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
Thumb
Synonyms
  • Feniramina
  • Pheniramine
  • Pheniraminum
Product Ingredients
IngredientUNIICASInChI Key
Pheniramine maleateNYW905655B132-20-7SSOXZAQUVINQSA-BTJKTKAUSA-N
International/Other Brands
AVIL
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Allergy Eye DropsPheniramine maleate (3 mg/mL) + Naphazoline hydrochloride (.25 mg/mL)Solution / dropsOphthalmicCVS Health2013-01-25Not applicableUs
Allergy Eye DropsPheniramine maleate (0.315 %) + Naphazoline hydrochloride (0.02675 %)Solution / dropsOphthalmicBausch & Lomb Inc2013-02-27Not applicableCanada
Allergy Eye DropsPheniramine maleate (3 mg/mL) + Naphazoline hydrochloride (.25 mg/mL)Solution / dropsOphthalmicChain Drug Consortium2014-01-10Not applicableUs
Antitussive Decong Antihistamine SyrPheniramine maleate (6.5 mg) + Dextromethorphan hydrobromide (15 mg) + Pyrilamine maleate (6.5 mg) + Phenylpropanolamine hydrochloride (13 mg)SyrupOralProdemdis Enr.1992-12-312001-04-26Canada
Bronchodex D CapPheniramine maleate (12.5 mg) + Chlorpheniramine maleate (1 mg) + Phenylpropanolamine hydrochloride (50 mg)Capsule, extended releaseOralProdemdis Enr.1981-12-312001-04-26Canada
Bronchodex PediatriquePheniramine maleate (5 mg) + Dextromethorphan hydrobromide (5 mg) + Guaifenesin (50 mg) + Pseudoephedrine hydrochloride (15 mg)SyrupOralTherapex Division De E Z Em Canada Inc1983-12-311997-07-22Canada
Bronchosirum Pour EnfantsPheniramine maleate (6.25 mg) + Dextromethorphan hydrobromide (15 mg) + Pyrilamine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg)SyrupOralBronchosirum Inc.1987-12-311997-08-05Canada
Caldomine Dh AdultePheniramine maleate (12.5 mg) + Hydrocodone bitartrate (5 mg) + Pyrilamine maleate (12.5 mg) + Phenylpropanolamine hydrochloride (25 mg)LiquidOralTechnilab Pharma Inc.1981-12-312001-04-04Canada
Caldomine Dh EnfantPheniramine maleate (6.25 mg) + Hydrocodone bitartrate (1.667 mg) + Pyrilamine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg)LiquidOralTechnilab Pharma Inc.1982-12-312001-04-04Canada
Calmylin AcePheniramine maleate (7.5 mg) + Codeine phosphate (10 mg) + Guaifenesin (100 mg)SyrupOralTeva1996-12-31Not applicableCanada
Categories
UNII
134FM9ZZ6M
CAS number
86-21-5
Weight
Average: 240.3434
Monoisotopic: 240.16264865
Chemical Formula
C16H20N2
InChI Key
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
IUPAC Name
dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine
SMILES
CN(C)CCC(C1=CC=CC=C1)C1=CC=CC=N1

