4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

• ChemBase ID: 874
• Molecular Formular: C13H21NO3
• Molecular Mass: 239.31074
• Monoisotopic Mass: 239.15214354
• SMILES: OC(CNC(C)(C)C)c1cc(c(O)cc1)CO
• Canonical SMILES: OCc1cc(ccc1O)C(CNC(C)(C)C)O
• 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
• InChIKey: NDAUXUAQIAJITI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
• IUPAC Traditional name: salbutamol
• Brand Name: Accuneb; Aerolin; Asmaven; Broncovaleas; Cetsim; Cobutolin; Ecovent; Loftan; Proventil; Rotahaler; Salbulin; Salbutard; Salbutine; Salbuvent; Solbutamol; Sultanol; Venetlin; Ventalin Inhaler; Ventolin; Ventolin Inhaler; Ventolin Rotacaps; Volma; Volmax; Xopenex; Airomir; Asthalin; Asthavent; Asmol; Buventol; ProAir; Salamol; ProAir HFA; Proventil HFA; Ventolin HFA; Xopenex HFA
• Synonyms: Salbutamol; α-[(tert-Butylamino)methyl]-4-hydroxy-m-xylene-α,α′-diol; Albuterol; Albuterol Sulfate; Salbutamol Sulfate; Salbutamol Sulphate; Albuterol Sulphate; Levalbuterol; Salbutamol; α-[(t-Butylamino)methyl]-4-hydroxy-m-xylene-α,α'-diol; α-[(叔丁基氨基)甲基]-4-羟基-间二甲苯-α,α′-二醇; 舒喘灵; 沙丁胺醇

Database IDs

• CAS Number: 18559-94-9
• EC Number: 242-424-0
• MDL Number: MFCD00148978
• Beilstein Number: 6405698
• PubChem SID: 24870392; 160964337; 46505312; 24278712
• PubChem CID: 2083

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.121162
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.306487
• LogD (pH = 7.4): -1.3223417
• Log P: 0.34441614
• Molar Refractivity: 67.8709 cm^3
• Polarizability: 26.575071 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.44
• LOG S: -2.05
• Solubility (Water): 2.15e+00 g/l

PROPERTIES

Physical Property

• Solubility: 3 mg/L
• Melting Point: 157°C
• Hydrophobicity(logP): 1.4

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: ZE4400000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22-43
• Safety Statements: 36; S:28-46-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... ADRB2(154)

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C13H21NO3

DETAILS

MP Biomedicals - 02156573

Free Base

DrugBank - DB01001

• Drug Groups: approved
• 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.
• Indication: For symptomatic relief and prevention of bronchospasm due to bronchial asthma, chronic bronchitis, and other chronic bronchopulmonary disorders such as COPD.
• Pharmacology: Salbutamol (INN) or albuterol (USAN), a moderately selective beta(2)-receptor agonist similar in structure to terbutaline, is widely used as a bronchodilator to manage asthma and other chronic obstructive airway diseases. The R-isomer, levalbuterol, is responsible for bronchodilation while the S-isomer increases bronchial reactivity. The R-enantiomer is sold in its pure form as Levalbuterol. The manufacturer of levalbuterol, Sepracor, has implied (although not directly claimed) that the presence of only the R-enantiomer produces fewer side-effects.
• Toxicity: LD₅₀=1100 mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hydrolyzed by esterases in tissue and blood to the active compound colterol. The drug is also conjugatively metabolized to salbutamol 4'-O-sulfate.
• Absorption: Systemic absorption is rapid following aerosol administration.
• Half Life: 1.6 hours
• Elimination: Approximately 72% of the inhaled dose is excreted in the urine within 24 hours, 28% as unchanged drug and 44% as metabolite.
• External Links: Wikipedia; RxList

Sigma Aldrich - S8260

Biochem/physiol Actions
β2-肾上腺素受体激动剂

Sigma Aldrich - 46725

Biochem/physiol Actions
β2-adrenoceptor agonist
Caution
sensitive to light
General description
Standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706019, T706030, T706020
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 46725

Biochem/physiol Actions
β2-adrenoceptor agonist
Caution
sensitive to light
General description
Standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706019, T706030, T706020
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC