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23031-32-5 molecular structure
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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 and InChIs

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

Cite this record

CBID:749 http://www.chembase.cn/molecule-749.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
23031-32-5
23031-25-6
PubChem SID
46506887
160964212
PubChem CID
5403

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.85872  H Acceptors
H Donor LogD (pH = 5.5) -1.8226097 
LogD (pH = 7.4) -0.726437  Log P 0.44103742 
Molar Refractivity 63.0359 cm3 Polarizability 24.725668 Å3
Polar Surface Area 72.72 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.55  LOG S -1.59 
Solubility (Water) 5.84e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
213 mg/mL expand Show data source
DMSO expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
246-248°C expand Show data source
Hydrophobicity(logP)
1.4 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Purity
98% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00871 external link
Item Information
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 external link
A B-Adrenergic receptor agonist. A Bronchodilator.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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