API Import of Sodium Oxybate obtained from Indian Customs Trade Statistics

Noramco Gamma Hydroxybutyric Acid Sodium

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1 US Medicaid Prescriptions, 3 Finished Drug Prices, 9 Annual Reports

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110 US Patents, 14 US Exclusivities, 1 Health Canada Patents

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110 US Patents
14 US Exclusivities
1 Health Canada Patents

Noramco Gamma-Hydroxybutyric Acid Sodium

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110

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Chemistry

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Also known as: 502-85-2, Sodium 4-hydroxybutyrate, Anetamin, 4-hydroxybutyric acid sodium salt, Sodium 4-hydroxybutanoate, Somsanit

Molecular Formula

C₄H₇NaO₃

Molecular Weight

126.09 g/mol

InChI Key

XYGBKMMCQDZQOZ-UHFFFAOYSA-M

FDA UNII

7G33012534

The sodium salt of 4-hydroxybutyric acid. It is used for both induction and maintenance of ANESTHESIA.

1 2D Structure

Sodium Oxybate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;4-hydroxybutanoate

2.1.2 InChI

InChI=1S/C4H8O3.Na/c5-3-1-2-4(6)7;/h5H,1-3H2,(H,6,7);/q;+1/p-1

2.1.3 InChI Key

XYGBKMMCQDZQOZ-UHFFFAOYSA-M

2.1.4 Canonical SMILES

C(CC(=O)[O-])CO.[Na+]

2.2 Other Identifiers

2.2.1 UNII

7G33012534

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4 Hydroxybutyrate Sodium

2. 4-hydroxybutyrate Sodium

3. Gamma Hydroxybutyrate

4. Gamma-hydroxybutyrate

5. Oxybate Sodium

6. Oxybate, Sodium

7. Oxybutyrate, Sodium

8. Sodium Gamma Hydroxybutyrate

9. Sodium Gamma-hydroxybutyrate

10. Sodium Oxybutyrate

11. Somsanit

12. Xyrem

2.3.2 Depositor-Supplied Synonyms

1. 502-85-2

2. Sodium 4-hydroxybutyrate

3. Anetamin

4. 4-hydroxybutyric Acid Sodium Salt

5. Sodium 4-hydroxybutanoate

6. Somsanit

7. Oxybate Sodium

8. Gamma Oh

9. Sodium Oxybate [usan]

10. Sodium Oxybutyrate

11. Catabate

12. Sodium Oxybat

13. Oxybate (sodium)

14. 4-hydroxybutyrate Sodium

15. Wy-3478

16. Butanoic Acid, 4-hydroxy-, Monosodium Salt

17. Gamma-hydroxybutyrate Sodium

18. Sodium Gamma-hydroxybutyrate

19. Sodium;4-hydroxybutanoate

20. Gamma-hydroxy Sodium Butyrate

21. Butanoic Acid, 4-hydroxy-, Sodium Salt

22. Eb 27

23. Hydroxybutyric Acid Monosodium Salt

24. 4-hydroxybutyric Acid Monosodium Salt

25. Wy 3478

26. .gamma.-hydroxybutyrate Sodium Salt

27. Nsc-84223

28. Sodium Oxybate (usan)

29. 7g33012534

30. Butyric Acid, 4-hydroxy-, Monosodium Salt

31. Butyric Acid, 4-hydroxy-, Sodium Salt

32. Natrium 4-hydroxybutyrat

33. Sodium-4-hydroxybutyrate

34. Sodium Oxybate (sodium 4-hydroxybutanoate)

35. Ghb Sodium Salt (sodium Gammahydroxybutyrate)

36. 4-hydroxybuttersaeure Natriumsalz

37. Gamma-hydroxybutyrate Sodium Salt

38. Ncgc00247714-01

39. Einecs 207-953-3

40. Nsc 84223

41. Gamma-hydroxybutyric Acid, Sodium Salt

42. Jzp-6

43. Sodium4-hydroxybutyrate

44. Acetamide,2,2-dichloro-n-[(1r,2r)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-,rel-

45. Unii-7g33012534

46. Xyrem (tn)

47. Sodium Gammahydroxybutyrate

48. Dsstox_cid_28866

49. Dsstox_rid_83135

50. Dsstox_gsid_48940

51. Schembl61823

52. Sodium Oxybate [hsdb]

53. Sodium Oxybate [vandf]

54. Dea No. 2012

55. Sodium Oxybate [mart.]

56. Chembl1200682

57. Dtxsid3048940

58. Oxybate Sodium [who-dd]

59. Sodium Oxybate [ema Epar]

60. Hms2091e15

61. Hy-b1187

62. Tox21_112871

63. Sodium Oxybate [orange Book]

64. Gamma Hydroxybutyric Acid Preparations

65. Xywav Component Sodium Oxybate

66. Akos006221428

67. Ccg-212465

68. Cs-4796

69. Db09072

70. Sodium Oxybate Component Of Xywav

71. Cas-502-85-2

72. Db-071156

73. Ft-0626615

74. D05866

75. H-4040

76. Sodium Salt Of Gamma-hydroxybutyric Acid

77. .gamma.-hydroxybutyrate Sodium Salt [mi]

