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Identification
NamePheniramine
Accession NumberDB01620
TypeSmall Molecule
GroupsApproved
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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AVILNot Available
Brand mixtures
NameLabellerIngredients
Allergy Eye DropsCVS Pharmacy
Antitussive Decong Antihistamine SyrProdemdis Enr.
Bronchodex D CapProdemdis Enr.
Bronchodex PediatriqueTherapex Division De E Z Em Canada Inc
Bronchosirum Pour EnfantsBronchosirum Inc.
Caldomine Dh AdulteTechnilab Pharma Inc.
Caldomine Dh EnfantTechnilab Pharma Inc.
Calmylin AceTeva Canada Limited
Care One Flu and Sore ThroatAmerican Sales Company
Centracol DM - SyrPrometic Pharma Inc.
Centracol Pediatrique - SyrPrometic Pharma Inc.
Citron Chaud Cumberland PwsProdemdis Enr.
Citron Chaud DM Cumberland PwsProdemdis Enr.
Citron Chaud DM Option + PwsProdemdis Enr.
Citron Chaud Extra FortPharmalab Inc.
Citron Chaud Réguliern DMPharmalab Inc.
Cold & FluPharmascience Inc
Cold & Flu Super StrengthPharmascience Inc
Cold Decongestant Long Acting CapNovopharm Limited
Cold StixLaboratoire Riva Inc
Cold Stix - Hot Lemon, Sugar-free; Sweetened With XylitolPnp Pharmaceuticals Inc
Cold Stix Super StrengthLaboratoire Riva Inc
Cold Stix-extra StrengthPnp Pharmaceuticals Inc
Cold Stix-regular StrengthPnp Pharmaceuticals Inc
Colds & CoughsThe Winning Combination Inc.
Cough & ColdPharmascience Inc
Cvs Pharmacy Cold and Sore Throat Lemon FlavorCVS Pharmacy
Diopticon A LiqDioptic Pharmaceuticals Inc
Diorouge LiqDioptic Pharmaceuticals Inc
Dristan Mentholated Nasal SprayWyeth Consumer Healthcare Inc.
Dristan Nasal MistPfizer Consumer Healthcare A Division Of Pfizer Canada Inc
Equaline Flu and Sore ThroatSupervalu Inc
Extra Strength PharmacitronPharmascience Inc
Eye Allergy ReliefWalgreen Company
Flu and Sore ThroatSafeway
Flu and Sore Throat Multi SymptomMeijer Distribution Inc
Flu and Sore Throat Soothing Warm ReliefCVS Pharmacy
Flu-away-extra StrengthPnp Pharmaceuticals Inc
Flu-away-regular StrengthPnp Pharmaceuticals Inc
Good Neighbor Pharmacy Flu and Sore ThroatAmerisource Bergen
Good Sense Flu and Sore ThroatL Perrigo Company
Hot Lemon Cold and Flu Relief Extra StrengthPharmanutrients Botanical Corporation
Hot Lemon Cold and Flu Relief Regular StrengthPharmanutrients Botanical Corporation
Hot Lemon Cough and Cold Relief DMPharmanutrients Botanical Corporation
Hot Lemon Cough and Colds Relief DMJamp Pharma Corporation
Hot Lemon Extra StrengthProdemdis Enr.
Hot Lemon for Colds PowderRandle Labs Inc.
Hot Lemon Regular - PwrProdemdis Enr.
Hot Lemon Relief Pck-pwsApotex Inc
Hot Lemon Relief - Extra StrengthJamp Pharma Corporation
Hot Lemon Relief Extra StrengthNorth Pacific Rim Marketing Inc.
Hot Lemon Relief for Cold Symptoms Ext StrPatheon Laboratories
Hot Lemon Relief for Cold Symptoms PwsPatheon Laboratories
Hot Lemon Relief for Symptoms Of Cold and Flu Extra StrengthPharmetics (2011) Inc
Hot Lemon Relief for Symptoms Of Cold and Flu FortePharmetics (2011) Inc
Hot Lemon Relief for Symptoms Of Cold and Flu Regular StrengthPharmetics (2011) Inc
Hot Lemon Relief for Symptoms Of Cough and ColdPharmetics (2011) Inc
Hot Lemon Relief PowderJamp Pharma Corporation
Hot Lemon Relief Powder Extra StrengthNutralife Health Products Ltd.
Hot Lemon Relief Powder Regular StrengthNutralife Health Products Ltd.
Hot Lemon Relief Regular StrengthJamp Pharma Corporation
Hot Lemon Relief-extra Strength Pck-pwsApotex Inc
Hot Liquid Relief for Symptoms Of Cold and CoughPharmetics (2011) Inc
Hot Liquid Relief for Symptoms Of Flu and Sore ThroatPharmetics (2011) Inc
Naphazoline Hci and Pheniramine MaleateAltaire Pharmaceuticals Inc.
Naphazoline Hydrochloride and Pheniramine MaleateWalgreens
Naphcon AAlcon Laboratories, Inc.
Neo Citran A PowderNovartis Consumer Health Canada Inc.
Neo Citran Extra StrengthSandoz Canada Inc
Neo Citran NutrasweetNovartis Consumer Health Canada Inc.
Neo Citran PowderNovartis Consumer Health Canada Inc.
Neocitran Cold & Cough NightNovartis Consumer Health Canada Inc.
