Details of the Drug

General Information of Drug (ID: DMZHUO5)

Drug Name

Phenylephrine

Synonyms

Cyclomydril; Dilatair; Dionephrine; Doktors; Duration; Fenilefrina; Isophrim; Isophrin; Mesaton; Mesatone; Mesatonum; Metaoxedrin; Metaoxedrine; Metaoxedrinum; Metasympatol; Metasynephrine; Metsatonum; Mezaton; Mydfrin; Neofrin; Neosynephrine; Nostril; Ocugestrin; Phenoptic; Phenylephrinum; Spersaphrine; Visadron; Alcon Efrin; Isopto Frin; Minims Phenylephrine; Nostril Spray Pump; Nostril Spray Pump Mild; Phenylephrine Minims; Prefrin Liquifilm; Relief Eye Drops for Red Eyes; Alconefrin Nasal Drops 12; Alconefrin Nasal Drops 25; Alconefrin Nasal Drops 50; Alconefrin Nasal Spray 25; Ah-Chew; Ak-dilate; Ak-nefrin; Fenilefrina [INN-Spanish]; I-Phrine; L-Phenylephedrine; L-Phenylephrine; M-Methylaminoethanolphenol; M-Oxedrine; M-Sympathol; M-Sympatol; M-Synephrine; Mydfrin (TN); Neo-Synephrine; Neo-Synephrine Nasal Drops; Neo-Synephrine Nasal Jelly; Neo-Synephrine Nasal Spray; Ocu-Phrin Sterile Eye Drops; Phenylephrine (INN); Phenylephrine Minims (TN); Phenylephrine [INN:BAN]; Phenylephrinum [INN-Latin]; R(-)-Phenylephrine; L-(3-Hydroxyphenyl)-N-methylethanolamine; L-1-(m-Hydroxyphenyl)-2-methylaminoethanol; L-m-Hydroxy-alpha-((methylamino)methyl)benzyl alcohol; L-alpha-Hydroxy-beta-methylamino-3-hydroxy-L-ethylbenzene; Tannins, compds. with (R)-3-hydroxy-alpha-((methylamino)methyl)benzenemethanol; Benzenemethanol, 3-hydroxy-alpha-((methylamino)methyl)-, (R)-(9CI); (-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol; (R)-2-Hydroxy-2-(3-hydroxyphenyl)-N-methylethylamine; (R)-3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol; 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol

Indication

Disease Entry	ICD 11	Status	REF
Fecal incontinence	ME07	Approved	[1]
Ophthalmic graves disease	5A02.0	Approved	[2], [3]

Therapeutic Class

Ophthalmologicals

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

167.2

Topological Polar Surface Area (xlogp)

-0.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [4]
Clearance: The clearance of drug is 2100 mL/min [5]
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 [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 minutes [6]
Metabolism: The drug is metabolized via the monoamine oxidase A, monoamine oxidase B, and SULT1A3 [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 4.98178 micromolar/kg/day [8]
Vd: The volume of distribution (Vd) of drug is 340 L [5]

Chemical Identifiers

Formula: C9H13NO2
IUPAC Name: 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
Canonical SMILES: CNC[C@@H](C1=CC(=CC=C1)O)O
InChI: 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

Cross-matching ID

PubChem CID: 6041
ChEBI ID: CHEBI:8093
CAS Number: 61-76-7
DrugBank ID: DB00388
TTD ID: D0O6IU
VARIDT ID: DR01201
ACDINA ID: D00528

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dopamine D2 receptor (D2R)	TTEX248	DRD2_HUMAN	Agonist	[9], [10]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Fecal incontinence

ICD Disease Classification

ME07

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine D2 receptor (D2R)	DTT	DRD2	2.50E-02	-0.08	-0.49

