| Version |
2.5 |
| Creation Date |
2005-06-13 13:24:05 |
| Update Date |
2009-04-16 16:48:16 |
| Primary Accession Number |
DB01114 |
| Secondary Accession Number |
|
| Name |
Chlorpheniramine |
| Drug Type |
|
| Description |
A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than promethazine. [PubChem] |
| Synonyms |
- Chloropheniramine
- Chlorophenylpyridamin
- Chlorophenylpyridamine
- Chloroprophenpyridamine
- Chlorphenamine
- Chlorpheniramine Maleate
- Chlorprophenpyridamine
- Clorfeniramina
- Dexchlorpheniramine
- Dexchlorpheniramine Maleate
|
| Brand Names |
- Aller-Chlor
- Allergican
- Allergisan
- Antagonate
- Chlo-Amine
- Chlor-Trimeton
- Chlor-Trimeton Allergy
- Chlor-Trimeton Repetabs
- Chlor-Tripolon
- Chlorate
- Chloropiril
- Cloropiril
- Efidac 24 Chlorpheniramine Maleate
- Gen-Allerate
- Haynon
- Histadur
- Kloromin
- Mylaramine
- Novo-Pheniram
- Pediacare Allergy Formula
- Phenetron
- Piriton
- Polaramine
- Polaronil
- Pyridamal 100
- Telachlor
- Teldrin
|
| Brand Mixtures |
- Alka Seltzer Plus Cold Medicine Evt (Acetylsalicylic Acid + Chlorpheniramine Maleate + Phenylpropanolamine Bitartrate)
- Alka-Seltzer Plus Cold Medicine - Evt (Acetylsalicylic Acid + Chlorpheniramine Maleate + Phenylpropanolamine Bitartrate)
- Allergy Sinus Medication - Caplet (Acetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride)
- Ana-Kit (2mg/Tab Orl, 1mg/Ml Liq Sc Im) (Chlorpheniramine Maleate + Epinephrine)
- Ana-Kit (Chlorpheniramine Maleate + Epinephrine Hcl)
- Anakit Insect Sting Treatment Kit (Chlorpheniramine Maleate + Epinephrine)
- Bronchodex D Cap (Chlorpheniramine Maleate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Children's Tylenol Cold Chewable Tablets (Acetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride)
- Children's Tylenol Cold Liquid (Acetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride)
- Children's Tylenol Cold Liquid with Dm (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Chlor Tripolon Decongest Syr (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Cold Decongestant Long Acting Cap (Chlorpheniramine Maleate + Pheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Coltalin Tablet (Acetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Contac Cold Capsules (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Contac Cold Extra Strength Capsules (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Contac Cough Cold and Flu Caplets (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride)
- Contact C Src (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Coricidin D Long Acting Tab (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Coricidin D Tab (Acetylsalicylic Acid + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Coricidin Sinus Headache Tab (Acetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Coricidin Tab (Acetylsalicylic Acid + Chlorpheniramine Maleate)
- Corsym Suspension (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Counteract Sinus and Allergy (Acetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Dristan Capsules (Acetylsalicylic Acid + Caffeine + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Extra Strength Allergy Plus Sinus Relief (Acetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride)
- Extra Strength Allergy Sinus Medication (Acetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride)
- Extra Strength Contac C - Src (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Extra Strength Nighttime Cold Relief-Caplet (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Extra Strength Tylenol Cold Nighttime Caplet (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Extra Strength Tylenol Cold and Flu Powder (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Extra Strength Tylenol Sinus Nighttime (Acetaminophen + Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride)
- Grippalin & C Tab (Acetaminophen + Chlorpheniramine Maleate + Vitamin C)
- Neocitran Total (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Omni-Tuss Sus (Chlorpheniramine + Codeine + Ephedrine As Resin Complex + Guaiacol Carbonate + Phenyltoloxamine)
- Once-a-Day Benylin Cold Cap (Chlorpheniramine Maleate + Pseudoephedrine Hydrochloride)
- Ornade Af Liquid (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Ornade Af Spansule Src (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Ornade Dm 10 Liq (Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride)
- Ornade Dm 15 Liq (Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride)
- Ornade Dm 30 Liq (Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Phenylpropanolamine Hydrochloride)
- Ornade Expectorant Cough Formula (Chlorpheniramine Maleate + Guaifenesin + Phenylpropanolamine Hydrochloride)
- Ornade Liquid (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Ornade Spansule Src (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Pendamine (Chlorpheniramine Maleate + Dexamethasone + Dihydrostreptomycin Sulfate + Penicillin G Procaine)
- Pentuss Srs (Chlorpheniramine Maleate + Codeine)
- Reg.Str.Cold Medic. (Night Time Relief)Caplet (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Regular Strength Tylenol Cold Nighttime Caplet (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Regular Strength Tylenol Cold and Flu Powder (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Rhinofebral (Chlorpheniramine Maleate + Acetaminophen + Vitamin C)
- Sine-Off Allergy Tab (Acetaminophen + Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Theraflu Flu Cold and Cough Medicine (Acetaminophen + Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
- Tri-Anamine Cold Syrup (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Triaminic Cold and Allergy Syrup (Chlorpheniramine Maleate + Phenylpropanolamine Hydrochloride)
- Triaminic Dm Expectorant Syr (Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Guaifenesin + Pseudoephedrine Hydrochloride)
- Triaminic Expectorant Syr (Chlorpheniramine Maleate + Guaifenesin + Pseudoephedrine Hydrochloride)
- Triaminicol Dm Syrup (Chlorpheniramine Maleate + Dextromethorphan Hydrobromide + Pseudoephedrine Hydrochloride)
|
| Chemical IUPAC Name |
3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine |
| Chemical Formula |
C16H19ClN2 |
| Chemical Structure |
 |
| CAS Registry Number |
132-22-9 |
| InChI Identifier |
InChI=1/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 |
| InChI Key |
SOYKEARSMXGVTM-UHFFFAOYAD |
| KEGG Drug |
D07398  |
| KEGG Compound |
C06905  |
| PubChem Compound |
2725  |
| PubChem Substance |
151743  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA448960  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
02265559  |
| RxList Link |
http://www.rxlist.com/cgi/generic/chlorpheniramine.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Chlorpheniramine  |
| FDA Label |
Not Available |
| Material Safety Data Sheet (MSDS) |
|
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
274.7880 |
| Monoisotopic Molecular Weight |
274.1237 |
| State |
Liquid |
| Melting Point |
142 oC (boiling point) |
| Experimental Water Solubility |
5.5 g/L
Source: PhysProp
|
| Predicted Water Solubility |
5.19e-02 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
3.2
Source: PhysProp
|
| Predicted LogP |
3.74
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-3.72
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
Not Available |
| pKa/Isoelectric Point |
9.13 |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
CN(C)CC[C@H](C1=CC=C(Cl)C=C1)C1=CC=CC=N1 |
| Canonical SMILES |
CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1 |
| Drug Category |
- Anti-Allergic Agents
- Antihistamines
- Antipruritics
- Histamine H1 Antagonists
|
| ATC Codes |
|
| AHFS Codes |
|
| Indication |
For the treatment of rhinitis, urticaria, allergy, common cold, asthma and hay fever. |
| Pharmacology |
In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Chlorpheniramine, is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies. |
| Mechanism of Action |
Chlorpheniramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. |
| Absorption |
Well absorbed in the gastrointestinal tract. |
| Toxicity |
LD50 = 306 mg/kg in humans, mild reproductive toxin to women of childbearing age. |
| Protein Binding |
72% |
| Biotransformation |
Primarily hepatic via Cytochrome P450 (CYP450) enzymes. |
| Half Life |
21-27 hours |
| Dosage Forms |
| Form |
Route |
| Syrup |
Oral |
| Tablet |
Oral |
| Tablet, extended release |
Oral |
|
| Patient Information |
Show  |
| Contraindications |
Show  |
| Interactions |
Show  |
| Drug Interactions |
| Drug |
Interaction |
| Donepezil |
Possible antagonism of action |
| Ethotoin |
The antihistamine increases the effect of hydantoin |
| Fosphenytoin |
The antihistamine increases the effect of hydantoin |
| Galantamine |
Possible antagonism of action |
| Mephenytoin |
The antihistamine increases the effect of hydantoin |
| Phenytoin |
The antihistamine increases the effect of hydantoin |
| Rivastigmine |
Possible antagonism of action |
|
| Food Interactions |
- Avoid alcohol.
- Take with food.
|
| Pathways |
Not Available
|
| General References |
- Drugs.com

