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Chemistry

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Also known as: D-biotin, 58-85-5, Vitamin h, Vitamin b7, Coenzyme r, Bioepiderm
Molecular Formula
C10H16N2O3S
Molecular Weight
244.31  g/mol
InChI Key
YBJHBAHKTGYVGT-ZKWXMUAHSA-N
FDA UNII
6SO6U10H04

Biotin
A water-soluble, enzyme co-factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk.
1 2D Structure

Biotin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
2.1.2 InChI
InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
2.1.3 InChI Key
YBJHBAHKTGYVGT-ZKWXMUAHSA-N
2.1.4 Canonical SMILES
C1C2C(C(S1)CCCCC(=O)O)NC(=O)N2
2.1.5 Isomeric SMILES
C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)O)NC(=O)N2
2.2 Other Identifiers
2.2.1 UNII
6SO6U10H04
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Biodermatin

2. Biokur

3. Biotin Gelfert

4. Biotin Hermes

5. Biotin Ratiopharm

6. Biotin-ratiopharm

7. Biotine Roche

8. Deacura

9. Gabunat

10. Gelfert, Biotin

11. Hermes, Biotin

12. Medebiotin

13. Medobiotin

14. Roche, Biotine

15. Rombellin

16. Vitamin H

2.3.2 Depositor-Supplied Synonyms

1. D-biotin

2. 58-85-5

3. Vitamin H

4. Vitamin B7

5. Coenzyme R

6. Bioepiderm

7. Bios Ii

8. Factor S

9. D(+)-biotin

10. Biodermatin

11. D-(+)-biotin

12. Medebiotin

13. (+)-biotin

14. Biotinum

15. Biotine

16. Meribin

17. Factor S (vitamin)

18. Lutavit H2

19. Biotina

20. 3h-biotin

21. Nsc 63865

22. Ccris 3932

23. Hsdb 346

24. Ritatin

25. Injacom H

26. 5-((3as,4s,6ar)-2-oxohexahydro-1h-thieno[3,4-d]imidazol-4-yl)pentanoic Acid

27. Cis-hexahydro-2-oxo-1h-thieno(3,4)imidazole-4-valeric Acid

28. Cis-tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric Acid

29. L-biotin

30. 1swk

31. 1swn

32. 1swr

33. Mfcd00005541

34. Rovimix H 2

35. D-biotin Factor S

36. 5-[(3as,4s,6ar)-2-oxo-hexahydro-1h-thieno[3,4-d]imidazolidin-4-yl]pentanoic Acid

37. Ai3-51198

38. 5-[(3as,4s,6ar)-2-oxohexahydro-1h-thieno[3,4-d]imidazol-4-yl]pentanoic Acid

39. 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic Acid

40. Cis-(+)-tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric Acid

41. (+)-cis-hexahydro-2-oxo-1h-thieno[3,4]imidazole-4-valeric Acid

42. (3as,4s,6ar)-hexahydro-2-oxo-1h-thieno(3,4-d)imidazole-4-valeric Acid

43. 1h-thieno(3,4-d)imidazole-4-pentanoic Acid, Hexahydro-2-oxo-, (3as-(3aalpha,4beta,6aalpha))-

44. 2'-keto-3,4-imidazolido-2-tetrahydrothiophene-n-valeric Acid

45. Chebi:15956

46. 6so6u10h04

47. 1h-thieno[3,4-d]imidazole-4-pentanoic Acid, Hexahydro-2-oxo-, (3as,4s,6ar)-

48. Nsc-63865

49. Hexahydro-2-oxo-1h-thieno(3,4-d)imidazole-4-pentanoic Acid, (3as-(3aalpha,4beta,6aalpha))-

50. 22377-59-9

51. D-biotin 10 Microg/ml In Acetonitrile

52. Md-1003

53. Beta-biotin

54. Biotin Impurity D - Mixture Of Diastereomers

55. Dsstox_cid_2679

56. Vitamin Bw

57. (3as,4s,6ar)-hexahydro-2-oxo-1h-thieno[3,4-d]imidazole-4-valeric Acid

58. (3as-(3aalpha,4b,6aalpha))-hexahydro-2-oxo-1h-thieno(3,4-d)imidaz- Ole-4-pentanoic Acid

