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2D Structure
Also known as: Niacinamide, 98-92-0, 3-pyridinecarboxamide, Pyridine-3-carboxamide, Nicotinic acid amide, Vitamin pp
Molecular Formula
C6H6N2O
Molecular Weight
122.12  g/mol
InChI Key
DFPAKSUCGFBDDF-UHFFFAOYSA-N
FDA UNII
25X51I8RD4

An important compound functioning as a component of the coenzyme NAD. Its primary significance is in the prevention and/or cure of blacktongue and PELLAGRA. Most animals cannot manufacture this compound in amounts sufficient to prevent nutritional deficiency and it therefore must be supplemented through dietary intake.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pyridine-3-carboxamide
2.1.2 InChI
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
2.1.3 InChI Key
DFPAKSUCGFBDDF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CN=C1)C(=O)N
2.2 Other Identifiers
2.2.1 UNII
25X51I8RD4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3 Pyridinecarboxamide

2. 3-pyridinecarboxamide

3. B 3, Vitamin

4. B3, Vitamin

5. Enduramide

6. Jenapharm, Nicotinsureamid

7. Niacinamide

8. Nicobion

9. Nicotinsureamid Jenapharm

10. Papulex

11. Vitamin B 3

12. Vitamin B3

13. Vitamin Pp

2.3.2 Depositor-Supplied Synonyms

1. Niacinamide

2. 98-92-0

3. 3-pyridinecarboxamide

4. Pyridine-3-carboxamide

5. Nicotinic Acid Amide

6. Vitamin Pp

7. Papulex

8. Aminicotin

9. Amixicotyn

10. Nicobion

11. Nicotylamide

12. Nikotinamid

13. Savacotyl

14. Benicot

15. Dipegyl

16. Endobion

17. Hansamid

18. Pelmine

19. Nicotinic Amide

20. Delonin Amide

21. Pelonin Amide

22. Vi-nicotyl

23. Austrovit Pp

24. Inovitan Pp

25. Nicosylamide

26. Nicotilamide

27. Nicotililamido

28. Amnicotin

29. Niacevit

30. Nicamina

31. Nicamindon

32. Nicofort

33. Nicomidol

34. Nicotamide

35. Nicovitina

36. Nicovitol

37. Nicozymin

38. Niocinamide

39. Niozymin

40. Niamide

41. Nicasir

42. Nicogen

43. Nicota

44. Nicotol

45. Nicovit

46. Niko-tamin

47. 3-carbamoylpyridine

48. Nicotine Acid Amide

49. Nandervit-n

50. Pyridine-3-carboxylic Acid Amide

51. Vitamin B

52. Niavit Pp

53. Nicotinamidum

54. Nicosan 2

55. Nicotine Amide

56. Beta-pyridinecarboxamide

57. Nikotinsaeureamid

58. Nicotylamidum

59. Mediatric

60. Nicotinsaureamid

61. Pyridine, 3-carbamoyl-

62. 3-pyridinecarboxylic Acid Amide

63. M-(aminocarbonyl)pyridine

64. Acid Amide

65. Factor Pp

66. Nicotinamida

67. Nicovel

68. Vitamin B (van)

69. Pelmin

70. Amid Kyseliny Nikotinove

71. Witamina Pp

72. Pp-faktor

73. Amide Pp

74. Nicotinsaureamid [german]

75. Nikotinsaeureamid [german]

76. Amid Kyseliny Nikotinove [czech]

77. Nicotinamidum [inn-latin]

78. Nicotinamida [inn-spanish]

79. Nam

80. Niacinamid

81. Nictoamide

82. Ccris 1901

83. Dipigyl

84. Hsdb 1237

85. Vi-noctyl

86. Ai3-02906

87. Nsc 13128

88. B-pyridinecarboxamide

89. Niacinamide [usp]

90. Nicotinamide [inn]

91. 3-(aminocarbonyl)pyridine

92. Mfcd00006395

93. Nsc-13128

94. Nsc-27452

95. .beta.-pyridinecarboxamide

96. Nicotinamide (vitamin B3)

97. Chembl1140

98. Mls000069714

99. Chebi:17154

100. 25x51i8rd4

101. Nsc13128

102. Niacinamide (usp)

103. Ncgc00093354-03

104. Ncgc00093354-05

105. Smr000058212

106. Nicotinamide 10 Microg/ml In Acetonitrile

107. Dsstox_cid_929

108. Niacinamide;nicotinic Acid Amide;vitamin B3

109. Wln: T6nj Cvz

110. Dsstox_rid_75873

111. Dsstox_gsid_20929

112. Niacinamide [usan]

113. Enduramide

114. Cas-98-92-0

115. B3, Vitamin

116. Vitamin B 3

117. B 3, Vitamin

118. 3 Pyridinecarboxamide

119. Sr-01000721872

120. Nicotinsaureamid Jenapharm

121. Einecs 202-713-4

122. Jenapharm, Nicotinsaureamid

123. Niacotinamide

124. Nicotinamid

125. Nicotin-amide

126. Unii-25x51i8rd4

127. Nicotinsaeureamid

