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Showing drug card for Pheniramine (DB01620)

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Version 2.5
Creation Date 2007-08-29 20:15:57
Update Date 2009-04-16 16:48:26
Primary Accession Number DB01620
Secondary Accession Number Not Available
Name Pheniramine
Drug Type
  • Approved
  • Small Molecule
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]
Synonyms
  1. 1-Phenyl-1-(2-pyridyl)-3-dimethylaminopropane
  2. 2-(3-Dimethylamino-1-phenylpropyl)pyridine
  3. 2-(alpha-(2-Dimethylaminoethyl)benzyl)pyridine
  4. 2-[.alpha.-(2-Dimethylaminoethyl)benzyl]pyridine
  5. 2-[.alpha.-[2-(Dimethylamino)ethyl]benzyl]pyridine
  6. Dimethyl(3-phenyl-3-(2-pyridyl)propyl)amine
  7. Feniramina [inn-spanish]
  8. Feniramine
  9. Pheniraminum [inn-latin]
  10. Propheniramine
  11. Prophenpyridamine
Brand Names
  1. AVIL
  2. Inhiston
  3. Metron
  4. Pyriton
  5. Trimeton
  6. Tripoton
Brand Mixtures
  1. AK Vernacon Oph Solution (Pheniramine Maleate + Phenylephrine Hydrochloride)
  2. Calmylin Ace (Codeine Phosphate + Guaifenesin + Pheniramine Maleate)
  3. Citron Chaud DM Option + PWS (Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C)
  4. Diopticon A Liquid (Naphazoline Hydrochloride + Pheniramine Maleate)
  5. Diorouge Liquid (Pheniramine Maleate + Phenylephrine Hydrochloride + Polyvinyl Alcohol)
  6. Dristan Decongestant Nasal Mist (Pheniramine Maleate + Phenylephrine Hydrochloride)
  7. Hot Lemon Cough and Colds Relief DM (Dextromethorphan Hydrobromide + Pheniramine Maleate + Phenylephrine Hydrochloride)
  8. Hot Lemon Extra Strength (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride + Vitamin C)
  9. Neo Citran Colds & Flu (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride)
  10. Neo Citran Extra Strength (Acetaminophen + Pheniramine Maleate + Phenylephrine Hydrochloride)
  11. Visine Advance Allergy (Naphazoline Hydrochloride + Pheniramine Maleate)
Chemical IUPAC Name N,N-dimethyl-3-phenyl-3-pyridin-2-ylpropan-1-amine
Chemical Formula C16H20N2
Chemical Structure Structure
CAS Registry Number 86-21-5
InChI Identifier InChI=1/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
InChI Key IJHNSHDBIRRJRN-UHFFFAOYAU
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 4761 Link Image
PubChem Substance 100679 Link Image
ChEBI ID Not Available
PharmGKB ID PA450907 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Pheniramine Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 240.3434
Monoisotopic Molecular Weight 240.1626
State Liquid
Melting Point < 25 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.77e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP 2.85 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.80 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN(C)CC[C@H](C1=CC=CC=C1)C1=CC=CC=N1
Canonical SMILES CN(C)CCC(C1=CC=CC=C1)C1=CC=CC=N1
Drug Category
  • Anti-Allergic Agents
  • Antipruritic Agents
  • Antipruritics
  • Histamine H1 Antagonists
ATC Codes Not Available
AHFS Codes Not Available
Indication Used to treat allergic conditions such as hay fever or urticaria.
Pharmacology 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.
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.
Absorption Not Available
Toxicity Not Available
Protein Binding Not Available
Biotransformation Hepatic hydroxylation, demethylation and glucuronidation.
