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Chemistry

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Also known as: 36505-84-7, Buspirona, Buspironum, Buspironum [inn-latin], Buspirona [inn-spanish], Gen-buspirone
Molecular Formula
C21H31N5O2
Molecular Weight
385.5  g/mol
InChI Key
QWCRAEMEVRGPNT-UHFFFAOYSA-N
FDA UNII
TK65WKS8HL

Buspirone
An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.
1 2D Structure

Buspirone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4.5]decane-7,9-dione
2.1.2 InChI
InChI=1S/C21H31N5O2/c27-18-16-21(6-1-2-7-21)17-19(28)26(18)11-4-3-10-24-12-14-25(15-13-24)20-22-8-5-9-23-20/h5,8-9H,1-4,6-7,10-17H2
2.1.3 InChI Key
QWCRAEMEVRGPNT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CCC2(C1)CC(=O)N(C(=O)C2)CCCCN3CCN(CC3)C4=NC=CC=N4
2.2 Other Identifiers
2.2.1 UNII
TK65WKS8HL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Anxut

2. Apo Buspirone

3. Apo-buspirone

4. Bespar

5. Busp

6. Buspar

7. Buspirone Hydrochloride

8. Gen Buspirone

9. Gen-buspirone

10. Hydrochloride, Buspirone

11. Lin Buspirone

12. Lin-buspirone

13. Mj 9022 1

14. Mj-9022-1

15. Mj90221

16. N-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-1-cyclopentanediacetamide

17. Neurosine

18. Novo Buspirone

19. Novo-buspirone

20. Nu Buspirone

21. Nu-buspirone

22. Pms Buspirone

23. Pms-buspirone

24. Ratio Buspirone

25. Ratio-buspirone

2.3.2 Depositor-Supplied Synonyms

1. 36505-84-7

2. Buspirona

3. Buspironum

4. Buspironum [inn-latin]

5. Buspirona [inn-spanish]

6. Gen-buspirone

7. Buspin

8. Buspirone Free Base

9. 8-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)-8-azaspiro[4.5]decane-7,9-dione

10. 8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4.5]decane-7,9-dione

11. 8-(4-(4-(2-pyrimidinyl)-1-piperizinyl)butyl)-8-azaspiro(4,5)decane-7,9-dione

12. Buspirone (inn)

13. Chembl49

14. Ansial

15. Tk65wks8hl

16. 8-azaspiro[4.5]decane-7,9-dione, 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-

17. Chebi:3223

18. Bci-024

19. 8-{4-[4-(pyrimidin-2-yl)piperazin-1-yl]butyl}-8-azaspiro[4.5]decane-7,9-dione

20. 8-[4-(4-pyrimidin-2-yl-piperazin-1-yl)-butyl]-8-aza-spiro[4.5]decane-7,9-dione

21. 8-azaspiro(4.5)decane-7,9-dione, 8-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)-

22. Ncgc00015162-04

23. Buspirone [inn]

24. Dsstox_cid_2707

25. Buspirone [inn:ban]

26. 8-azaspiro(4,5)decane-7,9-dione, 8-(4-(4-(2-pyrimidinyl)piperizinyl)butyl)-

27. Dsstox_rid_76696

28. Dsstox_gsid_22707

29. 116753-41-4

30. Buspirone-mdts

31. 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4,5]decane-7,9-dione

32. 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione

33. 8-{4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl}-8-azaspiro[4.5]decane-7,9-dione

34. 8-azaspiro[4.5]decane-7,9-dione,8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-

