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2 EU WC
32 KDMF
3 NDC API
27 Listed Suppliers
$ API Reference Price

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33 FDF Dossiers
6 Europe
27 Listed Dossiers

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Alpha Lipoic Acid

Synopsis

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Chemistry

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Also known as: Dl-thioctic acid, Alpha-lipoic acid, 1077-28-7, 5-(1,2-dithiolan-3-yl)pentanoic acid, Dl-alpha-lipoic acid, 1,2-dithiolane-3-pentanoic acid

Molecular Formula

C₈H₁₄O₂S₂

Molecular Weight

206.3 g/mol

InChI Key

AGBQKNBQESQNJD-UHFFFAOYSA-N

FDA UNII

73Y7P0K73Y

Alpha Lipoic Acid

An octanoic acid bridged with two sulfurs so that it is sometimes also called a pentanoic acid in some naming schemes. It is biosynthesized by cleavage of LINOLEIC ACID and is a coenzyme of oxoglutarate dehydrogenase (KETOGLUTARATE DEHYDROGENASE COMPLEX). It is used in DIETARY SUPPLEMENTS.

1 2D Structure

Alpha Lipoic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-(dithiolan-3-yl)pentanoic acid

2.1.2 InChI

InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)

2.1.3 InChI Key

AGBQKNBQESQNJD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CSSC1CCCCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

73Y7P0K73Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acid, Alpha-lipoic

2. Alpha Lipogamma

3. Alpha Lipoic Acid

4. Alpha Lipon Stada

5. Alpha Liponaure Heumann

6. Alpha Liponsaure Sofotec

7. Alpha Liponsaure Von Ct

8. Alpha Lippon Al

9. Alpha Vibolex

10. Alpha-lipogamma

11. Alpha-lipoic Acid

12. Alpha-lipon Stada

13. Alpha-liponaure Heumann

14. Alpha-liponsaure Sofotec

15. Alpha-liponsaure Von Ct

16. Alpha-lippon Al

17. Alpha-vibolex

18. Alphaflam

19. Alphalipogamma

20. Alphalipon Stada

21. Alphaliponaure Heumann

22. Alphaliponsaure Sofotec

23. Alphaliponsaure Von Ct

24. Alphalippon Al

25. Alphavibolex

26. Azulipont

27. Biomo Lipon

28. Biomo-lipon

29. Biomolipon

30. Duralipon

31. Espa Lipon

32. Espa-lipon

33. Espalipon

34. Fenint

35. Injekt, Thiogamma

36. Juthiac

37. Lipoic Acid

38. Liponsaure Ratiopharm

39. Liponsaure-ratiopharm

40. Liponsaureratiopharm

41. Mtw Alphaliponsaure

42. Mtw-alphaliponsaure

43. Mtwalphaliponsaure

44. Neurium

45. Pleomix Alpha

46. Pleomix Alpha N

47. Pleomix-alpha

48. Pleomix-alpha N

49. Pleomixalpha

50. Pleomixalpha N

51. Thioctacid

52. Thioctacide T

53. Thiogamma Injekt

54. Thiogamma Oral

55. Tromlipon

56. Verla Lipon

57. Verla-lipon

58. Verlalipon

2.3.2 Depositor-Supplied Synonyms

1. Dl-thioctic Acid

2. Alpha-lipoic Acid

3. 1077-28-7

4. 5-(1,2-dithiolan-3-yl)pentanoic Acid

5. Dl-alpha-lipoic Acid

6. 1,2-dithiolane-3-pentanoic Acid

7. Biletan

8. Alpha Lipoic Acid

9. 6,8-thioctic Acid

10. Thioctacid

11. Dl-6,8-thioctic Acid

12. 6-thioctic Acid

13. Lipothion

14. 62-46-4

15. 5-(dithiolan-3-yl)pentanoic Acid

16. Dl-lipoic Acid

17. Liposan

18. Thioctsan

19. Tioctacid

20. Rac-lipoate

21. 1,2-dithiolane-3-valeric Acid

22. 6,8-dithiooctanoic Acid

23. Alpha-liponsaeure

24. Dl-6-thioctic Acid

25. Thioctic Acid Dl-form

26. 5-(1,2-dithiolan-3-yl)valeric Acid

27. Alpha-liponic Acid

28. Thioktsaeure

29. Tioctidasi

30. (rs)-lipoic Acid

31. Espa-lipon

32. 5-(dithiolan-3-yl)valeric Acid

33. Acetate-replacing Factor

34. 6,8-thiotic Acid

35. Thioctansaeure

36. 6-thiotic Acid

37. .alpha.-lipoic Acid

38. Dl-1,2-dithiolane 3-valeric Acid

39. (+-)-lipoic Acid

40. Thioctate

41. Thioctic Acid [jan]

42. Thioctsaeure

43. Thiocacid

44. Thioctan

45. Liponic Acid

46. Thiooctic Acid

47. A-lipoic Acid

48. Dl-.alpha.-lipoic Acid

49. Acidum Thiocticum

50. (+/-)-1,2-dithiolane-3-pentanoic Acid

51. A-lipoicum Acidum

52. Dl-1,2-dithiolane-3-valeric Acid

53. Lipoate

54. Mfcd00005474

55. Nsc 90788

56. Lipoic Acid, Alpha

57. Lipoic Acid, Dl-

58. Nsc 628502

59. (+-)-1,2-dithiolane-3-pentanoic Acid

60. .alpha.-liponic Acid

61. Chebi:16494

62. Dl-1,2-dithiolan-3-valeriansaeure

63. (.+-.)-lipoic Acid

64. Nsc-90788

65. (rs)-.alpha.-lipoic Acid

66. 5-[3-(1,2-dithiolanyl)]pentanoic Acid

67. Chembl33864

68. Tioctic Acid

69. (.+-.)-.alpha.-lipoic Acid

70. 73y7p0k73y

71. 1,2-dithiolane-3-valeric Acid, (+-)-

72. Nsc90788

73. Nsc-628502

74. Thioctic Acid (jan)

75. Ncgc00016032-06

76. Dsstox_cid_5508

77. Protogen A

78. (+/-)-alpha-lipoic Acid

79. Dsstox_rid_77816

80. Dsstox_gsid_25508

81. (r)-(+)-alpha-lipoic Acid;r-(+)-thioctic Acid

82. Thioktsaeure [german]

83. Biomolipon

84. Duralipon

85. Alipure

86. Alphalipogamma

87. Thiotacid

88. Biomo Lipon

89. Espa Lipon

90. Alpha Lipogamma

91. Alpha-lipogamma

92. Pyruvate Oxidation Factor

93. Dl-thiocticacid

94. Pleomix Alpha

95. Thioctacide T

96. Verla Lipon

97. Alphalipon Stada

98. Alpha Lippon Al

99. Alpha-liponsaeure [german]

100. Alpha Lipon Stada

101. Alpha-lipon Stada

102. 5-(1,2)dithiolan-3-yl-pentanoic Acid

103. 5-[1,2]dithiolan-3-yl-pentanoic Acid

104. Liponsaureratiopharm

105. Alpha-lipon 300

106. Smr000058198

107. Cas-1077-28-7

108. Liponsaure-ratiopharm

109. (+-)-thioctic Acid

110. 5-(3-(1,2-dithiolanyl))pentanoic Acid