59. Dsstox_rid_76688

60. Dsstox_gsid_22679

61. Medobiotin

62. Deacura

63. Gabunat

64. Hexahydro-2-oxo-1h-thieno(3,4-d)imidazole-4-pentanoic Acid

65. Rombellin

66. Biokur

67. Biotine [inn-french]

68. Biotinum [inn-latin]

69. Biotina [inn-spanish]

70. Biotin Gelfert

71. Biotin Hermes

72. Biotine Roche

73. Gelfert, Biotin

74. Biotin Ratiopharm

75. Biotin-ratiopharm

76. Hermes, Biotin

77. Roche, Biotine

78. 1h-thieno(3,4-d)imidazole-4-pentanoic Acid, Hexahydro-2-oxo-, (3as,4s,6ar)-

79. 5-((3as,4s,6ar)-rel-2-oxohexahydro-1h-thieno[3,4-d]imidazol-4-yl)pentanoic Acid

80. Smr000112255

81. D(+)biotin

82. 5-(2-oxohexahydro-1h-thieno[3,4-d]imidazol-4-yl)pentanoic Acid

83. Einecs 200-399-3

84. Biotin [usp:inn:jan]

85. Hexahydro-2-oxo-1h-thieno[3,4-d]imidazole-4-pentanoic Acid

86. Unii-6so6u10h04

87. Delta-biotin

88. Vitamin-h

89. 1avd

90. 1ndj

91. 1stp

92. 1swg

93. 1swp

94. 2avi

95. 4bcs

96. 4ggz

97. 4jnj

98. Bioepiderm (tn)

99. Cas-58-85-5

100. Bios H

101. Ncgc00094984-04

102. 1h-thieno[3,4-d]imidazole-4-pentanoic Acid, Hexahydro-2-oxo-, [3as-(3aalpha,4beta,6aalpha)]-

103. Biotin111in

104. Delta-(+)-biotin

105. Biotin (8ci)

106. Delta-biotin Factor S

107. 1df8

108. 1n9m

109. 2gh7

110. 3t2w

111. 4bj8

112. Biotin [vandf]

113. Biotin [hsdb]

114. Biotin [inci]

115. Biotin [fcc]

116. Biotin [inn]

117. Biotin [jan]

118. Biotin [usp-rs]

119. Biotin [who-dd]

120. Prestwick0_000418

121. Prestwick1_000418

122. Prestwick2_000418

123. Prestwick3_000418

124. Biotin [mi]

125. Biotin [mart.]

126. Cid_253

127. D-biotin [vandf]

128. Bdbm12

129. Biotin Silver Nanoparticles

130. Bmse000227

131. Chembl857

132. Probes2_000006

133. Schembl8763

134. Biotin [ep Impurity]

135. Biotin [orange Book]

136. Biotin For System Suitability

137. Bspbio_000376

138. 22879-79-4

139. Biotin (jp17/usp/inn)

140. Mls001066402

141. Mls001074888

142. Mls001331736

143. Mls001333089

144. Biotin [ep Monograph]

145. D-biotin, Analytical Standard

146. Spbio_002315

147. Biotin [usp Monograph]

148. Bpbio1_000414

149. Cid_171548

150. Gtpl4787

151. Amf0005

152. 1n43

153. 2f01

154. Biotin, >=99.0% (t)

155. Hms1569c18

156. Hms2096c18

157. Hms2271o06

158. Hms3713c18

159. Hy-b0511

160. Tox21_113050

161. Tox21_302161

162. Ac8089

163. Bbl028095

164. Biotin, Tested According To Ph.eur.

165. S3130

166. Stk801941

167. Zinc35024346

168. Akos001287669

169. Tox21_113050_1

170. Ccg-220418

171. Db00121

172. 1h-thieno(3,4-d)imidazole-4-pentanoic Acid, Hexahydro-2-oxo-, (3as-(3aalpha,4b,6aalpha))-