128. 3-amidopyridine

129. Dea No. 1405

130. Nicotinamide,(s)

131. Vitamin B3 Amide

132. 3-yridinecarboxamide

133. Mediatric (salt/mix)

134. Niacin - Vitamin B3

135. 1yc5

136. Opera_id_775

137. Niacin (as Niacinamide)

138. Niacinamide [ii]

139. Niacinamide(vitamin B3)

140. Niacinamide [fcc]

141. Nicotinamide [mi]

142. Niacinamide [hsdb]

143. Niacinamide [inci]

144. Nicotinamide [jan]

145. Bmse000281

146. Molmap_000061

147. Ec 202-713-4

148. Niacinamide [vandf]

149. Schembl2926

150. Nicotinamide (jp17/inn)

151. Nicotinamidum [hpus]

152. Niacinamide [usp-rs]

153. Nicotinamide [mart.]

154. Mls001424246

155. Nicotinamide [who-dd]

156. Nicotinamide [who-ip]

157. Nicotinamide-(amide-[15n])

158. Schembl6278767

159. Sgcut00176

160. Zinc5878

161. Tpn Component Niacinamide

162. Dtxsid2020929

163. Schembl19978192

164. Bdbm27507

165. Niacinamide [orange Book]

166. Nicotinamide, Niacin, Vitamin B3

167. Hms2052m21

168. Hms2090b05

169. Hms2093h03

170. Hms2236j03

171. Hms3370f21

172. Hms3394m21

173. Hms3655m20

174. Hms3713b22

175. Hms3884a16

176. Nicotinamide [ep Impurity]

177. Pharmakon1600-01505397

178. Niacinamide [usp Monograph]

179. Nicotinamide [ep Monograph]

180. Bcp07322

181. Hy-b0150

182. Niacinamide Component Of Tpn

183. Nicotinamide (vitamin B3) Solution

184. Nsc27452

185. To_000073

186. Nicotinamide 1.0 Mg/ml In Methanol

187. Nicotinamide, >=98.5% (hplc)

188. Nicotinamide, >=99.5% (hplc)

189. Tox21_111202

190. Tox21_201716

191. Tox21_302776

192. Nicotinamidum [who-ip Latin]

193. Nsc759115

194. S1899

195. Stl163867

196. Akos005715850

197. Tox21_111202_1

198. Ccg-101149

199. Cs-1968

200. Db02701

201. Nc00399

202. Nsc-759115

203. Sb74497

204. Nicotinamide 100 Microg/ml In Methanol

205. Nicotinamide, >=98% (hplc), Powder

206. Ncgc00093354-04

207. Ncgc00093354-06

208. Ncgc00093354-09

209. Ncgc00256432-01

210. Ncgc00259265-01

211. Niacin (as Niacinamide) [vandf]

212. As-13845

213. Bn166252

214. Nicotinamide, Puriss., 99.0-101.0%

215. Sy024804

216. Nicotinamide, Tested According To Ph.eur.

217. Sbi-0206826.p001

218. Db-057754

219. Ft-0631517

220. Ft-0672696

221. Ft-0773644

222. N0078

223. N1651

224. Sw197779-3

225. En300-15612

226. Niacinamide, Meets Usp Testing Specifications

227. C00153

228. D00036

229. Nicotinamide (niacinamide), Analytical Standard

230. Ab00373895-13

231. Ab00373895_15

232. Ab00373895_16

233. Nicotinamide, Vetec(tm) Reagent Grade, >=98%

234. A845925

235. Ac-907/25014114

236. Q192423

237. Q-201470

238. Sr-01000721872-3

239. Sr-01000721872-4

240. Sr-01000721872-5

241. Z33546463

242. F2173-0513

243. Niacinamide;nicotinic Acid Amide;vitamin B3; Vitamin Pp

244. Nicotinamide, British Pharmacopoeia (bp) Reference Standard

245. A186b02e-6c70-4e54-9739-79398d439aaa

246. Nicotinamide, European Pharmacopoeia (ep) Reference Standard

247. Niacinamide, United States Pharmacopeia (usp) Reference Standard

248. Niacinamide, Pharmaceutical Secondary Standard; Certified Reference Material

249. Nicotinamide, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture

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

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 122.12 g/mol
Molecular Formula C6H6N2O
XLogP3-0.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass122.048012819 g/mol
Monoisotopic Mass122.048012819 g/mol
Topological Polar Surface Area56 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 Therapeutic Uses

Vitamin B Complex

National Library of Medicine's Medical Subject Headings. Niacinamide. Online file (MeSH, 2018). Available from, as of June 1, 2018: https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html