111. Alpha Liponsaure Von Ct

112. Tioctidasi Acetate Replacing Factor

113. Sr-01000737460

114. Dl-6,8-dithiooctanoic Acid

115. Lip(s2)

116. (rs)-alpha-lipoic Acid

117. Einecs 200-534-6

118. Einecs 214-071-2

119. (+-)-alpha-lipoic Acid

120. Brn 0081853

121. Brn 0122410

122. Unii-73y7p0k73y

123. Alpha Lipoic

124. Alphalipoic-acid

125. Dl-1,2-dithiolan-3-valeriansaeure [german]

126. Thioctic Acid [inn:ban:jan]

127. Hsdb 7818

128. Alpha-lipoic-acid

129. D,l-lipoic Acid

130. Thiotomin (tn)

131. Dl-a-lipoic Acid

132. D,l-thioctic Acid

133. Lipoic Acid (la)

134. Alpha -lipoic Acid

135. Rac ?-lipoic Acid

136. (rs)-thioctic Acid

137. Lipoic-acid

138. ()-alpha-lipoic Acid

139. Spectrum_001618

140. 5-(1,2-dithiolan-3-yl)-pentanoate

141. Thioctic Acid, Dl-form

142. R-(+)-alpalipoic Acid

143. 1,2-dithiolane-3-pentanoic Acid, (+-)-

144. Spectrum2_001605

145. Spectrum3_001188

146. Spectrum4_000217

147. Spectrum5_001298

148. (s)-(-)-thiocticacid

149. (+/-)-a-lipoic Acid

150. Cid_864

151. (.+-.)-thioctic Acid

152. Lipoic Acid, Alpha [nf]

153. Bmse000542

154. Epitope Id:150922

155. (+/-)-?-lipoic Acid

156. (.+/-.)-lipoic Acid

157. Thioctic Acid [mi]

158. Schembl51065

159. Bspbio_002835

160. Dl-thioctic Acid (oxidized)

161. Kbiogr_000853

162. Kbioss_002098

163. Thioctic Acid [hsdb]

164. Thioctic Acid [inci]

165. 5-19-07-00237 (beilstein Handbook Reference)

166. Mls000069736

167. Mls001332379

168. Mls001332380

169. Mls002153365

170. Divk1c_000912

171. Spectrum1503941

172. Spbio_001609

173. Thioctic Acid [mart.]

174. Thioctic Acid [who-dd]

175. Dtxsid7025508

176. Bdbm10515

177. Hms502n14

178. Kbio1_000912

179. Kbio2_002098

180. Kbio2_004666

181. Kbio2_007234

182. Kbio3_002335

183. A-lipoicum Acidum [hpus]

184. Alpha Lipoic Acid [vandf]

185. Alpha-lipoic Acid [vandf]

186. Ninds_000912

187. Thioctic Acid (alpha-lipoic Acid)

188. Hms1922m22

189. Hms3649h08

190. Hms3885i16

191. Pharmakon1600-01503941

192. Thioctic Acid, (+/-)-

193. Act14091

194. Albb-030318

195. Alpha Lipoic Acid [usp-rs]

196. Bcp13221

197. Bcp14048

198. Bcp18944

199. Hy-n0492

200. Thioctic Acid Dl-form [mi]

201. Tox21_110285

202. Tox21_201808

203. Tox21_303092

204. Ac7875

205. Bbl013878

206. Ccg-39063

207. Dl-1,2-dithiolane-3-pentanoic Acid

208. Nsc628502

209. Nsc758651

210. S3996

211. Stk801969

212. Thioctic Acid [ep Monograph]

213. ()-1,2-dithiolane-3-pentanoic Acid

214. Akos000121582

215. Akos016339634

216. Tox21_110285_1

217. Ab09328

218. Am84329

219. Cs-4370

220. Ks-1322

221. Nsc-758651

222. Sb49517

223. Idi1_000912

224. Alpha Lipoic Acid [usp Impurity]

225. Dl-thioctic Acid (oxidized) 25g

226. Ncgc00016032-02

227. Ncgc00016032-03

228. Ncgc00016032-04

229. Ncgc00016032-05

230. Ncgc00016032-07

231. Ncgc00016032-08

232. Ncgc00016032-09

233. Ncgc00016032-11

234. Ncgc00016032-14

235. Ncgc00090872-01

236. Ncgc00090872-02

237. Ncgc00090872-03

238. Ncgc00090872-04

239. Ncgc00090872-05

240. Ncgc00256970-01

241. Ncgc00259357-01

242. (+/-)-alpha-lipoic Acid, >=98.0%

243. .alpha.-lipoic Acid, (+/-)-

244. Ac-22673

245. Bp-31070

246. Nci60_042014

247. R)-(+)-

248. A-lipoic Acid Ooethyaoethaea

249. Sy010902

250. (r)-(+)-(c) Paragraph Sign-lipoic Acid

251. Sbi-0051871.p002

252. 5-(1,2-dithiolan-3-yl)pentanoic Acid #

253. Db-050522

254. ( Inverted Exclamation Marka)-a-lipoic Acid

255. 1,2-dithiolane-3-valeric Acid, (.+-.)-

256. Ft-0622068

257. Ft-0625429

258. Ft-0670812

259. Ft-0670813

260. L0058

261. 1,2-dithiolane-3-pentanoic Acid, (.+-.)-

262. 1,2-dithiolane-3-valeric Acid, (.+/-.)-

263. 1,2-dithiolane-3-pentanoic Acid, (.+/-.)-

264. C00725

265. D00086

266. Ab00052393_09

267. (+/-)?-?1,2-?dithiolane-?3-?pentanoic Acid

268. A801751

269. Q312229

270. 1,2-dithiolane-3-pentanoic Acid, (+-)- (9ci)