35. Cas-36505-84-7

36. Gen-buspirone (tn)

37. Einecs 253-072-2

38. Unii-tk65wks8hl

39. Brn 0964904

40. Spectrum_001756

41. Tocris-0962

42. Buspirone [mi]

43. Prestwick0_000369

44. Prestwick1_000369

45. Prestwick2_000369

46. Prestwick3_000369

47. Buspirone [vandf]

48. Lopac-b-7148

49. Biomol-nt_000108

50. Gtpl36

51. Buspirone [who-dd]

52. Buspironehydrochloride

53. Lopac0_000223

54. Schembl16398

55. Bspbio_000497

56. Kbioss_002236

57. Bidd:gt0519

58. Divk1c_000921

59. Spbio_002418

60. Bpbio1_000547

61. Bpbio1_001403

62. Dtxsid2022707

63. Kbio1_000921

64. Kbio2_002236

65. Kbio2_004804

66. Kbio2_007372

67. Ninds_000921

68. Hms2090k19

69. Zinc1530571

70. Tox21_110092

71. Tox21_302371

72. Bdbm50001859

73. Stk086268

74. Akos002313325

75. Tox21_110092_1

76. Ccg-204318

77. Db00490

78. Sdccgsbi-0050211.p004

79. 8-[4-[4-(pyrimidine-2-yl)-piperazine-1-yl]-butyl]-8-aza-spiro[4.5]decane-7,9-dione

80. Idi1_000921

81. Mrf-0000691

82. Buspirone 100 Microg/ml In Acetonitrile

83. Ncgc00015162-01

84. Ncgc00015162-02

85. Ncgc00015162-03

86. Ncgc00015162-05

87. Ncgc00015162-06

88. Ncgc00015162-07

89. Ncgc00015162-08

90. Ncgc00015162-10

91. Ncgc00015162-11

92. Ncgc00015162-22

93. Ncgc00016820-01

94. Ncgc00024905-01

95. Ncgc00024905-02

96. Ncgc00024905-03

97. Ncgc00255227-01

98. Buspirone 1000 Microg/ml In Acetonitrile

99. Sbi-0050211.p003

100. Cas-33386-08-2

101. Ab00053432

102. Ft-0621488

103. C06861

104. D07593

105. Ab00053432-12

106. Ab00053432_13

107. 505b847

108. A924049

109. L001110

110. Q412194

111. W-106606

112. Brd-k93461745-001-01-5

113. Brd-k93461745-003-03-7

114. Brd-k93461745-003-14-4

115. 8-(4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl)-8-azaspiro[4.5]decane-7,9-dione #

116. 8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4,5]decane-7,9-dione

117. 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]-butyl]-8-azaspiro[4.5]decane-7,9-dione

118. 8-[4-[4-(pyrimidine-2yl)-piperazine-1-yl]-butyl]-8-aza-spiro[4.5]decane-7.9-dione

119. (buspirone) 8-[4-(4-pyrimidin-2-yl-piperazin-1-yl)-butyl]-8-aza-spiro[4.5]decane-7,9-dione

120. 8-[4-(4-pyrimidin-2-yl-piperazin-1-yl)-butyl]-8-aza-spiro[4.5]decane-7,9-dione : (hydrochloride)

121. 8-[4-(4-pyrimidin-2-yl-piperazin-1-yl)-butyl]-8-aza-spiro[4.5]decane-7,9-dione; Hydrochloride(buspirone)

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 385.5 g/mol
Molecular Formula C21H31N5O2
XLogP32.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass385.24777525 g/mol
Monoisotopic Mass385.24777525 g/mol
Topological Polar Surface Area69.6 Ų
Heavy Atom Count28
Formal Charge0
Complexity529
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Indicated for the management of anxiety disorders or the short-term relief of the symptoms of anxiety.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The clinical effect of buspirone in alleviating the symptoms of generalized anxiety disorders typically takes 2 to 4 weeks to achieve. The delayed onset of action of buspirone suggests that the therapeutic effectiveness in generalized anxiety may involved more than its molecular mechanism of action at the 5-HT1A receptors, or buspirone may induce adaptations of 5-HT1A receptors. Buspirone was not shown to alter the psychomotor or cognitive function in healthy volunteers, and the risk of developing sedation is relatively low compared to other anxiolytics, such as benzodiazepines. Unlike benzodiazepines and barbiturates used in anxiety disorders, buspirone is not associated with a risk for developing physical dependence or withdrawal, or any significant interaction with central nervous system depressants such as ethanol. This is due to the lack of effects on GABA receptors. Buspirone also does not exhibit any anticonvulsant or muscle-relaxing properties, but may interfere with arousal reactions due to its inhibitory action on the aactivity of noradrenergic locus coerulus neurons. Despite its clinical effectiveness in generalized anxiety, buspirone demonstrated limited clinical effectiveness on panic disorders, severe anxiety, phobias, and obsessive compulsive disorders. The clinical effectiveness of the long-term use of buspirone, for more than 3 to 4 weeks, has not demonstrated in controlled trials but there were no observable significant adverse events in patients receiving buspirone for a year in a study of long-term use.