/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. Nicotinamide is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of June 1, 2018: https://clinicaltrials.gov/


Niacin and niacinamide are used to prevent niacin deficiency and to treat pellagra. Some clinicians prefer niacinamide for the treatment of pellagra because it lacks vasodilating effects. Pellagra may result from dietary deficiency, isoniazid therapy, or from decreased conversion of tryptophan to niacin in Hartnup disease or carcinoid tumors. /Included in US product label/

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


Although niacin and niacinamide have not been shown by well-controlled trials to have therapeutic value, the drugs have been used for the management of schizophrenic disorder, drug-induced hallucinations, chronic brain syndrome, hyperkinesis, unipolar depression, motion sickness, alcohol dependence, livedoid vasculitis, acne, and leprosy. /NOT included in US product label/

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


For more Therapeutic Uses (Complete) data for Nicotinamide (14 total), please visit the HSDB record page.


4.2 Drug Warning

Blood glucose concentration should be monitored periodically in patients receiving niacin or niacinamide, especially early in the course of therapy. Dosage requirements for antidiabetic agents (e.g., insulin, oral sulfonylureas) may change in diabetic patients.

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


Potential adverse effects on fetus: Higher levels in fetus than mother, but no fetal anomalies reported. Potential side effects on breast-fed infant: No adverse effects known . FDA Category: C (C = Studies in laboratory animals have revealed adverse effects on the fetus (teratogenic, embryocidal, etc.), but there are no controlled studies in pregnant women. The benefits from use of the drug in pregnant women may be acceptable despite its potential risks, or there are no laboratory animal studies or adequate studies in pregnant women.) /from table II/

Stockton, D.L. and A.S. Paller. J Am Acad Dermatol 23 (1):87-103 (1990)


Niacinamide /was administered/ daily as a liquid formulation to head and neck cancer patients receiving a 5- to 7-week course of radiotherapy. Niacinamide was administered orally 1.5 hr before irradiation. The daily dose was 80 mg/kg bw to a maximum of 6 g. A dose reduction to 60 mg/kg was introduced for patients with severe side-effects. ... Side-effects of niacinamide were monitored. In all patients, peak concentrations greater than 700 nM/mL could be obtained 0.25-3 hr after drug intake. During the first week of treatment, plasma concentrations at the time of irradiation were adequate in 82% of the samples. Nausea, with or without vomiting, occurred in 65% of patients. Tolerance improved after a 25% reduction of the dose in six of seven patients but plasma concentrations at the time of irradiation decreased below 700 nM/mL in four out of six patients. Other niacinamide side effects included gastrointestinal symptoms, flushing, dizziness, sweating, fatigue, and headache. The most powerful single predictor for severe niacinamide toxicity was the mean of the plasma concentration measured at the time of irradiation during the first week.

Cosmetic Ingredient Review (CIR) Expert Panel; Final Report of the Safety Assessment of Niacinamide and Niacin p.6; Intl J of Toxicology 24 (Suppl 5): 1-31 (2005). Available from, as of June 4, 2018: https://www.cir-safety.org/ingredients


Abnormal liver function test results (including increased serum concentrations of bilirubin, AST [SGOT], ALT [SGPT], and LDH), jaundice, and chronic liver damage have occurred during niacin and niacinamide therapy. Abnormal prothrombin time and hypoalbuminemia have also been reported.

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


For more Drug Warnings (Complete) data for Nicotinamide (6 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Vitamin B Complex

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


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Adenosine Receptor Agonists [MoA]; Adenosine Receptor Agonist [EPC]
5.3 ATC Code

A11HA01

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


A - Alimentary tract and metabolism

A11 - Vitamins

A11H - Other plain vitamin preparations

A11HA - Other plain vitamin preparations

A11HA01 - Nicotinamide


5.4 Absorption, Distribution and Excretion

14(C)Niacinamide was incorporated into an oil-in-water (o/w) skin cream and into a 30% (w/w) soap base and applied to the skin of female Colworth Wistar rats. The final concentration of niacinamide in the soap solution was approximately 0.3% (w/v) and was 1% (w/w) in the skin cream. Application of the skin cream and soap paste was made to rat skin at approximately 20 mg/sq cm. The cream was carefully massaged over 10 sq cm of skin for up to 5 min before covering with polythene-lined occlusive protective patches. The rats were placed in metabolism cages for 48 hr during which time all excreta was collected. At 48 hr, the animals were killed and the patch, carcass, and treated area of skin were assayed for 14(C). Up to 32% 14(C) was recovered in excreta and in the carcasses from rats treated with skin cream containing 14(C)Niacinamide and up to 30% from those treated with soap paste.

Cosmetic Ingredient Review (CIR) Expert Panel; Final Report of the Safety Assessment of Niacinamide and Niacin p.5; Intl J of Toxicology 24 (Suppl 5): 1-31 (2005). Available from, as of June 4, 2018: https://www.cir-safety.org/ingredients


Nicotinamide is efficiently absorbed from the gastrointestinal tract. At low doses, absorption is mediated via sodium-dependent facilitated diffusion. Passive diffusion is the principal mechanism of absorption at higher doses. Doses of up to three to four grams of nicotinamide are almost completely absorbed. Nicotinamide is transported via the portal circulation to the liver and via the systemic circulation to the various tissues of the body. Nicotinamide enters most cells by passive diffusion and enters erythrocytes by facilitated transport.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 452


Niacinamide is widely distributed /throughout/ body tissues.

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


Niacin and niacinamide are readily absorbed from the GI tract following oral administration, and niacinamide (no longer commercially available in the US) is readily absorbed from subcutaneous and IM injection sites.

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


For more Absorption, Distribution and Excretion (Complete) data for Nicotinamide (16 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

In amounts needed for physiologic function as a coenzyme (12-18 mg daily), niacin is converted to niacinamide; larger doses of niacin are converted to niacinamide to only a minor degree. Niacinamide is metabolized in the liver to N-methylniacinamide, other N-methylated derivatives, and nicotinuric acid (the glycine conjugate of niacin). These metabolites are excreted in urine. Following administration of physiologic doses of niacin or niacinamide, only a small amount of niacinamide is excreted unchanged in urine; however, following administration of larger doses, a greater proportion of niacin and niacinamide is excreted unchanged.

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


N1-Methyl-4-pyridone-3-carboxamide was detected on chromatograms of plasma extracts after oral administration of niacinamide to two human subjects.

Cosmetic Ingredient Review (CIR) Expert Panel; Final Report of the Safety Assessment of Niacinamide and Niacin p.6; Intl J of Toxicology 24 (Suppl 5): 1-31 (2005). Available from, as of June 4, 2018: https://www.cir-safety.org/ingredients


6-Hydroxynicotinamide and 6-hydroxynicotinic acid /were detected/ as urinary metabolites by comparison of ultraviolet, infrared, and mass spectra following intraperitoneal injections of 14(C)Niacin or 14(C)Niacinamide into rats.

Cosmetic Ingredient Review (CIR) Expert Panel; Final Report of the Safety Assessment of Niacinamide and Niacin p.8; Intl J of Toxicology 24 (Suppl 5): 1-31 (2005). Available from, as of June 4, 2018: https://www.cir-safety.org/ingredients


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 p.8; Intl J of Toxicology 24 (Suppl 5): 1-31 (2005). Available from, as of June 4, 2018: https://www.cir-safety.org/ingredients


For more Metabolism/Metabolites (Complete) data for Nicotinamide (7 total), please visit the HSDB record page.


5.6 Biological Half-Life

The mean half life values were 2.7 hr, 5.9 hr, and 8.1 hr after taking 1, 3, or 6 g of Niacinamide, respectively.

Cosmetic Ingredient Review (CIR) Expert Panel; Final Report of the Safety Assessment of Niacinamide and Niacin p.6; Intl J of Toxicology 24 (Suppl 5): 1-31 (2005). Available from, as of June 4, 2018: https://www.cir-safety.org/ingredients