271. J-002007

272. J-520421

273. Sr-01000737460-2

274. Sr-01000737460-6

275. 5-((3rs)-1,2-dithiolan-3-yl)pentanoic Acid

276. F2191-0208

277. .delta.-(3-(1,2-dithiacyclopentyl))pentanoic Acid

278. Thioctic Acid, European Pharmacopoeia (ep) Reference Standard

279. (+/-)-alpha-lipoic Acid, Bioreagent, Cell Culture Tested, >=99%

280. (+/-)-alpha-lipoic Acid, Synthetic, >=99% (titration), Powder

281. Alpha Lipoic Acid, United States Pharmacopeia (usp) Reference Standard

282. (r)-(+)-1,2-dithiolane-3-pentanoic Acid; R-(+)-thioctic Acid; R-(+)-alpha-lipoic Acid

283. Afae'a Centa' Nota Inverted Exclamation Markafasa'a

284. Afae'adaggeratrade Mark?-lipoic Acid

285. Thioctic Acid Containing Impurity B, European Pharmacopoeia (ep) Reference Standard

286. Thioctic Acid For System Suitability, European Pharmacopoeia (ep) Reference Standard

287. Thioctic Acid;1,2-dithiolane-3-pentanoic Acid;5-(1,2-dithiolan-3-yl)valeric Acid

2.3.3 Other Synonyms

1. 1200-22-2

2. (r)-lipoic Acid

3. Heparlipon

4. Lipoec

5. Tioctic Acid

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₈H₁₄O₂S₂
Molecular Weight	206.3 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	206.04352203 g/mol
Monoisotopic Mass	206.04352203 g/mol
Topological Polar Surface Area	87.9 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	150
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 Therapeutic Uses

/EXPERIMENTAL THERAPY/ The aim of this trial was to evaluate the effects of alpha-lipoic acid (ALA) on positive sensory symptoms and neuropathic deficits in diabetic patients with distal symmetric polyneuropathy (DSP). In this multicenter, randomized, double-blind, placebo-controlled trial, 181 diabetic patients in Russia and Israel received once-daily oral doses of 600 mg (n = 45) (ALA600), 1,200 mg (n = 47) (ALA1200), and 1,800 mg (ALA1800) of ALA (n = 46) or placebo (n = 43) for 5 weeks after a 1-week placebo run-in period. The primary outcome measure was the change from baseline of the Total Symptom Score (TSS), including stabbing pain, burning pain, paresthesia, and asleep numbness of the feet. Secondary end points included individual symptoms of TSS, Neuropathy Symptoms and Change (NSC) score, Neuropathy Impairment Score (NIS), and patients' global assessment of efficacy. Mean TSS did not differ significantly at baseline among the treatment groups and on average decreased by 4.9 points (51%) in ALA600, 4.5 (48%) in ALA1200, and 4.7 (52%) in ALA1800 compared with 2.9 points (32%) in the placebo group (all P < 0.05 vs. placebo). The corresponding response rates (> or = 50% reduction in TSS) were 62, 50, 56, and 26%, respectively. Significant improvements favoring all three ALA groups were also noted for stabbing and burning pain, the NSC score, and the patients' global assessment of efficacy. The NIS was numerically reduced. Safety analysis showed a dose-dependent increase in nausea, vomiting, and vertigo. CONCLUSIONS: Oral treatment with ALA for 5 weeks improved neuropathic symptoms and deficits in patients with DSP. An oral dose of 600 mg once daily appears to provide the optimum risk-to-benefit ratio.

PMID:17065669 Ziegler D E et al; Diabetes Care 29 (11): 2365-70 (2006)

/EXPERIMENTAL THERAPY/ Mitochondria produce reactive oxygen species that may contribute to vascular dysfunction. alpha-Lipoic acid and acetyl-L-carnitine reduce oxidative stress and improve mitochondrial function. In a double-blind crossover study, the authors examined the effects of combined alpha-lipoic acid/acetyl-L-carnitine treatment and placebo (8 weeks per treatment) on vasodilator function and blood pressure in 36 subjects with coronary artery disease. Active treatment increased brachial artery diameter by 2.3% (P=.008), consistent with reduced arterial tone. Active treatment tended to decrease systolic blood pressure for the whole group (P=.07) and had a significant effect in the subgroup with blood pressure above the median (151+/-20 to 142+/-18 mm Hg; P=.03) and in the subgroup with the metabolic syndrome (139+/-21 to 130+/-18 mm Hg; P=.03). Thus, mitochondrial dysfunction may contribute to the regulation of blood pressure and vascular tone....

