CLENBUTEROL

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H18Cl2N2O
Molecular Weight	277.1905
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)NCC(c1cc(c(c(c1)Cl)N)Cl)O

InChI

InChIKey=STJMRWALKKWQGH-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C12H18Cl2N2O
Molecular Weight	277.1905
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 194 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19245211	Agonist 2470		570.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 227 Sources: https://www.rlsnet.ru/tn_index_id_1750.htm	Primary		Approved 8043	SPIROPENT Approved Use Treatment of asthma, chroncic obstructive bronchitis, emphysema and other diseases.
Chronic obstructive pulmonary disease 191 Sources: https://www.rlsnet.ru/tn_index_id_1750.htm	Primary		Approved 8043	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
Clenbuterol-induced tardive dyskinesia.	1991 Oct	1742751
Is the "atypical" beta-receptor in the rat stomach fundus the rat beta 3 receptor?	1995 Jan	7815362
Early alterations of polyamine metabolism induced after acute administration of clenbuterol in mouse heart.	1999	10353628
The influence of indomethacin on the acth secretion induced by central stimulation of adrenergic receptors.	2000 Jun	10898105
[A case of immotile-dyskinetic cilia syndrome responding to clenbuterol hydrochloride and azithromycin].	2002 Jul	12382429
Role of myometrial activity in sperm transport through the genital tract and in fertilization in sows.	2002 May	12006096
Beta-adrenergic stimulation induces interleukin-18 expression via beta2-AR, PI3K, Akt, IKK, and NF-kappaB.	2004 Jun 25	15178407
Endotoxin-induced liver damage in rats is minimized by beta 2-adrenoceptor stimulation.	2004 Mar	15021963
Dobutamine inhibits phorbol-myristate-acetate-induced activation of nuclear factor-kappaB in human T lymphocytes in vitro.	2004 Nov	15502056
Dose-dependent apoptotic and necrotic myocyte death induced by the beta2-adrenergic receptor agonist, clenbuterol.	2005 Dec	16007677
[Resolution of clenbuterol hydrochloride enantiomers by thin-layer chromatography on silica gel impregnated with beta-cyclodextrin].	2005 Jul	16250460
Beta-adrenergic receptor modulation of the LPS-mediated depression in CYP1A activity in astrocytes.	2005 Mar 1	15710352
Adrenergic receptor agonists prevent bile duct injury induced by adrenergic denervation by increased cAMP levels and activation of Akt.	2006 Apr	16339297
[Use of ultrasensitive time-resolved fluoroimmunoassay for rapid detection of clenbuterol hydrochloride in urine].	2006 Nov	17290771
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
Pulmonary edema after electroconvulsive therapy in a patient treated for long-standing asthma with a beta2 stimulant.	2007 Mar	17435570
Metabolic responses to BRL37344 and clenbuterol in soleus muscle and C2C12 cells via different atypical pharmacologies and beta2-adrenoceptor mechanisms.	2008 Oct	18552870
Accumulation of the beta(2)-adrenergic agonist clenbuterol in mouse dark hair.	2009 Nov	19533101
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
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.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:55:18 UTC 2021` Edited by `admin` on `Fri Jun 25 21:55:18 UTC 2021`
Record UNII	XTZ6AXU7KN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLENBUTEROL

Official Name

English

CLENBUTEROL [MI]

Common Name

English

CLENBUTEROL [WHO-DD]

Common Name

English

CLENBUTEROL [INN]

Common Name

English

PLANIPART

Brand Name

English

NAB 365

Code

English

CONTRASPASMIN

Brand Name

English

NSC-758633

Code

English

Classification Tree Code System Code

WHO-VATC

QR03CC13