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Record Information
Version2.0
Creation Date2009-07-21 20:26:39 UTC
Update Date2014-12-24 20:25:51 UTC
Accession NumberT3D2757
Identification
Common NameTerfenadine
ClassSmall Molecule
DescriptionTerfenadine is only found in individuals that have used or taken this drug. In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.Terfenadine competes with histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. This reversible binding of terfenadine to H1-receptors suppresses the formation of edema, flare, and pruritus resulting from histaminic activity. As the drug does not readily cross the blood-brain barrier, CNS depression is minimal.
Compound Type
  • Amine
  • Anti-Allergic Agent
  • Anti-Arrhythmia Agent
  • Drug
  • Histamine Antagonist
  • Histamine H1 Antagonist, Non-Sedating
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(RS)-1-(4-tert-butylphenyl)-4-{4-[hydroxy(diphenyl)methyl]piperidin-1-yl}-butan-1-ol
Bronal
Daylert
Seldane
Servinin
Teldane
Terfed
Terfenadin
Terfenadin AL
Terfenadina
Terfénadine
Terfenadine FLX
Terfenadinum
Terfin
Ternadin
Trexyl
Triludan
Chemical FormulaC32H41NO2
Average Molecular Mass471.673 g/mol
Monoisotopic Mass471.314 g/mol
CAS Registry Number50679-08-8
IUPAC Name1-(4-tert-butylphenyl)-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-ol
Traditional Nameterfenadine
SMILESCC(C)(C)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3
InChI KeyInChIKey=GUGOEEXESWIERI-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylbutylamine
  • Phenylpropane
  • Aralkylamine
  • Piperidine
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Aromatic alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Blood
  • Heart
  • Liver
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point147°C
Boiling PointNot Available
Solubility0.0963 mg/L (at 25°C)
LogP7.1
Predicted Properties
PropertyValueSource
Water Solubility0.00046 g/LALOGPS
logP5.89ALOGPS
logP6.48ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.2ChemAxon
pKa (Strongest Basic)9.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity146.27 m³·mol⁻¹ChemAxon
Polarizability56.45 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0922300000-f2ebf7861ae9f28463f9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-1091031000-8a395a9531e2fce637a4JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0573-2592100000-35fee494c6fb22cf9279JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0000900000-577805b6e639de28dd59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0000900000-6ee8ace68773688ab606JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0000900000-8d9a4ec2424b97bb3b80JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-6770900000-9830d37d285444cff791JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-5920000000-909f0029205fa0a7663fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-2541900000-f3da0c526b0e748b9567JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0000900000-33f5717b3bed30143d5bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uki-0543900000-e5659b7fe1e1659acac9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-2981000000-03f1a2ca48b1a2d8e769JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0100900000-19b3063632e4afc820d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-5561900000-bac14174fc7e7f1ab7f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-9870000000-8b66dc183082f6b4a57fJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-001i-8890000000-2c6ad1195e498f463cbfJSpectraViewer | MoNA
Toxicity Profile
Route of ExposureOral. On the basis of a mass balance study using 14C labeled terfenadine the oral absorption of terfenadine was estimated to be at least 70%
Mechanism of ToxicityTerfenadine competes with histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. This reversible binding of terfenadine to H1-receptors suppresses the formation of edema, flare, and pruritus resulting from histaminic activity. As the drug does not readily cross the blood-brain barrier, CNS depression is minimal.
MetabolismTerfenadine is a prodrug, generally completely metabolized to the active form fexofenadine in the liver by the enzyme cytochrome P450 CYP3A4 isoform. Due to its near complete metabolism by the liver immediately after leaving the gut, terfenadine normally is not measurable in the plasma. (Wikipedia) Half Life: 3.5 hours
Toxicity ValuesLD50: 5000 mg/kg (Oral, mouse)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
Minimum Risk LevelNot Available
Health EffectsCardiotoxic at higher doses. In larger plasma concentrations, it may lead to toxic effects on the heart's rhythm (e.g. ventricular tachycardia and torsades de pointes). (Wikipedia)
SymptomsMild (e.g., headache, nausea, confusion), but adverse cardiac events including cardiac arrest, ventricular arrhythmias including torsades de pointes and QT prolongation have been reported.
Treatmentin cases of overdosage, cardiac monitoring for at least 24 hours is recommended and for as long as QTc is prolonged, along with standard measures to remove any unabsorbed drug. Treatment of the signs and symptoms of overdosage should be symptomatic and supportive after the acute stage. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00342
HMDB IDHMDB14486
PubChem Compound ID5405
ChEMBL IDCHEMBL17157
ChemSpider ID5212
KEGG IDC07463
UniProt IDNot Available
OMIM ID
ChEBI ID119569
BioCyc IDNot Available
CTD IDNot Available
Stitch IDTerfenadine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkTerfenadine
References
Synthesis Reference

Timothy G. Fawcett, Christian T. Goralski, David W. Ziettlow, “Preparation of polymorphically pure terfenadine.” U.S. Patent US4742175, issued April, 1975.