PMID:17396066 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2734271 McMackin CJ et al; J Clin Hypertens (Greenwich) 9 (4): 249-55 (2007)

/EXPERIMENTAL THERAPY/ Lipoic acid is an antioxidant that suppresses and treats an animal model of multiple sclerosis, experimental autoimmune encephalomyelitis. The purpose of this study was to determine the pharmacokinetics (PK), tolerability and effects on matrix metalloproteinase-9 (MMP-9) and soluble intercellular adhesion molecule-1 (sICAMP-1) of oral lipoic acid in patients with multiple sclerosis. Thirty-seven MS subjects were randomly assigned to one of four groups: placebo, lipoic acid 600 mg twice a day, lipoic acid 1200 mg once a day and lipoic acid 1200 mg twice a day. Subjects took study capsules for 14 days. ... Subjects taking 1200 mg lipoic acid had substantially higher peak serum lipoic acid levels than those taking 600 mg and that peak levels varied considerably among subjects. We also found a significant negative correlation between peak serum lipoic acid levels and mean changes in serum MMP-9 levels (T = -0.263, P =0.04). There was a significant dose response relationship between lipoic acid and mean change in serum sICAM-1 levels (P =0.03). ... Oral lipoic acid is generally well tolerated and appears capable of reducing serum MMP-9 and sICAM-1 levels. Lipoic acid may prove useful in treating MS by inhibiting MMP-9 activity and interfering with T-cell migration into the CNS.

PMID:15794388 Yadav V et al; Mult Scler 11 (2): 159-65 (2005)

/EXPERIMENTAL THERAPY/ Mitochondrial dysfunction and oxidative damage are highly involved in the pathogenesis of Parkinson's disease. Some mitochondrial antioxidants/nutrients that can improve mitochondrial function and/or attenuate oxidative damage have been implicated in Parkinson's disease therapy. However, few studies have evaluated the preventative effects of a combination of mitochondrial antioxidants/nutrients against Parkinson's disease, and even fewer have sought to optimize the doses of the combined agents. The present study examined the preventative effects of two mitochondrial antioxidant/nutrients, R-alpha-lipoic acid (LA) and acetyl-L-carnitine (ALC), in a chronic rotenone-induced cellular model of Parkinson's disease. We demonstrated that 4-week pretreatment with LA and/or ALC effectively protected SK-N-MC human neuroblastoma cells against rotenone-induced mitochondrial dysfunction, oxidative damage, and accumulation of alpha-synuclein and ubiquitin. Most notably, we found that when combined, LA and ALC worked at 100 to 1000 fold lower concentrations than they did individually. We also found that pretreatment with combined LA and ALC increased mitochondrial biogenesis and decreased production of reactive oxygen species through the upregulation of the peroxisome proliferator-activated receptor-gamma coactivator 1alpha as a possible underlying mechanism. This study provides important evidence that combining mitochondrial antioxidant/nutrients at optimal doses might be an effective and safe prevention strategy for Parkinson's disease. /R-alpha-lipoic acid/

PMID:18624765 Zhang H et al; J Cell Mol Med. 2008 Jun 20. (Epub ahead of print)

For more Therapeutic Uses (Complete) data for alpha-Lipoic acid (11 total), please visit the HSDB record page.

4.2 Drug Warning

Those with diabetes and problems with glucose intolerance are cautioned that supplemental alpha-lipoic acid may lower blood glucose levels. Blood glucose should be monitored and antidiabetic drug dose adjusted, if necessary, to avoid possible hypoglycemia.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 28

Because of lack of long-term safety data, alpha-lipoic acid should be avoided by pregnant and nursing mothers.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 28

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

Vitamin B Complex

A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)

