Chlorpheniramine
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Basic Info
| Common Name | Chlorpheniramine(F04784) |
| 2D Structure | |
| 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. |
| FRCD ID | F04784 |
| CAS Number | 132-22-9 |
| PubChem CID | 2725 |
| Formula | C16H19ClN2 |
| IUPAC Name | 3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine |
| InChI Key | SOYKEARSMXGVTM-UHFFFAOYSA-N |
| 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 |
| Canonical SMILES | CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2 |
| Isomeric SMILES | CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2 |
| Wikipedia | Chlorpheniramine |
| Synonyms |
Chloropheniramine
chlorpheniramine
Chlorphenamine
Chlorophenylpyridamine
Clorfeniramina
Teldrin
Chlor-trimeton
Clorfenamina
Haynon
Chlorpheniraminum
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pheniramines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pheniramines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| 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 |
| 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 274.792 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 5 |
| Complexity | 249 |
| Monoisotopic Mass | 274.124 |
| Exact Mass | 274.124 |
| XLogP | 3.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9620 |
| Human Intestinal Absorption | HIA+ | 0.9754 |
| Caco-2 Permeability | Caco2+ | 0.8749 |
| P-glycoprotein Substrate | Substrate | 0.6136 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8782 |
| Non-inhibitor | 0.9376 | |
| Renal Organic Cation Transporter | Inhibitor | 0.7916 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5988 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8026 |
| CYP450 2D6 Substrate | Substrate | 0.8919 |
| CYP450 3A4 Substrate | Substrate | 0.6472 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9096 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8932 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9023 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7501 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8702 |
| Inhibitor | 0.7145 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.9183 |
| Fish Toxicity | High FHMT | 0.7481 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9167 |
| Honey Bee Toxicity | Low HBT | 0.8583 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | II | 0.7386 |
| Carcinogenicity (Three-class) | Non-required | 0.7104 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1769 | LogS |
| Caco-2 Permeability | 1.3453 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.3361 | LD50, mol/kg |
| Fish Toxicity | 1.4017 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6943 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| The effect of Nesfatin-1 on food intake in neonatal chicks: role of CRF1 /CRF2and H1/ H3 receptors. | Vet Res Commun | 2018 Mar | 29280084 |
| Involvement of histaminergic and noradrenergic receptors in the oxytocin-induced food intake in neonatal meat-type chicks. | Vet Res Commun | 2017 Mar | 27975177 |
| Central histaminergic system interplay with suppressive effects of immune challenge on food intake in chicken. | Br Poult Sci | 2016 Apr | 26924422 |
| A Case of Anaphylaxis Induced by Contact with Young Radish (Raphanus sativus L). | Allergy Asthma Immunol Res | 2015 Jan | 25553270 |
| Effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin on scratching behavior in mice. | Int Immunopharmacol | 2010 Mar | 19969104 |
| The histamine H1 receptor is not involved in local control of mammary blood flow in dairy cows. | J Dairy Sci | 2008 Jun | 18487669 |
| Mechanisms of metabisulfite-induced bronchoconstriction: evidence for bradykinin B2-receptor stimulation. | J Appl Physiol (1985) | 1992 May | 1318295 |
| The importance of endogenous histamine relative to dietary histamine in the aetiology of scombrotoxicosis. | Food Addit Contam | 1991 Jul-Aug | 1806404 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Putative Polycomb group (PcG) protein. PcG proteins maintain the transcriptionally repressive state of genes, probably via a modification of chromatin, rendering it heritably changed in its expressibility (By similarity). Specifically binds to monomethylated and dimethylated 'Lys-20' on histone H4.
- Gene Name:
- MBTD1
- Uniprot ID:
- Q05BQ5
- Molecular Weight:
- 70546.805 Da
References
- Kireev D, Wigle TJ, Norris-Drouin J, Herold JM, Janzen WP, Frye SV: Identification of non-peptide malignant brain tumor (MBT) repeat antagonists by virtual screening of commercially available compounds. J Med Chem. 2010 Nov 11;53(21):7625-31. doi: 10.1021/jm1007374. [20931980 ]
- General Function:
- Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
- Specific Function:
- Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are retained intracellularly and undergo ubiquitin-dependent degradation.
- Gene Name:
- KCNH2
- Uniprot ID:
- Q12809
- Molecular Weight:
- 126653.52 Da
References
- Keseru GM: Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods. Bioorg Med Chem Lett. 2003 Aug 18;13(16):2773-5. [12873512 ]
- General Function:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [9537821 ]
- General Function:
- Serotonin:sodium symporter activity
- Specific Function:
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
- Gene Name:
- SLC6A4
- Uniprot ID:
- P31645
- Molecular Weight:
- 70324.165 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [9537821 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis.
