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

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	( + / - )

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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 316 Target ID: CHEMBL231 Sources: http://www.medicines.org.au/files/swpavilt.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/13743818	Antagonist 2849		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 8583	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 26 Sources: https://www.drugs.com/drp/pheniramine-maleate.html	Palliative	Approved 8583	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 8583	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 8583	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 8583	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
Accela ChemBio Inc	SY246337	http://www.accelachem.com/cn/search.html?keyword=SY246337&attname=GoodsCode
AHH Chemical co.,ltd	MT-57839	http://www.ahhchemical.com/product/MT-57839.html
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
eNovation Chemicals	D778952	https://www.enovationchem.com/ProductDetails.asp?ProductID=D778952
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
mcule	MCULE-7152203152	https://mcule.com/MCULE-7152203152/
Molcore	MC575266	https://www.molcore.com/product/86-21-5
OChem	11993	http://www.ocheminc.com/index.php?act=psearch&pid=086P215
Sigma-Aldrich	P-045_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/p045?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PH010134_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/ph010134
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

PubMed

Title	Date	PubMed
Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands.	2010-12-05	20869355
Use of potentially inappropriate medicines in elderly: A prospective study in medicine out-patient department of a tertiary care teaching hospital.	2010-04	20711374
Severe pulmonary adverse effects in lymphoma patients treated with cyclophosphamide, doxorubicin, vincristine, and prednisone (CHOP) regimen plus rituximab.	2010-03	20195409
Substance use and addiction research in India.	2010-01	21836677
Indian research on acute organic brain syndrome: Delirium.	2010-01	21836671
In vitro antibacterial activity of some systemic and topical antihistaminic preparations.	2009-12-01	20003827
Pouch colon associated with anorectal malformations fails to show spontaneous contractions but responds to acetylcholine and histamine in vitro.	2009-11	19944226
Halogenation effects of pheniramines on the complexation with beta-cyclodextrin.	2009-10-15	19540697
Acute renal failure caused by pheniramine maleate induced rhabdomyolysis: an unusual case.	2009-10	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.	2009-10	19794992
Antihistamine pretreatment to reduce incidence of withdrawal movement after rocuronium injection.	2009-10	19794987
Comparison of chiral separation of basic drugs in capillary electrophoresis and liquid chromatography using neutral and negatively charged cyclodextrins.	2009-07-10	19481637
Simultaneous determination of pseudoephdrine, pheniramine, guaifenisin, pyrilamine, chlorpheniramine and dextromethorphan in cough and cold medicines by high performance liquid chromatography.	2009-05-15	19269462
In situ forming polymeric drug delivery systems.	2009-05	20490289
Modulation of in vivo immunoglobulin production by endogenous histamine and H1R and H2R agonists and antagonists.	2009-04-11	21098875
Pheniramines and oxidative burst of blood phagocytes during ischaemia/reperfusion.	2009-04	19271141
Protective effect of pheniramines against mesenteric ischaemia/reperfusion-induced injury.	2009-04	19271140
Preparation and evaluation of orodispersible tablets of pheniramine maleate by effervescent method.	2009-03	20336216
A presentation of longstanding toxoplasmosis chorioretinitis.	2009-01	19111254
H1-antihistamines and oxidative burst of professional phagocytes.	2009	20027159
The effects of dithiaden on nitric oxide production by RAW 264.7 cells.	2008-12	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.	2008-12	19041066
Techniques of skin biopsy and practical considerations.	2008-07	20300359
Uniformly sized molecularly imprinted polymers for d-chlorpheniramine: influence of a porogen on their morphology and enantioselectivity.	2008-04-14	17644298
Evaluation of a new premedication protocol for administration of equine rabies immunoglobulin in patients with hypersensitivity.	2008-02-05	18240468
Possibilities of column coupling electrophoresis provided with a fiber-based diode array detection in enantioselective analysis of drugs in pharmaceutical and clinical samples.	2008-01-25	17905259
[Toxic epidermal necrolysis following dorzolamide eyedrops].	2008-01	18751332
Chiral separation of alkylamine antihistamines in pharmaceuticals by capillary isotachophoresis with charged cyclodextrin.	2007-11	18058316
Chemical profile of counterfeit buprenorphine vials seized in Tehran, Iran.	2007-10-25	17646070
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.	2007-08	17600843
First-generation H1 antihistamines found in pilot fatalities of civil aviation accidents, 1990-2005.	2007-05	17539447
High risk behaviors of injection drug users registered with harm reduction programme in Karachi, Pakistan.	2007-02-10	17291354
Intraoperative anaphylaxis with a complicated pulmonary hydatid cyst.	2007-02	17238900
Extra- and intracellular formation of reactive oxygen species by human neutrophils in the presence of pheniramine, chlorpheniramine and brompheniramine.	2006-12	17159800
Goat ureter - an alternative model for measuring ureteral peristalsis.	2006-08	17099295
Life-threatening facial edema due to pine caterpillar mimicking an allergic event.	2006-07-21	16854350
Antiradical effects of antihistamines in human blood. Structure-activity relationship.	2006-04	16547801
Pre-treatment of anaphylaxis, does it really work?	2005-12	16318672
Enantioselective determination of pheniramine in pharmaceuticals by capillary electrophoresis with charged cyclodextrin.	2005-07-01	15925245
A comparison of the clinical efficacy of pheniramine maleate/naphazoline hydrochloride ophthalmic solution and olopatadine hydrochloride ophthalmic solution in the conjunctival allergen challenge model.	2005-05	15978305
A case of pheniramine dependence.	2005-03	16492663
[Use of capillary isotachophoresis for the determination of pheniramine in granulated powders].	2005-03	15895972
Rapid identification and quantification of chlorpheniramine maleate or pheniramine maleate in pharmaceutical preparations by thin-layer chromatography-densitometry.	2005-01-29	15675442
Actual therapeutic management of allergic and hyperreactive nasal disorders.	2004	22073046
Conjunctival allergen challenge: models in the investigation of ocular allergy.	2003-07	12791217
Efficacy and safety of rectal thiopental, intramuscular cocktail and rectal midazolam for sedation in children undergoing neuroimaging.	2002-12	12421260
Contribution of the histaminergic receptor subtypes to histamine-induced cerebellar granular neurotoxicity.	2002-04-23	14506317
A phase II study of paclitaxel and cisplatin combination chemotherapy in recurrent or metastatic head and neck cancer.	2002-04	12017379
Uniformly sized molecularly imprinted polymer for d-chlorpheniramine. Evaluation of retention and molecular recognition properties in an aqueous mobile phase.	2002-03-01	12831185
[Antimycobacterial antihistaminics].	1989-08	2513793

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 `Mon Mar 31 17:50:53 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:53 GMT 2025`
Record UNII	NYW905655B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENIRAMINE MALEATE

Official Name

English

NAPHCON-A COMPONENT PHENIRAMINE MALEATE

Preferred Name

English

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

Common Name

English

PHENIRAMINE MALEATE [VANDF]

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

PHENIRAMINE MALEATE [JAN]

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

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