiki Link HMDB02182 Link_out
Metagene Link HMDB02182 Link_out
METLIN ID 699 Link_out
PubChem Compound 6041 Link_out
PDB ID Not Available
ChEBI ID 8093 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Amine oxidase [flavin-containing] A
Reactions: Not Available
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-2A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA2A
Uniprot ID: P08913 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-2B adrenergic receptor
Reactions: Not Available
Gene Name: ADRA2B
Uniprot ID: P18089 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-1A adrenergic receptor
Reactions: Not Available
Gene Name: ADRA1A
Uniprot ID: P35348 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-1B adrenergic receptor
Reactions: Not Available
Gene Name: ADRA1B
Uniprot ID: P35368 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ras GTPase-activating protein-binding protein 1
Reactions: Not Available
Gene Name: G3BP1
Uniprot ID: Q13283 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA