Salbutamol
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Basic Info
| Common Name | Salbutamol(F05491) |
| 2D Structure | |
| Description | Salbutamol is a short-acting, selective beta2-adrenergic receptor agonist used in the treatment of asthma and COPD. It is 29 times more selective for beta2 receptors than beta1 receptors giving it higher specificity for pulmonary beta receptors versus beta1-adrenergic receptors located in the heart. Salbutamol is formulated as a racemic mixture of the R- and S-isomers. The R-isomer has 150 times greater affinity for the beta2-receptor than the S-isomer and the S-isomer has been associated with toxicity. This lead to the development of levalbuterol, the single R-isomer of salbutamol. However, the high cost of levalbuterol compared to salbutamol has deterred wide-spread use of this enantiomerically pure version of the drug. Salbutamol is generally used for acute episodes of bronchospasm caused by bronchial asthma, chronic bronchitis and other chronic bronchopulmonary disorders such as chronic obstructive pulmonary disorder (COPD). It is also used prophylactically for exercise-induced asthma. |
| FRCD ID | F05491 |
| CAS Number | 18559-94-9 |
| PubChem CID | 2083 |
| Formula | C13H21NO3 |
| IUPAC Name | 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol |
| InChI Key | NDAUXUAQIAJITI-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3 |
| Canonical SMILES | CC(C)(C)NCC(C1=CC(=C(C=C1)O)CO)O |
| Isomeric SMILES | CC(C)(C)NCC(C1=CC(=C(C=C1)O)CO)O |
| Wikipedia | Salbutamol |
| Synonyms |
dl-Salbutamol
Salbutamol
albuterol
18559-94-9
Proventil
Sultanol
Volmax
Broncovaleas
Aerolin
dl-Albuterol
|
| Classifies |
Illegal Additives
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzyl alcohols |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzyl alcohols |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Benzyl alcohol - Phenol - Aralkylamine - 1-hydroxy-2-unsubstituted benzenoid - Secondary alcohol - 1,2-aminoalcohol - Secondary amine - Secondary aliphatic amine - Hydrocarbon derivative - Alcohol - Aromatic alcohol - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Amine - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 239.315 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 227 |
| Monoisotopic Mass | 239.152 |
| Exact Mass | 239.152 |
| XLogP | 0.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 17 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9659 |
| Human Intestinal Absorption | HIA+ | 0.9812 |
| Caco-2 Permeability | Caco2- | 0.7112 |
| P-glycoprotein Substrate | Substrate | 0.6840 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8781 |
| Non-inhibitor | 0.9673 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8974 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7661 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7897 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Non-substrate | 0.7074 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9197 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9287 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9343 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8834 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9564 |
| Non-inhibitor | 0.9288 | |
| AMES Toxicity | Non AMES toxic | 0.8409 |
| Carcinogens | Non-carcinogens | 0.8863 |
| Fish Toxicity | High FHMT | 0.6583 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9493 |
| Honey Bee Toxicity | High HBT | 0.5419 |
| Biodegradation | Not ready biodegradable | 0.9734 |
| Acute Oral Toxicity | III | 0.7801 |
| Carcinogenicity (Three-class) | Warning | 0.5392 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.2822 | LogS |
| Caco-2 Permeability | 0.4866 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5275 | LD50, mol/kg |
| Fish Toxicity | 1.6043 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.1839 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Determination of ractopamine and salbutamol in pig hair by liquid chromatography tandem mass spectrometry. | J Food Drug Anal | 2018 Apr | 29567243 |
| Highly stable aluminum-based metal-organic frameworks as biosensing platforms for assessment of food safety. | Biosens Bioelectron | 2017 May 15 | 28152486 |
| Ag/N-doped reduced graphene oxide incorporated with molecularly imprintedpolymer: An advanced electrochemical sensing platform for salbutamoldetermination. | Biosens Bioelectron | 2017 Apr 15 | 27898378 |
| A novel aptasensor for electrochemical detection of ractopamine, clenbuterol,salbutamol, phenylethanolamine and procaterol. | Biosens Bioelectron | 2016 Jun 15 | 26890828 |
| Rapid screening of toxic salbutamol, ractopamine, and clenbuterol in pork sample by high-performance liquid chromatography-UV method. | J Food Drug Anal | 2016 Apr | 28911579 |
| Metabolomic analysis of swine urine treated with β2-agonists by ultra-highperformance liquid chromatography-quadrupole time-of-flight mass spectrometry. | J Chromatogr A | 2015 Jun 26 | 25980694 |
| Development and validation of a sensitive method for simultaneous determination of eight β₂-agonists in pork by ultrasonic-assisted extraction and liquid chromatography/tandem mass spectrometry. | J Chromatogr Sci | 2015 Jan | 24771052 |
| Reactivity of β-blockers/agonists with aqueous permanganate. Kinetics and transformation products of salbutamol. | Water Res | 2015 Aug 1 | 25965887 |
| Evaluation of matrix solid-phase dispersion extraction for 11 β-agonists in swinefeed by liquid chromatography with electrospray ionization tandem massspectrometry. | J Sep Sci | 2014 Sep | 24981594 |
| Ultrasensitive and quantitative detection of a new β-agonist phenylethanolamine Aby a novel immunochromatographic assay based on surface-enhanced Raman scattering(SERS). | J Agric Food Chem | 2014 Nov 12 | 25343225 |
| Sulfonated polystyrene magnetic nanobeads coupled with immunochromatographicstrip for clenbuterol determination in pork muscle. | Talanta | 2014 Nov | 25127616 |
| Development of a highly sensitive and specific enzyme-linked immunosorbent assay (ELISA) for the detection of phenylethanolamine A in tissue and feed samples and confirmed by liquid chromatography tandem mass spectrometry (LC-MS/MS). | Talanta | 2013 Oct 15 | 24054641 |
| Electrochemical detection of toxic ractopamine and salbutamol in pig meat and human urine samples by using poly taurine/zirconia nanoparticles modified electrodes. | Colloids Surf B Biointerfaces | 2013 Oct 1 | 23732800 |
| Multiresidue analysis of nine β-agonists in animal muscles by LC-MS/MS based on anew polymer cartridge for sample cleanup. | J Sep Sci | 2013 Jun | 23504869 |
| Colorimetric detection of ractopamine and salbutamol using gold nanoparticlesfunctionalized with melamine as a probe. | Talanta | 2013 Aug 15 | 23708531 |
| Bronchiolitis. | BMJ Clin Evid | 2011 Apr 11 | 21486501 |
| Multicomponent mesofluidic system for the detection of veterinary drug residuesbased on competitive immunoassay. | Anal Biochem | 2010 Oct 1 | 20621709 |
| Determination of beta-agonists in pig feed, pig urine and pig liver usingcapillary electrophoresis with electrochemical detection. | Meat Sci | 2010 Jun | 20374903 |
| [Simultaneous determination of nine beta-agonist residues in animal derived foodsby ultra performance liquid chromatography-tandem mass spectrometry]. | Se Pu | 2008 Nov | 19253549 |
| Bronchiolitis. | BMJ Clin Evid | 2007 Oct 10 | 19450362 |
Targets
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- 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
- Baker JG: The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors. Br J Pharmacol. 2005 Feb;144(3):317-22. [15655528 ]