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Chemistry

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Also known as: Niacin, 59-67-6, Pyridine-3-carboxylic acid, 3-pyridinecarboxylic acid, 3-carboxypyridine, Wampocap
Molecular Formula
C6H5NO2
Molecular Weight
123.11  g/mol
InChI Key
PVNIIMVLHYAWGP-UHFFFAOYSA-N
FDA UNII
2679MF687A

Niacin
A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.
Niacin is a Nicotinic Acid.
1 2D Structure

Niacin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pyridine-3-carboxylic acid
2.1.2 InChI
InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
2.1.3 InChI Key
PVNIIMVLHYAWGP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CN=C1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
2679MF687A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3 Pyridinecarboxylic Acid

2. 3-pyridinecarboxylic Acid

3. Aluminum Salt, Niacin

4. Enduracin

5. Hydrochloride, Niacin

6. Induracin

7. Lithium Nicotinate

8. Niacin

9. Niacin Aluminum Salt

10. Niacin Ammonium Salt

11. Niacin Calcium Salt

12. Niacin Cobalt (2+) Salt

13. Niacin Copper (2+) Salt

14. Niacin Hydrochloride

15. Niacin Iron (2+) Salt

16. Niacin Lithium Salt

17. Niacin Lithium Salt, Hemihydrate

18. Niacin Magnesium Salt

19. Niacin Manganese (2+) Salt

20. Niacin Potassium Salt

21. Niacin Sodium Salt

22. Niacin Tartrate

23. Niacin Tosylate

24. Niacin Zinc Salt

25. Nicamin

26. Nico 400

27. Nico-400

28. Nico400

29. Nicobid

30. Nicocap

31. Nicolar

32. Nicotinate

33. Nicotinate, Lithium

34. Potassium Salt, Niacin

35. Sodium Salt, Niacin

36. Tartrate, Niacin

37. Tosylate, Niacin

38. Wampocap

2.3.2 Depositor-Supplied Synonyms

1. Niacin

2. 59-67-6

3. Pyridine-3-carboxylic Acid

4. 3-pyridinecarboxylic Acid

5. 3-carboxypyridine

6. Wampocap

7. Niaspan

8. Acidum Nicotinicum

9. Vitamin B3

10. Nicolar

11. Apelagrin

12. Pellagrin

13. Akotin

14. Daskil

15. Efacin

16. Pelonin

17. Linic

18. Nicamin

19. Nicobid

20. Nicocap

21. Enduracin

22. Nicodelmine

23. Niconacid

24. Nicotinipca

25. Pellagramin

26. Direktan

27. Nicacid

28. Nicangin

29. Peviton

30. Bionic

31. Diacin

32. Nicyl

33. Nyclin

34. Niac

35. Vitaplex N

36. Davitamon Pp

37. Nico-span

38. Tega-span

39. Nicocidin

40. Nicocrisina

41. Niconazid

42. Nicoside

43. Nicotamin

44. Nicotene

45. Nicovasan

46. Nicovasen

47. Nipellen

48. Sk-niacin

49. Naotin

50. Niacor

51. Nicodon

52. Niconat

53. Nicosan 3

54. Nicosyl

55. Nicotil

56. Tinic

57. 3-carboxylpyridine

58. Nicotine Acid

59. Slo-niacin

60. Nico

61. 3-picolinic Acid