Neocitran Cold & Sore ThroatGlaxosmithkline Consumer Healthcare Inc.
Neocitran Extra Strength Cold & Sinus NightGlaxosmithkline Consumer Healthcare Inc.
Odan-vernaconOdan Laboratories Ltd
Opcon-ABausch & Lomb Incorporated
Opti-tears AllergyAlcon Canada Inc
PharmacitronPharmascience Inc
Pharmacol DM SyrTherapex Division De E Z Em Canada Inc
Pharminicol DM SyrupTherapex Division De E Z Em Canada Inc
PulmorphanLaboratoire Riva Inc
Pulmorphan PediatriqueLaboratoire Riva Inc
Quality Choice Cold and Sore Throat Lemon FlavorChain Drug Marketing Association
Reactine Eye DropsMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
Rhume Et De LA Grippe (extra-fort)Prodemdis Enr.
Robitussin AcPfizer Consumer Healthcare A Division Of Pfizer Canada Inc
Robitussin Syrup With CodeineWyeth Consumer Healthcare Inc.
Rx Act Flu and Sore ThroatH E B
Scot-tussin Original Multi-symptom Cold and Allergy ReliefIri Sys, Llc
Scot-tussin Original Sf Multi-symptomScot Tussin Pharmacal Co., Inc.
Soothe AllergyBausch & Lomb Inc
Tantacol DM SyrTanta Pharmaceuticals Inc
Theraflu Cold and FluNovartis Consumer Health Canada Inc.
Theraflu Cold and Sore ThroatNovartis Consumer Health, Inc.
Theraflu Flu and Sore ThroatNovartis Consumer Health, Inc.
Theraflu Nighttime Cold and FluNovartis Consumer Health Canada Inc.
Theraflu Sinus and ColdNovartis Consumer Health, Inc.
Top Care Flu and Sore ThroatTopco Associates LLC
Topcare Cold and Sore Throat Lemon FlavorTopcare (Topco Associates Llc)
Triaminic Expectorant Dh SyrupNovartis Consumer Health Canada Inc.
Triaminic Time Release TabNovartis Consumer Health Canada Inc.
Triaminicin Colds & Flu CapletsNovartis Consumer Health Canada Inc.
Trisulfaminic SusShepherd Pharmaceuticals Inc.
Trisulfaminic TabShepherd Pharmaceuticals Inc.
Tussaminic C Forte SyrupNovartis Consumer Health Canada Inc.
Tussaminic C Pediatric SyrupNovartis Consumer Health Canada Inc.
Tussaminic Dh Forte SyrupNovartis Consumer Health Canada Inc.
Tussaminic Dh Pediatric SyrupNovartis Consumer Health Canada Inc.
Visine A Multi-action Eye Allergy ReliefJohnson & Johnson Consumer Inc.
Visine for Allergy With AntihistamineJohnson & Johnson Inc
Wal Flu Flu and Sore ThroatWalgreen Company
Walgreens Wal-flu Cold and Sore Throat Lemon FlavorWALGREEN CO.
Salts
Name/CASStructureProperties
Pheniramine maleate
ThumbNot applicableDBSALT001440
Categories
UNII134FM9ZZ6M
CAS number86-21-5
WeightAverage: 240.3434
Monoisotopic: 240.16264865
Chemical FormulaC16H20N2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPheniramines
Direct ParentPheniramines
Alternative Parents
Substituents
  • Pheniramine
  • Phenylpropylamine
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationPheniramine is an antihistamine used to treat allergic conditions such as hay fever or urticaria.
PharmacodynamicsPheniramine 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 actionAntihistamines 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic hydroxylation, demethylation and glucuronidation.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Dropsophthalmic
Capsule (sustained-release)oral
Solutionophthalmic
Liquidophthalmic
Spraynasal
Powder, for suspensionoral
Powder for solution
Package; powderoral
Powderoral
Package; powder for solutionoral
Solution/ dropsophthalmic
Powder for solutionoral
Syruporal
Liquidoral
Powder, for solutionoral
Tablet (extended-release)oral
Suspensionoral
Tabletoral
Granule, for solutionoral
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point181 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesR06AB05D04AA16
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Pheniramine.
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Pheniramine.
AmitriptylineAmitriptyline may increase the activities of Pheniramine.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Pheniramine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Pheniramine.
CabergolineCabergoline may increase the hypertensive activities of Pheniramine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Pheniramine.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Pheniramine.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Pheniramine.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Pheniramine.
DoxofyllineThe risk or severity of adverse effects can be increased when Pheniramine is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Pheniramine.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Pheniramine.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Pheniramine.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Pheniramine.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Pheniramine.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Pheniramine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Pheniramine.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Pheniramine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Pheniramine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Pheniramine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Pheniramine.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Pheniramine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Pheniramine.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Pheniramine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Pheniramine.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Pheniramine.
PhenelzinePhenelzine may increase the hypertensive activities of Pheniramine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Pheniramine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Pheniramine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Pheniramine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Pheniramine.
PrazosinPrazosin may decrease the vasoconstricting activities of Pheniramine.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Pheniramine.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Pheniramine.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Pheniramine.
TranylcypromineTranylcypromine may increase the hypertensive activities of Pheniramine.
Food InteractionsNot 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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
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 ]
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Drug created on August 29, 2007 14:15 / Updated on August 17, 2016 12:23