Clenbuterol

Common Name

Clenbuterol Description

Clenbuterol is only found in individuals that have used or taken this drug. It is a substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma. [PubChem]Clenbuterol is a Beta(2) agonist similar in some structural respects to salbutamol. Agonism of the beta(2) receptor stimliates adenylyl cyclase activity which litimately leads to downstream effects of smooth muscle relaxation in the bronchioles. Structure

Synonyms

Value Source (+-)-ClenbuterolChEBI 1-(4-amino-3,5-dichloro-Phenyl)-2-tert-butylamino-ethanolChEBI 4-amino-3,5-dichloro-alpha-(((1,1-Dimethylethyl)amino)methyl)benzenemethanolChEBI 4-amino-alpha-((Tert-butylamino)methyl)-3,5-dichlorobenzyl alcoholChEBI ClenbuterolumChEBI 4-amino-3,5-dichloro-a-(((1,1-Dimethylethyl)amino)methyl)benzenemethanolGenerator 4-amino-3,5-dichloro-α-(((1,1-dimethylethyl)amino)methyl)benzenemethanolGenerator 4-amino-a-((Tert-butylamino)methyl)-3,5-dichlorobenzyl alcoholGenerator 4-amino-α-((tert-butylamino)methyl)-3,5-dichlorobenzyl alcoholGenerator NAB 365MeSH NAB-365MeSH PlanipartMeSH

Chemical Formlia

C₁₂H₁₈Cl₂N₂O Average Molecliar Weight

277.19 Monoisotopic Molecliar Weight

276.079618622 IUPAC Name

1-(4-amino-3,5-dichlorophenyl)-2-(tert-butylamino)ethan-1-ol Traditional Name

clenbuterol CAS Registry Number

37148-27-9 SMILES

InChI Identifier

InChI Key

STJMRWALKKWQGH-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it. Kingdom

Organic compounds Super Class

Benzenoids Class

Benzene and substituted derivatives Sub Class

Halobenzenes Direct Parent

Dichlorobenzenes Alternative Parents

Aniline and substituted anilines

Aralkylamines

Aryl chlorides

Secondary alcohols

1,2-aminoalcohols

Dialkylamines

Primary amines

Organopnictogen compounds

Organochlorides

Hydrocarbon derivatives

Aromatic alcohols

Substituents

1,3-dichlorobenzene

Aniline or substituted anilines

Aralkylamine

Aryl chloride

Aryl halide

1,2-aminoalcohol

Secondary alcohol

Secondary aliphatic amine

Secondary amine

Hydrocarbon derivative

Primary amine

Organooxygen compound

Organonitrogen compound

Organochloride

Organohalogen compound

Organic nitrogen compound

Aromatic alcohol

Alcohol

Organic oxygen compound

Amine

Organopnictogen compound

Aromatic homomonocyclic compound

Molecliar Framework

Aromatic homomonocyclic compounds External Descriptors

substituted aniline (CHEBI:174690 )

secondary amino compound (CHEBI:174690 )

dichlorobenzene (CHEBI:174690 )

primary arylamine (CHEBI:174690 )

ethanolamines (CHEBI:174690 )

amino alcohol (CHEBI:174690 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Adrenergic beta-Agonists

Bronchodilator Agents

Sympathomimetics

Application

Pharmaceutical

Cellliar locations

Extracellliar

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.12e-01 g/LNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility0.11 mg/mLALOGPS logP2.94ALOGPS logP2.33ChemAxon logS-3.4ALOGPS pKa (Strongest Acidic)14.06ChemAxon pKa (Strongest Basic)9.63ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area58.28 ŲChemAxon Rotatable Bond Count4ChemAxon Refractivity73.38 m³·mol^-1ChemAxon Polarizability28.81 ųChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0zfr-0690000000-4ea9999e9adf3d869e7dView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0pb9-0090000000-4787e85eeb46d25e48ebView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0udi-0090000000-9081f080310110b928b2View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0uyi-0970000000-180db1557f9de0905570View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0159-0900000000-5607a3961d5b1b526acaView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0159-0900000000-f99c3fbb74f4657c8588View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-00lr-0900000000-1b8353b766cd0eb328a2View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0f8c-1900000000-b34f6b0fe72dbe12dc7bView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0zgl-4900000000-85c1e6d67f6eb7f4660cView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0udi-9600000000-6d5ae5d64081ef26b128View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Extracellliar

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01407

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01407

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01407 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB008487 KNApSAcK ID

Not Available Chemspider ID

2681 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Clenbuterol NuGOwiki Link

HMDB15477 Metagene Link

HMDB15477 METLIN ID

Not Available PubChem Compound

2783 PDB ID

Not Available ChEBI ID

174690

Product: Sibutramine (hydrochloride)

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

Enzymes

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.

Gene Name:

CYP1A1

Uniprot ID:

P04798

Molecular weight:

58164.815

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.

