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Identification
NameClenbuterol
Accession NumberDB01407
Typesmall molecule
Groupsapproved
Description

A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(±)-clenbuterolNot AvailableNot Available
1-(4-Amino-3,5-dichloro-phenyl)-2-tert-butylamino-ethanolNot AvailableNot Available
4-amino-α-((tert-butylamino)methyl)-3,5-dichlorobenzyl alcoholNot AvailableNot Available
ClenbuterolumLatinINN
SaltsNot Available
Brand names
NameCompany
MonoresValeas
SpiropentBoehringer Ingelheim
Brand mixturesNot Available
Categories
CAS number37148-27-9
WeightAverage: 277.19
Monoisotopic: 276.079618622
Chemical FormulaC12H18Cl2N2O
InChI KeySTJMRWALKKWQGH-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(4-amino-3,5-dichlorophenyl)-2-(tert-butylamino)ethan-1-ol
SMILES
CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassHalobenzenes
Direct parentDichlorobenzenes
Alternative parentsAnilines; Aryl Chlorides; Primary Aromatic Amines; Secondary Alcohols; 1,2-Aminoalcohols; Dialkylamines; Polyamines; Organochlorides
Substituentsaniline; aryl halide; primary aromatic amine; aryl chloride; 1,2-aminoalcohol; secondary alcohol; secondary aliphatic amine; secondary amine; polyamine; organohalogen; organochloride; primary amine; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
Pharmacology
IndicationUsed as a bronchodilator in the treatment of asthma patients.
PharmacodynamicsClenbuterol is a substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma. Although approved for use in some countries, as of fall, 2006, clenbuterol is not an ingredient of any therapeutic drug approved by the U.S. Food and Drug Administration.
Mechanism of actionClenbuterol 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.
Absorption89-98% orally
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half life36-39 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9484
Blood Brain Barrier + 0.8631
Caco-2 permeable + 0.5375
P-glycoprotein substrate Substrate 0.5588
P-glycoprotein inhibitor I Non-inhibitor 0.8863
P-glycoprotein inhibitor II Non-inhibitor 0.9627
Renal organic cation transporter Non-inhibitor 0.9052
CYP450 2C9 substrate Non-substrate 0.8142
CYP450 2D6 substrate Non-substrate 0.683
CYP450 3A4 substrate Non-substrate 0.5835
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.831
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5428
Ames test Non AMES toxic 0.8858
Carcinogenicity Non-carcinogens 0.5199
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.6024 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9704
hERG inhibition (predictor II) Non-inhibitor 0.8546
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point174-175.5Keck, J., Kruger, G., Machleidt, H., Noll, K., Engelhardt, G. and Eckenfels, A.; U S . Patent 3,536,712; October 27,1970: assigned to Boehringer lngelheim G.m.b.H. (Germany).
Predicted Properties
PropertyValueSource
water solubility1.12e-01 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 area58.28ChemAxon
rotatable bond count4ChemAxon
refractivity73.38ChemAxon
polarizability28.81ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceKeck, J., Kruger, G., Machleidt, H., Noll, K., Engelhardt, G. and Eckenfels, A.; U S . Patent

3,536,712; October 27,1970: assigned to Boehringer lngelheim G.m.b.H. (Germany).

General ReferenceNot Available
External Links
ResourceLink
PubChem Compound2783
PubChem Substance46508373
ChemSpider2681
BindingDB27958
ChEBI174690
ChEMBLCHEMBL49080
Therapeutic Targets DatabaseDAP000945
PharmGKBPA164745640
WikipediaClenbuterol
ATC CodesR03CC13R03AC14
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Beta-2 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Beta-2 adrenergic receptor P07550 Details

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
  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
  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
  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
  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
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

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. Pubmed

3. Beta-3 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-3 adrenergic receptor P13945 Details

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. Pubmed

4. Beta-nerve growth factor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: stimulator

Components

Name UniProt ID Details
Beta-nerve growth factor P01138 Details

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
  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
  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
  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
  5. Riaz SS, Tomlinson DR: Clenbuterol stimulates neurotrophic support in streptozotocin-diabetic rats. Diabetes Obes Metab. 1999 Jan;1(1):43-51. Pubmed

5. Tumor necrosis factor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: other/unknown

Components

Name UniProt ID Details
Tumor necrosis factor P01375 Details

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
  2. Yoshimura T: [Modulation of cytokine production from human mononuclear cells by several agents] Yakugaku Zasshi. 2000 Dec;120(12):1277-90. Pubmed
  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
  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
  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

Enzymes

1. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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. Epub 2009 Nov 24. Pubmed

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Drug created on July 17, 2007 06:33 / Updated on April 04, 2014 14:38