78. Butanoic Acid, 4-hydroxy-, Sodium Salt (1:1)

79. Q7553347

80. 90318-49-3

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₄H₇NaO₃
Molecular Weight	126.09 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	126.02928836 g/mol
Monoisotopic Mass	126.02928836 g/mol
Topological Polar Surface Area	60.4 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	64.3
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Xyrem
PubMed Health	Sodium Oxybate (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	Sodium oxybate, a CNS depressant, is the active ingredient in Xyrem. The chemical name for sodium oxybate is sodium 4-hydroxybutyrate. The molecular formula is C4H7NaO3, and the molecular weight is 126.09 g/mole. The chemical structure is:Sodium oxyb...
Active Ingredient	Sodium oxybate
Dosage Form	Solution
Route	Oral
Strength	500mg/ml
Market Status	Prescription
Company	Jazz Pharms

2 of 2
Drug Name	Xyrem
PubMed Health	Sodium Oxybate (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	Sodium oxybate, a CNS depressant, is the active ingredient in Xyrem. The chemical name for sodium oxybate is sodium 4-hydroxybutyrate. The molecular formula is C4H7NaO3, and the molecular weight is 126.09 g/mole. The chemical structure is:Sodium oxyb...
Active Ingredient	Sodium oxybate
Dosage Form	Solution
Route	Oral
Strength	500mg/ml
Market Status	Prescription
Company	Jazz Pharms

4.2 Drug Indication

For the treatment of cataplexy and excessive daytime sleepiness (EDS) associated with narcolepsy.

FDA Label

Treatment of narcolepsy with cataplexy in adult patients.

Substitution treatment for alcohol dependence within a framework of careful medical supervision along with continuous psychosocial support and social rehabilitation. Treatment should be initiated only in patients resistant to existing interventions or in patients for whom existing therapies are contra-indicated or not recommended. ,

5 Pharmacology and Biochemistry

5.1 Pharmacology

Sodium oxybate works through an unknown mechanism to treat narcolepsy by inducing sleep within about 5-15 minutes of administration.

5.2 MeSH Pharmacological Classification

Adjuvants, Anesthesia

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)

Anesthetics, Intravenous

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Central Nervous System Depression [PE]; Decreased Central Nervous System Organized Electrical Activity [PE]; Central Nervous System Depressant [EPC]

5.4 ATC Code

N07XX04

N07BB

B05XA02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N01 - Anesthetics

N01A - Anesthetics, general

N01AX - Other general anesthetics

N01AX11 - Sodium oxybate

N - Nervous system

N07 - Other nervous system drugs

N07X - Other nervous system drugs

N07XX - Other nervous system drugs

N07XX04 - Sodium oxybate

5.5 Absorption, Distribution and Excretion

Absorption

Absolute bioavailability is approximately 88%. Tmax of 30.7-51.9min.

Route of Elimination

The major metabolite is carbon dioxide which is cleared by expiration, less then 5% appears as the unchanged drug in the urine within 6-8 hours after dosing.

Volume of Distribution

Vd of 37.7-67.7

Clearance

Total clearance of 895-1361mL/min.

5.6 Metabolism/Metabolites

Animal studies indicate that the major elimination pathway is metabolism by the creation of carbon dioxide and water through the Krebs cycle and secondarily by beta-oxidation. In the primary pathway hydroxyacid-oxoacid transhydrogenase catalyzes the conversion of sodium oxybate to succinic semialdehyde which is then transformed to succinic acid by succinic semmialdehyde dehydrogenase. Succinic acid is then turned into carbon dioxide and water in the Krebs cycle. Succinic semialdehyde is also metabolised into carbon dioxide and water by a transhydrofenase in the presence of alpha ketoglutarate.

5.7 Biological Half-Life

0.5 to 1 hour.

5.8 Mechanism of Action

The exact mechanism of action is unknown. It is the sodium salt of the endogenous compound gamma hydroxybutyrate which is a metabolite of the GABA neurotransmitter and it's thought that it's therapeutic effects are mediated via GABA B actions at noradrenergic, dopaminergic and thalamocortical neurons.

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