5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol

• ChemBase ID: 749
• Molecular Formular: C12H19NO3
• Molecular Mass: 225.28416
• Monoisotopic Mass: 225.13649347
• SMILES: OC(CNC(C)(C)C)c1cc(O)cc(O)c1
• Canonical SMILES: OC(c1cc(O)cc(c1)O)CNC(C)(C)C
• InChI: InChI=1S/C12H19NO3/c1-12(2,3)13-7-11(16)8-4-9(14)6-10(15)5-8/h4-6,11,13-16H,7H2,1-3H3
• InChIKey: XWTYSIMOBUGWOL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol
• IUPAC Traditional name: terbutaline
• Brand Name: Brethaire; Brethine; Brican; Bricanyl; Bricar; Bricaril; Bricyn
• Synonyms: 2-tert-Butylamino-1-(3,5-dihydroxyphenyl)ethanol Hemisulfate; Brethaire; Brethine; Butalire; Monovent; Terbasmin; Terbul; Terbutaline Hemisulfate Salt; 5-(2-(tert-ButylaMino)-1-hydroxyethyl)benzene-1,3-diol; Terbutalina [Dcit]; Terbutaline Sulfate; Terbutalino [INN-Spanish]; Terbutalinum [INN-Latin]; Terbutalin; Terbutaline

Database IDs

• CAS Number: 23031-32-5; 23031-25-6
• PubChem SID: 160964212; 46506887
• PubChem CID: 5403

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.85872
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -1.8226097
• LogD (pH = 7.4): -0.726437
• Log P: 0.44103742
• Molar Refractivity: 63.0359 cm^3
• Polarizability: 24.725668 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.55
• LOG S: -1.59
• Solubility (Water): 5.84e+00 g/l

PROPERTIES

Physical Property

• Solubility: 213 mg/mL; DMSO; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 246-248°C
• Hydrophobicity(logP): 1.4

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 98%

DETAILS

DrugBank - DB00871

• Drug Groups: approved
• Description: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic. [PubChem]
• Indication: For the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible, obstructive airway disease, as well as symptomatic management of reversible bronchospasm associated with bronchitis and emphysema. Also used acute IV and sub-Q therapy in selected women to inhibit uterine contractions in preterm labor (tocolysis) and prolong gestation when beneficial.
• Pharmacology: Terbutaline is a relatively selective beta2-adrenergic bronchodilator that has little or no effect on alpha-adrenergic receptors. The drug has exerts a preferential effect on beta2-adrenergic receptors but stimulates beta-adrenergic receptors less selectively than relatively selective beta2-agonists. Terbutaline appears to have a greater stimulating effect on beta-receptors of the bronchial, vascular, and uterine smooth muscles (beta2 receptors) than on the beta-receptors of the heart (beta1 receptors). This drug relaxes smooth muscle and inhibits uterine contractions, but may also cause some cardiostimulatory effects and CNS stimulation.
• Toxicity: Terbutaline Sulfate: Oral LD₅₀(rat) = 8.7 g/kg; Oral LD₅₀(mouse) = 205 mg/kg; Oral LD₅₀(dog) = 1.5 g/kg; IP LD₅₀(rat)= 220 mg/kg ; IP LD₅₀(mouse) = 130 mg/kg; Oral LD₅₀(rabbit) = >8 g/kg; IV LD₅₀(mouse) = 36 mg/kg; IV LD₅₀(dog) = 116 mg/kg; IV LD₅₀(rabbit) = 110 mg/kg
• Affected Organisms: Humans and other mammals
• Absorption: Approximately 30-50% if administered orally and well absorbed subcutaneously.
• Half Life: 5.5-5.9 hours
• Elimination: About 90% of the drug was excreted in the urine at 96 hours after subcutaneous administration, with about 60% of this being unchanged drug. It appears that the sulfate conjugate is a major metabolite of terbutaline and urinary excretion is the primary route of elimination
• Clearance: * 311 +/- 112 mL/min
• References: Rhodes MC, Seidler FJ, Abdel-Rahman A, Tate CA, Nyska A, Rincavage HL, Slotkin TA: Terbutaline is a developmental neurotoxicant: effects on neuroproteins and morphology in cerebellum, hippocampus, and somatosensory cortex. J Pharmacol Exp Ther. 2004 Feb;308(2):529-37. Epub 2003 Nov 10. [Pubmed] ; Hochhaus G, Mollmann H: Pharmacokinetic/pharmacodynamic characteristics of the beta-2-agonists terbutaline, salbutamol and fenoterol. Int J Clin Pharmacol Ther Toxicol. 1992 Sep;30(9):342-62. [Pubmed] ; Haahtela T, Jarvinen M, Kava T, Kiviranta K, Koskinen S, Lehtonen K, Nikander K, Persson T, Reinikainen K, Selroos O, et al.: Comparison of a beta 2-agonist, terbutaline, with an inhaled corticosteroid, budesonide, in newly detected asthma. N Engl J Med. 1991 Aug 8;325(6):388-92. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - T109750

A B-Adrenergic receptor agonist. A Bronchodilator.

REFERENCES

• Rhodes MC, Seidler FJ, Abdel-Rahman A, Tate CA, Nyska A, Rincavage HL, Slotkin TA: Terbutaline is a developmental neurotoxicant: effects on neuroproteins and morphology in cerebellum, hippocampus, and somatosensory cortex. J Pharmacol Exp Ther. 2004 Feb;308(2):529-37. Epub 2003 Nov 10. Pubmed
• Hochhaus G, Mollmann H: Pharmacokinetic/pharmacodynamic characteristics of the beta-2-agonists terbutaline, salbutamol and fenoterol. Int J Clin Pharmacol Ther Toxicol. 1992 Sep;30(9):342-62. Pubmed
• Haahtela T, Jarvinen M, Kava T, Kiviranta K, Koskinen S, Lehtonen K, Nikander K, Persson T, Reinikainen K, Selroos O, et al.: Comparison of a beta 2-agonist, terbutaline, with an inhaled corticosteroid, budesonide, in newly detected asthma. N Engl J Med. 1991 Aug 8;325(6):388-92. Pubmed
• Akhtar, S., et al.: J. Vet. Pharmacol. Ther., 21, 388 (1998)
• Kasprowicz, D.J., et al.: J. Immunol., 165, 680 (2000)