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Details

Stereochemistry EPIMERIC
Molecular Formula C14H21NO2
Molecular Weight 235.322
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEREFRINE

SMILES

CN1C[C@H](OC1C(C)(C)C)C2=CC(O)=CC=C2

InChI

InChIKey=ORIOFGXXYYXLNY-UEWDXFNNSA-N
InChI=1S/C14H21NO2/c1-14(2,3)13-15(4)9-12(17-13)10-6-5-7-11(16)8-10/h5-8,12-13,16H,9H2,1-4H3/t12-,13?/m0/s1

HIDE SMILES / InChI

Molecular Formula C14H21NO2
Molecular Weight 235.322
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/204300lbl.pdf and https://www.drugs.com/pro/phenylephrine-and-chlorpheniramine-tablets.html

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

Curator's Comment: Phenylephrine does not cross the blood–brain barrier

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
55.0 nM [EC50]
5.9 nM [EC50]
154.88 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VAZCULEP

Approved Use

VAZCULEP (phenylephrine hydrochloride) is indicated for the treatment of clinically important hypotension resulting primarily from vasodilation in the setting of anesthesia.

Launch Date

1953
Diagnostic
Phenylephrine Hydrochloride Ophthalmic Solution

Approved Use

Indicated to dilate the pupil

Launch Date

1938
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1354 pg/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2959 pg/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4492 pg/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
955.8 pg × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2346 pg × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
3900 pg × h/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.89 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.93 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.64 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLEPHRINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
10 mg 1 times / day multiple, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 34 years
Health Status: unhealthy
Age Group: 34 years
Sex: M
Sources:
Disc. AE: Ischemic colitis...
AEs leading to
discontinuation/dose reduction:
Ischemic colitis (acute)
Sources:
40 mg 6 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 6 times / day
Route: oral
Route: multiple
Dose: 40 mg, 6 times / day
Sources:
unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Health Status: unhealthy
Age Group: 37.5 years (range: 19.0 - 77.0 years)
Sex: M+F
Sources:
Disc. AE: Chest pain, Jaw pain...
Other AEs: Nervous system disorders, Headache...
AEs leading to
discontinuation/dose reduction:
Chest pain (1 patient)
Jaw pain (1 patient)
Other AEs:
Nervous system disorders (3.6%)
Headache (2.7%)
Gastrointestinal disorders (8%)
Dry mouth (2.7%)
Nausea (3.6%)
Sources:
10 % 3 times / day multiple, ophthalmic
Recommended
Dose: 10 %, 3 times / day
Route: ophthalmic
Route: multiple
Dose: 10 %, 3 times / day
Sources:
healthy, > 1 year
Health Status: healthy
Age Group: > 1 year
Sources:
Other AEs: Eye pain, Blurred vision...
Other AEs:
Eye pain
Blurred vision
Photophobia
Allergic conjunctivitis
Sources:
250 ug single, intravenous
Recommended
Dose: 250 ug
Route: intravenous
Route: single
Dose: 250 ug
Sources:
unhealthy, adult
AEs

