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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
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C16H20N2
Molecular Weight 240.3434
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
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

Targets

Primary TargetPharmacologyConditionPotency
7.5 null [pKi]
Conditions
PubMed

PubMed

TitleDatePubMed
[Antimycobacterial antihistaminics].
1989 Aug
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
Techniques of skin biopsy and practical considerations.
2008 Jul
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
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
Preparation and evaluation of orodispersible tablets of pheniramine maleate by effervescent method.
2009 Mar
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
Pouch colon associated with anorectal malformations fails to show spontaneous contractions but responds to acetylcholine and histamine in vitro.
2009 Nov
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
Use of potentially inappropriate medicines in elderly: A prospective study in medicine out-patient department of a tertiary care teaching hospital.
2010 Apr
Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands.
2010 Dec 5
Substance use and addiction research in India.
2010 Jan
Indian research on acute organic brain syndrome: Delirium.
2010 Jan
Severe pulmonary adverse effects in lymphoma patients treated with cyclophosphamide, doxorubicin, vincristine, and prednisone (CHOP) regimen plus rituximab.
2010 Mar
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
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
Created
by admin
on Tue Oct 22 00:40:36 UTC 2019
Edited
by admin
on Tue Oct 22 00:40:36 UTC 2019
Record UNII
NYW905655B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENIRAMINE MALEATE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
2-(.ALPHA.-(2-DIMETHYLAMINOETHYL)BENZYL)PYRIDINE BIMALEATE
Common Name English
PHENIRAMINE MALEATE [VANDF]
Common Name English
PHENIRAMINE MALEATE [WHO-DD]
Common Name English
PHENIRAMINE MALEATE COMPONENT OF NAPHCON-A
Common Name English
PM-241
Code English
NAPHCON A
Brand Name English
PHENIRAMINE MALEATE [USP-RS]
Common Name English
2-(.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)BENZYL)PYRIDINE BIMALEATE
Common Name English
ANTOLOZINE
Brand Name English
OPCON-A COMPONENT PHENIRAMINE MALEATE
Common Name English
PHENIRAMINE MALEATE [USP]
Common Name English
VISINE-A COMPONENT PHENIRAMINE MALEATE
Common Name English
NAPHCON-A COMPONENT PHENIRAMINE MALEATE
Common Name English
PHENIRAMINE MALEATE [JAN]
Common Name English
PHENIRAMINE MALEATE COMPONENT OF VISINE-A
Common Name English
FERVEX
Brand Name English
PHENIRAMINE MALEATE [USAN]
Common Name English
N,N-DIMETHYL-3-PHENYL-3-(2-PYRIDYL)PROPYLAMINE HYDROGEN MALEATE
Systematic Name English
1-PHENYL-1-(2-PYRIDYL)-3-DIMETHYLAMINOPROPANE MALEATE
Systematic Name English
PHENIRAMINE MALEATE [EP]
Common Name English
INHISTON
Brand Name English
2-PYRIDINEPROPANAMINE, N,N-DIMETHYL-.GAMMA.-PHENYL-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
2-PYRIDINEPROPANAMINE, N,N-DIMETHYL-.GAMMA.-PHENYL-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
1-PHENYL-1-(2-PYRIDYL)-3-DIMETHAMINOPROPANE MALEINATE
Common Name English
DANERAL
Brand Name English
TRIMETOSE
Brand Name English
PROPHENPYRIDAMINE MALEATE
Common Name English
PHENIRAMINE MALEATE COMPONENT OF OPCON-A
Common Name English
TRIMETON
Brand Name English
PYRIDINE, 2-(.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)BENZYL)-, MALEATE (1:1)
Systematic Name English
PHENIRAMINE HYDROGEN MALEATE
Common Name English
PHENIRAMINE MALEATE [MI]
Common Name English
PHENIRAMINE MALEATE [MART.]
Common Name English
AVIL
Brand Name English
PHENIRAMINE MALEATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
CFR 21 CFR 341.12
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
Code System Code Type Description
MERCK INDEX
M8619
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
PRIMARY Merck Index
CAS
132-20-7
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
PRIMARY
EPA CompTox
132-20-7
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
PRIMARY
ECHA (EC/EINECS)
205-051-4
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
PRIMARY
RXCUI
266959
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
PRIMARY RxNorm
CAS
155683-11-7
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
SUPERSEDED
EVMPD
SUB03747MIG
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
PRIMARY
NCI_THESAURUS
C29358
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
PRIMARY
ChEMBL
CHEMBL1193
Created by admin on Tue Oct 22 00:40:36 UTC 2019 , Edited by admin on Tue Oct 22 00:40:36 UTC 2019
PRIMARY
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY