CLENBUTEROL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H18Cl2N2O.ClH
Molecular Weight	313.651
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1

InChI

InChIKey=OPXKTCUYRHXSBK-UHFFFAOYSA-N

InChI=1S/C12H18Cl2N2O.ClH/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;1H

HIDE SMILES / InChI

Description
Sources: http://rmtcnet.com/wp-content/uploads/2015/07/RMTC-Position-Paper-on-Clenbuterol.pdf
Curator's Comment: description was created based on several sources, including https://www.deadiversion.usdoj.gov/drug_chem_info/clenbuterol.pdf

Clenbuterol is agonist of beta2 adrenergic receptor. In some countries it is used as bronchodilator for treatment of asthma, but is not approved in USA. The drug is abused by bodybuilders and athletes for its ability to increase lean muscle mass and to reduce body fat. In 1998 FDA approved the clenbuterol-based Ventipulmin Syrup as a prescription-only drug for treatment of airway obstruction in horses.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19245211	Agonist 2678		570.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.rlsnet.ru/tn_index_id_1750.htm	Primary		Approved 8429	SPIROPENT Approved Use Treatment of asthma, chroncic obstructive bronchitis, emphysema and other diseases.
Chronic obstructive pulmonary disease 174 Sources: https://www.rlsnet.ru/tn_index_id_1750.htm	Primary		Approved 8429	CLENBUTEROL Approved Use Treatment of asthma, chroncic obstructive bronchitis, emphysema and other diseases.

PubMed

Title	Date	PubMed
[Novel quantitative assessment of the tremorogenic effects of the beta 2-mimetics clenbuterol and salbutamol after oral administration].	1985	3907640
Is the "atypical" beta-receptor in the rat stomach fundus the rat beta 3 receptor?	1995 Jan	7815362
Adrenergic agents inhibit rapid increases in cerebellar Purkinje cell glutamic acid decarboxylase (GAD67) mRNA levels after climbing fiber lesions or reserpine treatment.	1996 Mar 1	8774452
Clenbuterol and anabolic steroids: a previously unreported cause of myocardial infarction with normal coronary arteriograms.	1998 Aug	9715231
[A case of immotile-dyskinetic cilia syndrome responding to clenbuterol hydrochloride and azithromycin].	2002 Jul	12382429
Beta-adrenergic stimulation induces interleukin-18 expression via beta2-AR, PI3K, Akt, IKK, and NF-kappaB.	2004 Jun 25	15178407
Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro.	2004 Nov	15502056
[Enantiomeric resolution of clenbuterol hydrochloride using (2R, 3R)-Dicyclohexyl tartrate impregnated thin layer chromatography].	2005 Nov	16499011
An increase in murine skeletal muscle peroxisome proliferator-activated receptor-gamma coactivator-1alpha (PGC-1alpha) mRNA in response to exercise is mediated by beta-adrenergic receptor activation.	2007 Jul	17446185
Metabolic responses to BRL37344 and clenbuterol in soleus muscle and C2C12 cells via different atypical pharmacologies and beta2-adrenoceptor mechanisms.	2008 Oct	18552870
Solid substrate-room temperature phosphorimetry for the determination of residual clenbuterol hydrochloride based on the catalysis of sodium periodate oxidizing eosine Y.	2009 Apr 6	19298881
Beta2-adrenergic agonist-induced hypertrophy of the quadriceps skeletal muscle does not modulate disease severity in the rodent meniscectomy model of osteoarthritis.	2010 Apr	20060953
Beta(2)-adrenoceptor agonist clenbuterol reduces infarct size and myocardial apoptosis after myocardial ischaemia/reperfusion in anaesthetized rats.	2010 Jul	20590644
Antitussive effects of the leukotriene receptor antagonist montelukast in patients with cough variant asthma and atopic cough.	2010 Jun	20299826
Blocking beta2-adrenergic receptor attenuates acute stress-induced amyloid beta peptides production.	2010 Mar 4	20059989

Patents

Sample Use Guides

In Vivo Use Guide

For treatmen of airways obstruction the clenbuterol is administered orally, 15ml of syrop 2-3 times a day.

Route of Administration: Oral

In Vitro Use Guide

Affinity towards beta2 adrenergic receptors was measured using the recombinant receptor expressed in Sf-9 cells. Cell membrane homogenates were incubated with 0.15 nM of radioligand [3H]CGP1217 in the absence of presence of the clenbuterol. Following incubation, the samples were filtered rapidly under vacuum through through glass fiber filters, the filters were dried, and counted for radioactivity in a scintillation counter. Clenbuterol was binding to beta2 receptor with Ki of 0.58 uM.

Name

Type

Language

CLENBUTEROL HYDROCHLORIDE

Common Name

English

CLENBUTEROL HYDROCHLORIDE [EP IMPURITY]

Common Name

English

Clenbuterol hydrochloride [WHO-DD]

Common Name

English

NAB-365

Code

English

VENTIPULMIN

Brand Name

English

NAB 365 CL

Code

English

NAB-365CL

Code

English

CLENBUTEROL HYDROCHLORIDE [GREEN BOOK]

Common Name

English

CLENBUTEROL HYDROCHLORIDE [JAN]

Common Name

English

CLENBUTEROL HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

CLENBUTEROL HCL

Common Name

English

4-AMINO-.ALPHA.-((TERT-BUTYLAMINO)METHYL)-3,5-DICHLOROBENZYL ALCOHOL

Systematic Name

English

CLENBUTEROL HYDROCHLORIDE [MART.]

Common Name

English

CLENBUTEROL HYDROCHLORIDE [MI]

Common Name

English

CLENBUTEROL HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

SPIROPENT

Brand Name

English

CLENBUTEROL HYDROCHLORIDE [USP-RS]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149