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Also known as: 148553-50-8, Lyrica, (s)-3-(aminomethyl)-5-methylhexanoic acid, 3-isobutyl gaba, (3s)-3-(aminomethyl)-5-methylhexanoic acid, Ci-1008
Molecular Formula
C8H17NO2
Molecular Weight
159.23  g/mol
InChI Key
AYXYPKUFHZROOJ-ZETCQYMHSA-N
FDA UNII
55JG375S6M

Pregabalin
A gamma-aminobutyric acid (GABA) derivative that functions as a CALCIUM CHANNEL BLOCKER and is used as an ANTICONVULSANT as well as an ANTI-ANXIETY AGENT. It is also used as an ANALGESIC in the treatment of NEUROPATHIC PAIN and FIBROMYALGIA.
1 2D Structure

Pregabalin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S)-3-(aminomethyl)-5-methylhexanoic acid
2.1.2 InChI
InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m0/s1
2.1.3 InChI Key
AYXYPKUFHZROOJ-ZETCQYMHSA-N
2.1.4 Canonical SMILES
CC(C)CC(CC(=O)O)CN
2.1.5 Isomeric SMILES
CC(C)C[C@@H](CC(=O)O)CN
2.2 Other Identifiers
2.2.1 UNII
55JG375S6M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (r-)-3-isobutyl Gaba

