Drug Details

General Information of the Drug (ID: DR2449)
Name
Phenylephrine
Synonyms
phenylephrine; L-Phenylephrine; 59-42-7; Metasympatol; Mezaton; Metasynephrine; Neosynephrine; Metaoxedrin; m-Oxedrine; Metaoxedrine; Mesaton; Mesatone; Visadron; m-Sympatol; Isophrin; m-Synephrine; m-Sympathol; R(-)-Phenylephrine; Metaoxedrinum; Mesatonum; Neo-Synephrine; Fenilefrina; Phenylephrinum; m-Methylaminoethanolphenol; Isophrim; Ak-dilate; 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol; Mydfrin; Nostril; Cyclomydril; Alcon Efrin; l-(3-Hydroxyphenyl)-N-methylethanolamine; Dionephrine; Adrianol; Biomydrin; Neophryn; Prefrin; Rhinall; Isopto Frin; Prefrin Liquifilm; (-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol; (R)-3-(1-hydroxy-2-(methylamino)ethyl)phenol; Duo-Medihaler; l-1-(m-Hydroxyphenyl)-2-methylaminoethanol; UNII-1WS297W6MV; R(-)-Mezaton; CHEBI:8093; R-PHENYLEPHRINE; Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, (R)-; 1WS297W6MV; Benzyl alcohol, m-hydroxy-alpha-((methylamino)methyl)-, (-)-; Phenylephrine Tannate; Ah-Chew; 1416-03-1; Spersaphrine; Dilatair; Doktors; Duration; Neofrin; Ocugestrin; Phenoptic; Fenilefrina [INN-Spanish]; Phenylephrinum [INN-Latin]; Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-, (R)-; Ak-nefrin; I-Phrine; 61-76-7; Phenylephrine, l-; Nostril Spray Pump; Phenylephrine [INN:BAN]; Minims Phenylephrine; Hemorid; Nostril Spray Pump Mild; Alconefrin Nasal Drops 12; Alconefrin Nasal Drops 25; Alconefrin Nasal Drops 50; Alconefrin Nasal Spray 25; Neo-Synephrine Nasal Drops; Neo-Synephrine Nasal Jelly; Neo-Synephrine Nasal Spray; Ocu-Phrin Sterile Eye Drops; (-)-phenylephrine; (-)-m-Oxedrine; (R)-(-)-phenylephrine; Relief Eye Drops for Red Eyes; Phenylephrine (INN); (R)-(-)-Phenylephrine hydrochloride; HSDB 3383; UNII-DU5ATO7HYP; EINECS 200-424-8; Phenylephrine Minims (TN); phenylene; l-m-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol; AI3-02402; CCRIS 8464; l-alpha-Hydroxy-beta-methylamino-3-hydroxy-L-ethylbenzene; Phenylephrine HCI; Phenylephrine mixture with Tannins; EINECS 215-810-1; Mydfrin (Salt/Mix); Nostril (Salt/Mix); Prefrin (Salt/Mix); Adrianol (Salt/Mix); Neophryn (Salt/Mix); Biomydrin (Salt/Mix); R-(-)-Phenylephrine; Spectrum_001101; Ak-dilate (Salt/Mix); Ak-nefrin (Salt/Mix); DU5ATO7HYP; Alcon efrin (Salt/Mix); Spectrum2_001280; Spectrum3_000770; Spectrum4_000967; Spectrum5_001411; Lopac-P-6126; EC 200-424-8; Tannins, compds. with (R)-3-hydroxy-alpha-((methylamino)methyl)benzenemethanol; SCHEMBL4711; CHEMBL1215; Lopac0_000920; BSPBio_002420; GTPL485; KBioGR_001313; KBioSS_001581; BIDD:GT0157; DivK1c_000597; SPBio_001280; Benzyl alcohol, m-hydroxy-.alpha.-((methylamino)methyl)-, (-)-; (R)-2-Hydroxy-2-(3-hydroxyphenyl)-N-methylethylamine; component of Entex (Salt/Mix); component of Relief (Salt/Mix); DTXSID9023465; component of Comhist (Salt/Mix); component of Demazin (Salt/Mix); KBio1_000597; KBio2_001581; KBio2_004149; KBio2_006717; KBio3_001640; AB-101 (PHENYLEPHRINE); component of Vasosulf (Salt/Mix); component of Zincfrin (Salt/Mix); NINDS_000597; ZINC113355; component of Cerose dm (Salt/Mix); component of Prefrin-a (Salt/Mix); HY-B0769; component of Cyclomydril (Salt/Mix); ANW-42493; BDBM50067212; MFCD00044749; Neo-Synephrine Pediatric Nasal Drops; PDSP1_001108; PDSP2_001092; component of Decongestant (Salt/Mix); component of Dristan cold (Salt/Mix); Ocu-Phrin Sterile Ophthalmic Solution; AKOS006282042; CCG-205002; CS-6187; DB00388; J8.601K; MCULE-8302708533; SDCCGSBI-0050895.P005; component