U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H20N2.C4H4O4
Molecular Weight 356.4156
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PHENIRAMINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN(C)CCC(C1=CC=CC=C1)C2=CC=CC=N2

InChI

InChIKey=SSOXZAQUVINQSA-BTJKTKAUSA-N
InChI=1S/C16H20N2.C4H4O4/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16;5-3(6)1-2-4(7)8/h3-10,12,15H,11,13H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C16H20N2
Molecular Weight 240.3434
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.5 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AVIL
Palliative
Visine-A
Primary
AVIL
Preventing
AVIL
Primary
AVIL

Cmax

ValueDoseCo-administeredAnalytePopulation
274 ng/mL
30.5 mg single, oral
PHENIRAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
5768 ng × h/mL
30.5 mg single, oral
PHENIRAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
17 h
30.5 mg single, oral
PHENIRAMINE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Histamine (100 uM)-induced contractions was blocked by pheniramine (0.32 uM) by 74% in neonatal small intestinal smooth muscle of dilated pre-atretic part of intestinal atresia.
Substance Class Chemical
Record UNII
NYW905655B
Record Status Validated (UNII)
Record Version