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
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
| 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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00388https://www.ncbi.nlm.nih.gov/pubmed/?2008281 | https://www.ncbi.nlm.nih.gov/pubmed/8272415Curator'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
Sources: http://www.drugbank.ca/drugs/DB00388https://www.ncbi.nlm.nih.gov/pubmed/?2008281 | https://www.ncbi.nlm.nih.gov/pubmed/8272415
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22391890
Curator's Comment: Phenylephrine does not cross the blood–brain barrier
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL229 Sources: http://www.drugbank.ca/drugs/DB00388 |
55.0 nM [EC50] | ||
Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25813897 |
5.9 nM [EC50] | ||
Target ID: CHEMBL326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8831777 |
154.88 nM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | VAZCULEP Approved UseVAZCULEP (phenylephrine hydrochloride) is indicated for the treatment of clinically important
hypotension resulting primarily from vasodilation in the setting of anesthesia. Launch Date1953 |
|||
| Diagnostic | Phenylephrine Hydrochloride Ophthalmic Solution Approved UseIndicated to dilate the pupil Launch Date1938 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1354 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
955.8 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.89 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
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
| Dose | Population | Adverse 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 |
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) Other AEs:Jaw pain (1 patient) Nervous system disorders (3.6%) Sources: Headache (2.7%) Gastrointestinal disorders (8%) Dry mouth (2.7%) Nausea (3.6%) |
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 Sources: Blurred vision Photophobia Allergic conjunctivitis |
250 ug single, intravenous Recommended Dose: 250 ug Route: intravenous Route: single Dose: 250 ug Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
| 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
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16510159/ Page: 10.0 |
yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26406609
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
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Edited
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| Record UNII |
378U019DHG
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Validated (UNII)
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| Code System | Code | Type | Description | ||
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Berefrine
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CC-78
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6987
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378U019DHG
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C166649
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DTXSID10869448
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105567-83-7
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20055419
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C050817
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CHEMBL2104659
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100000086049
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SUB05780MIG
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