173. Biotin, Meets Usp Testing Specifications

174. Biotin, Saj Special Grade, >=98.0%

175. Ncgc00179580-01

176. Ncgc00179580-02

177. Ncgc00179580-04

178. Ncgc00255377-01

179. 56846-45-8

180. Ac-19998

181. Bp-20441

182. Biotin, >=99% (tlc), Lyophilized Powder

183. Biotin, Vetec(tm) Reagent Grade, >=99%

184. Ab00374191

185. B0463

186. 58b855

187. C00120

188. D00029

189. M02926

190. Ab00374191-08

191. Ab00374191_11

192. A929752

193. Biotin, Plant Cell Culture Tested, >=99% (tlc)

194. Q181354

195. Sr-01000765521

196. Biotin, Certified Reference Material, Tracecert(r)

197. Q-200929

198. Sr-01000765521-2

199. Brd-k89210380-001-03-8

200. Brd-k89210380-001-13-7

201. 6ae43aa3-bc3d-4c49-9db9-5913a2401eb6

202. Biotin, European Pharmacopoeia (ep) Reference Standard

203. F2173-0855

204. Hexahydro-2-oxo-1h-thieno(3,4-d)imidazole-4-pentanoate

205. Z210803762

206. Biotin, United States Pharmacopeia (usp) Reference Standard

207. Cis-(+)-tetrahydro-2-oxothieno[3,4]imidazoline-4-valerate

208. (+)-cis-hexahydro-2-oxo-1h-thieno[3,4]imidazole-4-valerate

209. 5-(2-oxohexahydro-1h-thieno[3,4-d]imidazol-4-yl)pentanoate

210. Daunorubicin Hydrochloride, Antibiotic For Culture Media Use Only

211. (3as,4s,6ar)-hexahydro-2-oxo-1h-thieno[3,4-d]imidazole-4-valerate

212. Biotin, Pharmaceutical Secondary Standard; Certified Reference Material

213. 1h-thieno[3,4-d]imidazole-4-pentanoic Acid, Hexahydro-2-oxo-, (3as,4s,6ar)- (9ci)

214. 5-((3ar,6s,6as)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic Acid

215. 5-[(3ar,6s,6as)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanoic Acid

216. Biotin For System Suitability, European Pharmacopoeia (ep) Reference Standard

217. Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1h-thieno[3,4-d]imidazole-4-pentanoate

218. Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1h-thieno[3,4-d]imidazole-4-pentanoic Acid

219. Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1h-thieno[3,4-d]imidazole-4-pentanoate

220. Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1h-thieno[3,4-d]imidazole-4-pentanoic Acid

221. Biotin, Pharmagrade, Usp, Meets Fcc Testing Specifications, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production.

222. Biotin, Powder, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture, Suitable For Plant Cell Culture, >=99%

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 244.31 g/mol
Molecular Formula C10H16N2O3S
XLogP30.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass244.08816355 g/mol
Monoisotopic Mass244.08816355 g/mol
Topological Polar Surface Area104 Ų
Heavy Atom Count16
Formal Charge0
Complexity298
Isotope Atom Count0
Defined Atom Stereocenter Count3
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

The B vitamins are indicated for prevention and treatment of vitamin B deficiency. Vitamin B deficiency may occur as a result of inadequate nutrition or intestinal malabsorption but does not occur in healthy individuals receiving an adequate balanced diet. Simple nutritional deficiency of individual B vitamins is rare since dietary inadequacy usually results in multiple deficiencies. For prophylaxis of biotin deficiency, dietary improvement, rather than supplementatin, is advisable. For teatment of biotin deficiency, supplementation is preferred. /Included in US product labeling/

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


Large doses of biotin ... are administered to babies with infantile seborrhea and to individuals with genetic alterations of biotin-dependent enzymes. patients who receive long-term parenteral nutrition should be given vitamin formulations that contain biotin.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1763


(VET): Biotin is used as a feed additive for poultry and swine.

