Details of the Drug

General Information of Drug (ID: DM5URA2)

Drug Name

Chlorpheniramine

Synonyms

Allergican; Allergisan; Antagonate; Chloropheniramine; Chlorophenylpyridamin; Chlorophenylpyridamine; Chloropiril; Chloroprophenpyridamine; Chlorphenamine; Chlorphenaminum; Chlorpheniraminum; Chlorprophenpyridamine; Clofeniramina; Clorfenamina; Clorfeniramina; Cloropiril; Haynon; Hayon; Histadur; ISOCLOR; Kloromin; Phenetron; PiriIton; Piriton; Polaronil; Telachlor; Teldrin; Chlorphenamine [INN]; Clorfeniramina [Italian]; Pediacare Allergy Formula; [3H]Chlorpheniramine; Aller-Chlor; Chlo-amine; Chlor-Pro; Chlor-Trimeton Repetabs; Chlor-trimeton; Chlorphenamine (INN); Chlorphenaminum [INN-Latin]; Clofeniramina (TN); Clorfenamina [INN-Spanish]; Comakin (TN); Gen-Allerate; Novo-Pheniram; Piriton (TN); Chlor-Trimeton (TN); Chlor-Tripolon (TN); CHLORPHENIRAMINE (SEE ALSO: CHLORPHENIRAMINE MALEATE (CAS113-92-8)); Gamma-(4-Chlorophenyl)-gamma-(2-pyridyl)propyldimethylamine; Gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine; 1-(p-Chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamine; 1-(p-Chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropane; 2-(p-Chloro-alpha-(2-(dimethylamino)ethyl)benzyl)pyridine; 3-(4-chlorophenyl)-N,N-dimethyl-3-(pyridin-2-yl)propan-1-amine; 3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine; 3-(p-Chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine; 4-Chloropheniramine

Indication

Disease Entry	ICD 11	Status	REF
Allergic rhinitis	CA08.0	Approved	[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)

274.79

Logarithm of the Partition Coefficient (xlogp)

3.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 2.5 mL/min/kg [3]
Elimination: 10% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 22 hours [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.48399 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.7% [3]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 3.3 L/kg [3]

Chemical Identifiers

Formula: C16H19ClN2
IUPAC Name: 3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
Canonical SMILES: CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2
InChI: InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
InChIKey: SOYKEARSMXGVTM-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 2725
ChEBI ID: CHEBI:52010
CAS Number: 113-92-8
DrugBank ID: DB01114
TTD ID: D0B7NG
VARIDT ID: DR00595
INTEDE ID: DR0304
ACDINA ID: D00123

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	[5]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Multidrug resistance-associated protein 1 (ABCC1)	DTSYQGK	MRP1_HUMAN	Substrate	[6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[7]
Cytochrome P450 2D6 (CYP2D6)	DECB0K3	CP2D6_HUMAN	Substrate	[8]
Cytochrome P450 3A5 (CYP3A5)	DEIBDNY	CP3A5_HUMAN	Substrate	[7]
Cytochrome P450 3A7 (CYP3A7)	DERD86B	CP3A7_HUMAN	Substrate	[7]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cholinesterase (BCHE)	OTOH3WQ9	CHLE_HUMAN	Gene/Protein Processing	[9]
Cytochrome P450 2D6 (CYP2D6)	OTZJC802	CP2D6_HUMAN	Drug Response	[10]
Heat shock factor protein 1 (HSF1)	OTYNJ4KP	HSF1_HUMAN	Gene/Protein Processing	[11]
Phosphatidylcholine translocator ABCB4 (ABCB4)	OTE6PY83	MDR3_HUMAN	Gene/Protein Processing	[12]
Potassium voltage-gated channel subfamily H member 2 (KCNH2)	OTZX881H	KCNH2_HUMAN	Gene/Protein Processing	[13]
Prostaglandin G/H synthase 2 (PTGS2)	OT75U9M4	PGH2_HUMAN	Gene/Protein Processing	[14]
Transmembrane protease serine 2 (TMPRSS2)	OTN44YQ5	TMPS2_HUMAN	Gene/Protein Processing	[15]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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
Multidrug resistance-associated protein 1 (ABCC1)	DTP	MRP1	3.67E-01	-1.78E-01	-9.02E-01
Cytochrome P450 3A5 (CYP3A5)	DME	CYP3A5	9.57E-01	9.43E-03	1.29E-01
Cytochrome P450 2D6 (CYP2D6)	DME	CYP2D6	8.70E-01	2.98E-02	1.22E-01
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	1.76E-01	1.26E-01	8.27E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Chlorpheniramine

