Human Metabolome Database: Showing metabocard for Chlorpheniramine (HMDB01944)

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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

3.6

Creation Date

2006-05-18 09:20:41 UTC

Update Date

2017-03-02 21:26:47 UTC

HMDB ID

HMDB01944

Secondary Accession Numbers

HMDB04994

Metabolite Identification

Common Name

Chlorpheniramine

Description

Chlorpheniramine is 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; Chlorphenamine or chlorpheniramine, commonly marketed as its salt chlorphenamine maleate (Chlor- Trimeton, Piriton, Chlor- Tripolon), is a first generation antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria.- wikipedia.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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
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	MeSH
Chlor-tripolon	MeSH
Chlorpro	MeSH
cloro-Trimeton	MeSH
Kloromin	MeSH
Maleate, chlorpheniramine	MeSH
Piriton	MeSH
Rugby brand OF chlorpheniramine maleate	MeSH
Schering-plough brand OF chlorpheniramine maleate	MeSH
Tannate, chlorpheniramine	MeSH
Bayer brand OF chlorpheniramine maleate	MeSH
chlo-Amine	MeSH
Chlorphenamine	MeSH
Hogil brand 1 OF chlorpheniramine maleate	MeSH
Llorens brand OF chlorpheniramine maleate	MeSH
Schering brand OF chlorpheniramine maleate	MeSH
Vortech brand 1 OF chlorpheniramine maleate	MeSH
antihistaminico Llorens	MeSH
Chlorprophenpyridamine	MeSH
Chlorspan 12	MeSH
Chlortab-4	MeSH
Halsey drug brand OF chlorpheniramine maleate	MeSH
Stafford-miller brand OF chlorpheniramine maleate	MeSH
Vortech brand 3 OF chlorpheniramine maleate	MeSH
Chlor-100	MeSH
Chlorpheniramine tannate	MeSH
Efidac 24	MeSH
Hogil brand 2 OF chlorpheniramine maleate	MeSH
Intra brand OF chlorpheniramine maleate	MeSH
Schein brand OF chlorpheniramine maleate	MeSH
Vortech brand 2 OF chlorpheniramine maleate	MeSH

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

This 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.

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

Status

Expected but not Quantified

Origin

Drug

Biofunction

Not Available

Application

Not Available

Cellular locations

Membrane (predicted from logP)

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	130 - 135 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	160.0 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.052 mg/mL	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-01b9-3900000000-ea4ccfd2afe05f49fc7a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-004i-0090000000-9e46eb080de95d4f8f8e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-014i-1920000000-d2d2acf559d9070a1d47	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0zfr-6190000000-2ca3230cde716588805e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0290000000-03651b7b90a1745fdf23	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0uy0-0960000000-1f750af75fe542c6c06f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	Not Available
MS	Mass Spectrum (Electron Ionization)	splash10-0zfr-6490000000-8e58cd1c686f23a7dac6	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biofluid Locations

Not Available

Tissue Location

Skin

Pathways

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Predicted Concentrations

Biofluid	Value	Original age	Original sex	Original condition	Comments
Blood	0-4 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0-2 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

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB022759

KNApSAcK ID

Not Available

Chemspider ID

2624

KEGG Compound ID

C06905

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

NuGOwiki Link

Metagene Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

52010

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 (HMDB01944)

Structure for HMDB01944 (Chlorpheniramine)

Enzymes