2. (s)-3-(aminomethyl)-5-methylhexanoic Acid

3. (s+)-3-isobutyl Gaba

4. 1008, Ci

5. 3 Isobutyl Gaba

6. 3-(aminomethyl)-5-methylhexanoic Acid

7. 3-isobutyl Gaba

8. Ci 1008

9. Ci-1008

10. Ci1008

11. Gaba, 3-isobutyl

12. Lyrica

2.3.2 Depositor-Supplied Synonyms

1. 148553-50-8

2. Lyrica

3. (s)-3-(aminomethyl)-5-methylhexanoic Acid

4. 3-isobutyl Gaba

5. (3s)-3-(aminomethyl)-5-methylhexanoic Acid

6. Ci-1008

7. (s)-pregabalin

8. Hexanoic Acid, 3-(aminomethyl)-5-methyl-, (3s)-

9. Vronogabic

10. Ci 1008

11. Pregabalin Mylan

12. Pregabalin Sandoz

13. Pd 144723

14. Pd-144723

15. Pregabalin Zentiva

16. Pregabalin Sandoz Gmbh

17. (s)-3-isobutyl Gaba

18. Chembl1059

19. Chebi:64356

20. (3s)-3-(aminomethyl)-5-methyl-hexanoic Acid

21. 55jg375s6m

22. Ynp-1807

23. Nsc-759256

24. Hexanoic Acid, 3-(aminomethyl)-5-ethyl-, (3s)-

25. (r-)-3-isobutyl Gaba

26. Pregabalin [usan]

27. Hexanoic Acid, 3-(aminomethyl)-5-methyl-, (s)-

28. Pregabalina

29. Pregabaline

30. Nervalin

31. Pregablin

32. Unii-55jg375s6m

33. Hsdb 7530

34. Pregabalin [usan:inn:ban:jan]

35. Ncgc00095186-01

36. Pregabalin- Bio-x

37. Lyrica (tn)

38. Mfcd00917044

39. Lyrica Cr

40. Pregabalin [mi]

41. (s)-3-(aminomethyl)-5-methylhexanoicacid

42. Pregabalin [inn]

43. Pregabalin [jan]

44. Pregabalin [hsdb]

45. Pregabalin [vandf]

46. Pregabalin [mart.]

47. Schembl8227

48. Dsstox_cid_25950

49. Dsstox_rid_81246

50. Pregabalin [usp-rs]

51. Pregabalin [who-dd]

52. Dsstox_gsid_45950

53. Pregabalin (jan/usan/inn)

54. Pregabalin [ema Epar]

55. Pregabalin Mylan Pharma

56. (s)-(+)-4-amino-3-(2-methylpropyl)butanoic Acid

57. Gtpl5484

58. Zinc5152

59. Dea No. 2782

60. Pregabalin, >=97% (nmr)

61. Dtxsid1045950

62. Pregabalin [orange Book]

63. Pregabalin [ep Monograph]

64. Hms3715j16

65. Pregabalin [usp Monograph]

66. Pregabalin 1.0 Mg/ml In Methanol

67. Tox21_111475

68. Bdbm50164279

69. Akos001476611

70. Akos005145504

71. Lyrica;ci-1008;pd-144723

72. Ac-1158

73. Ccg-221247

74. Cs-1247

75. Db00230

76. Ks-5378

77. Nsc 759256

78. (s)-3-aminomethyl-5-methylhexanoic Acid

79. Ncgc00346738-01

80. 121ge001

81. Bp163672

82. Hy-17414

83. (s)-3-aminomethyl-5-methyl-hexanoic Acid

84. Am20080369

85. Cas-148553-50-8

86. P2840

87. En300-92104

88. (3s)-3-(aminomethyl)-5-methyl Hexanoic Acid

89. (s)-(+)-3-aminomethyl-5-methylhexanoic Acid

90. D02716

91. Ab01563007_01

92. 553p508

93. A808784

94. Q412174

95. Sr-01000942257

96. Sr-01000942257-2

97. Pregabalin, Europepharmacopoeia (ep) Reference Standard

98. Z2757554242

99. 1414928-41-8

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 159.23 g/mol
Molecular Formula C8H17NO2
XLogP3-1.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass159.125928785 g/mol
Monoisotopic Mass159.125928785 g/mol
Topological Polar Surface Area63.3 Ų
Heavy Atom Count11
Formal Charge0
Complexity123
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameLyrica
PubMed HealthPregabalin (By mouth)
Drug ClassesAnticonvulsant, Neuropathic Pain Agent
Drug LabelPregabalin is described chemically as (S)-3-(aminomethyl)-5-methylhexanoic acid. The molecular formula is C8H17NO2 and the molecular weight is 159.23. The chemical structure of pregabalin is:Pregabalin is a white to off-white, crystalline solid with...
Active IngredientPregabalin
Dosage FormCapsule; Solution
Routeoral; Oral
Strength20mg/ml; 200mg; 25mg; 150mg; 300mg; 75mg; 100mg; 50mg; 225mg
Market StatusPrescription
CompanyPf Prism; Cp Pharms

2 of 4  
Drug NamePregabalin
PubMed HealthPregabalin (By mouth)
Drug ClassesAnticonvulsant, Neuropathic Pain Agent
Drug LabelPregabalin is described chemically as (S)-3-(aminomethyl)-5-methylhexanoic acid. The molecular formula is C8H17NO2 and the molecular weight is 159.23. The chemical structure of pregabalin is:Pregabalin is a white to off-white, crystalline solid with...
Active IngredientPregabalin
Dosage FormCapsule; Solution
Routeoral; Oral
Strength20mg/ml; 200mg; 25mg; 150mg; 300mg; 75mg; 100mg; 50mg; 225mg
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Apotex; Lupin; Sandoz; Watson Labs; Actavis Elizabeth; Teva Pharms; Wockhardt Usa

3 of 4  
Drug NameLyrica
PubMed HealthPregabalin (By mouth)
Drug ClassesAnticonvulsant, Neuropathic Pain Agent
Drug LabelPregabalin is described chemically as (S)-3-(aminomethyl)-5-methylhexanoic acid. The molecular formula is C8H17NO2 and the molecular weight is 159.23. The chemical structure of pregabalin is:Pregabalin is a white to off-white, crystalline solid with...
Active IngredientPregabalin
Dosage FormCapsule; Solution
Routeoral; Oral
Strength20mg/ml; 200mg; 25mg; 150mg; 300mg; 75mg; 100mg; 50mg; 225mg
Market StatusPrescription
CompanyPf Prism; Cp Pharms