Gene Name:

CYP1A2

Uniprot ID:

P05177

Molecular weight:

58406.915

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

General function:

Involved in G-protein coupled receptor protein signaling pathway

Specific function:

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity

Gene Name:

ADRB1

Uniprot ID:

P08588

Molecular weight:

51322.1

References

1. Baker JG: The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors. Br J Pharmacol. 2010 Jul;160(5):1048-61. doi: 10.1111/j.1476-5381.2010.00754.x. [PubMed:20590599 ]

General function:

Involved in G-protein coupled receptor protein signaling pathway

Specific function:

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine

Gene Name:

ADRB2

Uniprot ID:

P07550

Molecular weight:

46458.3

References

1. Zhu Y, Culmsee C, Roth-Eichhorn S, Krieglstein J: Beta(2)-adrenoceptor stimulation enhances latent transforming growth factor-beta-binding protein-1 and transforming growth factor-beta1 expression in rat hippocampus after transient forebrain ischemia. Neuroscience. 2001;107(4):593-602. [PubMed:11720783 ]
2. Ryall JG, Gregorevic P, Plant DR, Sillence MN, Lynch GS: Beta 2-agonist fenoterol has greater effects on contractile function of rat skeletal muscles than clenbuterol. Am J Physiol Regul Integr Comp Physiol. 2002 Dec;283(6):R1386-94. Epub 2002 Sep 5. [PubMed:12388476 ]
3. Choo JJ, Horan MA, Little RA, Rothwell NJ: Anabolic effects of clenbuterol on skeletal muscle are mediated by beta 2-adrenoceptor activation. Am J Physiol. 1992 Jul;263(1 Pt 1):E50-6. [PubMed:1322047 ]
4. Sillence MN, Matthews ML, Spiers WG, Pegg GG, Lindsay DB: Effects of clenbuterol, ICI118551 and sotalol on the growth of cardiac and skeletal muscle and on beta 2-adrenoceptor density in female rats. Naunyn Schmiedebergs Arch Pharmacol. 1991 Oct;344(4):449-53. [PubMed:1685013 ]
5. Mazzanti G, Di Sotto A, Daniele C, Battinelli L, Brambilla G, Fiori M, Loizzo S, Loizzo A: A pharmacodynamic study on clenbuterol-induced toxicity: beta1- and beta2-adrenoceptors involvement in guinea-pig tachycardia in an in vitro model. Food Chem Toxicol. 2007 Sep;45(9):1694-9. Epub 2007 Mar 12. [PubMed:17449161 ]
6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

General function:

Involved in tumor necrosis factor receptor binding

Specific function:

Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation

Gene Name:

TNF

Uniprot ID:

P01375

Molecular weight:

25644.1

References

1. Izeboud CA, Mocking JA, Monshouwer M, van Miert AS, Witkamp RF: Participation of beta-adrenergic receptors on macrophages in modulation of LPS-induced cytokine release. J Recept Signal Transduct Res. 1999 Jan-Jul;19(1-4):191-202. [PubMed:10071758 ]
2. Yoshimura T: [Modulation of cytokine production from human mononuclear cells by several agents]. Yakugaku Zasshi. 2000 Dec;120(12):1277-90. [PubMed:11193379 ]
3. Izeboud CA, Hoebe KH, Grootendorst AF, Nijmeijer SM, van Miert AS, Witkamp RR, Rodenburg RJ: Endotoxin-induced liver damage in rats is minimized by beta 2-adrenoceptor stimulation. Inflamm Res. 2004 Mar;53(3):93-9. Epub 2004 Feb 16. [PubMed:15021963 ]
4. Laan TT, Bull S, Pirie RS, Fink-Gremmels J: Evaluation of cytokine production by equine alveolar macrophages exposed to lipopolysaccharide, Aspergillus fumigatus, and a suspension of hay dust. Am J Vet Res. 2005 Sep;66(9):1584-9. [PubMed:16261833 ]
5. van den Hoven R, Duvigneau JC, Hartl RT, Gemeiner M: Clenbuterol affects the expression of messenger RNA for interleukin 10 in peripheral leukocytes from horses challenged intrabronchially with lipopolysaccharides. Vet Res Commun. 2006 Nov;30(8):921-8. [PubMed:17139543 ]

General function:

Involved in receptor binding

Specific function:

Nerve growth factor is important for the development and maintenance of the sympathetic and sensory nervous systems. It stimulates division and differentiation of sympathetic and embryonic sensory neurons

Gene Name:

NGF

Uniprot ID:

P01138

Molecular weight:

26958.5

References

1. Culmsee C, Semkova I, Krieglstein J: NGF mediates the neuroprotective effect of the beta2-adrenoceptor agonist clenbuterol in vitro and in vivo: evidence from an NGF-antisense study. Neurochem Int. 1999 Jul;35(1):47-57. [PubMed:10403429 ]
2. Semkova I, Krieglstein J: Neuroprotection mediated via neurotrophic factors and induction of neurotrophic factors. Brain Res Brain Res Rev. 1999 Aug;30(2):176-88. [PubMed:10525174 ]
3. Puls I, Beck M, Giess R, Magnus T, Ochs G, Toyka KV: [Clenbuterol in amyotrophic lateral sclerosis. No indication for a positive effect]. Nervenarzt. 1999 Dec;70(12):1112-5. [PubMed:10637819 ]
4. Samina Riaz S, Tomlinson DR: Pharmacological modulation of nerve growth factor synthesis: a mechanistic comparison of vitamin D receptor and beta(2)-adrenoceptor agonists. Brain Res Mol Brain Res. 2000 Dec 28;85(1-2):179-88. [PubMed:11146120 ]
5. Riaz SS, Tomlinson DR: Clenbuterol stimulates neurotrophic support in streptozotocin-diabetic rats. Diabetes Obes Metab. 1999 Jan;1(1):43-51. [PubMed:11221812 ]

General function:

Involved in G-protein coupled receptor protein signaling pathway

Specific function:

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis

Gene Name:

ADRB3

Uniprot ID:

P13945

Molecular weight:

43518.6

References

1. Baker JG: The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors. Br J Pharmacol. 2010 Jul;160(5):1048-61. doi: 10.1111/j.1476-5381.2010.00754.x. [PubMed:20590599 ]

PMID: 8863814

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