Details of the Drug

General Information of Drug (ID: DMCH7RU)

Drug Name

Pheniramine

Synonyms

Avil; Feniramina; Feniramine; Histapyridamine; Metron; Pheniraminum; Propheniramine; Prophenpyridamine; Pyriton; Trimeton; Tripoton; Pheniramine Bimaleate; Avil (TN); Feniramina [INN-Spanish]; P-Aminosalicylsaures salz; Pheniramine (INN); Pheniramine [INN:BAN]; Pheniraminum [INN-Latin]; PHENIRAMINE (SEE ALSO PHENIRAMINE MALEATE 132-20-7); Dimethyl(3-phenyl-3-(2-pyridyl)propyl)amine; N,N-Dimethyl-3-phenyl-3-(2-pyridyl)propylamine; N,N-dimethyl-3-phenyl-3-pyridin-2-ylpropan-1-amine; 1-Phenyl-1-(2-pyridyl)-3-dimethylaminopropane; 2-(3-Dimethylamino-1-phenylpropyl)pyridine; 2-(alpha-(2-Dimethylaminoethyl)benzyl)pyridine; 2-Pyridinepropanamine, N,N-dimethyl-gamma-phenyl-(9CI); 2-[.alpha.-(2-Dimethylaminoethyl)benzyl]pyridine; 2-[.alpha.-[2-(Dimethylamino)ethyl]benzyl]pyridine; 3-Phenyl-3-(2-pyridyl)-N,N-dimethylpropylamine; 3-Phenyl-3-(2-pyridyl)-N,N-dimethylpropylanine

Indication

Disease Entry	ICD 11	Status	REF
Allergic rhinitis	CA08.0	Approved	[1]
Common cold	CA00	Approved	[1]
Cough	MD12	Approved	[1]
Fever	MG26	Approved	[1]
Hay fever	CA08.00	Approved	[2]
Headache	8A80-8A84	Approved	[1]
Seasonal allergic rhinitis	CA08.01	Approved	[1]
Urticaria	EB00-EB05	Approved	[1]
Vasomotor/allergic rhinitis	CA08	Approved	[1]
Pruritus	EC90	Investigative	[1]
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Therapeutic Class

Antiallergic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

240.34

Logarithm of the Partition Coefficient (xlogp)

2.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 173-294 ng/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1-2.5 h [3]
Bioavailability: 99% of drug becomes completely available to its intended biological destination(s) [4]
Elimination: Pheniramine is eliminated via renal excretion, and 24.3% of pheniramine is present in the urine as the parent drug [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 8 - 17 hours [3]
Metabolism: The drug is metabolized via the N-dealkylation to N-didesmethylpheniramine and N-desmethylpheniramine [5]

Chemical Identifiers

Formula: C16H20N2
IUPAC Name: N,N-dimethyl-3-phenyl-3-pyridin-2-ylpropan-1-amine
Canonical SMILES: CN(C)CCC(C1=CC=CC=C1)C2=CC=CC=N2
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
InChIKey: IJHNSHDBIRRJRN-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4761
ChEBI ID: CHEBI:91591
CAS Number: 86-21-5
DrugBank ID: DB01620
TTD ID: D04OBB

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Histamine H1 receptor (H1R)	TTTIBOJ	HRH1_HUMAN	Antagonist	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Allergic rhinitis

ICD Disease Classification

CA08.0

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Histamine H1 receptor (H1R)	DTT	HRH1	6.74E-01	0.13	0.43

Molecular Expression Atlas (MEA)

MEA Detail

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References

1	Pheniramine FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7267).
3	Pharmacokinetics of pheniramine (Avil) and metabolites in healthy subjects after oral and intravenous administration. Int J Clin Pharmacol Ther Toxicol. 1985 Jan;23(1):59-62.
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Kimko HC, Cross JT, Abernethy DR: Pharmacokinetics and clinical effectiveness of methylphenidate. Clin Pharmacokinet. 1999 Dec;37(6):457-70. doi: 10.2165/00003088-199937060-00002.
6	Role of central histaminergic system in lorazepam withdrawal syndrome in rats. Pharmacol Biochem Behav. 2001 Apr;68(4):777-82.