5.2 ATC Code

A - Alimentary tract and metabolism

A16 - Other alimentary tract and metabolism products

A16A - Other alimentary tract and metabolism products

A16AX - Various alimentary tract and metabolism products

A16AX01 - Thioctic acid

5.3 Absorption, Distribution and Excretion

To determine the concentration of alpha-lipoic acid in the aqueous humour and investigate if its topical instillation can increase quantities. Methods: Seventy patients selected to undergo cataract surgery were randomly divided into two groups. Group 1 was used as a control group; for the patients in Group 2, a single instillation of alpha-lipoic acid eye drops (1%) was administered. Immediately before surgery an aliquot of 40-120 microL of aqueous humour was aspirated. The individual aspirations were combined to constitute pools representing time intervals with respect to administration. The levels of alpha-lipoic acid in the aqueous humour were measured using gas chromatography/mass-spectrometry. Pool 0 was created by combining the samples of aqueous humour obtained from the patients in Group 1, the control group, and the level of alpha-lipoic acid was 27.5 + 2.6 ng/mL; in the other pools the time interval between the administration of the eye drops and sampling was respectively 23 minutes, 53 minutes, 72 minutes, 93 minutes and 114 minutes, and the level of alpha-lipoic acid was 33.0 + 10.8 ng/mL; 52.0 + 2.5 ng/mL; 86.7 + 2.5 ng/mL; 91.2 + 2.5 ng/mL; 80.3 + 2.5 ng/mL. /The/ study demonstrates the presence of alpha-lipoic acid in the aqueous humour and indicates that its concentration increases after it is administered in the form of eye drops, reaching maximum values after around 93 minutes. The concentrations that are achieved in the anterior chamber allow us to theorise the possibility of exploiting the antioxidant properties of alpha-lipoic acid.

PMID:20456443 Cagini C et al; Clin Experiment Ophthalmol 38 (6): 572-6 (2010)

R(+)-alpha-lipoic acid is a natural occurring compound that acts as an essential cofactor for certain dehydrogenase complexes. The redox couple alpha-lipoic acid/dihydrolipoic acid possesses potent antioxidant activity. Exogenous racemic alpha-lipoic acid orally administered for the symptomatic treatment of diabetic polyneuropathy is readily and nearly completely absorbed, with a limited absolute bioavailability of about 30% caused by high hepatic extraction. Although the pharmacokinetics of the parent drug have been well characterized in humans, relatively little is known regarding the excretion of alpha-lipoic acid and the pharmacokinetics of any metabolites in humans. In the present study, plasma concentration-time courses, urinary excreted amounts, and pharmacokinetic parameters of alpha-lipoic acid metabolites were evaluated in 9 healthy volunteers after multiple once-daily oral administration of 600 mg racemic alpha-lipoic acid. The primary metabolic pathways of alpha-lipoic acid in man, S-methylation and beta-oxidation, were quantitatively confirmed by an HPLC-electrochemical assay newly established prior to the beginning of this study. Major circulating metabolites were the S-methylated beta-oxidation products 4,6-bismethylthio-hexanoic acid and 2,4-bismethylthio-butanoic acid, whereas its conjugated forms accounted for the major portion excreted in urine. There was no statistically significant difference in the pharmacokinetic parameters Cmax, AUC, and tmax between day 1 and day 4. Despite the prolonged half-lives of the major metabolites compared to the parent drug, no evidence of accumulation was found. Mean values of 12.4% of the administered dose were recovered in the urine after 24 hours as the sum of alpha-lipoic acid and its metabolites. The results of the present study revealed that urinary excretion of alpha-lipoic acid and five of its main metabolites does not play a significant role in the elimination of alpha-lipoic acid. Therefore, biliary excretion, further electrochemically inactive degradation products, and complete utilization of alpha-lipoic acid as a primary substrate in the endogenous metabolism should be considered.

PMID:14551180 Teichert J et al; J Clin Pharmacol 43 (11):1257-67 (2003)

In an open-label, parallel-group study involving 16 patients (8 with severely reduced renal function, 8 with end-stage renal disease needing hemodialysis), the effect of renal function on the pharmacokinetics, metabolism, and safety `of alpha-lipoic acid (thioctic acid) was evaluated by comparing the pharmacokinetic parameters with those of a reference group of 8 healthy subjects. Alpha-lipoic acid 600 mg was administered orally once daily for 4 days, and the pharmacokinetic parameters were measured on days 1 and 4. The mean percentage of the administered dose excreted in urine as parent compound was 0.2 and 0.05 in healthy subjects and subjects with severely reduced renal function, respectively. Assuming a bioavailability of 30%, this represents 0.67% and 0.17% of the bioavailable amount of alpha-lipoic acid, respectively. The percentage of total urinary recovered amounts of alpha-lipoic acid and 5 of its metabolites was 12.0 on both days. The respective values for patients with severe kidney damage were 5.2% (day 1) and 6.4% (day 4). The total percentage of the administered dose removed by hemodialysis was 4.0 in patients with end-stage renal disease. Renal clearance of alpha-lipoic acid and its major metabolites, 6,8-bismethylthio-octanoic acid, 4,6-bismethylthio-hexanoic acid and 2,4-bismethylthio-butanoic acid, were significantly decreased in subjects with kidney damage compared to the reference group. Apparent total clearance of alpha-lipoic acid was poorly correlated with creatinine clearance. There is strong evidence that alpha-lipoic acid is mainly excreted by nonrenal mechanism or further degraded to smaller units in the catabolic process. The significantly increased area under the curve values of 4,6-bismethylthio-hexanoic acid and half-lives of 2,4-bismethylthio-butanoic acid on both days in patients with severely reduced function and end-stage renal disease were not considered to be clinically relevant. Although trough levels of both metabolites tend to increase slightly in these subjects, no accumulation effects were detected. We conclude that the pharmacokinetics of alpha-lipoic acid are not influenced by creatinine clearance and are unaffected in subjects with severely reduced kidney function or end-stage renal disease. Hemodialysis did not significantly contribute to the clearance of alpha-lipoic acid. Hence, dose adjustment of alpha-lipoic acid is not necessary in patients with renal dysfunction.

