PHENIRAMINE MALEATE

US Approved OTC

First approved in 1948

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 Search

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: http://www.medicines.org.au/files/swpavilt.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/13743818	Antagonist 2778		7.5 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Allergic conditions 7 Sources: http://www.news-medical.net/drugs/Avil.aspx http://www.medicines.org.au/files/swpavilt.pdf	Primary	Approved 8429	AVIL Approved Use Allergic 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.
Eye diseases 25 Sources: https://www.drugs.com/drp/pheniramine-maleate.html	Palliative	Approved 8429	Visine-A Approved Use Visine-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.
Meniere's disease 16 Sources: http://www.news-medical.net/drugs/Avil.aspx http://www.medicines.org.au/files/swpavilt.pdf	Primary	Approved 8429	AVIL Approved Use Allergic 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.
Motion sickness 43 Sources: http://www.news-medical.net/drugs/Avil.aspx http://www.medicines.org.au/files/swpavilt.pdf	Preventing	Approved 8429	AVIL Approved Use Allergic 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.
Neurodermatitis 5 Sources: http://www.news-medical.net/drugs/Avil.aspx http://www.medicines.org.au/files/swpavilt.pdf	Primary	Approved 8429	AVIL Approved Use Allergic 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.

C_max

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

T_1/2

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

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY575266	https://www.001chemical.com/chem/86-21-5
3B Scientific (Wuhan) Corp	3B2-1890	http://www.3bsc.com/index/pro_info.php?id=58394
AHH Chemical co.,ltd	MT-57839	http://www.ahhchemical.com/product/MT-57839.html
Accela ChemBio Inc	SY246337	http://www.accelachem.com/cn/search.html?keyword=SY246337&attname=GoodsCode
Aurora Fine Chemicals LLC	A17.921.637	http://online.aurorafinechemicals.com/info?ID=A17.921.637
ChemMol	49426112	http://www.chemmol.com/chemmol/49426112.html
Clearsynth	CS-O-11352	http://www.clearsynth.com/en/CSO11352.html
Debye Scientific	DB-056919	http://www.debyesci.com/cas_86-21-5.html
Finetech	FT-0603298	http://www.finetechnology-ind.com/prod/detail/pub/86-21-5.html
Glentham Life Sciences	GP1934	http://www.glentham.com/products/product/GP1934/
LGC Standards	LGCAMP0059.01-01	https://www.lgcstandards.com/US/en/p/LGCAMP0059.01-01
LGC Standards	LGCFOR0059.01	https://www.lgcstandards.com/US/en/p/LGCFOR0059.01
LGC Standards	MM0059.01	https://www.lgcstandards.com/US/en/p/MM0059.01
Molcore	MC575266	https://www.molcore.com/product/86-21-5
OChem	11993	http://www.ocheminc.com/index.php?act=psearch&pid=086P215
Sigma-Aldrich	PH010134_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/ph010134
Sigma-Aldrich	P-045_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/p045?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S595388	https://www.smolecule.com/products/s595388
THE BioTek	bt-460207	https://www.thebiotek.com/product/others/bt-460207
Vitas-M Laboratory	STL329242	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL329242&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
eNovation Chemicals	D778952	https://www.enovationchem.com/ProductDetails.asp?ProductID=D778952
mcule	MCULE-7152203152	https://mcule.com/MCULE-7152203152/