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Phenylephrine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Methylene blue	DMJAPE7	Major	Additive hypertensive effects by the combination of Phenylephrine and Methylene blue.	Acquired methaemoglobinaemia [3A93]	[21]
Droxidopa	DM5YF4M	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Droxidopa.	Autonomic nervous system disorder [8D87]	[22]
Linezolid	DMGFPU2	Major	Additive hypertensive effects by the combination of Phenylephrine and Linezolid.	Bacterial infection [1A00-1C4Z]	[23]
Sotalol	DML60TN	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Sotalol.	Cardiac arrhythmia [BC9Z]	[24]
Levomilnacipran	DMV26S8	Moderate	Increased risk of rapid heart rate by the combination of Phenylephrine and Levomilnacipran.	Chronic pain [MG30]	[25]
Selegiline	DM6034S	Major	Increased risk of hyperpyrexia by the combination of Phenylephrine and Selegiline.	Depression [6A70-6A7Z]	[21]
Duloxetine	DM9BI7M	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Duloxetine.	Depression [6A70-6A7Z]	[25]
Isocarboxazid	DMAF1NB	Major	Increased risk of hyperpyrexia by the combination of Phenylephrine and Isocarboxazid.	Depression [6A70-6A7Z]	[21]
Milnacipran	DMBFE74	Moderate	Increased risk of rapid heart rate by the combination of Phenylephrine and Milnacipran.	Depression [6A70-6A7Z]	[25]
Tranylcypromine	DMGB5RE	Major	Increased risk of hyperpyrexia by the combination of Phenylephrine and Tranylcypromine.	Depression [6A70-6A7Z]	[21]
Desvenlafaxine	DMHD4PE	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Desvenlafaxine.	Depression [6A70-6A7Z]	[25]
Phenelzine	DMHIDUE	Major	Additive hypertensive effects by the combination of Phenylephrine and Phenelzine.	Depression [6A70-6A7Z]	[21]
Nadolol	DMW6GVL	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Nadolol.	Essential hypertension [BA00]	[24]
Carteolol	DMFMDOB	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Carteolol.	Glaucoma [9C61]	[24]
Metipranolol	DMJMVKI	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Metipranolol.	Glaucoma [9C61]	[24]
Levobetaxolol	DMSREPX	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Levobetaxolol.	Glaucoma [9C61]	[24]
Levobunolol	DMTNFCQ	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Levobunolol.	Glaucoma [9C61]	[24]
Ergotamine	DMKR3C5	Major	Additive hypertensive effects by the combination of Phenylephrine and Ergotamine.	Headache [8A80-8A84]	[26]
Carvedilol	DMHTEAO	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Carvedilol.	Heart failure [BD10-BD1Z]	[24]
Procarbazine	DMIK367	Major	Increased risk of hyperpyrexia by the combination of Phenylephrine and Procarbazine.	Hodgkin lymphoma [2B30]	[21]
Acebutolol	DM0TI4U	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Acebutolol.	Hypertension [BA00-BA04]	[24]
Bisoprolol	DM3UZ95	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Bisoprolol.	Hypertension [BA00-BA04]	[24]
Penbutolol	DM4ES8F	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Penbutolol.	Hypertension [BA00-BA04]	[24]
Nebivolol	DM7F1PA	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Nebivolol.	Hypertension [BA00-BA04]	[24]
Pindolol	DMD2NV7	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Pindolol.	Hypertension [BA00-BA04]	[24]
Labetalol	DMK8U72	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Labetalol.	Hypertension [BA00-BA04]	[24]
Propranolol	DM79NTF	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Propranolol.	Migraine [8A80]	[24]
Ozanimod	DMT6AM2	Major	Increased risk of hyperpyrexia by the combination of Phenylephrine and Ozanimod.	Multiple sclerosis [8A40]	[21]
Sibutramine	DMFJTDI	Moderate	Increased risk of rapid heart rate by the combination of Phenylephrine and Sibutramine.	Obesity [5B80-5B81]	[27]
Safinamide	DM0YWJC	Moderate	Decreased metabolism of Phenylephrine caused by Safinamide mediated inhibition of non-CYP450 enzyme.	Parkinsonism [8A00]	[28]
Rasagiline	DM3WKQ4	Moderate	Additive hypertensive effects by the combination of Phenylephrine and Rasagiline.	Parkinsonism [8A00]	[21]
Ergonovine	DM0VEC1	Major	Additive hypertensive effects by the combination of Phenylephrine and Ergonovine.	Postpartum haemorrhage [JA43]	[26]