- Wikipedia

- RxList

|
| Organisms Affected |
|
| Phase 1 Metabolizing Enzymes |
- Cytochrome P450 3A4 (CYP3A4)
- Cytochrome P450 2D6 (CYP2D6)
|
| Targets |
- 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 |
|
| 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  |
| Target 1 UniProtKB/Swiss-Prot ID |
P35367  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
HRH1_HUMAN  |
| 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  |
| Target 1 GenAtlas ID |
HRH1  |
| Target 1 HGNC ID |
HGNC:5182  |
| Target 1 Chromosome Location |
3 |
| Target 1 Locus |
3p25 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- 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
]
- 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
]
|
| Target 1 Drug References |
- Hasenohrl RU, Kuhlen A, Frisch C, Galosi R, Brandao ML, Huston JP: Comparison of intra-accumbens injection of histamine with histamine H1-receptor antagonist chlorpheniramine in effects on reinforcement and memory parameters. Behav Brain Res. 2001 Oct 15;124(2):203-11. [PubMed
]
- Tagawa M, Kano M, Okamura N, Higuchi M, Matsuda M, Mizuki Y, Arai H, Iwata R, Fujii T, Komemushi S, Ido T, Itoh M, Sasaki H, Watanabe T, Yanai K: Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-chlorpheniramine, a classical antihistamine. Br J Clin Pharmacol. 2001 Nov;52(5):501-9. [PubMed
]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed
]
- Nicholson AN, Pascoe PA, Turner C, Ganellin CR, Greengrass PM, Casy AF, Mercer AD: Sedation and histamine H1-receptor antagonism: studies in man with the enantiomers of chlorpheniramine and dimethindene. Br J Pharmacol. 1991 Sep;104(1):270-6. [PubMed
]
- Yasuda SU, Wellstein A, Likhari P, Barbey JT, Woosley RL: Chlorpheniramine plasma concentration and histamine H1-receptor occupancy. Clin Pharmacol Ther. 1995 Aug;58(2):210-20. [PubMed
]
- Salata JJ, Jurkiewicz NK, Wallace AA, Stupienski RF 3rd, Guinosso PJ Jr, Lynch JJ Jr: Cardiac electrophysiological actions of the histamine H1-receptor antagonists astemizole and terfenadine compared with chlorpheniramine and pyrilamine. Circ Res. 1995 Jan;76(1):110-9. [PubMed
]
|