Albuterol

Title: Albuterol
CAS Registry Number: 18559-94-9
CAS Name: a1-[[(1,1-Dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol
Additional Names: a1-[(tert-butylamino)methyl]-4-hydroxy-m-xylene-a,-diol; 2-(tert-butylamino)-1-(4-hydroxy-3-hydroxymethylphenyl)ethanol; 4-hydroxy-3-hydroxymethyl-a-[(tert-butylamino)methyl]benzyl alcohol; salbutamol
Manufacturers' Codes: AH-3365
Molecular Formula: C13H21NO3
Molecular Weight: 239.31
Percent Composition: C 65.25%, H 8.84%, N 5.85%, O 20.06%
Literature References: b-Adrenergic agonist. Prepn: L. H. C. Lunts et al., ZA 6705591; eidem, US 3644353 (1968, 1972 both to Allen & Hanburys). Synthesis and structure-activity studies: D. T. Collin et al., J. Med. Chem. 13, 674 (1970). Prepn of isomers: C. J. Hawkins, G. T. Klease, ibid. 16, 856 (1973); R. P. Bakale, Spec. Chem. 15, 249 (1995). Absolute configuration of isomers: D. Hartley, D. Middlemiss, J. Med. Chem. 14, 895 (1971). Pharmacology: R. T. Brittain et al., Nature 219, 862 (1968); V. A. Cullum et al., Br. J. Pharmacol. 35, 141 (1969). Metabolism: L. E. Martin et al., Eur. J. Pharmacol. 14, 183 (1971). Clinical comparison of levalbuterol with racemate: H. S. Nelson et al., J. Allergy Clin. Immunol. 102, 943 (1998). Comprehensive description: H. Y. Aboul-Enein et al., Anal. Profiles Drug Subs. 10, 665-689 (1981). Review of clinical experience in asthma and in preterm labor: A. H. Price, S. P. Clissold, Drugs 38, 77-122 (1989); of toxicology: S. E. Libretto, Arch. Toxicol. 68, 213-216 (1994). Review of clinical trials for add-on therapy to inhaled steroids: S. Shrewsbury et al., Br. Med. J. 320, 1368-1373 (2000).
Properties: Crystalline powder from ethanol-ethyl acetate or ethyl acetate-cyclohexane, mp 151° (Lunts); 157-158° (Collin). Sol in most organic solvents.
Melting point: mp 151° (Lunts); 157-158° (Collin)
Derivative Type: Sulfate
CAS Registry Number: 51022-70-9
Trademarks: Aerolin (3M Pharma); Asmaven (APS); Cobutolin (Cox); Ecovent (Ecosol); Loftan (GSK); Proventil (Schering-Plough); Salbulin (3M Pharma); Salbumol (GSK); Salbutard (Lusofarmaco); Salbuvent (Nycomed); Sultanol (GSK); Venetlin (Sankyo); Ventilastin (Viatris); Ventodisks (GSK); Ventolin (GSK); Volmax (GSK)
Molecular Formula: (C13H21NO3)2.H2SO4
Molecular Weight: 576.70
Percent Composition: C 54.15%, H 7.69%, N 4.86%, O 27.74%, S 5.56%
Properties: White crystalline powder. Sol in water; slightly sol in ethanol.
Derivative Type: (R)-Form
CAS Registry Number: 34391-04-3
Additional Names: Levalbuterol; levosalbutamol
Derivative Type: (R)-Form hydrochloride
CAS Registry Number: 50293-90-8
Trademarks: Xopenex (Sepracor)
Molecular Formula: C13H21NO3.HCl
Molecular Weight: 275.77
Percent Composition: C 56.62%, H 8.04%, N 5.08%, O 17.41%, Cl 12.86%
Properties: Crystallized as the monohydrate; changes crystalline form at 175°; dec 188-195°. [a]D20 -32.2° (c = 0.1 in water).
Optical Rotation: [a]D20 -32.2° (c = 0.1 in water)
Therap-Cat: Bronchodilator; tocolytic.
Keywords: ?Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives; Tocolytic.
Alclofenac Alclometasone Aldicarb Aldioxa Aldol

Salbutamol
Salbutamol.svg
Salbutamol-S-enantiomer-3D-balls.png
(S)-Salbutamol
Systematic (IUPAC) name
(RS)-4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
Clinical data
Pregnancy cat. A (AU) C (US)
Legal status Pharmacist Only (S3) (AU) F (prescription)[1] (CA) POM (UK) -only (US)
Routes Oral, inhalational, IV
Pharmacokinetic data
Metabolism Hepatic
Half-life 1.6 hours
Excretion Renal
Identifiers
CAS number 18559-94-9 YesY
ATC code R03AC02 R03CC02
PubChem CID 2083
IUPHAR ligand 558
DrugBank DB01001
ChemSpider 1999 YesY
UNII QF8SVZ843E YesY
KEGG D02147 YesY
ChEBI CHEBI:2549 N
ChEMBL CHEMBL714 YesY
Chemical data
Formula C13H21NO3 
Mol. mass 239.311
 N (what is this?)  (verify)

Salbutamol (INN) or albuterol (USAN) is a short-acting β2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and chronic obstructive pulmonary disease.[2] It is marketed as Ventolin among other brand names.

Salbutamol was the first selective β2-receptor agonist to be marketed in 1968. It was first sold by Allen & Hanburys (UK) under the brand name Ventolin, and has been used for the treatment of asthma ever since.[3] It was approved for use in the US by the FDA in May 1982.[4]

Salbutamol sulfate is sold in the USA as Ventolin HFA,[5] ProAir HFA,[6] or Proventil HFA,[7] and is also available in extended release tablets.[8] It is usually given by the inhaled route for direct effect on bronchial smooth muscle. This is usually achieved through a metered dose inhaler (MDI), nebulizer or other proprietary delivery devices (e.g. Rotahaler or Autohaler). In these forms of delivery, the maximal effect of salbutamol can take place within five to 20 minutes of dosing, though some relief is immediately seen. It can also be given intravenously.[9]