PHENYLEPHRINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H13NO2
Molecular Weight	167.205
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CNC[C@H](O)C1=CC(O)=CC=C1

InChI

InChIKey=SONNWYBIRXJNDC-VIFPVBQESA-N

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

HIDE SMILES / InChI

Molecular Formula	C9H13NO2
Molecular Weight	167.205
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Berefrine (also known as phenylephrine oxazolidine), a prodrug of phenylephrine, is a mydriatic agent. Berefrine was developed for improving ocular absorption and reducing systemic side effects.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Alpha-1a adrenergic receptor 66	Agonist 2,678	55.0 nM [EC50]
Alpha-1b adrenergic receptor 44	Agonist 2,678	5.9 nM [EC50]
Alpha-1d adrenergic receptor 36	Agonist 2,678	154.88 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypotension 28	Primary		Approved 8,429	VAZCULEP
Eye diseases 25	Diagnostic		Approved 8,429	Phenylephrine Hydrochloride Ophthalmic Solution

C_max

Value	Dose	Analyte	Population
1354 pg/mL	10 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens
2959 pg/mL	20 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens
4492 pg/mL	30 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
955.8 pg × h/mL	10 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens
2346 pg × h/mL	20 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens
3900 pg × h/mL	30 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.89 h	10 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens
1.93 h	20 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens
1.64 h	30 mg single, oral	PHENYLEPHRINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
10 mg 1 times / day multiple, oral	unhealthy, 34 years	Disc. AE: Ischemic colitis...
40 mg 6 times / day multiple, oral Highest studied dose	unhealthy, 37.5 years (range: 19.0 - 77.0 years)	Disc. AE: Chest pain, Jaw pain... Other AEs: Nervous system disorders, Headache...
10 % 3 times / day multiple, ophthalmic Recommended	healthy, > 1 year	Other AEs: Eye pain, Blurred vision...
250 ug single, intravenous Recommended	unhealthy, adult

Showing 1 to 4 of 4 entries

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AEs

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AE	Significance	Dose	Population
Ischemic colitis	acute Disc. AE	10 mg 1 times / day multiple, oral	unhealthy, 34 years
Chest pain	1 patient Disc. AE	40 mg 6 times / day multiple, oral Highest studied dose	unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Jaw pain	1 patient Disc. AE	40 mg 6 times / day multiple, oral Highest studied dose	unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Dry mouth	2.7%	40 mg 6 times / day multiple, oral Highest studied dose	unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Headache	2.7%	40 mg 6 times / day multiple, oral Highest studied dose	unhealthy, 37.5 years (range: 19.0 - 77.0 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1A2 701

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1,692	inducer 1,573	yes

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PubMed

Show entries

Title	Date	PubMed
Epidural phenylephrine attenuates hypotension induced by alkalinized lidocaine epidural anesthesia.	1999 Jun	10357338
Bupivacaine inhibits baroreflex control of heart rate in conscious rats.	2000 Jan	10638917
Roles of tissue transglutaminase in ethanol-induced inhibition of hepatocyte proliferation and alpha 1-adrenergic signal transduction.	2000 Jul 21	10801782
Fine structure and plasticity of barosensitive neurons in the nucleus of solitary tract.	2000 Jul 3	10861511
The Rho effector, PKN, regulates ANF gene transcription in cardiomyocytes through a serum response element.	2000 Jun	10843871

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Patents

Sample Use Guides

In Vivo Use Guide

VAZCULEP (phenylephrine hydrochloride) Injection, 10 mg/mL, is injected intravenously either as a bolus or in a dilute solution as a continuous infusion. Dilute before administration. Dosing for treatment of hypotension during anesthesia Bolus intravenous injection: 40 mcg to 100 mcg every 1-2 minutes as needed, not to exceed 200 mcg. Intravenous infusion: 10 mcg/min to 35 mcg/min, titrating to effect, not to exceed 200 mcg/min.

Route of Administration: Intravenous

In Vitro Use Guide

The hypertrophic phenotype of neonatal rat cardiomyocyte cultures (cardiomyocyte size, sarcomeric organization, total protein synthesis, c-fos expression) mediated by phenylephrine (10 uM) was counteracted by the selective A1 receptor agonist

Substance Class	Chemical
Record UNII	1WS297W6MV
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

PHENYLEPHRINE

Official Name

English

J8.601K

Code

English

M-SYMPATHOL

Common Name

English

M-SYNEPHRINE

Common Name

English

AB-101 (PHENYLEPHRINE)

Code

English

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Classification Tree

Code System

Code

Allergy symptoms

LIVERTOX

773

Sympathomimetics

WHO-VATC

QR01BA03

Sympathomimetics, excl. antiglaucoma preparations

WHO-VATC

QS01FB01

Sympathomimetics, plain

WHO-VATC

QR01AA04

Adrenergic and dopaminergic agents

WHO-VATC

QC01CA06

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Code System

Code

Type

Description

NCI_THESAURUS

C62067

PRIMARY

CAS

59-42-7

PRIMARY

RXCUI

8163

PRIMARY

MESH

D010656

PRIMARY

ChEMBL

CHEMBL1215

PRIMARY

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Related Record

Type

Details


					DU5ATO7HYP

PHENYLEPHRINE TANNATE

SALT/SOLVATE -> PARENT

Amount:


					27O3Q5ML57

PHENYLEPHRINE BITARTRATE

SALT/SOLVATE -> PARENT

Amount:


					Q7A4S7HOP4

ALPHA-1B ADRENERGIC RECEPTOR

TARGET -> AGONIST

Comments:

Binding Assay

Qualification:

IC50

Amount:

12.3 MICROMOLAR (average)


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

95 % (average)


					3T7136LE8K

ALPHA-1A ADRENERGIC RECEPTOR

TARGET -> AGONIST

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					2YHZ5B4FDS

PHENYLEPHRINE GLUCURONIDE

METABOLITE -> PARENT

Amount:

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Type

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					Y4FM912JTR

PHENYLEPHRONE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					OON2Y3767M

BENZYLPHENYLEPHRONE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					F2BGC076EB

NORFENEFRINE, (R)-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

[<0.1] PERCENT PEAK AREA (limits)


					O2JO4751KY

BENZYLPHENYLEPHRINE

IMPURITY -> PARENT

Qualification:

EP

Amount:

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Type

Details


					1WS297W6MV

PHENYLEPHRINE

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount
Volume of Distribution	PHARMACOKINETIC	[2.63 to 7.76] Liters/Kilogram (average)

Vdss	PHARMACOKINETIC	340 LITERS [184 to 543] (average)

Biological Half-life	PHARMACOKINETIC	[2.1 to 3.4] hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator