Human Metabolome Database: Showing metabocard for Chlorpheniramine (HMDB0001944)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

enzymes (5) Show 5 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2006-05-18 09:20:41 UTC

Update Date

2020-04-22 23:33:18 UTC

HMDB ID

HMDB0001944

Secondary Accession Numbers

HMDB0004994
HMDB01944
HMDB04994

Metabolite Identification

Common Name

Chlorpheniramine

Description

Chlorpheniramine, also known as clofeniramina or haynon, belongs to the class of organic compounds known as pheniramines. Pheniramines 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. Chlorpheniramine is a drug. Chlorpheniramine is a very strong basic compound (based on its pKa). In humans, chlorpheniramine is involved in chlorphenamine h1-antihistamine action. Chlorpheniramine is a bitter tasting compound. Chlorpheniramine is a potentially toxic compound. The dextrorotatory stereoisomer, dexchlorpheniramine, has been reported to possess Kd values of 15 nM for the H1 receptor and 1,300 nM for the muscarinic acetylcholine receptors in human brain tissue. The halogenated alkylamine antihistamines all exhibit optical isomerism, and chlorphenamine in the indicated products is racemic chlorphenamine maleate, whereas dexchlorphenamine is the dextrorotary stereoisomer. Chlorphenamine is combined with a narcotic (hydrocodone) in the product Tussionex, which is indicated for treatment of cough and upper respiratory symptoms associated with allergy or cold in adults and children 6 years of age and older. In one example, 4-chlorophenylacetonitrile is reacted with 2-chloropyridine in the presence of sodium amide to form 4-chlorophenyl(2-pyridyl)acetonitrile. It has only weak affinity for the norepinephrine and dopamine transporters (Kd 1,440 nM and 1,060 nM, respectively).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(p-Chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropane	ChEBI
1-(p-Chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamine	ChEBI
2-[p-Chloro-alpha-[2-(dimethylamino)ethyl]benzyl]pyridine	ChEBI
3-(p-Chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine	ChEBI
Chlorophenylpyridamine	ChEBI
Chlorphenamin	ChEBI
Chlorphenaminum	ChEBI
Chlorpheniraminum	ChEBI
Clofeniramina	ChEBI
Clorfenamina	ChEBI
Clorfeniramina	ChEBI
gamma-(4-Chlorophenyl)-gamma-(2-pyridyl)propyldimethylamine	ChEBI
gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	ChEBI
Haynon	ChEBI
Chlorphenamine	Kegg
2-[p-Chloro-a-[2-(dimethylamino)ethyl]benzyl]pyridine	Generator
2-[p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine	Generator
g-(4-Chlorophenyl)-g-(2-pyridyl)propyldimethylamine	Generator
Γ-(4-chlorophenyl)-γ-(2-pyridyl)propyldimethylamine	Generator
g-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	Generator
Γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	Generator
Chlor-trimeton	HMDB
Chloropheniramine maleate	HMDB
Chlorphenamine hydrogen maleate	HMDB
Chlorphenamine maleate	HMDB
Chlorpheniaramine maleate	HMDB
Chlorpheniramine maleate	HMDB
Teldrin	HMDB
Aller-chlor	HMDB
Chlor-tripolon	HMDB
Chlorpro	HMDB
Cloro-trimeton	HMDB
Kloromin	HMDB
Maleate, chlorpheniramine	HMDB
Piriton	HMDB
Rugby brand OF chlorpheniramine maleate	HMDB
Schering-plough brand OF chlorpheniramine maleate	HMDB
Tannate, chlorpheniramine	HMDB
Bayer brand OF chlorpheniramine maleate	HMDB
Chlo-amine	HMDB
Hogil brand 1 OF chlorpheniramine maleate	HMDB
Llorens brand OF chlorpheniramine maleate	HMDB
Schering brand OF chlorpheniramine maleate	HMDB
Vortech brand 1 OF chlorpheniramine maleate	HMDB
Antihistaminico llorens	HMDB
Chlorprophenpyridamine	HMDB
Chlorspan 12	HMDB
Chlortab-4	HMDB
Halsey drug brand OF chlorpheniramine maleate	HMDB
Stafford-miller brand OF chlorpheniramine maleate	HMDB
Vortech brand 3 OF chlorpheniramine maleate	HMDB
Chlor-100	HMDB
Chlorpheniramine tannate	HMDB
Efidac 24	HMDB
Hogil brand 2 OF chlorpheniramine maleate	HMDB
Intra brand OF chlorpheniramine maleate	HMDB
Schein brand OF chlorpheniramine maleate	HMDB
Vortech brand 2 OF chlorpheniramine maleate	HMDB

Chemical Formula

C₁₆H₁₉ClN₂

Average Molecular Weight

274.788

Monoisotopic Molecular Weight

274.123676325

IUPAC Name

[3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine

Traditional Name

chlorpheniramine

CAS Registry Number

113-92-8

SMILES

CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1

InChI Identifier

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

InChI Key

SOYKEARSMXGVTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pheniramines. Pheniramines 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

Substituents

Pheniramine
Chlorobenzene
Halobenzene
Aralkylamine
Aryl chloride
Benzenoid
Monocyclic benzene moiety
Aryl halide
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:52010 )
pyridines (CHEBI:52010 )
monochlorobenzenes (CHEBI:52010 )

Ontology

Disposition

Route of exposure:

Enteral:

Gastrointestinal

Biological location:

Organ and components:

Skin

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Chlorphenamine H1-Antihistamine Action

Role

Biological role:

Serotonin uptake inhibitor

Industrial application:

Drug

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	130 - 135 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	160 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	3.74	ALOGPS
logP	3.58	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.85 m³·mol⁻¹	ChemAxon
Polarizability	30.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zfr-6290000000-2ca3230cde716588805e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zfr-6290000000-2ca3230cde716588805e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9380000000-f4a0f7b13adeafb1762d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-01b9-3900000000-ea4ccfd2afe05f49fc7a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-004i-0090000000-9e46eb080de95d4f8f8e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-014i-1920000000-d2d2acf559d9070a1d47	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0zfr-6190000000-2ca3230cde716588805e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0uy0-0960000000-1f750af75fe542c6c06f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0290000000-03651b7b90a1745fdf23	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0uy0-0960000000-1f750af75fe542c6c06f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-9b4d486e9c2c7712ca4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-0190000000-2c96b165338a445b284d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-3960000000-73025748bd5a00459938	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-90a6e640c735788d17ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1090000000-89ac3cf688134ba8a50b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01tc-6490000000-4242ef7cec7b0b0a7393	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0zfr-6490000000-8e58cd1c686f23a7dac6	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Epidermis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Chlorphenamine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01114

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022759

KNApSAcK ID

Not Available

Chemspider ID

2624

KEGG Compound ID

C06905

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorpheniramine

METLIN ID

1734

PubChem Compound

2725

PDB ID

Not Available

ChEBI ID

52010

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Bantz EW, Dolen WK, Chadwick EW, Nelson HS: Chronic chlorpheniramine therapy: subsensitivity, drug metabolism, and compliance. Ann Allergy. 1987 Nov;59(5):341-6. [PubMed:3688558 ]
Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83. [PubMed:12417888 ]
MSDS [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

3. Serum albumin

General function:: Involved in transport
Specific function:: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:: ALB
Uniprot ID:: P02768
Molecular weight:: 69365.9

Enzyme Details

4. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
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:: 55783.6

Enzyme Details

5. Histamine H4 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The H4 subclass of histamine receptors could mediate the histamine signals in peripheral tissues. Displays a significant level of constitutive activity (spontaneous activity in the absence of agonist)
Gene Name:: HRH4
Uniprot ID:: Q9H3N8
Molecular weight:: 44495.4

Showing metabocard for Chlorpheniramine (HMDB0001944)

Structure for HMDB0001944 (Chlorpheniramine)

Enzymes