- Gene Name:
- HTR2C
- Uniprot ID:
- P28335
- Molecular Weight:
- 51820.705 Da
References
- Wainscott DB, Lucaites VL, Kursar JD, Baez M, Nelson DL: Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences. J Pharmacol Exp Ther. 1996 Feb;276(2):720-7. [8632342 ]
- General Function:
- Histamine receptor activity
- 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:
- 44495.375 Da
References
- Nguyen T, Shapiro DA, George SR, Setola V, Lee DK, Cheng R, Rauser L, Lee SP, Lynch KR, Roth BL, O'Dowd BF: Discovery of a novel member of the histamine receptor family. Mol Pharmacol. 2001 Mar;59(3):427-33. [11179435 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Polycomb group (PcG) protein that specifically recognizes and binds mono- and dimethyllysine residues on target proteins, therey acting as a 'reader' of a network of post-translational modifications. PcG proteins maintain the transcriptionally repressive state of genes: acts as a chromatin compaction factor by recognizing and binding mono- and dimethylated histone H1b/HIST1H1E at 'Lys-26' (H1bK26me1 and H1bK26me2) and histone H4 at 'Lys-20' (H4K20me1 and H4K20me2), leading to condense chromatin and repress transcription. Recognizes and binds p53/TP53 monomethylated at 'Lys-382', leading to repress p53/TP53-target genes. Also recognizes and binds RB1/RB monomethylated at 'Lys-860'. Participates in the ETV6-mediated repression. Probably plays a role in cell proliferation. Overexpression induces multinucleated cells, suggesting that it is required to accomplish normal mitosis.
- Gene Name:
- L3MBTL1
- Uniprot ID:
- Q9Y468
- Molecular Weight:
- 83882.985 Da
References
- Kireev D, Wigle TJ, Norris-Drouin J, Herold JM, Janzen WP, Frye SV: Identification of non-peptide malignant brain tumor (MBT) repeat antagonists by virtual screening of commercially available compounds. J Med Chem. 2010 Nov 11;53(21):7625-31. doi: 10.1021/jm1007374. [20931980 ]
- Specific Function:
- Putative Polycomb group (PcG) protein. PcG proteins maintain the transcriptionally repressive state of genes, probably via a modification of chromatin, rendering it heritably changed in its expressibility. Required for normal maturation of myeloid progenitor cells (By similarity).
- Gene Name:
- L3MBTL3
- Uniprot ID:
- Q96JM7
- Molecular Weight:
- 88336.035 Da
References
- Kireev D, Wigle TJ, Norris-Drouin J, Herold JM, Janzen WP, Frye SV: Identification of non-peptide malignant brain tumor (MBT) repeat antagonists by virtual screening of commercially available compounds. J Med Chem. 2010 Nov 11;53(21):7625-31. doi: 10.1021/jm1007374. [20931980 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Putative Polycomb group (PcG) protein. PcG proteins maintain the transcriptionally repressive state of genes, probably via a modification of chromatin, rendering it heritably changed in its expressibility (By similarity).
- Gene Name:
- L3MBTL4
- Uniprot ID:
- Q8NA19
- Molecular Weight:
- 71121.56 Da
References
- Kireev D, Wigle TJ, Norris-Drouin J, Herold JM, Janzen WP, Frye SV: Identification of non-peptide malignant brain tumor (MBT) repeat antagonists by virtual screening of commercially available compounds. J Med Chem. 2010 Nov 11;53(21):7625-31. doi: 10.1021/jm1007374. [20931980 ]
- General Function:
- Platelet activating factor receptor activity
- Specific Function:
- Receptor for platelet activating factor, a chemotactic phospholipid mediator that possesses potent inflammatory, smooth-muscle contractile and hypotensive activity. Seems to mediate its action via a G protein that activates a phosphatidylinositol-calcium second messenger system.
- Gene Name:
- PTAFR
- Uniprot ID:
- P25105
- Molecular Weight:
- 39203.075 Da
References
- Piwinski JJ, Wong JK, Green MJ, Ganguly AK, Billah MM, West RE Jr, Kreutner W: Dual antagonists of platelet activating factor and histamine. Identification of structural requirements for dual activity of N-Acyl-4-(5,6-dihydro-11H-benzo [5,6]cyclohepta-[1,2-b]pyridin-11-ylidene)piperidines. J Med Chem. 1991 Jan;34(1):457-61. [1671420 ]
- General Function:
- Monoamine transmembrane transporter activity
- Specific Function:
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A3
- Uniprot ID:
- Q01959
- Molecular Weight:
- 68494.255 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [9537821 ]
- General Function:
- Histamine receptor activity
- 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:
- 55783.61 Da
- 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.
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- General Function:
- Serotonin receptor activity
- Specific Function:
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of dopamine and 5-hydroxytryptamine release, 5-hydroxytryptamine uptake and in the regulation of extracellular dopamine and 5-hydroxytryptamine levels, and thereby affects neural activity. May play a role in the perception of pain. Plays a role in the regulation of behavior, including impulsive behavior. Required for normal proliferation of embryonic cardiac myocytes and normal heart development. Protects cardiomyocytes against apoptosis. Plays a role in the adaptation of pulmonary arteries to chronic hypoxia. Plays a role in vasoconstriction. Required for normal osteoblast function and proliferation, and for maintaining normal bone density. Required for normal proliferation of the interstitial cells of Cajal in the intestine.
- Gene Name:
- HTR2B
- Uniprot ID:
- P41595
- Molecular Weight:
- 54297.41 Da
References
- Wainscott DB, Lucaites VL, Kursar JD, Baez M, Nelson DL: Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences. J Pharmacol Exp Ther. 1996 Feb;276(2):720-7. [8632342 ]