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V24 41


Biotin is used to treat the biotin-responsive inborn errors of metabolism holocarboxylase synthetase deficiency and biotinidase deficiency. Holocarboxylase deficiency is the most common cause of neonatal multiple carboxylase deficiency. Biotinidase deficiency is the most common cause of late-onset multiple carboxylase deficiency.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.52 (2001)


For more Therapeutic Uses (Complete) data for BIOTIN (11 total), please visit the HSDB record page.


4.2 Drug Warning

Biotin deficiency, which can occur by the feeding of uncooked egg whites or by the omission of biotin from the diet, can cause alopecia and a characteristic scaly, erythematous dermatitis around body orifices in infants, children, and adults. For adults, prolonged biotin deficiency can result in depression, lethargy, hallucinations, and paresthesias of the extremities.

PMID:11800048 Fiume MZ, Cosmetic Ingredient Review Expert Panel; Int J Toxicol 20 (Suppl 4):1-12 (2001)


Biotin has not been proven effective in the treatment of acne, seborrheic eczema, or alopecia.

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


4.3 Drug Indication

For nutritional supplementation, also for treating dietary shortage or imbalance.


Treatment of multiple sclerosis


5 Pharmacology and Biochemistry
5.1 Pharmacology

Biotin is a water-soluble B-complex vitamin which is composed of an ureido ring fused with a tetrahydrothiophene ring, which attaches a valeric acid substituent at one of its carbon atoms. Biotin is used in cell growth, the production of fatty acids, metabolism of fats, and amino acids. It plays a role in the Kreb cycle, which is the process in which energy is released from food. Biotin not only assists in various metabolic chemical conversions, but also helps with the transfer of carbon dioxide. Biotin is also helpful in maintaining a steady blood sugar level. Biotin is often recommended for strengthening hair and nails. Consequenty, it is found in many cosmetic and health products for the hair and skin. Biotin deficiency is a rare nutritional disorder caused by a deficiency of biotin. Initial symptoms of biotin deficiency include: Dry skin, Seborrheic dermatitis, Fungal infections, rashes including erythematous periorofacial macular rash, fine and brittle hair, and hair loss or total alopecia. If left untreated, neurological symptoms can develop, including mild depression, which may progress to profound lassitude and, eventually, to somnolence; changes in mental status, generalized muscular pains (myalgias), hyperesthesias and paresthesias. The treatment for biotin deficiency is to simply start taking some biotin supplements. A lack of biotin in infants will lead to a condition called seborrheic dermatitis or "cradle cap". Biotin deficiencies are extremely rare in adults but if it does occur, it will lead to anemia, depression, hair loss, high blood sugar levels, muscle pain, nausea, loss of appetite and inflamed mucous membranes.


5.2 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.)


5.3 ATC Code

A - Alimentary tract and metabolism

A11 - Vitamins

A11H - Other plain vitamin preparations

A11HA - Other plain vitamin preparations

A11HA05 - Biotin


5.4 Absorption, Distribution and Excretion

Absorption

Systemic - approximately 50%


The intestine is exposed to biotin from a few sources: the diet, biotin supplements and biotin synthesized by bacteria in the large intestine. Dietary biotin exists in free and protein-bound forms. Protein-bound biotin is digested by proteases and peptidases to biotin-containing oligopeptides and biocytin (epsilon-N-biotinyl-L-lysine). Biocytin and the biotin-containing oligopeptides are converted to biotin via the enzyme biotinidase. Biotin - both dietary-derived biotin and supplementary biotin - is efficiently absorbed from the small intestine. At doses of biotin derived from food, biotin appears to be transported into enterocytes by a sodium -dependent carrier. At higher doses of biotin,absorption appears to occur by passive diffusion. Absorption of the biotin produced by the colonic microflora, appears to occur by a carrier mediated process in the proximal large intestine.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.52 (2001)


Elimination: Primarily in urine.

