CLENBUTEROL

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H18Cl2N2O
Molecular Weight	277.19
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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	277.19
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 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
Effect of clenbuterol on skeletal muscle atrophy in mice induced by the glucocorticoid dexamethasone.	1992 May	1351811
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
Early alterations of polyamine metabolism induced after acute administration of clenbuterol in mouse heart.	1999	10353628
beta1 to beta3 switch in control of cyclic adenosine monophosphate during brown adipocyte development explains distinct beta-adrenoceptor subtype mediation of proliferation and differentiation.	1999 Sep	10465291
The influence of indomethacin on the acth secretion induced by central stimulation of adrenergic receptors.	2000 Jun	10898105
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
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
Antitussive effects of the leukotriene receptor antagonist montelukast in patients with cough variant asthma and atopic cough.	2010 Jun	20299826

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 Dec 15 15:40:55 GMT 2023` Edited by `admin` on `Fri Dec 15 15:40:55 GMT 2023`
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