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Chemistry

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Also known as: 23031-25-6, Terbutalin, Brican, Brethine, Bricaril, Bricar

Molecular Formula

C₁₂H₁₉NO₃

Molecular Weight

225.28 g/mol

InChI Key

XWTYSIMOBUGWOL-UHFFFAOYSA-N

FDA UNII

N8ONU3L3PG

A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.

1 2D Structure

Terbutaline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

XWTYSIMOBUGWOL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C)NCC(C1=CC(=CC(=C1)O)O)O

2.2 Other Identifiers

2.2.1 UNII

N8ONU3L3PG

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Arubendol

2. Asthmoprotect

3. Brethaire

4. Brethine

5. Bricanyl

6. Bricanyl Sa

7. Butaliret

8. Butalitab

9. Contimit

10. Kwd 2019

11. Kwd-2019

12. Kwd2019

13. Monovent

14. Taziken

15. Tedipulmo

16. Terbasmin

17. Terbul

18. Terbutalin Al

19. Terbutalin Ratiopharm

20. Terbutalin Stada

21. Terbutalin Von Ct

22. Terbutalin-ratiopharm

23. Terbutaline Sulfate

24. Terbuturmant

2.3.2 Depositor-Supplied Synonyms

1. 23031-25-6

2. Terbutalin

3. Brican

4. Brethine

5. Bricaril

6. Bricar

7. Bricyn

8. Brethaire

9. Bricanyl

10. Terbutalinum

11. Terbutalina [dcit]

12. Terbutalina

13. Terbutalinum [inn-latin]

14. 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol

15. Terbutalino [inn-spanish]

16. (+-)-terbutaline

17. Asthmasian

18. Terbutaline Hemisulfate

19. 5-(2-(tert-butylamino)-1-hydroxyethyl)benzene-1,3-diol

20. Terbutaline (inn)

21. 46719-29-3

22. 1,3-benzenediol, 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-

23. Kwd-2019

24. Aerodur; Brican; Bricar

25. N8onu3l3pg

26. 5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-1,3-benzenediol

27. Chebi:9449

28. 1,3-benzenediol, 5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-

29. 23031-25-6 (free Base)

30. (+-)-5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-1,3-benzenediol

31. Terbutalino

32. 5-{2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl}benzene-1,3-diol

33. Terbutaline [inn]

34. 1,3-benzenediol, 5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-, (+-)-