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


Protein binding: Primarily to plasma proteins.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.


Absorption: approximately 50%.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.


For more Absorption, Distribution and Excretion (Complete) data for BIOTIN (32 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Biotin is excreted in the urine as biotin, bisnorbiotin, biotin sulfoxide, biotin sulfone, bisnorbiotin methyl ketone and tetranobiotin-1-sulfoxide.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.52 (2001)


Biotin is catabolized to a number of different metabolites, including bisnorbiotin, biotin sulfoxide, biotin sulfone, bisonorbiotin methylketone and tetranorbiotin-1-sulfoxide.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.52 (2001)


More than 95% of the biotin is free in the skim fraction of human milk. The concentration of biotin varies substantially in some women and exceeds that in serum by one to two order of magnitude, suggesting that there is a transport system into milk. The biotin metabolite bisnorbiotin accounts for approximately 50%. In early and transitional human milk, the biotin metabolite biotin sulfoxide accounts for about 10% of the total biotin plus metabolites. With postpartum maturation, the biotin concentration increases, but the bisnorbiotin and biotin sulfoxide concentrations still account for 25% and 8% at 5 weeks postpartum. Current studies provide no evidence for a soluble biotin-binding protein or any other mechanism that traps biotin in human milk.

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 35 (2005)


On a molar basis, biotin accounts for approximately half of the total avidin-binding substances in human serum and urine. Biocytin, bisnorbiotin, bisnorbiotin methylketone, biotin sulfoxide, and biotin sulfone form most of the balance. Biotin metabolism is accelerated in some individuals by anticonvulsants and during pregnancy, thereby increasing the ratio of biotin metabolites to biotin excreted in urine.

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 35 (2005)


An alternate fate to being incorporated into carboxylases or unchanged excretion is catabolism to an inactive metabolite before excretion in urine. About half of biotin undergoes metabolism before excretion. Two principal pathways of biotin catabolism have been identified in mammals. In the first pathway, the valeric acid side chain of biotin is degraded by beta oxidation. This leads to the formation of bisnorbiotin, tetranorbiotin, and related intermediates that are known to result from beta-oxidation of fatty acids. The cellular site of this beta-oxidation of biotin is uncertain. Nonenzymatic decarboxylation of the unstable beta-ketobiotin and beta-keto-bisnorbiotin leads to formation of bisnorbiotin methylketone and tetranorbiotin methylketone, which appear in urine. In the second pathway, the sulfur in the thiophane ring of biotin is oxidized, leading to the formation of biotin L-sulfoxide, biotin D-sulfoxide, and biotin sulfone. Combined oxidation of the ring sulfur and beta-oxidation of the side chain lead to metabolites such as bisnorbiotin sulfone. In mammals, degradation of the biotin ring to release carbon dioxide and urea is quantitatively minor.

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 35 (2005)


5.6 Mechanism of Action

Biotin is necessary for the proper functioning of enzymes that transport carboxyl units and fix carbon dioxide, and is required for various metabolic functions, including gluconeogenesis, lipogenesis, fatty acid biosynthesis, propionate metabolism, and catabolism of branched-chain amino acids.


