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Identification
NameClenbuterol
Accession NumberDB01407
TypeSmall Molecule
GroupsApproved, Vet Approved
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
(+-)-Clenbuterol
(±)-clenbuterol
1-(4-Amino-3,5-dichloro-phenyl)-2-tert-butylamino-ethanol
4-amino-3,5-Dichloro-alpha-(((1,1-dimethylethyl)amino)methyl)benzenemethanol
4-amino-alpha-((Tert-butylamino)methyl)-3,5-dichlorobenzyl alcohol
4-amino-α-((tert-butylamino)methyl)-3,5-dichlorobenzyl alcohol
CLENBUTEROL
Clenbuterolum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MonoresValeas
SpiropentBoehringer Ingelheim
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Clenbuterol hydrochloride
ThumbNot applicableDBSALT001621
Categories
UNIIXTZ6AXU7KN
CAS number37148-27-9
WeightAverage: 277.19
Monoisotopic: 276.079618622
Chemical FormulaC12H18Cl2N2O
InChI KeyInChIKey=STJMRWALKKWQGH-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as substituted anilines. These are organic compound containing an aniline group substituted at one or more positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilines
Direct ParentSubstituted anilines
Alternative Parents
Substituents
  • Substituted aniline
  • 1,3-dichlorobenzene
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Primary aromatic amine
  • Aryl halide
  • Aryl chloride
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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.
Related Articles
Absorption89-98% orally
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9484
Blood Brain Barrier+0.8631
Caco-2 permeable+0.5375
P-glycoprotein substrateSubstrate0.5588
P-glycoprotein inhibitor INon-inhibitor0.8863
P-glycoprotein inhibitor IINon-inhibitor0.9627
Renal organic cation transporterNon-inhibitor0.9052
CYP450 2C9 substrateNon-substrate0.8142
CYP450 2D6 substrateNon-substrate0.683
CYP450 3A4 substrateNon-substrate0.5835
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5428
Ames testNon AMES toxic0.8858
CarcinogenicityNon-carcinogens0.5199
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6024 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9704
hERG inhibition (predictor II)Non-inhibitor0.8546
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 Solubility0.112 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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.38 m3·mol-1ChemAxon
Polarizability28.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 ReferencesNot Available
External Links
ATC CodesR03AC14R03CC13
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.9 KB)
Interactions
Drug Interactions
Drug
AcetaminophenThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Acetaminophen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Acetylsalicylic acid.
AminophyllineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Aminophylline.
AmphetamineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Clenbuterol.
BenzphetamineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Benzphetamine.
ButalbitalThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Caffeine.
CocaineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Cocaine.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dopamine.
DoxapramThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Doxapram.
DronabinolDronabinol may increase the tachycardic activities of Clenbuterol.
DyphyllineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Epinephrine.
FenoterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Fenoterol.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Formoterol.
IndacaterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Clenbuterol.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Ipratropium bromide.
IsomethepteneThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Isometheptene.
LevonordefrinThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Clenbuterol.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Lisdexamfetamine.
MepivacaineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Mepivacaine.
MethamphetamineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Midodrine.
ModafinilThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Modafinil.
NabiloneNabilone may increase the tachycardic activities of Clenbuterol.
NaphazolineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Naphazoline.
NorepinephrineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Norepinephrine.
OlodaterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Olodaterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Oxymetazoline.
PhendimetrazineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Phendimetrazine.
PheniramineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Pheniramine.
PhentermineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Phenylephrine.
PirbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Pirbuterol.
PropylhexedrineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Propylhexedrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Racepinephrine.
SalbutamolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Salmeterol.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Clenbuterol.
TerbutalineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Terbutaline.
TheophyllineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Theophylline.
TriprolidineThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Vilanterol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein homodimerization activity
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:
46458.32 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Receptor signaling protein activity
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. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular Weight:
51322.1 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein homodimerization activity
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:
43518.615 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
stimulator
General Function:
Receptor signaling protein activity
Specific Function:
Nerve growth factor is important for the development and maintenance of the sympathetic and sensory nervous systems. Extracellular ligand for the NTRK1 and NGFR receptors, activates cellular signaling cascades through those receptor tyrosine kinase to regulate neuronal proliferation, differentiation and survival. Inhibits metalloproteinase dependent proteolysis of platelet glycoprotein VI (PubM...
Gene Name:
NGF
Uniprot ID:
P01138
Molecular Weight:
26958.53 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other/unknown
General Function:
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. Impairs ...
Gene Name:
TNF
Uniprot ID:
P01375
Molecular Weight:
25644.15 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d 24-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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
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 ]
Comments
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Drug created on July 17, 2007 06:33 / Updated on August 17, 2016 12:23