Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C16H20N2.ClH |
| Molecular Weight | 276.804 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN(C)CCC(C1=CC=CC=C1)C2=CC=CC=N2
InChI
InChIKey=LAWLMXPSCYHMNV-UHFFFAOYSA-N
InChI=1S/C16H20N2.ClH/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16;/h3-10,12,15H,11,13H2,1-2H3;1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C16H20N2 |
| Molecular Weight | 240.3434 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionSources: https://www.drugs.com/drp/pheniramine-maleate.html | http://www.news-medical.net/drugs/Avil.aspxCurator's Comment: Description was created based on several sources, including http://www.druginfosys.com/drug.aspx?drugcode=561&type=1 | https://www.drugbank.ca/drugs/DB01620
Sources: https://www.drugs.com/drp/pheniramine-maleate.html | http://www.news-medical.net/drugs/Avil.aspx
Curator's Comment: Description was created based on several sources, including http://www.druginfosys.com/drug.aspx?drugcode=561&type=1 | https://www.drugbank.ca/drugs/DB01620
Pheniramine is an antihistamine used to treat allergic conditions such as hay fever or urticaria. It is generally sold in combination with other medications, rather than as a stand-alone drug. Allergies are caused by an excessive type 1 hypersensitivity response of the body to allergens, mediated by inappropriate histamine signalling. By inhibiting the binding of histamine, antihistamines decrease the normal histamine response from cells, consequently decreasing allergic symptoms. Antihistamines such as pheniramine appear to compete with histamine for histamine H1- receptor sites on effector cells. The antihistamines antagonize those pharmacological effects of histamine which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release. Antihistamines suppress the histamine-induced wheal (swelling) and flare (vasodilation) response by blocking the binding of histamine to its receptors on nerves, vascular smooth muscle, glandular cells, endothelium, and mast cells. They effectively exert competitive antagonism of histamine for H1-receptors. Pheniramine is marketed under the trade name Avil and Visine-A among others).
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 7.5 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | AVIL Approved UseAllergic conditions including hay fever, drug rashes, angioneurotic oedema, serum sickness,
allergic conjunctivitis, food allergy etc.
· Conditions of the respiratory tract that are accompanied by increased secretion, including
vasomotor rhinitis and acute rhinitis.
· All itching skin conditions, including neurodermatitis, eczema of any origin, lichen planus,
acute and chronic urticaria, pruritis of the anus or genitals, pruritus in icterus and diabetes,
radiation sickness etc.
· Prevention and treatment of motion sickness.
· Prevention and treatment of nausea, vomiting and vertigo due to Menière’s disease and other
labyrinthine disturbances. |
|||
| Palliative | Visine-A Approved UseVisine-A is an antihistamine/redness reliever eye drop, formerly available by prescription only, that provides temporary relief of itchy, red eyes due to pollen, ragweed, grass, animal hair and dander. |
|||
| Primary | AVIL Approved UseAllergic conditions including hay fever, drug rashes, angioneurotic oedema, serum sickness,
allergic conjunctivitis, food allergy etc.
· Conditions of the respiratory tract that are accompanied by increased secretion, including
vasomotor rhinitis and acute rhinitis.
· All itching skin conditions, including neurodermatitis, eczema of any origin, lichen planus,
acute and chronic urticaria, pruritis of the anus or genitals, pruritus in icterus and diabetes,
radiation sickness etc.
· Prevention and treatment of motion sickness.
· Prevention and treatment of nausea, vomiting and vertigo due to Menière’s disease and other
labyrinthine disturbances. |
|||
| Preventing | AVIL Approved UseAllergic conditions including hay fever, drug rashes, angioneurotic oedema, serum sickness,
allergic conjunctivitis, food allergy etc.
· Conditions of the respiratory tract that are accompanied by increased secretion, including
vasomotor rhinitis and acute rhinitis.
· All itching skin conditions, including neurodermatitis, eczema of any origin, lichen planus,
acute and chronic urticaria, pruritis of the anus or genitals, pruritus in icterus and diabetes,
radiation sickness etc.
· Prevention and treatment of motion sickness.