In human tissues biotin is a cofactor for the enzymatic carboxylation of four substrates: pyruvate, acetyl coenzyme A (CoA), propionyl CoA, and beta-methylcrotonyl CoA. As such, it plays an important role in both carbohydrate and fat metabolism. Carbon dioxide fixation occurs in a two-step reaction, the first involving binding of carbon dioxide to the biotin moiety of the holoenzyme, and the second involving transfer of the biotin-bound carbon dioxide to an appropriate acceptor.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1763


Biotin functions in carbon dioxide fixation reactions in intermediate metabolism, transferring the carboxyl group to acceptor molecules. It acts similarly in decarboxylation reactions. Biotin is essential in human metabolism for its part in the previously described enzymatic steps, in catalyzing deamination of amino acids, and in oleic acid synthesis. Biotin is a cofactor for the enzymatic carboxylation of pyruvate, acetyl coenzyme A (CoA), propionyl CoA, and beta-methylcrotonyl CoA, and, therefore, plays an important role in carbohydrate and fat metabolism.

PMID:11800048 Fiume MZ, Cosmetic Ingredient Review Expert Panel; Int J Toxicol 20 (Suppl 4):1-12 (2001)


Protein folding in the endoplasmic reticulum (ER) depends on Ca2+; uptake of Ca2+ into the ER is mediated by sarco/endoplasmic reticulum Ca2+-ATPase 3 (SERCA3). The 5'-flanking region of the SERCA3 gene (ATP2A3) contains numerous binding sites for the transcription factors Sp1 and Sp3. Biotin affects the nuclear abundance of Sp1 and Sp3, which may act as transcriptional activators or repressors. Here we determined whether biotin affects the expression of the SERCA3 gene and, thus, protein folding in human lymphoid cells. Jurkat cells were cultured in media containing 0.025 nmol/L biotin (denoted "deficient") or 10 nmol/L biotin ("supplemented"). The transcriptional activity of the full-length human SERCA3 promoter was 50% lower in biotin-supplemented cells compared to biotin-deficient cells. Biotin-dependent repressors bind to elements located 731 to 1312 bp upstream from the transcription start site in the SERCA3 gene. The following suggest that low expression of SERCA3 in biotin-supplemented cells impaired folding of secretory proteins in the ER, triggering unfolded protein response: (i) sequestration of Ca2+ in the ER decreased by 14 to 24% in response to biotin supplementation; (ii) secretion of interleukin-2 into the extracellular space decreased by 75% in response to biotin supplementation; (iii) the nuclear abundance of stress-induced transcription factors increased in response to biotin supplementation; and (iv) the abundance of stress-related proteins such ubiquitin activating enzyme 1, growth arrest and DNA damage 153 gene, X-box binding protein 1 and phosphorylated eukaryotic translation initiation factor 2alpha increased in response to biotin supplementation. Collectively, this study suggests that supplements containing pharmacological doses of biotin may cause cell stress by impairing protein folding in the ER.

PMID:16109482 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1473219 Griffin JB et al; J Nutr Biochem 17(4):272-81 (2006)


Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various human tissues. Many biotin-dependent gene products play roles in signal transduction and localize to the cell nucleus, consistent with a role for biotin in cell signaling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; at least seven biotinylation sites have been identified in human histones. Biotinylation of histones appears to play a role in cell proliferation, gene silencing, and the cellular response to DNA repair. Roles for biotin in cell signaling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology.

PMID:16011464 Zempleni J; Annu Rev Nutr 25:175-96 (2005)


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30-Jan-2021
27-Feb-2025
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DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL...DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL;0.02MG/VIAL;0.001MG/VIAL;5MG/VIAL;0.01MG/VIAL;0.14MG/VIAL;17MG/VIAL;0.2MG/VIAL;1MG/VIAL;1.4MG/VIAL;EQ 1.2MG BASE/VIAL;0.7MG/VIAL;7MG/VIAL

USFDA APPLICATION NUMBER - 18920

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DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/...DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/ML;12MCG/ML;40 IU/ML;1MCG/ML;3MG/ML;120MCG/ML;8MG/ML;1.2MG/ML;0.72MG/ML;1.2MG/ML;660 IU/ML;0.03MG/ML

