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
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 |
|
| Dermal exposure to strychnine. | 2001 Jul-Aug |
|
| Chiral separation of pheniramine-like 3-phenyl-3-heteroarylpropylamines by CE and HPLC methods. | 2001 Jun |
|
| 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 |
|
| Rapid identification and quantification of chlorpheniramine maleate or pheniramine maleate in pharmaceutical preparations by thin-layer chromatography-densitometry. | 2004 Nov-Dec |
|
| Pre-treatment of anaphylaxis, does it really work? | 2005 Dec |
|
| Enantioselective determination of pheniramine in pharmaceuticals by capillary electrophoresis with charged cyclodextrin. | 2005 Jul 1 |
|
| A case of pheniramine dependence. | 2005 Mar |
|
| [Use of capillary isotachophoresis for the determination of pheniramine in granulated powders]. | 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 |
|
| Evaluation of a new premedication protocol for administration of equine rabies immunoglobulin in patients with hypersensitivity. | 2007 Apr-Jun |
|
| 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 |
|
| High risk behaviors of injection drug users registered with harm reduction programme in Karachi, Pakistan. | 2007 Feb 10 |
|
| First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005. | 2007 May |
|
| Chiral separation of alkylamine antihistamines in pharmaceuticals by capillary isotachophoresis with charged cyclodextrin. | 2007 Nov |
|
| 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 |
|
| The effects of dithiaden on nitric oxide production by RAW 264.7 cells. | 2008 Dec |
|
| The lollipop with strawberry aroma may be promising in reduction of infusion-related nausea and vomiting during the infusion of cryopreserved peripheral blood stem cells. | 2008 Dec |
|
| [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 |
|
| H1-antihistamines and oxidative burst of professional phagocytes. | 2009 |
|
| Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion. | 2009 Apr |
|
| 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 |
|
| Preparation and evaluation of orodispersible tablets of pheniramine maleate by effervescent method. | 2009 Mar |
|
| Simultaneous determination of pseudoephdrine, pheniramine, guaifenisin, pyrilamine, chlorpheniramine and dextromethorphan in cough and cold medicines by high performance liquid chromatography. | 2009 May 15 |
|
| Pouch colon associated with anorectal malformations fails to show spontaneous contractions but responds to acetylcholine and histamine in vitro. | 2009 Nov |
|
| Halogenation effects of pheniramines on the complexation with beta-cyclodextrin. | 2009 Oct 15 |
|
| Substance use and addiction research in India. | 2010 Jan |
|
| Indian research on acute organic brain syndrome: Delirium. | 2010 Jan |
|
| Modulation of in vivo immunoglobulin production by endogenous histamine and H1R and H2R agonists and antagonists. | 2010 Sep-Oct |
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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
LIVERTOX |
769
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
||
|
WHO-ATC |
R06AB05
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
||
|
WHO-ATC |
D04AA16
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
||
|
WHO-VATC |
QR06AB05
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
||
|
NCI_THESAURUS |
C29578
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID0023454
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
155683-10-6
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
SUPERSEDED | |||
|
CHEMBL1193
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
SUB09768MIG
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
201-656-2
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
134FM9ZZ6M
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
86-21-5
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
DB01620
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
134FM9ZZ6M
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
100000082237
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
8132
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | RxNorm | ||
|
m8619
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | Merck Index | ||
|
47965
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
2132
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
D010632
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
105
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
PHENIRAMINE
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
4761
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
7267
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY | |||
|
C61889
Created by
admin on Sat Dec 16 16:30:29 GMT 2023 , Edited by admin on Sat Dec 16 16:30:29 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