· Prevention and treatment of nausea, vomiting and vertigo due to Menière’s disease and other
labyrinthine disturbances. |
|||
| Primary | AVIL Approved UseAllergic conditions including hay fever, drug rashes, angioneurotic oedema, serum sickness,
allergic conjunctivitis, food allergy etc.
· Conditions of the respiratory tract that are accompanied by increased secretion, including
vasomotor rhinitis and acute rhinitis.
· All itching skin conditions, including neurodermatitis, eczema of any origin, lichen planus,
acute and chronic urticaria, pruritis of the anus or genitals, pruritus in icterus and diabetes,
radiation sickness etc.
· Prevention and treatment of motion sickness.
· Prevention and treatment of nausea, vomiting and vertigo due to Menière’s disease and other
labyrinthine disturbances. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
274 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3988394/ |
30.5 mg single, oral dose: 30.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENIRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5768 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3988394/ |
30.5 mg single, oral dose: 30.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENIRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3988394/ |
30.5 mg single, oral dose: 30.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENIRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Antimycobacterial antihistaminics]. | 1989 Aug |
|
| Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures. | 2001 Apr |
|
| Comparison of lytic cocktail, chloral hydrate and midazolam for pediatric sedation. | 2001 Oct |
|
| A phase II study of paclitaxel and cisplatin combination chemotherapy in recurrent or metastatic head and neck cancer. | 2002 Apr |
|
| Efficacy and safety of rectal thiopental, intramuscular cocktail and rectal midazolam for sedation in children undergoing neuroimaging. | 2002 Dec |
|
| Uniformly sized molecularly imprinted polymer for d-chlorpheniramine. Evaluation of retention and molecular recognition properties in an aqueous mobile phase. | 2002 Mar 1 |
|
| Conjunctival allergen challenge: models in the investigation of ocular allergy. | 2003 Jul |
|
| Contribution of the histaminergic receptor subtypes to histamine-induced cerebellar granular neurotoxicity. | 2003 May-Jun |
|
| Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
|
| A case of pheniramine dependence. | 2005 Mar |
|
| Antiradical effects of antihistamines in human blood. Structure-activity relationship. | 2006 Apr |
|
| Goat ureter - an alternative model for measuring ureteral peristalsis. | 2006 Aug |
|
| Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine. | 2006 Dec |
|
| Life-threatening facial edema due to pine caterpillar mimicking an allergic event. | 2006 Jul-Aug |
|
| Enantioselective analysis of pheniramine in urine by charged CD-mediated CZE provided with a fiber-based DAD and an on-line sample pretreatment by capillary ITP. | 2007 Aug |
|
| Intraoperative anaphylaxis with a complicated pulmonary hydatid cyst. | 2007 Feb |
|
| Chemical profile of counterfeit buprenorphine vials seized in Tehran, Iran. | 2007 Oct 25 |
|
| Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity. | 2008 Apr 14 |
|
| [Toxic epidermal necrolysis following dorzolamide eyedrops]. | 2008 Jan |
|
| Possibilities of column coupling electrophoresis provided with a fiber-based diode array detection in enantioselective analysis of drugs in pharmaceutical and clinical samples. | 2008 Jan 25 |
|
| Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion. | 2009 Apr |
|
| Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury. | 2009 Apr |
|
| A presentation of longstanding toxoplasmosis chorioretinitis. | 2009 Jan |
|
| Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins. | 2009 Jul 10 |
|
| In situ forming polymeric drug delivery systems. | 2009 May |
|
| Pouch colon associated with anorectal malformations fails to show spontaneous contractions but responds to acetylcholine and histamine in vitro. | 2009 Nov |
|
| Substance use and addiction research in India. | 2010 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Could also be used topically https://www.drugs.com/drp/pheniramine-maleate.html
Each Avil (Pheniramine maleate) tablet contains 45.3mg pheniramine maleate. In adults and children over 10 years of age, treatment is commenced with half a tablet
taken up to three times daily. This dose may be increased to one tablet taken up to three times daily
if required. Children 5-10 years of age: half a tablet up to three times daily. Avil tablets are not
recommended in children under 5 years of age.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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| Record UNII |
10P41DI6MI
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| Record Status |
Validated (UNII)
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| Record Version |
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