AEs

AESignificanceDosePopulation
Ischemic colitis acute
Disc. AE
10 mg 1 times / day multiple, oral
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 34 years
Health Status: unhealthy
Age Group: 34 years
Sex: M
Sources:
Chest pain 1 patient
Disc. AE
40 mg 6 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 6 times / day
Route: oral
Route: multiple
Dose: 40 mg, 6 times / day
Sources:
unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Health Status: unhealthy
Age Group: 37.5 years (range: 19.0 - 77.0 years)
Sex: M+F
Sources:
Jaw pain 1 patient
Disc. AE
40 mg 6 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 6 times / day
Route: oral
Route: multiple
Dose: 40 mg, 6 times / day
Sources:
unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Health Status: unhealthy
Age Group: 37.5 years (range: 19.0 - 77.0 years)
Sex: M+F
Sources:
Dry mouth 2.7%
40 mg 6 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 6 times / day
Route: oral
Route: multiple
Dose: 40 mg, 6 times / day
Sources:
unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Health Status: unhealthy
Age Group: 37.5 years (range: 19.0 - 77.0 years)
Sex: M+F
Sources:
Headache 2.7%
40 mg 6 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 6 times / day
Route: oral
Route: multiple
Dose: 40 mg, 6 times / day
Sources:
unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Health Status: unhealthy
Age Group: 37.5 years (range: 19.0 - 77.0 years)
Sex: M+F
Sources:
Nausea 3.6%
40 mg 6 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 6 times / day
Route: oral
Route: multiple
Dose: 40 mg, 6 times / day
Sources:
unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Health Status: unhealthy
Age Group: 37.5 years (range: 19.0 - 77.0 years)
Sex: M+F
Sources:
Nervous system disorders 3.6%
40 mg 6 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 6 times / day
Route: oral
Route: multiple
Dose: 40 mg, 6 times / day
Sources:
unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Health Status: unhealthy
Age Group: 37.5 years (range: 19.0 - 77.0 years)
Sex: M+F
Sources:
Gastrointestinal disorders 8%
40 mg 6 times / day multiple, oral
Highest studied dose
Dose: 40 mg, 6 times / day
Route: oral
Route: multiple
Dose: 40 mg, 6 times / day
Sources:
unhealthy, 37.5 years (range: 19.0 - 77.0 years)
Health Status: unhealthy
Age Group: 37.5 years (range: 19.0 - 77.0 years)
Sex: M+F
Sources:
Allergic conjunctivitis
10 % 3 times / day multiple, ophthalmic
Recommended
Dose: 10 %, 3 times / day
Route: ophthalmic
Route: multiple
Dose: 10 %, 3 times / day
Sources:
healthy, > 1 year
Health Status: healthy
Age Group: > 1 year
Sources:
Blurred vision
10 % 3 times / day multiple, ophthalmic
Recommended
Dose: 10 %, 3 times / day
Route: ophthalmic
Route: multiple
Dose: 10 %, 3 times / day
Sources:
healthy, > 1 year
Health Status: healthy
Age Group: > 1 year
Sources:
Eye pain
10 % 3 times / day multiple, ophthalmic
Recommended
Dose: 10 %, 3 times / day
Route: ophthalmic
Route: multiple
Dose: 10 %, 3 times / day
Sources:
healthy, > 1 year
Health Status: healthy
Age Group: > 1 year
Sources:
Photophobia
10 % 3 times / day multiple, ophthalmic
Recommended
Dose: 10 %, 3 times / day
Route: ophthalmic
Route: multiple
Dose: 10 %, 3 times / day
Sources:
healthy, > 1 year
Health Status: healthy
Age Group: > 1 year
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Contribution of ryanodine receptor subtype 3 to ca2+ responses in Ca2+-overloaded cultured rat portal vein myocytes.
2001-04-06
In vivo regulation of Na/Ca exchanger expression by adrenergic effectors.
2001-03
Endothelial cell protein kinase G inhibits release of EDHF through a PKG-sensitive cation channel.
2001-03
Reciprocal regulation of cGMP-mediated vasorelaxation by soluble and particulate guanylate cyclases.
2001-03
Endogenous estrogen mediates vascular reactivity and distensibility in pregnant rat mesenteric arteries.
2001-03
Topical phenylephrine increases anal canal resting pressure in patients with faecal incontinence.
2001-03
Regulation of slow wave frequency by IP(3)-sensitive calcium release in the murine small intestine.
2001-03
EDHF contributes to strain-related differences in pulmonary arterial relaxation in rats.
2001-03
The transient receptor potential protein homologue TRP6 is the essential component of vascular alpha(1)-adrenoceptor-activated Ca(2+)-permeable cation channel.
2001-02-16
Flow (shear stress)-induced endothelium-dependent dilation is altered in mice lacking the gene encoding for dystrophin.
2001-02-13
Nitric oxide contributes to vascular smooth muscle relaxation in contracting fast-twitch muscles.
2001-02-07
Heat, but not mechanical hyperalgesia, following adrenergic injections in normal human skin.
2001-02-01
Influence of a multideficient diet from northeastern Brazil on resting blood pressure and baroreflex sensitivity in conscious, freely moving rats.
2001-02
Effects of salt intake and angiotensin II on vascular reactivity to endothelin-1.
2001-02
Reflex cardiovascular responses originating in exercising muscles of mice.
2001-02
Smooth muscle-targeted overexpression of insulin-like growth factor I results in enhanced vascular contractility.
2001-02
Nitric oxide-mediated arteriolar dilation after endothelial deformation.
2001-02
Vascular NAD(P)H oxidase is distinct from the phagocytic enzyme and modulates vascular reactivity control.
2001-02
Regulation of mitogen-activated protein kinases in cardiac myocytes through the small G protein Rac1.
2001-02
Interaction of rapid nongenomic cardiovascular aldosterone effects with the adrenergic system.
2001-02
