DrugBank: Pheniramine (DB01620)

targets (1)

Identification

Name

Pheniramine

Accession Number

DB01620

Type

small molecule

Groups

approved

Description

One of the histamine H1 antagonists with little sedative action. It is used in treatment of hay fever, rhinitis, allergic dermatoses, and pruritus. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

1-Phenyl-1-(2-pyridyl)-3-dimethylaminopropane
2-(3-Dimethylamino-1-phenylpropyl)pyridine
2-(alpha-(2-Dimethylaminoethyl)benzyl)pyridine
2-[.alpha.-(2-Dimethylaminoethyl)benzyl]pyridine
2-[.alpha.-[2-(Dimethylamino)ethyl]benzyl]pyridine
Dimethyl(3-phenyl-3-(2-pyridyl)propyl)amine
Feniramina [inn-spanish]
Feniramine
Pheniraminum [inn-latin]
Propheniramine
Prophenpyridamine

Brand names

AVIL
Inhiston
Metron
Pyriton
Trimeton
Tripoton

Brand name mixtures

AK Vernacon Oph Solution (Pheniramine Maleate + Phenylephrine Hydrochloride)
Calmylin Ace (Codeine Phosphate + Guaifenesin + Pheniramine Maleate)
Citron Chaud DM Option + PWS (Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C)
Diopticon A Liquid (Naphazoline Hydrochloride + Pheniramine Maleate)
Diorouge Liquid (Pheniramine Maleate + Phenylephrine Hydrochloride + Polyvinyl Alcohol)
Dristan Decongestant Nasal Mist (Pheniramine Maleate + Phenylephrine Hydrochloride)
Hot Lemon Cough and Colds Relief DM (Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride)
Hot Lemon Extra Strength (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C)
Neo Citran Colds & Flu (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride)
Neo Citran Extra Strength (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride)
Visine Advance Allergy (Naphazoline Hydrochloride + Pheniramine Maleate)

Categories

Antipruritic Agents
Antipruritics
Anti-Allergic Agents
Histamine H1 Antagonists

CAS number

86-21-5

Weight

Average: 240.3434
Monoisotopic: 240.162648650

Chemical Formula

C₁₆H₂₀N₂

InChI Key

InChIKey=IJHNSHDBIRRJRN-UHFFFAOYSA-N

InChI

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

Plain Text

IUPAC Name

dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine

SMILES

CN(C)CCC(C1=CC=CC=C1)C1=NC=CC=C1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Pheniramines

Substructures

Pheniramines
Pyridines and Derivatives
Benzene and Derivatives
Aliphatic and Aryl Amines
Heterocyclic compounds
Aromatic compounds
Phenylpropylamines
Imines

Pharmacology

Indication

Pheniramine is an antihistamine used to treat allergic conditions such as hay fever or urticaria.

Pharmacodynamics

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.

Mechanism of action

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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic hydroxylation, demethylation and glucuronidation.

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Powder	Oral
Solution	Oral
Solution / drops	Oral
Tablet	Oral

Prices

Not Available

Patents

Not Available

Properties

State

liquid

Melting point

< 25 oC

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	3.77e-01 g/l	ALOGPS
logP	2.85	ALOGPS
logP	2.98	ChemAxon Molconvert
logS	-2.80	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	2	ChemAxon Molconvert
hydrogen donor count	0	ChemAxon Molconvert
polar surface area	16.13	ChemAxon Molconvert
rotatable bond count	5	ChemAxon Molconvert
refractivity	76.05	ChemAxon Molconvert
polarizability	28.41	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	4761
PubChem Substance	46505932
ChemSpider	4597
BindingDB	50017656
Therapeutic Targets Database	DAP001063
PharmGKB	PA450907
Drug Product Database	0
Wikipedia	http://en.wikipedia.org/wiki/Pheniramine

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Not Available

Targets
1. Histamine H1 receptor Pharmacological action: yes Actions: antagonist In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system Organism class: human UniProt ID: P35367 Gene: HRH1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Leurs R, Bast A, Timmerman H: High affinity, saturable [3H]mepyramine binding sites on rat liver plasma membrane do not represent histamine H1-receptors. A warning. Biochem Pharmacol. 1989 Jul 1;38(13):2175-80. Pubmed Yanni JM, Stephens DJ, Parnell DW, Spellman JM: Preclinical efficacy of emedastine, a potent, selective histamine H1 antagonist for topical ocular use. J Ocul Pharmacol. 1994 Winter;10(4):665-75. Pubmed Nath C, Gupta MB: Role of central histaminergic system in lorazepam withdrawal syndrome in rats. Pharmacol Biochem Behav. 2001 Apr;68(4):777-82. Pubmed Karadag CH, Ulugol A, Dokmeci D, Dokmeci I: The role of histamine H1-receptors in the anticonvulsive effect of morphine against maximal electroconvulsive shock in mice. Jpn J Pharmacol. 1996 Jun;71(2):109-12. Pubmed Nosal R, Drabikova K, Jancinova V, Moravcova J, Lojek A, Ciz M, Macickova T, Pecivova J: H1-antihistamines and oxidative burst of professional phagocytes. Neuro Endocrinol Lett. 2009;30 Suppl 1:133-6. Pubmed Gepdiremen A, Buyukokuroglu ME, Hacimuftuoglu A, Suleyman H: Contribution of the histaminergic receptor subtypes to histamine-induced cerebellar granular neurotoxicity. Pol J Pharmacol. 2003 May-Jun;55(3):383-8. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system

Organism class: human
UniProt ID: P35367 Link_out

Gene: HRH1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Leurs R, Bast A, Timmerman H: High affinity, saturable [3H]mepyramine binding sites on rat liver plasma membrane do not represent histamine H1-receptors. A warning. Biochem Pharmacol. 1989 Jul 1;38(13):2175-80. Pubmed
Yanni JM, Stephens DJ, Parnell DW, Spellman JM: Preclinical efficacy of emedastine, a potent, selective histamine H1 antagonist for topical ocular use. J Ocul Pharmacol. 1994 Winter;10(4):665-75. Pubmed
Nath C, Gupta MB: Role of central histaminergic system in lorazepam withdrawal syndrome in rats. Pharmacol Biochem Behav. 2001 Apr;68(4):777-82. Pubmed
Karadag CH, Ulugol A, Dokmeci D, Dokmeci I: The role of histamine H1-receptors in the anticonvulsive effect of morphine against maximal electroconvulsive shock in mice. Jpn J Pharmacol. 1996 Jun;71(2):109-12. Pubmed
Nosal R, Drabikova K, Jancinova V, Moravcova J, Lojek A, Ciz M, Macickova T, Pecivova J: H1-antihistamines and oxidative burst of professional phagocytes. Neuro Endocrinol Lett. 2009;30 Suppl 1:133-6. Pubmed
Gepdiremen A, Buyukokuroglu ME, Hacimuftuoglu A, Suleyman H: Contribution of the histaminergic receptor subtypes to histamine-induced cerebellar granular neurotoxicity. Pol J Pharmacol. 2003 May-Jun;55(3):383-8. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments

Drug created on August 29, 2007 14:15 / Updated on September 03, 2011 16:59

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.