USFDA APPLICATION NUMBER - 21163

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DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/...DOSAGE - SOLUTION;INTRAVENOUS - 2 IU/ML;40MG/ML;12MCG/ML;40 IU/ML;1MCG/ML;3MG/ML;120MCG/ML;8MG/ML;1.2MG/ML;0.72MG/ML;1.2MG/ML;660 IU/ML;30MCG/ML

USFDA APPLICATION NUMBER - 21163

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DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;...DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;0.06MG/VIAL;0.005MG/VIAL;15MG/VIAL;0.005MG/VIAL;0.6MG/VIAL;40MG/VIAL;6MG/VIAL;3.6MG/VIAL;6MG/VIAL;1MG/VIAL;10MG/VIAL;0.15MG/VIAL

USFDA APPLICATION NUMBER - 21625

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DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006...DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006MG/ML;0.05MCG/ML;1.5MG/ML;0.0005MG/ML;0.06MG/ML;4MG/ML;0.6MG/ML;0.36MG/ML;0.6MG/ML;0.1MG/ML;1MG/ML

USFDA APPLICATION NUMBER - 8809

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ABOUT THIS PAGE

Looking for 58-85-5 / Biotin API manufacturers, exporters & distributors?

Biotin manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Biotin 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 Biotin manufacturer or Biotin supplier for your needs.

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

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

API | Excipient name

Biotin

Synonyms

D-biotin, 58-85-5, Vitamin h, Vitamin b7, Coenzyme r, Bioepiderm

Cas Number

58-85-5

Unique Ingredient Identifier (UNII)

6SO6U10H04

About Biotin

A water-soluble, enzyme co-factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid Manufacturers

A cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid, including repackagers and relabelers. The FDA regulates cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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 cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid Suppliers

A cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid supplier is an individual or a company that provides cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid active pharmaceutical ingredient (API) or cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid finished formulations upon request. The cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid suppliers may include cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid API manufacturers, exporters, distributors and traders.

click here to find a list of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid USDMF

A cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid DMF (Drug Master File) is a document detailing the whole manufacturing process of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid active pharmaceutical ingredient (API) in detail. Different forms of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid DMFs exist exist since differing nations have different regulations, such as cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid DMF submitted to regulatory agencies in the US is known as a USDMF. cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid USDMF includes data on cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid suppliers with USDMF on PharmaCompass.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid Drug Master File in Japan (cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid JDMF) empowers cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid JDMF during the approval evaluation for pharmaceutical products. At the time of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid suppliers with JDMF on PharmaCompass.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid KDMF

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

Pharmaceutical companies submit a cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid Drug Master File in Korea (cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid. The MFDS reviews the cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid KDMF as part of the drug registration process and uses the information provided in the cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid KDMF to evaluate the safety and efficacy of the drug.

After submitting a cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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 cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid API can apply through the Korea Drug Master File (KDMF).

click here to find a list of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid suppliers with KDMF on PharmaCompass.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CEP

A cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CEP of the European Pharmacopoeia monograph is often referred to as a cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid Certificate of Suitability (COS). The purpose of a cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid to their clients by showing that a cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CEP has been issued for it. The manufacturer submits a cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CEP (COS) as part of the market authorization procedure, and it takes on the role of a cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CEP holder for the record. Additionally, the data presented in the cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid DMF.

A cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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 cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid suppliers with CEP (COS) on PharmaCompass.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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 cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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 cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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 cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid suppliers with NDC on PharmaCompass.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid GMP

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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 cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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 cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid GMP manufacturer or cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid GMP API supplier for your needs.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CoA

A cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CoA (Certificate of Analysis) is a formal document that attests to cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid's compliance with cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid specifications and serves as a tool for batch-level quality control.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid CoA mostly includes findings from lab analyses of a specific batch. For each cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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.

cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid may be tested according to a variety of international standards, such as European Pharmacopoeia (cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid EP), cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid 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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