Half Life Not Available
Dosage Forms
Form Route
Powder Oral
Solution Oral
Solution / drops Oral
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Histamine H1 receptor
Drug Target 1 [top]
Target 1 ID 492
Target 1 Name Histamine H1 receptor
Target 1 Synonyms Not Available
Target 1 Gene Name HRH1
Target 1 Protein Sequence >Histamine H1 receptor 
MSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLYAVRSERKLHT
VGNLYIVSLSVADLIVGAVVMPMNILYLLMSKWSLGRPLCLFWLSMDYVASTASIFSVFI
LCIDRYRSVQQPLRYLKYRTKTRASATILGAWFLSFLWVIPILGWNHFMQQTSVRREDKC
ETDFYDVTWFKVMTAIINFYLPTLLMLWFYAKIYKAVRQHCQHRELINRSLPSFSEIKLR
PENPKGDAKKPGKESPWEVLKRKPKDAGGGSVLKSPSQTPKEMKSPVVFSQEDDREVDKL
YCFPLDIVHMQAAAEGSSRDYVAVNRSHGQLKTDEQGLNTHGASEISEDQMLGDSQSFSR
TDSDTTTETAPGKGKLRSGSNTGLDYIKFTWKRLRSHSRQYVSGLHMNRERKAAKQLGFI
MAAFILCWIPYFIFFMVIAFCKNCCNEHLHMFTIWLGYINSTLNPLIYPLCNENFKKTFK
RILHIRS
Target 1 Number of Residues 495
Target 1 Molecular Weight 55785
Target 1 Theoretical pI 9.58
Target 1 GO Classification
Function
amine receptor activity
histamine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 Specific Function 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 30-49
  • 64-83
  • 102-123
  • 146-165
  • 190-210
  • 419-438
  • 451-470
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 510296 Link Image
Target 1 UniProtKB/Swiss-Prot ID P35367 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name HRH1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1464 bp 
ATGAGCCTCCCCAATTCCTCCTGCCTCTTAGAAGACAAGATGTGTGAGGGCAACAAGACC
ACTATGGCCAGCCCCCAGCTGATGCCCCTGGTGGTGGTCCTGAGCACTATCTGCTTGGTC
ACAGTAGGGCTCAACCTGCTGGTGCTGTATGCCGTACGGAGTGAGCGGAAGCTCCACACT
GTGGGGAACCTGTACATCGTCAGCCTCTCGGTGGCGGACTTGATCGTGGGTGCCGTCGTC
ATGCCTATGAACATCCTCTACCTGCTCATGTCCAAGTGGTCACTGGGCCGTCCTCTCTGC
CTCTTTTGGCTTTCCATGGACTATGTGGCCAGCACAGCGTCCATTTTCAGTGTCTTCATC
CTGTGCATTGATCGCTACCGCTCTGTCCAGCAGCCCCTCAGGTACCTTAAGTATCGTACC
AAGACCCGAGCCTCGGCCACCATTCTGGGGGCCTGGTTTCTCTCTTTTCTGTGGGTTATT
CCCATTCTAGGCTGGAATCACTTCATGCAGCAGACCTCGGTGCGCCGAGAGGACAAGTGT
GAGACAGACTTCTATGATGTCACCTGGTTCAAGGTCATGACTGCCATCATCAACTTCTAC
CTGCCCACCTTGCTCATGCTCTGGTTCTATGCCAAGATCTACAAGGCCGTACGACAACAC
TGCCAGCACCGGGAGCTCATCAATAGGTCCCTCCCTTCCTTCTCAGAAATTAAGCTGAGG
CCAGAGAACCCCAAGGGGGATGCCAAGAAACCAGGGAAGGAGTCTCCCTGGGAGGTTCTG
AAAAGGAAGCCAAAAGATGCTGGTGGTGGATCTGTCTTGAAGTCACCATCCCAAACCCCC
AAGGAGATGAAATCCCCAGTTGTCTTCAGCCAAGAGGATGATAGAGAAGTAGACAAACTC
TACTGCTTTCCACTTGATATTGTGCACATGCAGGCTGCGGCAGAGGGGAGTAGCAGGGAC
TATGTAGCCGTCAACCGGAGCCATGGCCAGCTCAAGACAGATGAGCAGGGCCTGAACACA
CATGGGGCCAGCGAGATATCAGAGGATCAGATGTTAGGTGATAGCCAATCCTTCTCTCGA
ACGGACTCAGATACCACCACAGAGACAGCACCAGGCAAAGGCAAATTGAGGAGTGGGTCT
AACACAGGCCTGGATTACATCAAGTTTACTTGGAAGAGGCTCCGCTCGCATTCAAGACAG
TATGTATCTGGGTTGCACATGAACCGCGAAAGGAAGGCCGCCAAACAGTTGGGTTTTATC
ATGGCAGCCTTCATCCTCTGCTGGATCCCTTATTTCATCTTCTTCATGGTCATTGCCTTC
TGCAAGAACTGTTGCAATGAACATTTGCACATGTTCACCATCTGGCTGGGCTACATCAAC
TCCACACTGAACCCCCTCATCTACCCCTTGTGCAATGAGAACTTCAAGAAGACATTCAAG
AGAATTCTGCATATTCGCTCCTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID HRH1 Link Image
Target 1 GenAtlas ID HRH1 Link Image
Target 1 HGNC ID HGNC:5182 Link Image
Target 1 Chromosome Location 3
Target 1 Locus 3p25
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Fukui H, Fujimoto K, Mizuguchi H, Sakamoto K, Horio Y, Takai S, Yamada K, Ito S: Molecular cloning of the human histamine H1 receptor gene. Biochem Biophys Res Commun. 1994 Jun 15;201(2):894-901. [PubMed Link Image]
  2. De Backer MD, Gommeren W, Moereels H, Nobels G, Van Gompel P, Leysen JE, Luyten WH: Genomic cloning, heterologous expression and pharmacological characterization of a human histamine H1 receptor. Biochem Biophys Res Commun. 1993 Dec 30;197(3):1601-8. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  3. 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 Link Image]
  4. 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 Link Image]

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.