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Trimeprazine	DMEMV9D	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Trimeprazine.	Vasomotor/allergic rhinitis [CA08]	[16]
Acrivastine	DMTIGA0	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Acrivastine.	Vasomotor/allergic rhinitis [CA08]	[17]
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Coadministration of a Drug Treating the Disease Different from Chlorpheniramine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Phenyltoloxamine	DMKAEQW	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Phenyltoloxamine.	Allergic/hypersensitivity disorder [4A80-4A8Z]	[16]
Desipramine	DMT2FDC	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Desipramine.	Attention deficit hyperactivity disorder [6A05]	[17]
Cariprazine	DMJYDVK	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Cariprazine.	Bipolar disorder [6A60]	[17]
Acetylcholine	DMDF79Z	Moderate	Antagonize the effect of Chlorpheniramine when combined with Acetylcholine.	Cataract [9B10]	[18]
Umeclidinium	DM4E8O9	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Umeclidinium.	Chronic obstructive pulmonary disease [CA22]	[19]
Tiotropium	DMFDC0Q	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Tiotropium.	Chronic obstructive pulmonary disease [CA22]	[19]
Revefenacin	DMMP5SI	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Revefenacin.	Chronic obstructive pulmonary disease [CA22]	[19]
Isocarboxazid	DMAF1NB	Moderate	Additive CNS depression effects by the combination of Chlorpheniramine and Isocarboxazid.	Depression [6A70-6A7Z]	[20]
OPC-34712	DMHG57U	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and OPC-34712.	Depression [6A70-6A7Z]	[17]
Clomipramine	DMINRKW	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Clomipramine.	Depression [6A70-6A7Z]	[17]
Doxepin	DMPI98T	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Doxepin.	Depression [6A70-6A7Z]	[16]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Chlorpheniramine and Esketamine.	Depression [6A70-6A7Z]	[21]
Mepenzolate	DM8YU2F	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Mepenzolate.	Digestive system disease [DE2Z]	[17]
Solifenacin	DMG592Q	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Solifenacin.	Functional bladder disorder [GC50]	[17]
Mirabegron	DMS1GYT	Moderate	Decreased metabolism of Chlorpheniramine caused by Mirabegron mediated inhibition of CYP450 enzyme.	Functional bladder disorder [GC50]	[22]
Procarbazine	DMIK367	Moderate	Additive CNS depression effects by the combination of Chlorpheniramine and Procarbazine.	Hodgkin lymphoma [2B30]	[20]
Cobicistat	DM6L4H2	Moderate	Decreased metabolism of Chlorpheniramine caused by Cobicistat mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[23]
Givosiran	DM5PFIJ	Moderate	Decreased metabolism of Chlorpheniramine caused by Givosiran mediated inhibition of CYP450 enzyme.	Inborn porphyrin/heme metabolism error [5C58]	[24]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Chlorpheniramine caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[25]
ITI-007	DMUQ1DO	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and ITI-007.	Insomnia [7A00-7A0Z]	[17]
Dacomitinib	DMOH8VY	Moderate	Decreased metabolism of Chlorpheniramine caused by Dacomitinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[26]
Vemurafenib	DM62UG5	Moderate	Decreased metabolism of Chlorpheniramine caused by Vemurafenib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[27]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Chlorpheniramine and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[28]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Chlorpheniramine and Lasmiditan.	Migraine [8A80]	[29]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Chlorpheniramine and Flibanserin.	Mood disorder [6A60-6E23]	[30]
Panobinostat	DM58WKG	Moderate	Decreased metabolism of Chlorpheniramine caused by Panobinostat mediated inhibition of CYP450 enzyme.	Multiple myeloma [2A83]	[31]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Chlorpheniramine caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[32]
Nilotinib	DM7HXWT	Moderate	Decreased metabolism of Chlorpheniramine caused by Nilotinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[33]
Rolapitant	DM8XP26	Moderate	Decreased metabolism of Chlorpheniramine caused by Rolapitant mediated inhibition of CYP450 enzyme.	Nausea/vomiting [MD90]	[34]
Cyclizine	DM9G7BS	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Cyclizine.	Nausea/vomiting [MD90]	[17]
Bupropion	DM5PCS7	Moderate	Decreased metabolism of Chlorpheniramine caused by Bupropion mediated inhibition of CYP450 enzyme.	Nicotine use disorder [6C4A]	[35]
Lorcaserin	DMG6OYJ	Moderate	Decreased metabolism of Chlorpheniramine caused by Lorcaserin mediated inhibition of CYP450 enzyme.	Obesity [5B80-5B81]	[36]
Methylscopolamine	DM5VWOB	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Methylscopolamine.	Peptic ulcer [DA61]	[17]