PMID:15703366 Teichert J et al; J Clin Pharmacol 45 (3): 313-28 (2005)

Alpha-lipoic aicd is absorbed from the small intestine and distributed to the liver via the portal circulation and to various tissues in the body via the systemic circulation.The natural R-enantiomer is more readily absorbed than the L-enantiomer and is the more active form. Alpha-lipoic acid readily crosses the blood-brain barrier. It is found, after its distribution to the various body tissues, intracellularly, intramitochondrialy and extracellularly.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 26

5.4 Metabolism/Metabolites

Alpha-lipoic acid is metabolized to its reduced form, dihydrolipoic acid by mitochondrial lipoamide dehydrogenase. Dihydroipoic acid, together with lipoic acid, form a redox couple. It is also metabolized to lipoamide, which functions as the lipoic acid cofactor in the multienzyme complexes that catalyze the oxidative decarboxylations of pyruvate and alpha-ketoglutarate. Alpha-lipoic acid may be metabolized to dithiol octanoic acid, which can undergo catabolism.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 26

The excretion and biotransformation of rac-alpha-lipoic acid (LA), which is used for the symptomatic treatment of diabetic polyneuropathy, were investigated following single oral dosing of [(14)C]LA to mice (30 mg/kg), rats (30 mg/kg), dogs (10 mg/kg), and unlabeled LA to humans (600 mg). More than 80% of the radioactivity given was renally excreted. Metabolite profiles obtained by radiometric high-performance liquid chromatography revealed that LA was extensively metabolized irrespective of the species. Based on a new on-line liquid chromatography/tandem mass spectroscopy assay developed for negative ions, LA and a total of 12 metabolites were identified. Mitochondrial beta-oxidation played the paramount role in the metabolism of LA. Simultaneously, the circulating metabolites were subjected to reduction of the 1,2-dithiolane ring and subsequent S-methylation. In addition, evidence is given for the first time that the methyl sulfides formed were partly oxidized to give sulfoxides, predominantly in dogs. The disulfoxide of 2,4-bismethylmercapto-butanoic acid, the most polar metabolite identified, was the major metabolite in dogs. Furthermore, new data are presented that suggest conjugation with glycine occurred as a separate metabolic pathway in competition with beta-oxidation, predominantly in mice.

PMID:11353754 Schupke H et al; Drug Metab Dispos 29 (6): 855-62 (2001)

5.5 Mechanism of Action

Alpha-lipoic acid (LA) shows a protective effect on oxidative stress-induced apoptosis while it induces apoptosis in various cancer cells. Intracellular Ca(2+) plays a central role in triggering apoptotic pathways. In the present study, we aim to investigate whether LA induces apoptosis in lung cancer cells and whether Ca(2+) is involved in LA-induced apoptosis. We found that LA decreased cell viability and increased DNA fragmentation of the cells. LA activated the caspase-independent pathway, determined by upregulation of poly(ADP-ribose) polymerase (PARP) and increased the nuclear level of apoptosis-inducing factor and caspase-dependent apoptotic pathway, determined by increased levels of cytochrome c and PARP-1 cleavage product. LA-induced apoptotic alterations were inhibited in the cells treated with Ca(2+) chelator BAPTA-AM. In conclusion, LA induces apoptosis through caspase-independent and caspase-dependent pathways, which is mediated by intracellular Ca(2+).