MSDSLink
General References
  1. Drugs.com [Link]
  2. RxList: The Internet Drug Index (2009). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.058 uMNot AvailableBindingDB 50017376
Inhibitory0.32 uMNot AvailableBindingDB 50017376
IC500.03 uMNot AvailableBindingDB 50017376
IC500.05 uMNot AvailableBindingDB 50017376
IC500.056 uMNot AvailableBindingDB 50017376
IC500.129 uMNot AvailableBindingDB 50017376
IC500.2 uMNot AvailableBindingDB 50017376
IC500.204 uMNot AvailableBindingDB 50017376
IC500.312 uMNot AvailableBindingDB 50017376
IC5056 uMNot AvailableBindingDB 50017376
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  2. Imai YN, Ryu S, Oiki S: Docking model of drug binding to the human ether-a-go-go potassium channel guided by tandem dimer mutant patch-clamp data: a synergic approach. J Med Chem. 2009 Mar 26;52(6):1630-8. doi: 10.1021/jm801236n. [19260734 ]
  3. Du LP, Tsai KC, Li MY, You QD, Xia L: The pharmacophore hypotheses of I(Kr) potassium channel blockers: novel class III antiarrhythmic agents. Bioorg Med Chem Lett. 2004 Sep 20;14(18):4771-7. [15324906 ]
  4. Pearlstein RA, Vaz RJ, Kang J, Chen XL, Preobrazhenskaya M, Shchekotikhin AE, Korolev AM, Lysenkova LN, Miroshnikova OV, Hendrix J, Rampe D: Characterization of HERG potassium channel inhibition using CoMSiA 3D QSAR and homology modeling approaches. Bioorg Med Chem Lett. 2003 May 19;13(10):1829-35. [12729675 ]
  5. Pearlstein R, Vaz R, Rampe D: Understanding the structure-activity relationship of the human ether-a-go-go-related gene cardiac K+ channel. A model for bad behavior. J Med Chem. 2003 May 22;46(11):2017-22. [12747773 ]
  6. Mihalic JT, Fan P, Chen X, Chen X, Fu Y, Motani A, Liang L, Lindstrom M, Tang L, Chen JL, Jaen J, Dai K, Li L: Discovery of a novel melanin concentrating hormone receptor 1 (MCHR1) antagonist with reduced hERG inhibition. Bioorg Med Chem Lett. 2012 Jun 1;22(11):3781-5. doi: 10.1016/j.bmcl.2012.04.006. Epub 2012 Apr 7. [22542010 ]
  7. Rajamani R, Tounge BA, Li J, Reynolds CH: A two-state homology model of the hERG K+ channel: application to ligand binding. Bioorg Med Chem Lett. 2005 Mar 15;15(6):1737-41. [15745831 ]
  8. 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 ]
  9. Tobita M, Nishikawa T, Nagashima R: A discriminant model constructed by the support vector machine method for HERG potassium channel inhibitors. Bioorg Med Chem Lett. 2005 Jun 2;15(11):2886-90. [15911273 ]
  10. Jia L, Sun H: Support vector machines classification of hERG liabilities based on atom types. Bioorg Med Chem. 2008 Jun 1;16(11):6252-60. doi: 10.1016/j.bmc.2008.04.028. Epub 2008 Apr 16. [18448342 ]
  11. Cavalli A, Poluzzi E, De Ponti F, Recanatini M: Toward a pharmacophore for drugs inducing the long QT syndrome: insights from a CoMFA study of HERG K(+) channel blockers. J Med Chem. 2002 Aug 29;45(18):3844-53. [12190308 ]
  12. Aslanian R, Piwinski JJ, Zhu X, Priestley T, Sorota S, Du XY, Zhang XS, McLeod RL, West RE, Williams SM, Hey JA: Structural determinants for histamine H(1) affinity, hERG affinity and QTc prolongation in a series of terfenadine analogs. Bioorg Med Chem Lett. 2009 Sep 1;19(17):5043-7. doi: 10.1016/j.bmcl.2009.07.047. Epub 2009 Aug 5. [19660947 ]
  13. Zhu BY, Jia ZJ, Zhang P, Su T, Huang W, Goldman E, Tumas D, Kadambi V, Eddy P, Sinha U, Scarborough RM, Song Y: Inhibitory effect of carboxylic acid group on hERG binding. Bioorg Med Chem Lett. 2006 Nov 1;16(21):5507-12. Epub 2006 Aug 22. [16931010 ]
  14. Zhang HC, Derian CK, McComsey DF, White KB, Ye H, Hecker LR, Li J, Addo MF, Croll D, Eckardt AJ, Smith CE, Li Q, Cheung WM, Conway BR, Emanuel S, Demarest KT, Andrade-Gordon P, Damiano BP, Maryanoff BE: Novel indolylindazolylmaleimides as inhibitors of protein kinase C-beta: synthesis, biological activity, and cardiovascular safety. J Med Chem. 2005 Mar 24;48(6):1725-8. [15771419 ]
  15. Friemel A, Zunkler BJ: Interactions at human ether-a-go-go-related gene channels. Toxicol Sci. 2010 Apr;114(2):346-55. doi: 10.1093/toxsci/kfq011. Epub 2010 Jan 13. [20071423 ]
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
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.04 uMNot AvailableBindingDB 50017376
IC500.094 uMNot AvailableBindingDB 50017376
IC500.295 uMNot AvailableBindingDB 50017376
IC500.563 uMNot AvailableBindingDB 50017376
Dissociation0.03548 uMNot AvailableBindingDB 50017376
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
  2. Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [9485522 ]