of Histalet forte (Salt/Mix); component of Ru-tuss liquid (Salt/Mix); IDI1_000597; component of Pv tussin syrup (Salt/Mix); component of Ru-tuss tablets (Salt/Mix); NCGC00015825-01; NCGC00015825-02; NCGC00024257-03; NCGC00024257-05; NCGC00024257-06; NCGC00024257-07; NCGC00024257-19; AM100999; AS-13635; R780; component of Hycomine compound (Salt/Mix); SBI-0050895.P004; AB0018328; component of Dristan nasal mist (Salt/Mix); P0395; 1400-EP2281815A1; 1400-EP2295409A1; 1400-EP2301933A1; 1400-EP2305640A2; 1400-EP2311827A1; 1400-EP2314590A1; 3-[(1R)-1-hydroxy-2-methylaminoethyl]phenol; C07441; D08365; J10016; M-2869; AB00053522_11; AB00053522_12; 044P749; 3-[1-Hydroxy-2-(methylamino)ethyl]phenol, (R)-; A832309; AT-057/40243664; Q421910; 3-[(1R)-2-(methylamino)-1-oxidanyl-ethyl]phenol; Q-201560; (-)-m-Hydroxy-.alpha.-(methylaminomethyl)benzyl alcohol; l-m-Hydroxy-.alpha.-((methylamino)methyl)benzyl alcohol; (R)-3-Hydroxy-.alpha.-[(methylamino)methyl]benzenemethanol; UNII-RH8FKZ05H0 component SONNWYBIRXJNDC-VIFPVBQESA-N; 3-[(1R)-1-Hydroxy-2-(methylamino)ethyl]phenol, AldrichCPR; l-.alpha.-Hydroxy-.beta.-methylamino-3-hydroxy-l-ethylbenzene; (-)- m-Hydroxy-a-[(methylamino)methyl]benzyl alcohol hydrochloride; Benzenemethanol, 3-hydroxy-a-[(methylamino)methyl]-, (.alpha.R)-; Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, (R)- (9CI); 1228015-39-1
    Click to Show/Hide
Molecular Type
Small molecule
Disease Thyrotoxicosis [ICD-11: 5A02] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Clearance
The clearance of drug is 2100 mL/min
Elimination
86% of a dose of phenylephrine is recovered in the urine with 16% as the unmetabolized drug, 57% as the inactive meta-hydroxymendelic acid, and 8% as inactive sulfate conjugates
Half-life
The concentration or amount of drug in body reduced by one-half in 5 minutes
Metabolism
The drug is metabolized via the monoamine oxidase A, monoamine oxidase B, and SULT1A3
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 4.98178 micromolar/kg/day
Vd
The volume of distribution (Vd) of drug is 340 L
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C9H13NO2
PubChem CID
6041
Canonical SMILES
CNCC(C1=CC(=CC=C1)O)O
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
InChIKey
SONNWYBIRXJNDC-VIFPVBQESA-N
CAS Number
CAS 61-76-7
ChEBI ID
CHEBI:8093
TTD Drug ID
D0O6IU
DrugBank ID
DB00388
Target and Pathway
Target(s) Dopamine D2 receptor (D2R)  Molecule Info  [2]
KEGG Pathway Rap1 signaling pathway Click to Show/Hide
2 cAMP signaling pathway
3 Neuroactive ligand-receptor interaction
4 Gap junction
5 Dopaminergic synapse
6 Parkinson's disease
7 Cocaine addiction
8 Alcoholism
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Heterotrimeric G-protein signaling pathway-Gq alpha and Go alpha mediated pathway
3 Dopamine receptor mediated signaling pathway
4 Nicotine pharmacodynamics pathway
Reactome Dopamine receptors Click to Show/Hide
2 G alpha (i) signalling events
WikiPathways Hypothetical Network for Drug Addiction Click to Show/Hide
2 Monoamine GPCRs
3 GPCRs, Class A Rhodopsin-like
4 Genes and (Common) Pathways Underlying Drug Addiction
5 GPCR ligand binding
6 GPCR downstream signaling
7 Nicotine Activity on Dopaminergic Neurons
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 485).
Reference 2 MMP-2 induced vein relaxation via inhibition of [Ca2+]e-dependent mechanisms of venous smooth muscle contraction. Role of RGD peptides. J Surg Res. 2010 Apr;159(2):755-64.