62. Nicotinsaure

63. Nico-400

64. Acide Nicotinique

65. Pyridine-beta-carboxylic Acid

66. Nicagin

67. Anti-pellagra Vitamin

68. Caswell No. 598

69. Pp Factor

70. Kyselina Nikotinova

71. P.p. Factor

72. Pellagra Preventive Factor

73. S115

74. Nicotinsaure [german]

75. Acido Nicotinico

76. 3-pyridylcarboxylic Acid

77. M-pyridinecarboxylic Acid

78. Kyselina Nikotinova [czech]

79. Mfcd00006391

80. Niacine

81. Ccris 1902

82. Pyridine-carboxylique-3

83. Epa Pesticide Chemical Code 056701

84. Acide Nicotinique [inn-french]

85. Acido Nicotinico [inn-spanish]

86. Acidum Nicotinicum [inn-latin]

87. Hsdb 3134

88. Pyridine-carboxylique-3 [french]

89. Ai3-18994

90. Pyridinecarboxylic Acid, 3-

91. Niacin [usp]

92. Sr 4390

93. Brn 0109591

94. Niacin Extended Release

95. Nicotinic Acid [inn]

96. Nah

97. Chembl573

98. Beta-pyridinecarboxylic Acid

99. Nsc-169454

100. Mls000069603

101. Pyridine-.beta.-carboxylic Acid

102. Chebi:15940

103. Niacin (usp)

104. 2679mf687a

105. P.p. Factor-pellagra Preventive Factor

106. Cas-59-67-6

107. Ncgc00016268-02

108. Smr000059024

109. Dsstox_cid_932

110. [5, 6-3h]-niacin

111. Dsstox_rid_75875

112. Dsstox_gsid_20932

113. Niacin [usan]

114. Nicotinicacid

115. Nio

116. Niacin (nicotinic Acid)

117. Sr-01000722017

118. 36321-41-2

119. Einecs 200-441-0

120. Niaspan Titration Starter Pack

121. Nsc 169454

122. Pellagra

123. Nikotinsaeure

124. Ncotnc Acd

125. Unii-2679mf687a

126. Preventative Factor

127. Antipellagra Vitamin

128. Niaspan (tn)

129. 3pyrcooh

130. [3h]nicotinic Acid

131. Niacor (tn)

132. Nicotinic Acid,(s)

133. [3h]-nicotinic Acid

134. Spectrum_001063

135. 3-pyridinecarboxylicacid

136. Nicotinic Acid, Ph Eur

137. Niacin [vandf]

138. Niacin [hsdb]

139. Niacin [inci]

140. 5-pyridinecarboxylic Acid

141. Niacin [fcc]

142. Niacin [usp-rs]

143. Opera_id_1346

144. Prestwick0_000881

145. Prestwick1_000881

146. Prestwick2_000881

147. Prestwick3_000881

148. Pyridine-3-carbonic Acid

149. Spectrum2_000006

150. Spectrum3_000515

151. Spectrum4_000965

152. Spectrum5_001287

153. Vitamin B-3

154. 3-pyridyl Carboxylic Acid

155. Nicotinic Acid-d3(major)

156. Wln: T6nj Cvq

157. 3-pyridine Carboxylic Acid

158. Bmse000104

159. Nicotinic Acid, >=98%

160. Nicotinic Acid, Usp Grade

161. Ec 200-441-0

162. Schembl1433

163. Nicotinic Acid [mi]

164. Oprea1_514398

165. Vitamin B3 [vandf]

166. Bspbio_000662

167. Bspbio_002069

168. Kbiogr_001309

169. Kbioss_001543

170. Niacin [orange Book]

171. Nicotinic Acid [jan]

172. 5-22-02-00057 (beilstein Handbook Reference)

173. Bidd:gt0644

174. Divk1c_000695

175. Nicotinic Acid (jp17/inn)

176. Simcor Component Niacin

177. Spectrum1500430

178. .beta.-pyridinecarboxylic Acid

179. Spbio_000011

180. Spbio_002881

181. Advicor Component Niacin

182. Niacin [usp Monograph]

183. Nicotinic Acid [vandf]

184. Bpbio1_000730

185. Gtpl1588

186. Gtpl1594

187. Zinc1795

188. Nicotinic Acid [mart.]

189. Dtxsid1020932

190. Nicotinic Acid [who-dd]

191. Nicotinic Acid [who-ip]

192. Bdbm23515

193. Hms502c17

194. Kbio1_000695

195. Kbio2_001543

196. Kbio2_004111

197. Kbio2_006679

198. Kbio3_001569

199. Abt-919

200. Niacin Component Of Simcor

201. Nicotinic Acid [ema Epar]

202. Ninds_000695

203. Hms1570b04

204. Hms1920p17

205. Hms2091h22

206. Hms2097b04

207. Hms2236a05

208. Hms3259k21

209. Hms3371e07

210. Hms3655k08

211. Hms3714b04

212. Niacin Component Of Advicor

213. Pharmakon1600-01500430

214. Nicotinic Acid, Analytical Standard

215. Bcp16301

216. Hy-b0143

217. Str00112

218. Tox21_110337

219. Tox21_201420

220. Tox21_302904

221. Ac8691

222. Bbl037343

223. Ccg-38340

224. Nicotinic Acid [ep Impurity]

225. Nicotinic Acid, For Synthesis, 99%

226. Nsc169454

227. Nsc757241

228. S1744

229. Stk301803

230. Nicotinic Acid (vitamin B3) Solution

231. Nicotinic Acid [ep Monograph]

232. Akos000118980

233. Nicotinic Acid, >=99.5% (hplc)

234. Tox21_110337_1

235. Am81316

236. Cs-1946

237. Db00627

238. Nc00524

239. Nicotinic Acid 1.0 Mg/ml In Methanol

240. Nsc-757241

241. Ps-4255

242. Sdccgmls-0066610.p001

243. Idi1_000695

244. Ncgc00016268-01

245. Ncgc00016268-03

246. Ncgc00016268-04

247. Ncgc00016268-05

248. Ncgc00016268-08

249. Ncgc00016268-09

250. Ncgc00094734-01

251. Ncgc00094734-02

252. Ncgc00256537-01

253. Ncgc00258971-01

254. Ac-22484

255. Acidum Nicotinicum [who-ip Latin]

256. Bp-21419

257. Nci60_001041

258. Nicotinic Acid, Nist(r) Srm(r) 148

259. Nicotinic Acid, Plant Cell Culture Tested

260. Sy011111

261. Nicotinic Acid 100 Microg/ml In Methanol

262. Sbi-0051456.p003

263. Db-007765

264. Nicotinic Acid [matrix For Maldi-tof/ms]

265. Ab00052050

266. Ft-0600004

267. Ft-0672715

268. Ft-0672716

269. Ft-0672717

270. Ft-0672718

271. Ft-0773496

272. N0082

273. N1103

274. Nicotinic Acid 10 Microg/ml In Acetonitrile

275. Nicotinic Acid, Purum, >=99.0% (hplc)

276. Sw197229-3

277. C00253

278. D00049

279. Nicotinic Acid, Saj Special Grade, >=99.5%

280. Ab00052050-13

281. Ab00052050_14

282. Ab00052050_15

283. Nicotinic Acid, Meets Usp Testing Specifications

284. Ac-907/25014105

285. L001199

286. Methyl Nicotinate Impurity A [ep Impurity]

287. Nicotinic Acid, Vetec(tm) Reagent Grade, >=98%

288. Q134658

289. J-523605

290. Sr-01000722017-2

291. Sr-01000722017-3

292. Sr-01000722017-4

293. Z56755709

294. 3ddb011e-f3a6-45b6-a2d2-77b2a6e8936e

295. F2191-0082

296. Niacin, United States Pharmacopeia (usp) Reference Standard

297. Nicotinic Acid, Certified Reference Material, Tracecert(r)

298. Nicotinic Acid, European Pharmacopoeia (ep) Reference Standard

299. Nicotinic Acid, Matrix Substance For Maldi-ms, >=99.5% (hplc)

300. Nicotinic Acid, For Inorganic Trace Analysis, >=99.999% (metals Basis)

301. Niacin (nicotinic Acid), Pharmaceutical Secondary Standard; Certified Reference Material

302. 101113-41-1

303. Nicotinic Acid (vitamin B3) Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

304. Nicotinic Acid, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture, Suitable For Plant Cell Culture, >=98%

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 123.11 g/mol
Molecular Formula C6H5NO2
XLogP30.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass123.032028402 g/mol
Monoisotopic Mass123.032028402 g/mol
Topological Polar Surface Area50.2 Ų
Heavy Atom Count9
Formal Charge0
Complexity114
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 Information
1 of 6  
Drug NameNiacin
PubMed HealthNiacin (By mouth)
Drug ClassesAntihyperlipidemic, Nutriceutical, Nutritive Agent
Drug LabelNIASPAN (niacin tablet, film-coated extended-release), contains niacin, which at therapeutic doses is an antihyperlipidemic agent. Niacin (nicotinic acid, or 3-pyridinecarboxylic acid) is a white, crystalline powder, very soluble in water, with the f...
Active IngredientNiacin
Dosage FormTablet, extended release; Tablet
RouteOral
Strength500mg; 750mg; 1gm
Market StatusPrescription
CompanyWockhardt; Lupin; Sun Pharma Global; Barr

2 of 6  
Drug NameNiacor
Drug LabelNiacin or nicotinic acid, a water-soluble B-complex vitamin and antihyperlipidemic agent, is 3-pyridinecarboxylic acid. It is a white, crystalline powder, sparingly soluble in water. It has the following structural formula:Each NIACOR Tablet, for o...
Active IngredientNiacin
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyUpsher Smith

3 of 6  
Drug NameNiaspan
Drug LabelNIASPAN (niacin tablet, film-coated extended-release), contains niacin, which at therapeutic doses is an antihyperlipidemic agent. Niacin (nicotinic acid, or 3-pyridinecarboxylic acid) is a white, crystalline powder, very soluble in water, with the f...
Active IngredientNiacin
Dosage FormTablet, extended release
RouteOral
Strength500mg; 750mg; 1gm
Market StatusPrescription
CompanyAbbvie

4 of 6  
Drug NameNiacin
PubMed HealthNiacin (By mouth)
Drug ClassesAntihyperlipidemic, Nutriceutical, Nutritive Agent
Drug LabelNIASPAN (niacin tablet, film-coated extended-release), contains niacin, which at therapeutic doses is an antihyperlipidemic agent. Niacin (nicotinic acid, or 3-pyridinecarboxylic acid) is a white, crystalline powder, very soluble in water, with the f...
Active IngredientNiacin
Dosage FormTablet, extended release; Tablet
RouteOral
Strength500mg; 750mg; 1gm
Market StatusPrescription
CompanyWockhardt; Lupin; Sun Pharma Global; Barr

5 of 6  
Drug NameNiacor
Drug LabelNiacin or nicotinic acid, a water-soluble B-complex vitamin and antihyperlipidemic agent, is 3-pyridinecarboxylic acid. It is a white, crystalline powder, sparingly soluble in water. It has the following structural formula:Each NIACOR Tablet, for o...
Active IngredientNiacin
Dosage FormTablet
RouteOral
Strength500mg
Market StatusPrescription
CompanyUpsher Smith

6 of 6  
Drug NameNiaspan
Drug LabelNIASPAN (niacin tablet, film-coated extended-release), contains niacin, which at therapeutic doses is an antihyperlipidemic agent. Niacin (nicotinic acid, or 3-pyridinecarboxylic acid) is a white, crystalline powder, very soluble in water, with the f...
Active IngredientNiacin
Dosage FormTablet, extended release
RouteOral
Strength500mg; 750mg; 1gm
Market StatusPrescription
CompanyAbbvie

4.2 Therapeutic Uses

Hypolipidemic Agents, Vasodilator Agents, Vitamin B Complex

National Library of Medicine's Medical Subject Headings. Citalopram. Online file (MeSH, 2018). Available from, as of February 2, 2018: https://meshb.nlm.nih.gov/search


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Niacin included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of February 2, 2018: https://clinicaltrials.gov/


Niacin is used as an adjunct to dietary therapy in patients with a history of myocardial infarction (MI) and hypercholesterolemia to reduce the risk of recurrent nonfatal MI. Extended-release niacin in fixed combination with lovastatin is used in patients for whom treatment with both extended-release niacin and lovastatin is appropriate. /Included in US product label/

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1936


Niacin, in combination with a bile acid sequestrant, also is used to slow the progression or promote regression of atherosclerosis in patients with clinical evidence of coronary heart disease who have elevated cholesterol concentrations. Extended-release niacin in fixed combination with lovastatin is used in patients for whom treatment with both extended-release niacin and lovastatin is appropriate. /Included in US product label/

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1936


For more Therapeutic Uses (Complete) data for Nicotinic acid (31 total), please visit the HSDB record page.


4.3 Drug Warning

Concomitant administration of niacin with alcohol, hot drinks, or spicy foods may increase the risk of flushing or pruritus; these beverages or foods should be avoided at the time of drug ingestion.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1937


Decreased glucose tolerance has been reported in patients receiving niacin in controlled clinical trials. Therefore, the manufacturers and many clinicians suggest that patients with (or those at risk of developing) diabetes mellitus be observed closely. The ACC/AHA cholesterol management guideline recommends that fasting blood glucose concentrations or glycosylated hemoglobin (hemoglobin A1c, HbA1c) be obtained before initiation of therapy, following an increase in niacin dosage, and periodically (e.g., every 6 months) thereafter. If niacin is used in diabetic or potentially diabetic patients, dosages of niacin and/or antidiabetic agents should be adjusted appropriately. Niacin should be discontinued if hyperglycemia persists.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1939


Niacin should be used with caution in patients with unstable angina, acute myocardial infarction (MI), or coronary heart disease (CHD), particularly when these patients also are receiving vasoactive drugs such as nitrates, calcium-channel blockers, or adrenergic blocking agents. Since niacin therapy has been associated with small, but statistically significant, increases in prothrombin time (PT), the drug, alone or in fixed combination with lovastatin, should be used with caution in patients undergoing surgery. PT and platelet count should be monitored closely in patients receiving niacin concomitantly with anticoagulants.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1939


Because hyperuricemia has been reported with niacin therapy, the drug should be used with caution in patients predisposed to gout. The ACC/AHA cholesterol management guideline recommends that uric acid concentrations be obtained before initiation of therapy, following an increase in niacin dosage, and periodically (e.g., every 6 months) thereafter. Niacin should be discontinued if acute gout occurs.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1939


For more Drug Warnings (Complete) data for Nicotinic acid (33 total), please visit the HSDB record page.


4.4 Drug Indication

Niacin is indicated to prevent vitamin deficiencies in pediatric and adult patients receiving parenteral nutrition as part of multivitamin intravenous injections. Niacin oral tablets are indicated as a monotherapy or in combination with simvastatin or lovastatin to treat primary hyperlipidemia and mixed dyslipidemia. It can also be used to reduce the risk of nonfatal myocardial infarctions in patients with a history of myocardial infarction and hyperlipidemia. Niacin is also indicated with bile acid binding resins to treat atherosclerosis in patients with coronary artery disease and hyperlipidemia or to treat primary hyperlipidemia. Finally niacin is indicated to treat severe hypertriglyceridemia.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Niacin is a B vitamin used to treat vitamin deficiencies as well as hyperlipidemia, dyslipidemia, hypertriglyceridemia, and to reduce the risk of myocardial infarctions. Niacin acts to decrease levels of very low density lipoproteins and low density lipoproteins, while increasing levels of high density lipoproteins. Niacin has a wide therapeutic window with usual oral doses between 500mg and 2000mg. Patients with diabetes, renal failure, uncontrolled hypothyroidism, and elderly patients taking niacin with simvastatin or lovastatin are at increased risk of myopathy and rhabdomyolysis.


5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Hypolipidemic Agents

Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS. (See all compounds classified as Hypolipidemic Agents.)


Vitamin B Complex

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


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
NIACIN
5.3.2 FDA UNII
2679MF687A
5.3.3 Pharmacological Classes
Nicotinic Acids [CS]; Nicotinic Acid [EPC]
5.4 ATC Code

C - Cardiovascular system

C04 - Peripheral vasodilators

C04A - Peripheral vasodilators

C04AC - Nicotinic acid and derivatives

C04AC01 - Nicotinic acid


C - Cardiovascular system

C10 - Lipid modifying agents

C10A - Lipid modifying agents, plain

C10AD - Nicotinic acid and derivatives

C10AD02 - Nicotinic acid


5.5 Absorption, Distribution and Excretion

Absorption

In patients with chronic kidney disease, the Cmax is 0.06g/mL for a 500mg oral dose, 2.42g/mL for a 1000mg oral dose, and 4.22g/mL for a 1500mg oral dose. The Tmax is 3.0 hours for a 1000mg or 1500mg oral dose. The AUC is 1.44g\*h/mL for a 500mg oral dose, 6.66g\*h/mL for a 1000mg oral dose, and 12.41g\*h/mL for a 1500mg oral dose. These values did not drastically differ in patients requiring dialysis.


Route of Elimination

69.5% of a dose of niacin is recovered in urine. 37.9% of the recovered dose was N-methyl-2-pyridone-5-carboxamide, 16.0% was N-methylnicotinamide, 11.6% was nicotinuric acid, and 3.2% was niacin.


Volume of Distribution

Data regarding the volume of distribution of niacin is not readily available.


Clearance

Data regarding the clearance of niacin is not readily available.


/MILK/ Niacin is distributed in human milk.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1940


Niacin is rapidly and extensively (60-76% of dose) absorbed following oral administration. Peak plasma concentrations of niacin following administration of an immediate-release (Niacor) or extended-release (Niaspan) niacin preparation generally are attained within 30-60 minutes or 4-5 hours after oral administration, respectively. The bioavailability of 1 tablet containing 1 g of extended-release niacin in fixed combination with 40 mg of lovastatin (Advicor 1 g/40 mg) differs from that of 2 tablets each containing 500 mg of extended-release niacin in fixed combination with 20 mg of lovastatin (Advicor 500 mg/20 mg). ... Peak plasma concentrations of niacin and metabolites following oral administration of Niaspan extended-release tablets appear to be slightly higher in women than in men, possibly because of differences in metabolism. Limited data suggest that women may exhibit greater antilipemic response to niacin than men, possibly because of gender-specific differences in the metabolic rate or volume of distribution of the drug.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1941


Niacin is distributed mainly to the liver, kidney, and adipose tissue.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1941


Niacin and its metabolites are rapidly excreted in urine. Following oral administration of single and multiple doses of an immediate-release (Niacor) or extended-release (Niaspan) niacin preparation, approximately 88 or 60-76% of the dose, respectively, was excreted in urine as unchanged drug and inactive metabolites.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1941


For more Absorption, Distribution and Excretion (Complete) data for Nicotinic acid (10 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

The metabolism of niacin is poorly described in the literature, but the metabolites niacinamide, niacinamide N-oxide, nicotinuric acid, N1-methyl-2-pyridone-5-carboxamide, N1-methyl-4-pyridone-5-carboxamide, and trigonelline have been identified in human urine.


... Nicotinamide is the main substance that is transported between the different tissues as a precursor of nicotinamide adenine dinucleotide (NAD) synthesis. The liver, kidneys, brain and erythrocytes prefer nicotinic acid as a precursor for NAD synthesis, but testes and ovaries prefer nicotinamide. NAD nucleosidase cleaves NAD with nicotinamide as one of the products. This can be deamidated to form nicotinic acid (and re-converted to NAD) or methylated and released via urine. Excretion of the amide (and its metabolites) tends to be more extensive compared to the acid.

Organization for Economic Cooperation and Development; Screening Information Data Set for 3-Pyridinecarboxamide (Nicotinamide) CAS #: 98-92-0 p.40 (2005). Available from, as of July 23, 2018: https://www.inchem.org/pages/sids.html


Niacin is rapidly metabolized and undergoes extensive first-pass metabolism. The drug is converted to several metabolites, including nicotinuric acid (NUA), nicotinamide, and nicotinamide adenine dinucleotide (NAD). At doses used to treat hyperlipoproteinemia, the principal metabolic pathways appear to be saturable, and niacin is thought to exhibit nonlinear, dose-dependent pharmacokinetics. Nicotinamide does not appear to exert antilipemic effects; the activity of other metabolites on lipoprotein fractions currently are unknown.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1941


After doses of 100 mg of niacin (total dose of 200 mg), the urinary excretion of alkalihydrolyzable niacin derivatives and of N1-methylnicotinamide increased from 6.0 to 14.6 mg and from 2.8 to 5.7 mg after 3 hr in four human subjects, respectively. Chromatographic results showed the major metabolite in the urine to be nicotinuric acid, forming 92-99% of the alkalihydrolysable derivatives. Niacinamide (1-4%) was the other metabolite. There was no free niacin in the urine except in one subject who had intense flushing of the skin soon after ingesting the niacin. In these four subjects, there was a large increase in the excretion of N1-methylnicotinamide, which varied from 6.9 to 16.6 mg/3 hr. The small rise in the tertiary nicotinyl derivatives (0.9 to 1.8 mg) was solely due to niacinamide, since no other nicotinyl compound could be detected on the paper chromatograms. Urine from undosed subjects, averaged 0.53 mg N1-methylnicotinamide for a period of 3 hr. The total content of tertiary alkali-hydrolyzable derivative of niacin ranged from 0.2 to 0.3 mg within 3 hr.

Cosmetic Ingredient Review (CIR) Expert Panel; Final Report of the Safety Assessment of Niacinamide and Niacin; Intl J of Toxicology 24 (Suppl 5): p.7 (2005).


N1-methyl-4- pyridone-3-carboxamide is a major metabolite of niacin and niacinamide which has been found to be synthesized from N1- methylnicotinamide.

Cosmetic Ingredient Review (CIR) Expert Panel; Final Report of the Safety Assessment of Niacinamide and Niacin; Intl J of Toxicology 24 (Suppl 5): p.8 (2005). Available from, as of July 23, 218: https://www.cir-safety.org/ingredients


For more Metabolism/Metabolites (Complete) data for Nicotinic acid (8 total), please visit the HSDB record page.


5.7 Biological Half-Life

The half life of niacin is 0.9h, nicotinuric acid is 1.3h, and nicotinamide is 4.3h.


/The authors/ describe a case of massive oral niacin overdose that resulted in severe persistent hypotension without the manifestation of cutaneous flushing. ... A 56-year-old male with a history of schizophrenia presented to the emergency department after orally ingesting 11,000 mg of niacin. ... Serum niacin levels were 8.2 ug/mL and 5.6 ug/mL at 48 and 96 hours post ingestion, respectively, giving an apparent half-life of 87 hours. ...

PMID:16496499 Mularski RA et al; Clin Toxicol (Phila) 44 (1): 81-4 (2006)


Half-life about 45 min.

Knoben, J.E. and P.O. Anderson (eds.) Handbook of Clinical Drug Data. 6th ed. Bethesda, MD: Drug Intelligence Publications, Inc. 1988., p. 502


The plasma half-life of niacin has been reported to range from 20-60 minutes.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 1941


5.8 Mechanism of Action

Niacin performs a number of functions in the body and so has many mechanisms, not all of which have been fully described. Niacin can decrease lipids and apolipoprotein B (apo B)-containing lipoproteins by modulating triglyceride synthesis in the liver, which degrades apo B, or by modulating lipolysis in adipose tissue. Niacin inhibits hepatocyte diacylglycerol acyltransferase-2. This action prevents the final step of triglyceride synthesis in hepatocytes, limiting available triglycerides for very low density lipoproteins (VLDL). This activity also leads to intracellular degradation of apo B and decreased production of low density lipoproteins, the catabolic product of VLDL. Niacin also inhibits a high density lipoprotein (HDL) catabolism receptor, which increases the levels and half life of HDL.


Prolonged niacin treatment elicits beneficial effects on the plasma lipid and lipoprotein profile that is associated with a protective CVD risk profile. Acute niacin treatment inhibits nonesterified fatty acid release from adipocytes and stimulates prostaglandin release from skin Langerhans cells, but the acute effects diminish upon prolonged treatment, while the beneficial effects remain. To gain insight in the prolonged effects of niacin on lipid metabolism in adipocytes, we used a mouse model with a human-like lipoprotein metabolism and drug response [female APOE*3-Leiden.CETP (apoE3 Leiden cholesteryl ester transfer protein) mice] treated with and without niacin for 15 weeks. The gene expression profile of gonadal white adipose tissue (gWAT) from niacin-treated mice showed an upregulation of the "biosynthesis of unsaturated fatty acids" pathway, which was corroborated by quantitative PCR and analysis of the FA ratios in gWAT. Also, adipocytes from niacin-treated mice secreted more of the PUFA DHA ex vivo. This resulted in an increased DHA/arachidonic acid (AA) ratio in the adipocyte FA secretion profile and in plasma of niacin-treated mice. Interestingly, the DHA metabolite 19,20-dihydroxy docosapentaenoic acid (19,20-diHDPA) was increased in plasma of niacin-treated mice. Both an increased DHA/AA ratio and increased 19,20-diHDPA are indicative for an anti-inflammatory profile and may indirectly contribute to the atheroprotective lipid and lipoprotein profile associated with prolonged niacin treatment.

PMID:25320342 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4242446 Heemskerk MM et al; J Lipid Res 55 (12): 2532-40 (2014)


/The study objective was/ to determine the effects of niacin on adiponectin and markers of adipose tissue inflammation in a mouse model of obesity. Male C57BL/6 mice were placed on a control or high-fat diet (HFD) and were maintained on such diets for the duration of the study. After 6 weeks on the control or high fat diets, vehicle or niacin treatments were initiated and maintained for 5 weeks. Identical studies were conducted concurrently in HCA2 (-/-) (niacin receptor(-/-)) mice. Niacin increased serum concentrations of the anti-inflammatory adipokine, adiponectin by 21% in HFD-fed wild-type mice, but had no effect on lean wild-type or lean or HFD-fed HCA2 (-/-) mice. Niacin increased adiponectin gene and protein expression in the HFD-fed wild-type mice only. The increases in adiponectin serum concentrations, gene and protein expression occurred independently of changes in expression of PPARgamma C/EBPalpha or SREBP-1c (key transcription factors known to positively regulate adiponectin gene transcription) in the adipose tissue. Further, niacin had no effect on adipose tissue expression of ERp44, Ero1-Lalpha, or DsbA-L (key ER chaperones involved in adiponectin production and secretion). However, niacin treatment attenuated HFD-induced increases in adipose tissue gene expression of MCP-1 and IL-1beta in the wild-type HFD-fed mice. Niacin also reduced the expression of the pro-inflammatory M1 macrophage marker CD11c in HFD-fed wild-type mice. Niacin treatment attenuates obesity-induced adipose tissue inflammation through increased adiponectin and anti-inflammatory cytokine expression and reduced pro-inflammatory cytokine expression in a niacin receptor-dependent manner.

PMID:23967184 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3742781 Wanders D et al; PLoS One 8 (8): e71285 (2013)


Nicotinic acid (niacin), a vitamin of the B complex, has been used for almost 50 years as a lipid-lowering drug. The pharmacological effect of nicotinic acid requires doses that are much higher than those provided by a normal diet. Its primary action is to decrease lipolysis in adipose tissue by inhibiting hormone-sensitive triglyceride lipase. This anti-lipolytic effect of nicotinic acid involves the inhibition of cyclic adenosine monophosphate (cAMP) accumulation in adipose tissue through a G(i)-protein-mediated inhibition of adenylyl cyclase. A G-protein-coupled receptor for nicotinic acid has been proposed in adipocytes. Here, we show that the orphan G-protein-coupled receptor, "protein upregulated in macrophages by interferon-gamma" (mouse PUMA-G, human HM74), is highly expressed in adipose tissue and is a nicotinic acid receptor. Binding of nicotinic acid to PUMA-G or HM74 results in a G(i)-mediated decrease in cAMP levels. In mice lacking PUMA-G, the nicotinic acid-induced decrease in free fatty acid (FFA) and triglyceride plasma levels was abrogated, indicating that PUMA-G mediates the anti-lipolytic and lipid-lowering effects of nicotinic acid in vivo. The identification of the nicotinic acid receptor may be useful in the development of new drugs to treat dyslipidemia.