Pharmacology

Indication

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

Structured Indications
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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
UNuclear receptor subfamily 1 group I member 3Not AvailableHuman
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
PathwayCategory
Pheniramine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Pheniramine.Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative activities of Pheniramine.Experimental
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Pheniramine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Pheniramine.Experimental, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Pheniramine.Approved, Illicit
BenzphetamineBenzphetamine may decrease the sedative activities of Pheniramine.Approved, Illicit
Benzylpenicilloyl PolylysinePheniramine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Pheniramine.Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Pheniramine.Illicit, Withdrawn
DextroamphetamineDextroamphetamine may decrease the sedative activities of Pheniramine.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Pheniramine.Approved, Illicit
GepefrineGepefrine may decrease the sedative activities of Pheniramine.Experimental
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Pheniramine.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Pheniramine.Approved
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Pheniramine.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Pheniramine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Pheniramine.Investigational
MephentermineMephentermine may decrease the sedative activities of Pheniramine.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Pheniramine.Approved, Illicit
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Pheniramine.Experimental
MidomafetamineMidomafetamine may decrease the sedative activities of Pheniramine.Experimental, Illicit, Investigational
MMDAMMDA may decrease the sedative activities of Pheniramine.Experimental, Illicit
PhenterminePhentermine may decrease the sedative activities of Pheniramine.Approved, Illicit
PseudoephedrinePseudoephedrine may decrease the sedative activities of Pheniramine.Approved
RitobegronRitobegron may decrease the sedative activities of Pheniramine.Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB15557
PubChem Compound
4761
PubChem Substance
46505932
ChemSpider
4597
BindingDB
50017656
ChEBI
91591
ChEMBL
CHEMBL1193
Therapeutic Targets Database
DAP001063
PharmGKB
PA164744506
Wikipedia
Pheniramine
ATC Codes
R06AB05 — PheniramineD04AA16 — Pheniramine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidOral
Capsule, extended releaseOral
SprayNasal
Kit; powderOral
PowderOral
Kit; powder, for solutionOral
SolutionOphthalmic
Solution / dropsOphthalmic
SyrupOral
Powder, for solutionOral
Tablet, extended releaseOral
SuspensionOral
TabletOral
Powder, for suspensionOral
Granule, for solutionOral
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)181 °C at 1.30E+01 mm HgPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.377 mg/mLALOGPS
logP2.85ALOGPS
logP2.98ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity76.05 m3·mol-1ChemAxon
Polarizability28.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9719
Blood Brain Barrier+0.9657
Caco-2 permeable+0.9034
P-glycoprotein substrateSubstrate0.6248
P-glycoprotein inhibitor INon-inhibitor0.9048
P-glycoprotein inhibitor IINon-inhibitor0.966
Renal organic cation transporterInhibitor0.7942
CYP450 2C9 substrateNon-substrate0.7957
CYP450 2D6 substrateSubstrate0.7888
CYP450 3A4 substrateSubstrate0.5421
CYP450 1A2 substrateNon-inhibitor0.9442
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.5302
CYP450 2C19 inhibitorNon-inhibitor0.7433
CYP450 3A4 inhibitorNon-inhibitor0.9034
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9161
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9375
BiodegradationNot ready biodegradable0.9876
Rat acute toxicity2.9748 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9031
hERG inhibition (predictor II)Non-inhibitor0.516
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0920000000-fd728bb396d025cac3f0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-7af6ac1b513c7f2f33a9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-ea7e67a76460b33d8306
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-f5daabe4b8aedf8605e6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014j-0900000000-4ccd8055b59ae6eabc90
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-1900000000-deb31ec7e47ca6a0e3ff
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-1900000000-add8b8849c3db116e181
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-2900000000-c38a45f14fb4ab5b1687
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014r-3900000000-1f2c04e07e8c46a0c722
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0910000000-549410c48d9c44650beb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-669fdf1a00514df13bf2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-59e6f9e272a364ed620a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-a9b1b534a7a36bdaf014
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-0900000000-0d3c0ba161b03c4cc7d5

Taxonomy

Description
This compound belongs to the class of organic compounds known as pheniramines. These are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pheniramines
Direct Parent
Pheniramines
Alternative Parents
Aralkylamines / Benzene and substituted derivatives / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Pheniramine / Aralkylamine / Benzenoid / Monocyclic benzene moiety / Heteroaromatic compound / Tertiary aliphatic amine / Tertiary amine / Azacycle / Organic nitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
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 catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
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:17016423]
  2. 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:2567596]
  3. 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:7714410]
  4. 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:11526976]
  5. 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:8835636]
  6. 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:20027159]
  7. 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:14506317]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
Gene Name
NR1I3
Uniprot ID
Q14994
Uniprot Name
Nuclear receptor subfamily 1 group I member 3
Molecular Weight
39942.145 Da
References
  1. Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [PubMed:20869355]

Drug created on August 29, 2007 14:15 / Updated on December 01, 2017 17:23