ABIRATERONE	DM8V75C	Moderate	Decreased metabolism of Chlorpheniramine caused by ABIRATERONE mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[37]
Levomepromazine	DMIKFEL	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Levomepromazine.	Psychotic disorder [6A20-6A25]	[17]
Quetiapine	DM1N62C	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Quetiapine.	Schizophrenia [6A20]	[17]
Aripiprazole	DM3NUMH	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Aripiprazole.	Schizophrenia [6A20]	[17]
Iloperidone	DM6AUFY	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Iloperidone.	Schizophrenia [6A20]	[17]
Paliperidone	DM7NPJS	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Paliperidone.	Schizophrenia [6A20]	[17]
Molindone	DMAH70G	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Molindone.	Schizophrenia [6A20]	[17]
Thiothixene	DMDINC4	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Thiothixene.	Schizophrenia [6A20]	[17]
Asenapine	DMSQZE2	Moderate	Additive anticholinergic effects by the combination of Chlorpheniramine and Asenapine.	Schizophrenia [6A20]	[17]
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⏷ Show the Full List of 42 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Hydrazine yellow	E00409	164825	Colorant
methylparaben	E00149	7456	Antimicrobial preservative
Oleic acid	E00421	445639	Emulsifying agent; Penetration agent; Solubilizing agent
Quinoline yellow WS	E00309	24671	Colorant
Sodium benzoate	E00432	517055	Antimicrobial preservative; lubricant
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Calcium hydrogenphosphate	E00294	24441	Diluent
Calcium sulfate anhydrous	E00303	24497	Desiccant; Diluent
Carmellose sodium	E00625	Not Available	Disintegrant
Crospovidone	E00626	Not Available	Disintegrant
Ethanethiol	E00116	6343	Flavoring agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Rosin	E00470	5280656	Binding agent; Film/membrane-forming agent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triethyl citrate	E00128	6506	Plasticizing agent; Solvent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
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⏷ Show the Full List of 27 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Chlorpheniramine 12 mg tablet	12 mg	12 HR Extended Release Oral Tablet	Oral
Chlorpheniramine 4 mg tablet	4 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	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: 6976).
2	BDDCS applied to over 900 drugs
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4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization. J Pharmacol Sci. 2008 May;107(1):66-79.
6	Carrier mediated transport of chlorpheniramine and chlorcyclizine across bovine olfactory mucosa: implications on nose-to-brain transport. J Pharm Sci. 2005 Mar;94(3):613-24.
7	Drug Interactions Flockhart Table
8	The roles of CYP2D6 and stereoselectivity in the clinical pharmacokinetics of chlorpheniramine. Br J Clin Pharmacol. 2002 May;53(5):519-25.
9	Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity. Toxicol Appl Pharmacol. 1975 Feb;31(2):179-90.
10	Impact of CYP2D6*10 on H1-antihistamine-induced hypersomnia. Eur J Clin Pharmacol. 2006 Dec;62(12):995-1001. doi: 10.1007/s00228-006-0210-3. Epub 2006 Nov 7.
11	A Gene Expression Biomarker Predicts Heat Shock Factor 1 Activation in a Gene Expression Compendium. Chem Res Toxicol. 2021 Jul 19;34(7):1721-1737. doi: 10.1021/acs.chemrestox.0c00510. Epub 2021 Jun 25.
12	Evaluating the Role of Multidrug Resistance Protein 3 (MDR3) Inhibition in Predicting Drug-Induced Liver Injury Using 125 Pharmaceuticals. Chem Res Toxicol. 2017 May 15;30(5):1219-1229. doi: 10.1021/acs.chemrestox.7b00048. Epub 2017 May 4.
13	Block of HERG k channel by classic histamine h(1) receptor antagonist chlorpheniramine. Korean J Physiol Pharmacol. 2009 Jun;13(3):215-20. doi: 10.4196/kjpp.2009.13.3.215. Epub 2009 Jun 30.
14	An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
15	Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
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25	Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
26	Product Information. Vizimpro (dacomitinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
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28	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
29	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
30	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
31	Product Information. Farydak (panobinostat). Novartis Pharmaceuticals, East Hanover, NJ.
32	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
33	Product Information. Tasigna (nilotinib). Novartis Pharmaceuticals, East Hanover, NJ.
34	Product Information. Varubi (rolapitant). Tesaro Inc., Waltham, MA.
35	Dufresne RL, Weber SS, Becker RE "Bupropion hydrochloride." Drug Intell Clin Pharm 18 (1984): 957-64. [PMID: 6439541]
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37	Product Information. Zytiga (abiraterone). Centocor Inc, Malvern, PA.