  3. 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. [8001268 ]
  4. Wood-Baker R, Smith R, Holgate ST: A double-blind, placebo controlled study of the effect of the specific histamine H1-receptor antagonist, terfenadine, in chronic severe asthma. Br J Clin Pharmacol. 1995 Jun;39(6):671-5. [7654486 ]
  5. Phillips GD, Polosa R, Holgate ST: The effect of histamine-H1 receptor antagonism with terfenadine on concentration-related AMP-induced bronchoconstriction in asthma. Clin Exp Allergy. 1989 Jul;19(4):405-9. [2569356 ]
  6. Rafferty P, Holgate ST: Terfenadine (Seldane) is a potent and selective histamine H1 receptor antagonist in asthmatic airways. Am Rev Respir Dis. 1987 Jan;135(1):181-4. [2879489 ]
  7. Zhang MQ, Wada Y, Sato F, Timmerman H: (Piperidinylalkoxy)chromones: novel antihistamines with additional antagonistic activity against leukotriene D4. J Med Chem. 1995 Jun 23;38(13):2472-7. [7608912 ]
  8. Abou-Gharbia M, Moyer JA, Nielsen ST, Webb M, Patel U: New antihistamines: substituted piperazine and piperidine derivatives as novel H1-antagonists. J Med Chem. 1995 Sep 29;38(20):4026-32. [7562938 ]
  9. Walsh DA, Franzyshen SK, Yanni JM: Synthesis and antiallergy activity of 4-(diarylhydroxymethyl)-1-[3-(aryloxy)propyl]piperidines and structurally related compounds. J Med Chem. 1989 Jan;32(1):105-18. [2562852 ]
  10. Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
  11. Aslanian R, Piwinski JJ, Zhu X, Priestley T, Sorota S, Du XY, Zhang XS, McLeod RL, West RE, Williams SM, Hey JA: Structural determinants for histamine H(1) affinity, hERG affinity and QTc prolongation in a series of terfenadine analogs. Bioorg Med Chem Lett. 2009 Sep 1;19(17):5043-7. doi: 10.1016/j.bmcl.2009.07.047. Epub 2009 Aug 5. [19660947 ]
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC501.1 uMNot AvailableBindingDB 50017376
IC501.4 uMNot AvailableBindingDB 50017376
IC501.8 uMNot AvailableBindingDB 50017376
IC502.5 uMNot AvailableBindingDB 50017376
IC502.7 uMNot AvailableBindingDB 50017376
References
  1. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [12699389 ]
  2. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [11716514 ]
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC502.9 uMNot AvailableBindingDB 50017376
References
  1. Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [10212017 ]
  2. Abou-Gharbia M, Moyer JA, Nielsen ST, Webb M, Patel U: New antihistamines: substituted piperazine and piperidine derivatives as novel H1-antagonists. J Med Chem. 1995 Sep 29;38(20):4026-32. [7562938 ]
General Function:
Steroid hydroxylase activity
Specific Function:
This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible for the epoxidation of endogenous cardiac arachidonic acid pools.
Gene Name:
CYP2J2
Uniprot ID:
P51589
Molecular Weight:
57610.165 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC508.1 uMNot AvailableBindingDB 50017376
References
  1. Lafite P, Dijols S, Buisson D, Macherey AC, Zeldin DC, Dansette PM, Mansuy D: Design and synthesis of selective, high-affinity inhibitors of human cytochrome P450 2J2. Bioorg Med Chem Lett. 2006 May 15;16(10):2777-80. Epub 2006 Feb 21. [16495056 ]
General Function:
Vitamin d3 25-hydroxylase 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 (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC500.32 uMNot AvailableBindingDB 50017376
References
  1. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [12699389 ]
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [10212017 ]
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [10212017 ]
General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular Weight:
53048.65 Da
References
  1. Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [10212017 ]
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM5
Uniprot ID:
P08912
Molecular Weight:
60073.205 Da
References
  1. Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [10212017 ]
General Function:
Tachykinin receptor activity
Specific Function:
This is a receptor for the tachykinin neuropeptide substance P. It is probably associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinity of this receptor to tachykinins is: substance P > substance K > neuromedin-K.
Gene Name:
TACR1
Uniprot ID:
P25103
Molecular Weight:
46250.5 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50>10 uMNot AvailableBindingDB 50017376
References
  1. Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]