PMID:12563315 Tunaru S et al; Nat Med 9 (3): 352-5 (2003)


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04-Jan-2022
30-May-2025
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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 1GM ...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 1GM **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20381

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 500M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 500MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20381

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 750M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 750MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20381

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ABOUT THIS PAGE

Looking for 59-67-6 / Niacin API manufacturers, exporters & distributors?

Niacin manufacturers, exporters & distributors 1

13

PharmaCompass offers a list of Niacin API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Niacin manufacturer or Niacin supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Niacin manufacturer or Niacin supplier.

PharmaCompass also assists you with knowing the Niacin API Price utilized in the formulation of products. Niacin API Price is not always fixed or binding as the Niacin Price is obtained through a variety of data sources. The Niacin Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Niacin

Synonyms

59-67-6, Pyridine-3-carboxylic acid, 3-pyridinecarboxylic acid, 3-carboxypyridine, Wampocap, Niaspan

Cas Number

59-67-6

Unique Ingredient Identifier (UNII)

2679MF687A

About Niacin

A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.

Niacin Manufacturers

A Niacin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Niacin, including repackagers and relabelers. The FDA regulates Niacin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Niacin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Niacin manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Niacin Suppliers

A Niacin supplier is an individual or a company that provides Niacin active pharmaceutical ingredient (API) or Niacin finished formulations upon request. The Niacin suppliers may include Niacin API manufacturers, exporters, distributors and traders.

click here to find a list of Niacin suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Niacin USDMF

A Niacin DMF (Drug Master File) is a document detailing the whole manufacturing process of Niacin active pharmaceutical ingredient (API) in detail. Different forms of Niacin DMFs exist exist since differing nations have different regulations, such as Niacin USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Niacin DMF submitted to regulatory agencies in the US is known as a USDMF. Niacin USDMF includes data on Niacin's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Niacin USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Niacin suppliers with USDMF on PharmaCompass.

Niacin KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Niacin Drug Master File in Korea (Niacin KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Niacin. The MFDS reviews the Niacin KDMF as part of the drug registration process and uses the information provided in the Niacin KDMF to evaluate the safety and efficacy of the drug.

After submitting a Niacin KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Niacin API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Niacin suppliers with KDMF on PharmaCompass.

Niacin CEP

A Niacin CEP of the European Pharmacopoeia monograph is often referred to as a Niacin Certificate of Suitability (COS). The purpose of a Niacin CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Niacin EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Niacin to their clients by showing that a Niacin CEP has been issued for it. The manufacturer submits a Niacin CEP (COS) as part of the market authorization procedure, and it takes on the role of a Niacin CEP holder for the record. Additionally, the data presented in the Niacin CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Niacin DMF.

A Niacin CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Niacin CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Niacin suppliers with CEP (COS) on PharmaCompass.

Niacin WC

A Niacin written confirmation (Niacin WC) is an official document issued by a regulatory agency to a Niacin manufacturer, verifying that the manufacturing facility of a Niacin active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Niacin APIs or Niacin finished pharmaceutical products to another nation, regulatory agencies frequently require a Niacin WC (written confirmation) as part of the regulatory process.

click here to find a list of Niacin suppliers with Written Confirmation (WC) on PharmaCompass.

Niacin NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Niacin as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Niacin API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Niacin as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Niacin and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Niacin NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Niacin suppliers with NDC on PharmaCompass.

Niacin GMP

Niacin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Niacin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Niacin GMP manufacturer or Niacin GMP API supplier for your needs.

Niacin CoA

A Niacin CoA (Certificate of Analysis) is a formal document that attests to Niacin's compliance with Niacin specifications and serves as a tool for batch-level quality control.

Niacin CoA mostly includes findings from lab analyses of a specific batch. For each Niacin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Niacin may be tested according to a variety of international standards, such as European Pharmacopoeia (Niacin EP), Niacin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Niacin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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