PubMed

Title	Date	PubMed
[Antimycobacterial antihistaminics].	1989 Aug	2513793
A phase II study of paclitaxel and cisplatin combination chemotherapy in recurrent or metastatic head and neck cancer.	2002 Apr	12017379
Efficacy and safety of rectal thiopental, intramuscular cocktail and rectal midazolam for sedation in children undergoing neuroimaging.	2002 Dec	12421260
Uniformly sized molecularly imprinted polymer for d-chlorpheniramine. Evaluation of retention and molecular recognition properties in an aqueous mobile phase.	2002 Mar 1	12831185
Conjunctival allergen challenge: models in the investigation of ocular allergy.	2003 Jul	12791217
Contribution of the histaminergic receptor subtypes to histamine-induced cerebellar granular neurotoxicity.	2003 May-Jun	14506317
Actual therapeutic management of allergic and hyperreactive nasal disorders.	2004	22073046
Rapid identification and quantification of chlorpheniramine maleate or pheniramine maleate in pharmaceutical preparations by thin-layer chromatography-densitometry.	2004 Nov-Dec	15675442
Pre-treatment of anaphylaxis, does it really work?	2005 Dec	16318672
Enantioselective determination of pheniramine in pharmaceuticals by capillary electrophoresis with charged cyclodextrin.	2005 Jul 1	15925245
A case of pheniramine dependence.	2005 Mar	16492663
[Use of capillary isotachophoresis for the determination of pheniramine in granulated powders].	2005 Mar	15895972
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	15978305
Antiradical effects of antihistamines in human blood. Structure-activity relationship.	2006 Apr	16547801
Goat ureter - an alternative model for measuring ureteral peristalsis.	2006 Aug	17099295
Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine.	2006 Dec	17159800
Life-threatening facial edema due to pine caterpillar mimicking an allergic event.	2006 Jul-Aug	16854350
Evaluation of a new premedication protocol for administration of equine rabies immunoglobulin in patients with hypersensitivity.	2007 Apr-Jun	18240468
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	17600843
Intraoperative anaphylaxis with a complicated pulmonary hydatid cyst.	2007 Feb	17238900
High risk behaviors of injection drug users registered with harm reduction programme in Karachi, Pakistan.	2007 Feb 10	17291354
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.	2007 May	17539447
Chiral separation of alkylamine antihistamines in pharmaceuticals by capillary isotachophoresis with charged cyclodextrin.	2007 Nov	18058316
Chemical profile of counterfeit buprenorphine vials seized in Tehran, Iran.	2007 Oct 25	17646070
Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity.	2008 Apr 14	17644298
The effects of dithiaden on nitric oxide production by RAW 264.7 cells.	2008 Dec	21218118
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	19041066
[Toxic epidermal necrolysis following dorzolamide eyedrops].	2008 Jan	18751332
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	17905259
Techniques of skin biopsy and practical considerations.	2008 Jul	20300359
H1-antihistamines and oxidative burst of professional phagocytes.	2009	20027159
Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion.	2009 Apr	19271141
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury.	2009 Apr	19271140
In vitro antibacterial activity of some systemic and topical antihistaminic preparations.	2009 Dec 1	20003827
A presentation of longstanding toxoplasmosis chorioretinitis.	2009 Jan	19111254
Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins.	2009 Jul 10	19481637
Preparation and evaluation of orodispersible tablets of pheniramine maleate by effervescent method.	2009 Mar	20336216
In situ forming polymeric drug delivery systems.	2009 May	20490289
Simultaneous determination of pseudoephdrine, pheniramine, guaifenisin, pyrilamine, chlorpheniramine and dextromethorphan in cough and cold medicines by high performance liquid chromatography.	2009 May 15	19269462
Pouch colon associated with anorectal malformations fails to show spontaneous contractions but responds to acetylcholine and histamine in vitro.	2009 Nov	19944226
Acute renal failure caused by pheniramine maleate induced rhabdomyolysis: an unusual case.	2009 Oct	20436692
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	19794992
Antihistamine pretreatment to reduce incidence of withdrawal movement after rocuronium injection.	2009 Oct	19794987
Halogenation effects of pheniramines on the complexation with beta-cyclodextrin.	2009 Oct 15	19540697
Use of potentially inappropriate medicines in elderly: A prospective study in medicine out-patient department of a tertiary care teaching hospital.	2010 Apr	20711374
Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands.	2010 Dec 5	20869355
Substance use and addiction research in India.	2010 Jan	21836677
Indian research on acute organic brain syndrome: Delirium.	2010 Jan	21836671
Severe pulmonary adverse effects in lymphoma patients treated with cyclophosphamide, doxorubicin, vincristine, and prednisone (CHOP) regimen plus rituximab.	2010 Mar	20195409
Modulation of in vivo immunoglobulin production by endogenous histamine and H1R and H2R agonists and antagonists.	2010 Sep-Oct	21098875

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.

Name

Type

Language

PHENIRAMINE MALEATE

Official Name

English

2-(.ALPHA.-(2-DIMETHYLAMINOETHYL)BENZYL)PYRIDINE BIMALEATE

Common Name

English

PHENIRAMINE MALEATE [VANDF]

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

PHENIRAMINE MALEATE [USP MONOGRAPH]

Common Name

English

Pheniramine maleate [WHO-DD]

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 MONOGRAPH]

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

NSC-757270

Code

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 MALEATE [EP IMPURITY]

Common 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