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Alphaxolone

Alphaxolone

Synopsis, Chemistry

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Also known as: Alphaxalone, 23930-19-0, 5alpha-pregnan-3alpha-ol-11,20-dione, Alfaxalonum [inn-latin], Alfaxalona [inn-spanish], Gr 2/234

Molecular Formula

C₂₁H₃₂O₃

Molecular Weight

332.5 g/mol

InChI Key

DUHUCHOQIDJXAT-OLVMNOGESA-N

FDA UNII

BD07M97B2A

Alfaxalone is a synthetic neuroactive steroid, with anesthetic activity. Upon administration, alfaxalone binds to the gamma-aminobutyric acid (GABA)-A cell surface receptor, thereby enhancing the inhibitory actions of GABA-A in the brain. This leads to modulation of neuronal cell membrane chloride ion transport and induction and maintenance of anesthesia.

1 2D Structure

Alphaxolone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R,5S,8S,9S,10S,13S,14S,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one

2.1.2 InChI

InChI=1S/C21H32O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h13-17,19,23H,4-11H2,1-3H3/t13-,14+,15-,16+,17-,19+,20-,21+/m0/s1

2.1.3 InChI Key

DUHUCHOQIDJXAT-OLVMNOGESA-N

2.1.4 Canonical SMILES

CC(=O)C1CCC2C1(CC(=O)C3C2CCC4C3(CCC(C4)O)C)C

2.1.5 Isomeric SMILES

CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC(=O)[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C

2.2 Other Identifiers

2.2.1 UNII

BD07M97B2A

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alfaxolone

2. Alphaxalone

3. Alphaxalone, (3alpha)-isomer

4. Alphaxalone, (3alpha,5beta)-isomer

5. Alphaxalone, (3beta,5alpha)-isomer

6. Alphaxalone, (3beta,5beta)-isomer

7. Delta(16)-alfaxalone

8. Hydroxy-5 Alpha-pregnane-11,20-dione

2.3.2 Depositor-Supplied Synonyms

1. Alphaxalone

2. 23930-19-0

3. 5alpha-pregnan-3alpha-ol-11,20-dione

4. Alfaxalonum [inn-latin]

5. Alfaxalona [inn-spanish]

6. Gr 2/234

7. Phaxan

8. 3alpha-hydroxy-5alpha-pregnane-11,20-dione

9. (3r,5s,8s,9s,10s,13s,14s,17s)-17-acetyl-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-11-one

10. Alfadione

11. Mls000069684

12. Mls001076262

13. Bd07m97b2a

14. Chembl190279

15. Chebi:34531

16. Alfaxalone (inn)

17. Ncgc00023100-03

18. Smr000058494

19. (3a,5a)-3-hydroxypregnane-11,20-dione

20. Alfaxalone [inn]

21. Dsstox_cid_2576

22. Dsstox_rid_76638

23. Alphaxolone

24. Dsstox_gsid_22576

25. Alfaxalona

26. Alfaxalonum

27. Sr-01000000168

28. Brn 3217240

29. Unii-bd07m97b2a

30. 3alpha-hydroxy-5alpha-pregnan-11,20-dion

31. 5alpha-alphaxalone

32. Alfaxalone [inn:ban:dcf:jan]

33. 3-alpha-hydroxy-5-alpha-pregnane-11,20-dione

34. (3-alpha,5-alpha)-3-hydroxypregnane-11,20-dione

35. Cas-23930-19-0

36. Alfaxalone [mi]

37. 3.alpha.-hydroxy-5.alpha.-pregnane-11,20-dione

38. Alfaxalone [jan]

39. Opera_id_1629

40. Prestwick0_001002

41. Prestwick1_001002

42. Prestwick2_001002

43. Prestwick3_001002

44. Alfaxalone [mart.]

45. Alfaxalone [who-dd]

46. (3alpha,5alpha)-3-hydroxypregnane-11,20-dione

47. Bidd:pxr0037

48. Lopac0_000929

49. Pregnane-11,20-dione, 3-hydroxy-, (3a,5a)-

50. Schembl57756

51. Bspbio_001123

52. 4-08-00-02091 (beilstein Handbook Reference)

53. 5-alpha-pregnane-11,20-dione, 3-alpha-hydroxy-

54. Spbio_003004

55. Bpbio1_001237

56. Gtpl5461

57. Alfaxalone [green Book]

58. Dtxsid9022576

59. Pregnane-11,20-dione, 3-hydroxy-, (3-alpha,5-alpha)-

60. Hms1571i05

61. Hms2098i05

62. Hms2236n05

63. Hms3262j20

64. Hms3715i05

65. Zinc4081122

66. Tox21_110884

67. Tox21_500929

68. Bdbm50164570

69. Akos024457399

70. Tox21_110884_1

71. Ccg-205010

72. Db11371

73. Lp00929

74. Sdccgsbi-0050903.p002

75. 5alpha-pregnane-3alpha-ol-11,20-dione

76. Ncgc00023100-04

77. Ncgc00023100-05

78. Ncgc00023100-06

79. Ncgc00023100-08

80. Ncgc00261614-01

81. Gr-2/234

82. (3?,5?)-3-hydroxypregnane-11,20-dione

83. Ab00384358

84. B7253

85. Eu-0100929

86. D07282

87. P 5052

88. Sr-01000076070

89. J-015280

90. Q3611058

91. Sr-01000000168-2

92. Sr-01000000168-3

93. Sr-01000076070-1

94. Brd-k41445866-001-03-0

95. 5alpha-pregnan-3alpha-ol-11,20-dione, Powder, >=98% (tlc)

96. (3beta,5alpha,8alpha,9beta,10alpha)-3-hydroxypregnane-11,20-dione

97. (3r,5s,8s,9s,10s,13s,14s,17s)-17-acetyl-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-one

98. Ey4

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₂O₃
Molecular Weight	332.5 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	332.23514488 g/mol
Monoisotopic Mass	332.23514488 g/mol
Topological Polar Surface Area	54.4 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	569
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Neurosteroids

Endogenous compounds or drugs that affect neuronal excitability through modulation of specific ionotropic receptors (e.g., GABA-A RECEPTORS). Endogenous neurosteroids are steroid hormones de novo synthesized by neurons and glial cells from steroid metabolite precursors (e.g., PREGNENOLONE). (See all compounds classified as Neurosteroids.)

Anesthetics

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site. (See all compounds classified as Anesthetics.)

4.2 ATC Code

N - Nervous system

N01 - Anesthetics

N01A - Anesthetics, general

N01AX - Other general anesthetics

N01AX05 - Alfaxalone