Relaxation of rat aorta by adenosine in diabetes with and without hypertension: role of endothelium.
2001-01-19
The dual-specificity phosphatase MKP-1 limits the cardiac hypertrophic response in vitro and in vivo.
2001-01-19
Catecholamine inotropes as growth factors for Staphylococcus epidermidis and other coagulase-negative staphylococci.
2001-01-15
Receptor reserve analysis of the human alpha(2C)-adrenoceptor using.
2001-01-12
Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum.
2001-01-05
Insulin-induced relaxation of rat mesenteric artery is mediated by Ca(2+)-activated K(+) channels.
2001-01-05
Dietary restriction in pregnant rats causes gender-related hypertension and vascular dysfunction in offspring.
2001-01-01
Methylene blue as a successful treatment alternative for pharmacologically induced priapism.
2001-01
Detection and characterization of cholinergic oscillatory control in the forehead microvasculature in response to systemic alpha-agonist infusion in healthy volunteers.
2001-01
A N-terminal PTHrP peptide fragment void of a PTH/PTHrP-receptor binding domain activates cardiac ET(A) receptors.
2001-01
Activity of cardiorespiratory networks revealed by transsynaptic virus expressing GFP.
2001-01
Involvement of Ca2+ -activated K+ channels in ginsenosides-induced aortic relaxation in rats.
2001-01
Effects of LY117018 and the estrogen analogue, 17alpha-ethinylestradiol, on vascular reactivity, platelet aggregation, and lipid metabolism in the insulin-resistant JCR:LA-cp male rat: role of nitric oxide.
2001-01
Effect of dietary vitamin E supplementation on vascular reactivity of thoracic aorta in streptozotocin-diabetic rats.
2001-01
Increased dilator response to heptanol and octanol in aorta from DOCA-salt-hypertensive rats.
2001-01
In vivo measurement of pulsewave velocity in small vessels using intravascular MR.
2001-01
Exercise attenuates alpha-adrenergic-receptor responsiveness in skeletal muscle vasculature.
2001-01
Catecholamine responses to alpha-adrenergic blockade during exercise in women acutely exposed to altitude.
2001-01
Should the angiotensin II antagonists be discontinued before surgery?
2001-01
Effects of acute and chronic hypertension on the labyrinthine barriers in rat.
2001-01
CYP4A1 antisense oligonucleotide reduces mesenteric vascular reactivity and blood pressure in SHR.
2001-01
Acute hypertension inhibits thirst stimulated by ANG II, hyperosmolality, or hypovolemia in rats.
2001-01
[Ca(2+)](i) signaling in renal arterial smooth muscle cells of pregnant rat is enhanced during inhibition of NOS.
2001-01
Substance P and NPY differentially potentiate ATP and adrenergic stimulated vasopressin and oxytocin release.
2001-01
Endothelin and nitric oxide mediate reduced myogenic reactivity of small renal arteries from pregnant rats.
2001-01
A metabolic fragment of bradykinin, Arg-Pro-Pro-Gly-Phe, protects against the deleterious effects of lipopolysaccharide in rats.
2001-01
alpha-Adrenoceptor stimulation-mediated negative inotropism and enhanced Na(+)/Ca(2+) exchange in mouse ventricle.
2001-01
Inducible and neuronal nitric oxide synthase involvement in lipopolysaccharide-induced sphincteric dysfunction.
2001-01
Hepatic neovascularization after partial portal vein ligation: novel mechanism of chronic regulation of blood flow.
2001-01
Evidence of alpha-adrenoceptor-mediated chronotropic action in children.
2000-12-31
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Also used as Ophthalmic Solution or oral tablets http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203510s000lbl.pdf https://www.drugs.com/dosage/chlorpheniramine-phenylephrine.html
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
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
Created
by admin
on Mon Mar 31 17:58:31 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:31 GMT 2025
Record UNII
378U019DHG
Record Status Validated (UNII)
Record Version
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Name Type Language
BEREFRINE [USAN]
Preferred Name English
BEREFRINE
INN   USAN  
INN   USAN  
Official Name English
PHENOL, 3-(2-(1,1-DIMETHYLETHYL)-3-METHYL-5-OXAZOLIDINYL)-
Systematic Name English
berefrine [INN]
Common Name English
M-((2R,5R)-2-TERT-BUTYL-3-METHYL-5-OXAZOLIDINYL)PHENOL MIXTURE WITH M-((2S,5R)-2-TERT-BUTYL-3-METHYL-5-OXAZOLIDINYL)PHENOL
Common Name English
3-((5R)-2-TERT-BUTYL-3-METHYL-1,3-OXAZOLIDIN-5-YL)PHENOL
Systematic Name English
Phenylephrine oxazolidine
Common Name English
2-T-BUTYL-3-METHYL-5-(M-HYDROXYPHENYL)-1,3-OXAZOLIDINE
Systematic Name English
BUREFRINE
Common Name English
Code System Code Type Description
WIKIPEDIA
Berefrine
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
USAN
CC-78
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
INN
6987
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
FDA UNII
378U019DHG
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
NCI_THESAURUS
C166649
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
EPA CompTox
DTXSID10869448
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
CAS
105567-83-7
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
PUBCHEM
20055419
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
MESH
C050817
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
ChEMBL
CHEMBL2104659
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
SMS_ID
100000086049
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
EVMPD
SUB05780MIG
Created by admin on Mon Mar 31 17:58:31 GMT 2025 , Edited by admin on Mon Mar 31 17:58:31 GMT 2025
PRIMARY
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