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⏷ Show the Full List of 32 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 27	E00381	83511	Colorant
D&C red no. 28	E00491	6097185	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Brushite	E00392	104805	Diluent
Calcium hydrogenphosphate	E00294	24441	Diluent
Carboxymethylcellulose sodium	E00621	Not Available	Adsorbent; Binding agent; Disintegrant; Emulsifying agent; Suspending agent; Viscosity-controlling agent
Carmellose sodium	E00625	Not Available	Disintegrant
Dextrin	E00359	62698	Binding agent; Diluent; Microencapsulating agent; Stiffening agent; Suspending agent; Viscosity-controlling agent
Dextrose monohydrate	E00538	22814120	Binding agent; Diluent; Flavoring agent; Tonicity agent
Magnesium silicate	E00596	72941442	Anticaking agent; Glidant; Lubricant
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 2000	E00649	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium citrate dihydrate	E00369	71474	Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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⏷ Show the Full List of 25 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Phenylephrine 10 mg tablet	10 mg	Oral Tablet	Oral
Phenylephrine 5 mg tablet	5 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800019494)
2	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).
3	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040654.
4	BDDCS applied to over 900 drugs
5	FDA Approved Drug Products: Phenylephrine Solution for Intravenous Injection
6	Pharmacokinetics of oral decongestants. Pharmacotherapy. 1993 Nov-Dec;13(6 Pt 2):116S-128S; discussion 143S-146S.
7	Forgue ST, Patterson BE, Bedding AW, Payne CD, Phillips DL, Wrishko RE, Mitchell MI: Tadalafil pharmacokinetics in healthy subjects. Br J Clin Pharmacol. 2006 Mar;61(3):280-8. doi: 10.1111/j.1365-2125.2005.02553.x.
8	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
9	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.
10	Intracellular Ca2+ and adrenergic responsiveness of cardiac myocytes in streptozotocin-induced diabetes. Clin Exp Pharmacol Physiol. 1999 Apr;26(4):347-53.
11	The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74.
12	Dopaminergic synapses in the matrix of the ventrolateral striatum after chronic haloperidol treatment. Synapse. 2002 Aug;45(2):78-85.
13	CYP2D6 and DRD2 genes differentially impact pharmacodynamic sensitivity and time course of prolactin response to perphenazine. Pharmacogenet Genomics. 2007 Nov;17(11):989-93.
14	Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. Bioorg Med Chem. 2005 Jan 3;13(1):77-87.
15	Screening of domperidone in wastewater by high performance liquid chromatography and solid phase extraction methods. Talanta. 2006 Jan 15;68(3):928-31.
16	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: 3639).
17	Receptor reserve-dependent properties of antipsychotics at human dopamine D2 receptors. Eur J Pharmacol. 2009 Apr 1;607(1-3):35-40.
18	[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome]. Nervenarzt. 2007 Mar;78(3):264, 266-8, 270-1.
19	Modulatory role of dopamine D2 receptors and fundamental role of L-type Ca2+ channels in the induction of long-term potentiation in the basolateral... Eur J Pharmacol. 2009 Mar 15;606(1-3):90-3.
20	Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
21	Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
22	Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
23	Hendershot PE, Antal EJ, Welshman IR, Batts DH, Hopkins NK "Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr." J Clin Pharmacol 41 (2001): 563-72. [PMID: 11361053]
24	Cass E, Kadar D, Stein HA "Hazards of phenylephrine topical medication in persons taking propranolol." Can Med Assoc J 120 (1979): 1261-2. [PMID: 221086]
25	Product Information. Cymbalta (duloxetine). Lilly, Eli and Company, Indianapolis, IN.
26	Barthel W, Glusa E, Koth W "Interactions of dihydroergotamine with etilefrine in human leg veins in vitro and in situ." Int J Clin Pharmacol Ther Toxicol 25 (1987): 63-9. [PMID: 2881898]
27	Product Information. Meridia (sibutramine). Knoll Pharmaceutical Company, Whippany, NJ.
28	Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".