4 of 4  
Drug NamePregabalin
PubMed HealthPregabalin (By mouth)
Drug ClassesAnticonvulsant, Neuropathic Pain Agent
Drug LabelPregabalin is described chemically as (S)-3-(aminomethyl)-5-methylhexanoic acid. The molecular formula is C8H17NO2 and the molecular weight is 159.23. The chemical structure of pregabalin is:Pregabalin is a white to off-white, crystalline solid with...
Active IngredientPregabalin
Dosage FormCapsule; Solution
Routeoral; Oral
Strength20mg/ml; 200mg; 25mg; 150mg; 300mg; 75mg; 100mg; 50mg; 225mg
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Apotex; Lupin; Sandoz; Watson Labs; Actavis Elizabeth; Teva Pharms; Wockhardt Usa

4.2 Therapeutic Uses

Pregabalin is indicated for management of post-herpetic neuralgia. /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 2412


Pregabalin is indicated for management of neuropathic pain associated with diabetic peripheral neuropathy. /Included in US product labe/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 2412


Pregabalin is indicated as an adjunctive therapy for adult patients with partial onset seizures. /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 2412


The U.S. Food and Drug Administration ... has approved Lyrica (pregabalin), the first drug to treat fibromyalgia, a disorder characterized by pain, fatigue and sleep problems.

FDA; FDA News (P07-107). Available from, as of July 31, 2007: https://www.fda.gov/bbs/topics/NEWS/2007/NEW01656.html


4.3 Drug Warning

Known hypersensitivity to pregabalin or any ingredient in the formulation.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2247


Because of the possibility of increased seizure frequency, anticonvulsant drugs, including pregabalin, should be withdrawn gradually and dosage reduced slowly over at least 1 week. Abrupt discontinuance of pregabalin has been associated with insomnia, nausea, headache, and diarrhea.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2247


In controlled studies, blurred vision, which was reported in 6 or 2% of patients receiving pregabalin or placebo, respectively, resolved in the majority of cases with continued dosing; less than 1% of patients required discontinuance of the drug. In addition, decreased visual acuity was reported in 7 or 5% of patients receiving pregabalin or placebo, respectively, while visual field changes were detected in 13 or 12% of patients receiving the drug or placebo, respectively, and funduscopic changes were observed in 2% of patients receiving pregabalin or placebo. The clinical importance of these ophthalmologic findings has not been elucidated. If visual disturbance persists, further ocular assessment should be considered, while more frequent assessment is recommended in patients who already are monitored for ocular conditions.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2247


Weight gain, which was related to dosage and duration of exposure to pregabalin, has been reported in patients receiving pregabalin. Weight gain did not appear to be associated with baseline body mass index (BMI), gender, or age and was not limited to patients with edema.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 2247


For more Drug Warnings (Complete) data for PREGABALIN (20 total), please visit the HSDB record page.


4.4 Drug Indication

Pregabalin is indicated for the management of neuropathic pain associated with diabetic peripheral neuropathy, postherpetic neuralgia, fibromyalgia, neuropathic pain associated with spinal cord injury, and as adjunctive therapy for the treatment of partial-onset seizures in patients 1 month of age and older.


FDA Label


* Neuropathic pain:

- Lyrica is indicated for the treatment of peripheral and central neuropathic pain in adults.

* Epilepsy :

- Lyrica is indicated as adjunctive therapy in adults with partial seizures with or without secondary generalisation.

* Generalised anxiety disorder:

- Lyrica is indicated for the treatment of generalised anxiety disorder (GAD) in adults.


* Epilepsy :

Pregabalin Mylan Pharma is indicated as adjunctive therapy in adults with partial seizures with or without secondary generalisation.

* Generalised Anxiety Disorder:

Pregabalin Mylan Pharma is indicated for the treatment of Generalised Anxiety Disorder (GAD) in adults.


* Neuropa