PMID:19723049 Choi SY et al; Ann N Y Acad Sc 1171: 149-55 (2009)

Alpha-lipoic acid is known to increase insulin sensitivity in vivo and to stimulate glucose uptake into adipose and muscle cells in vitro. In this study, alpha-lipoic acid was demonstrated to stimulate the autophosphorylation of insulin receptor and glucose uptake into 3T3-L1 adipocytes by reducing the thiol reactivity of intracellular proteins. To elucidate mechanism of this effect, role of protein thiol groups and H(2)O(2) in insulin receptor autophosphorylation and glucose uptake was investigated in 3T3-L1 adipocytes following stimulation with alpha-lipoic acid. Alpha-lipoic acid or insulin treatment of adipocytes increased intracellular level of oxidants, decreased thiol reactivity of the insulin receptor beta-subunit, increased tyrosine phosphorylation of the insulin receptor, and enhanced glucose uptake. Alpha-lipoic acid or insulin-stimulated glucose uptake was inhibited (i) by alkylation of intracellular, but not extracellular, thiol groups downstream of insulin receptor activation, and (ii) by diphenylene iodonium at the level of the insulin receptor autophosphorylation. alpha-Lipoic acid also inhibited protein tyrosine phosphatase activity and decreased thiol reactivity of protein tyrosine phosphatase 1B. These findings indicate that oxidants produced by alpha-lipoic acid or insulin are involved in activation of insulin receptor and in inactivation of protein tyrosine phosphatases, which eventually result in elevated glucose uptake into 3T3-L1 adipocytes.

PMID:12948866 Cho KJ et al; Biochem Pharmacol 66 (5): 849-58 (2003)

Reactive oxygen (ROS) and nitrogen oxide (RNOS) species are produced as by-products of oxidative metabolism. A major function for ROS and RNOS is immunological host defense. Recent evidence indicate that ROS and RNOS may also function as signaling molecules. However, high levels of ROS and RNOS have been considered to potentially damage cellular macromolecules and have been implicated in the pathogenesis and progression of various chronic diseases. alpha-Lipoic acid and dihydrolipoic acid exhibit direct free radical scavenging properties and as a redox couple, with a low redox potential of -0.32 V, is a strong reductant. Several studies provided evidence that alpha-lipoic acid supplementation decreases oxidative stress and restores reduced levels of other antioxidants in vivo. However, there is also evidence indicating that alpha-lipoic acid and dihydrolipoic acid may exert prooxidant properties in vitro. alpha-Lipoic acid and dihydrolipoic acid were shown to promote the mitochondrial permeability transition in permeabilized hepatocytes and isolated rat liver mitochondria. Dihydrolipoic acid also stimulated superoxide anion production in rat liver mitochondria and submitochondrial particles. alpha-Lipoic acid was recently shown to stimulate glucose uptake into 3T3-L1 adipocytes by increasing intracellular oxidant levels and/or facilitating insulin receptor autophosphorylation presumably by oxidation of critical thiol groups present in the insulin receptor beta-subunit. Whether alpha-lipoic acid and/or dihydrolipoic acid-induced oxidative protein modifications contribute to their versatile effects observed in vivo warrants further investigation.

PMID:12127266 Moini H et al; Toxicol Appl Pharmacol 182 (1): 84-90 (2002)

This study investigated the effect of alpha-lipoic acid (ALA) in concentration range 0.7-5.0 mM on the intracellular level of reduced glutathione, the cell cycle phase distribution, the structure of microfilaments and microtubules of normal (3T3) and transformed (3T3-SV40) fibroblasts. We obtained that ALA increased the glutathione content in transformed cells, but did not change its level in normal cells, induced cell cycle arrest of 3T3 cells (but not 3T3-SV40 cells), and disrupted actin microfilaments in cells of both lines. The effect of ALA was compared with N-acetylcysteine (NAC) action. The whole complex of findings allows us to affirm that each of these antioxidants acts on its own target molecules in normal and transformed cells and activates different signal and metabolic pathways in these cells. But at the same time the intermediate steps of ALA and NAC action can be common (alteration of the intracellular level of glutathione, reorganization of actin cytoskeleton, etc.).

PMID:20141032 Vakhromova EA et al; Tsitologiia 51 (12): 971-7 (2009)

For more Mechanism of Action (Complete) data for alpha-Lipoic acid (7 total), please visit the HSDB record page.

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