Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C16H20N2 |
| Molecular Weight | 240.3434 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC(C1=CC=CC=C1)C2=CC=CC=N2
InChI
InChIKey=IJHNSHDBIRRJRN-UHFFFAOYSA-N
InChI=1S/C16H20N2/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
| 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 |
|
| Role of central histaminergic system in lorazepam withdrawal syndrome in rats. | 2001 Apr |
|
| Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures. | 2001 Apr |
|
| pH-independent large-volume sample stacking of positive or negative analytes in capillary electrophoresis. | 2001 Jan |
|
| Dermal exposure to strychnine. | 2001 Jul-Aug |
|
| A phase II study of paclitaxel and cisplatin combination chemotherapy in recurrent or metastatic head and neck cancer. | 2002 Apr |
|
| Uniformly sized molecularly imprinted polymer for d-chlorpheniramine. Evaluation of retention and molecular recognition properties in an aqueous mobile phase. | 2002 Mar 1 |
|
| Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
|
| Pre-treatment of anaphylaxis, does it really work? | 2005 Dec |
|
| A case of pheniramine dependence. | 2005 Mar |
|
| A comparison of the clinical efficacy of pheniramine maleate/naphazoline hydrochloride ophthalmic solution and olopatadine hydrochloride ophthalmic solution in the conjunctival allergen challenge model. | 2005 May |
|
| 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 |
|
| Intraoperative anaphylaxis with a complicated pulmonary hydatid cyst. | 2007 Feb |
|
| High risk behaviors of injection drug users registered with harm reduction programme in Karachi, Pakistan. | 2007 Feb 10 |
|
| Chemical profile of counterfeit buprenorphine vials seized in Tehran, Iran. | 2007 Oct 25 |
|
| [Toxic epidermal necrolysis following dorzolamide eyedrops]. | 2008 Jan |
|
| H1-antihistamines and oxidative burst of professional phagocytes. | 2009 |
|
| Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury. | 2009 Apr |
|
| In vitro antibacterial activity of some systemic and topical antihistaminic preparations. | 2009 Dec 1 |
|
| A presentation of longstanding toxoplasmosis chorioretinitis. | 2009 Jan |
|
| In situ forming polymeric drug delivery systems. | 2009 May |
|
| Simultaneous determination of pseudoephdrine, pheniramine, guaifenisin, pyrilamine, chlorpheniramine and dextromethorphan in cough and cold medicines by high performance liquid chromatography. | 2009 May 15 |
|
| Acute renal failure caused by pheniramine maleate induced rhabdomyolysis: an unusual case. | 2009 Oct |
|
| Weekly paclitaxel and trastuzumab as a first-line therapy in patients with HER2-overexpressing metastatic breast cancer: magnitude of HER2/neu amplification as a predictive factor for efficacy. | 2009 Oct |
|
| Antihistamine pretreatment to reduce incidence of withdrawal movement after rocuronium injection. | 2009 Oct |
|
| Halogenation effects of pheniramines on the complexation with beta-cyclodextrin. | 2009 Oct 15 |
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 |
134FM9ZZ6M
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| Record Status |
Validated (UNII)
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LIVERTOX |
769
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WHO-ATC |
R06AB05
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WHO-ATC |
D04AA16
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WHO-VATC |
QR06AB05
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NCI_THESAURUS |
C29578
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| Code System | Code | Type | Description | ||
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DTXSID0023454
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155683-10-6
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CHEMBL1193
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SUB09768MIG
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201-656-2
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134FM9ZZ6M
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86-21-5
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DB01620
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134FM9ZZ6M
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100000082237
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8132
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m8619
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47965
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2132
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D010632
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105
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PHENIRAMINE
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4761
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7267
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C61889
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