5.2 MeSH Pharmacological Classification

Anti-Anxiety Agents

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)


Serotonin Receptor Agonists

Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS. (See all compounds classified as Serotonin Receptor Agonists.)


5.3 ATC Code

N - Nervous system

N05 - Psycholeptics

N05B - Anxiolytics

N05BE - Azaspirodecanedione derivatives

N05BE01 - Buspirone


5.4 Absorption, Distribution and Excretion

Absorption

Buspirone is rapidly absorbed following oral administration. Bioavailability is low and variable (approximately 5%) due to extensive first pass metabolism. While absorption of buspirone is decreased with concomitant food intake, the first-pass metabolism of the drug is also decreased, resulting in an increased bioavailability as well as increased Cmax and AUC. Following oral administration of single oral doses of 20 mg, the Cmax ranged from 1 to 6 ng/mL and the Tmax ranged from 40 to 90 minutes.


Route of Elimination

A single-dose pharmacokinetic studies using 14C-labeled buspirone demonstrated that about 29-63% of the dose administered was excreted in the urine within 24 hours, primarily in the form of metabolites. About 18% to 38% of the dose was eliminated via fecal excretion.


Volume of Distribution

In a pharmacokinetic study assessing buspirone over the dose range of 10 to 40 mg, the volume of distribution was 5.3 L/kg.


Clearance

In a pharmacokinetic study assessing buspirone over the dose range of 10 to 40 mg, the systemic clearance was 1.7 L/h/kg.


5.5 Metabolism/Metabolites

Buspirone is extensively metabolized upon administration, where it primarily undergoes hepatic oxidation mediated by the CYP3A4 enzyme. Hydroxylated derivatives are produced, including a pharmacologically active metabolite 1-pyrimidinylpiperazine (1-PP). In animal studies, 1-PP possessed about one quarter of the pharmacological activity of buspirone.


5.6 Biological Half-Life

In a single-dose pharmacokinetic study of 14C-labeled buspirone, the average elimination half-life of unchanged buspirone following administration of single doses ranging from 10 to 40 mg was about 2 to 3 hours.


5.7 Mechanism of Action

The therapeutic action of buspirone in generalized anxiety disorders is thought to be mainly derived from its interaction with two major 5-HT1A receptor subtypes that are involved in the brain's anxiety and fear circuitry to enhance the serotonergic activity in these brain areas. Buspirone acts as a full agonist at presynaptic 5-HT1A receptors, or 5-HT1A autoreceptors, expressed at dorsal raphe while acting as a partial agonist at the postsynaptic 5-HT1A receptors expressed on hippocampus and cortex. 5-HT1A receptors function as inhibitory autoreceptors by being expressed on the soma or dendrites of serotonergic neurons or mediate postsynaptic actions of 5-HT by being highly expressed on the corticolimbic circuits. They are inhibitory G-protein coupled receptors that couple to Gi/Go proteins. When activated, presynaptic 5-HT1A autoreceptors causes neuron hyperpolarization and reduces the firing rate of the serotonergic neuron, thereby decreasing extracellular 5-HT levels in the neuron's projection areas. Activated postsynaptic 5-HT1A receptors promote hyperpolarization to released 5-HT on pyramidal neurons. The anxiolytic action of buspirone is mainly thought to arise from the interaction at presynaptic 5-HT1A autoreceptors. Acting as a potent agonist in these receptors, buspirone initially causes activation of these autoreceptors and inhibition of 5-HT release. It is proposed that buspirone induces desensitization of somatodendritic autoreceptors over time, which may explain the delayed onset of action of the drug. Desensitization of the autoreceptors ultimately results in heightened excitation of serotonergic neurons and enhanced 5-HT release. Buspirone also displays a weak affinity for serotonin 5HT2 receptors and acts as a weak antagonist on dopamine D2 autoreceptors, although there is not much evidence that the action at these receptors contribute to the anxiolytic effect of buspirone. It acts as an antagonist at presynaptic dopamine D3 and D4 receptors and may bind to alpha-1 adrenergic receptors as a partial agonist.


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27-Jan-2021
29-Jul-2024
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Quantity (KGS) & Unit rate (USD/KGS) over time

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