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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:41 UTC
HMDB IDHMDB0015477
Secondary Accession Numbers
  • HMDB15477
Metabolite Identification
Common NameClenbuterol
DescriptionClenbuterol 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 stimulates adenylyl cyclase activity which ultimately leads to downstream effects of smooth muscle relaxation in the bronchioles.
Structure
Data?1582753301
Synonyms
ValueSource
(+-)-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
ContraspasminKegg
PlanipartKegg
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 365HMDB
NAB-365HMDB
Chemical FormulaC12H18Cl2N2O
Average Molecular Weight277.19
Monoisotopic Molecular Weight276.079618622
IUPAC Name1-(4-amino-3,5-dichlorophenyl)-2-(tert-butylamino)ethan-1-ol
Traditional Nameclenbuterol
CAS Registry Number37148-27-9
SMILES
CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1
InChI Identifier
InChI=1S/C12H18Cl2N2O/c1-12(2,3)16-6-10(17)7-4-8(13)11(15)9(14)5-7/h4-5,10,16-17H,6,15H2,1-3H3
InChI KeySTJMRWALKKWQGH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.11 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9420000000-6706d3b9f245093754baSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-6090000000-db6af9c796c9356caa5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0zfr-0690000000-4ea9999e9adf3d869e7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0pb9-0090000000-4787e85eeb46d25e48ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-9081f080310110b928b2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0uyi-0970000000-180db1557f9de0905570Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0159-0900000000-5607a3961d5b1b526acaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0159-0900000000-f99c3fbb74f4657c8588Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00lr-0900000000-1b8353b766cd0eb328a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0f8c-1900000000-b34f6b0fe72dbe12dc7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0zgl-4900000000-85c1e6d67f6eb7f4660cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-9600000000-6d5ae5d64081ef26b128Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0090000000-acf898225ec20e842aceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zg0-1290000000-aa684358fbffa4f3acfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9i-6960000000-debe05c32ecf29e7984aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1090000000-e97792f89d018fba93a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-3290000000-864348c3a99c8de29569Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-6910000000-cf0a09b5733af5af5dd0Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01407 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01407 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01407
Phenol Explorer Compound IDNot Available
FooDB IDFDB008487
KNApSAcK IDNot Available
Chemspider ID2681
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClenbuterol
METLIN IDNot Available
PubChem Compound2783
PDB IDNot Available
ChEBI ID174690
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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 ]