35. Terbutaline [inn:ban]

36. Asthmasian (tn)

37. Einecs 245-385-8

38. Unii-n8onu3l3pg

39. Brn 2370513

40. Sr-01000000174

41. Bricanyl (salt/mix)

42. Terbutaline,(+/-)

43. Brethaire (salt/mix)

44. Spectrum_001030

45. Terbutaline [mi]

46. Prestwick0_000391

47. Prestwick1_000391

48. Prestwick2_000391

49. Prestwick3_000391

50. Spectrum2_001327

51. Spectrum3_000593

52. Spectrum4_000870

53. Spectrum5_001262

54. Terbutaline [vandf]

55. Schembl4391

56. Chembl1760

57. Lopac0_001126

58. Oprea1_823972

59. Bspbio_000601

60. Bspbio_002066

61. Gtpl560

62. Kbiogr_001539

63. Kbioss_001510

64. Terbutaline [who-dd]

65. Divk1c_000078

66. Spbio_001453

67. Spbio_002522

68. Bpbio1_000663

69. Terbutaline Sulfate (salt/mix)

70. Dtxsid7021310

71. Bdbm25770

72. Hy-b0802a

73. Kbio1_000078

74. Kbio2_001510

75. Kbio2_004078

76. Kbio2_006646

77. Kbio3_001566

78. Ninds_000078

79. Benzyl Alcohol, Alpha-((t-butylamino)methyl)-3,5-dihydroxy-

80. Pdsp1_000158

81. Pdsp2_000157

82. Akos015889885

83. Ccg-205201

84. Db00871

85. Sdccgsbi-0051094.p005

86. Idi1_000078

87. Ncgc00016010-03

88. Ncgc00016010-04

89. Ncgc00016010-06

90. Ncgc00016010-16

91. Ncgc00089821-02

92. Sbi-0051094.p004

93. Ab00053548

94. Cs-0013822

95. Ft-0674864

96. C07129

97. D08570

98. Ab00053548_15

99. 031t256

100. A816514

101. L000594

102. Q424340

103. J-014950

104. Sr-01000000174-2

105. 1-(3',5'-dihydroxyphenyl)-2-(t-butylamino)-ethanol

106. Brd-a50157456-065-02-4

107. Brd-a50157456-065-12-3

108. 5-[2-(tert-butylamino)-1-hydroxyethyl]-1,3-benzenediol #

109. 5-[2-(tert-butylamino)-1-oxidanyl-ethyl]benzene-1,3-diol

110. 5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-diol, 5

111. Benzyl Alcohol, .alpha.-((t-butylamino)methyl)-3,5-dihydroxy-

112. (rs)-5-(2-(tert-butylamino)-1-hydroxyethyl)benzene-1,3-diol

113. 1164563-86-3

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₉NO₃
Molecular Weight	225.28 g/mol
XLogP3	0.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	225.13649347 g/mol
Monoisotopic Mass	225.13649347 g/mol
Topological Polar Surface Area	72.7 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	205
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Terbutaline sulfate
Drug Label	Terbutaline Sulfate, USP, the active ingredient of Terbutaline Sulfate Injection, USP, is a betaadrenergic agonist bronchodilator available as a sterile, nonpyrogenic, aqueous solution in vials, for subcutaneous administration. Each milliliter of...
Active Ingredient	Terbutaline sulfate
Dosage Form	Tablet; Injectable
Route	Injection; Oral
Strength	2.5mg; 1mg/ml; 5mg
Market Status	Prescription
Company	Bedford; Hikma Farmaceutica; United Biomedcl; Fresenius Kabi Usa; Lannett; Impax Labs; Akorn

2 of 2
Drug Name	Terbutaline sulfate
Drug Label	Terbutaline Sulfate, USP, the active ingredient of Terbutaline Sulfate Injection, USP, is a betaadrenergic agonist bronchodilator available as a sterile, nonpyrogenic, aqueous solution in vials, for subcutaneous administration. Each milliliter of...
Active Ingredient	Terbutaline sulfate
Dosage Form	Tablet; Injectable
Route	Injection; Oral
Strength	2.5mg; 1mg/ml; 5mg
Market Status	Prescription
Company	Bedford; Hikma Farmaceutica; United Biomedcl; Fresenius Kabi Usa; Lannett; Impax Labs; Akorn

4.2 Drug Indication

Terbutaline is indicated for prevention and reversal of bronchospasm in patients at least 12 years old, with asthma and reversible bronchospasm associated with bronchitis and emphysema.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Terbutaline is a beta-2 adrenergic receptor agonist indicated to treat reversibly bronchospasm in asthmatic patients with bronchitis and emphysema. It has a short duration as the inhaled form is taken up to three times daily, and the therapeutic window is wide.

5.2 MeSH Pharmacological Classification

Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

Adrenergic beta-2 Receptor Agonists

Compounds bind to and activate ADRENERGIC BETA-2 RECEPTORS. (See all compounds classified as Adrenergic beta-2 Receptor Agonists.)

Sympathomimetics

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)

Tocolytic Agents

Drugs that prevent preterm labor and immature birth by suppressing uterine contractions (TOCOLYSIS). Agents used to delay premature uterine activity include magnesium sulfate, beta-mimetics, oxytocin antagonists, calcium channel inhibitors, and adrenergic beta-receptor agonists. The use of intravenous alcohol as a tocolytic is now obsolete. (See all compounds classified as Tocolytic Agents.)

5.3 ATC Code

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03A - Adrenergics, inhalants

R03AC - Selective beta-2-adrenoreceptor agonists

R03AC03 - Terbutaline

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03C - Adrenergics for systemic use

R03CC - Selective beta-2-adrenoreceptor agonists

R03CC03 - Terbutaline

5.4 Absorption, Distribution and Excretion

Absorption

A 0.5 mg subcutaneous dose of terbutaline reaches a mean C_max of 9.6 ng/mL, with a median T_max of 0.5 hours, and a mean AUC of 29.4 14.2 h\*ng/mL. A 5 mg oral terbutaline tablet reaches a mean C_max of 8.3 3.9 ng/mL with a median T_max of 2 hours, and a mean AUC of 54.6 26.8 h\*ng/mL. A 5 mg oral terbutaline solution reaches a mean C_max of 8.6 3.6 ng/mL, with a median T_max of 1.5 hours, and a mean AUC of 53.1 23.5 h\*ng/mL. Oral terbutaline has an oral bioavailability of 14-15%.

Route of Elimination

An oral dose of terbutaline is 40% eliminated in the urine after 72 hours. The major metabolite in the urine was the sulphate conjugated form of terbutaline. Parenteral doses of terbutaline are 90% eliminated in the urine, with approximately 2/3 as the unchanged parent drug. Less than 1% of a dose of terbutaline is eliminated in the feces.

Volume of Distribution

Terbutaline has a mean volume of distribution of 1.6 L/kg.

Clearance

The average clearance of terbutaline is 3.0 mL/min/kg.

5.5 Metabolism/Metabolites

Terbutaline is sulphated or glucuronidated prior to elimination.

5.6 Biological Half-Life

An oral dose of terbutaline has an elimination half life of 3.4 hours, while a subcutaneous dose has an elimination half life of 2.9 hours.

5.7 Mechanism of Action

Terbutaline is a selective beta-2 adrenergic receptor agonist. Agonism of these receptors in bronchioles activates adenylyl cyclase, increasing intracellular cyclic adenosine monophosphate (cAMP). Increased cAMP decreases intracellular calcium, activating protein kinase A, inactivating myosin light-chain kinase, activating myosin light-chain phosphatase, and finally relaxing smooth muscle in the bronchiole.

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