List of Analytical Solutions of NCGC00024497-03 on PharmaCompass.com.

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Chemistry

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Also known as: 2-aminoethanesulfonic acid, 107-35-7, Ethanesulfonic acid, 2-amino-, L-taurine, Tauphon, 2-aminoethylsulfonic acid
Molecular Formula
C2H7NO3S
Molecular Weight
125.15  g/mol
InChI Key
XOAAWQZATWQOTB-UHFFFAOYSA-N
FDA UNII
1EQV5MLY3D

Taurine
A conditionally essential nutrient, important during mammalian development. It is present in milk but is isolated mostly from ox bile and strongly conjugates bile acids.
1 2D Structure

Taurine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-aminoethanesulfonic acid
2.1.2 InChI
InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)
2.1.3 InChI Key
XOAAWQZATWQOTB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CS(=O)(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
1EQV5MLY3D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Taufon

2. Tauphon

3. Taurine Hydrochloride

4. Taurine Zinc Salt (2:1)

5. Taurine, Monopotassium Salt

2.3.2 Depositor-Supplied Synonyms

1. 2-aminoethanesulfonic Acid

2. 107-35-7

3. Ethanesulfonic Acid, 2-amino-

4. L-taurine

5. Tauphon

6. 2-aminoethylsulfonic Acid

7. 2-sulfoethylamine

8. 2-aminoethane-1-sulfonic Acid

9. O-due

10. Aminoethylsulfonic Acid

11. Taufon

12. Aminoethanesulfonic Acid

13. Beta-aminoethylsulfonic Acid

14. Taurinum [latin]

15. Taurina [spanish]

16. Fema No. 3813

17. Taurine [inn]

18. Ccris 4721

19. Nci-c60606

20. Ai3-18307

21. Nsc32428

22. Nsc-32428

23. 1eqv5mly3d

24. 2-aminoethane Sulfonic Acid

25. .beta.-aminoethylsulfonic Acid

26. 1-aminoethane-2-sulfonic Acid

27. Chebi:15891

28. Ncgc00015997-06

29. Dsstox_cid_1304

30. Dsstox_rid_76069

31. Dsstox_gsid_21304

32. Aminoethylsulfonic Acid (jan)

33. Taurine Hydrochloride

34. 2-amino-ethanesulfonic Acid

35. Taurina

36. Taurinum

37. Aminoethylsulfonic Acid [jan]

38. Cas-107-35-7

39. Smr000326743

40. Sr-01000076144

41. 2-aminoethanesulfonicacid

42. Einecs 203-483-8

43. Unii-1eqv5mly3d

44. Nsc 32428

45. Taurine [usp:inn:ban]

46. Taurineold

47. Taukard

48. Taurate

49. Hsdb 8167

50. Aminoethylsulfonate

51. Taurine,(s)

52. Taurine (tn)

53. B-aminoethylsulfonate

54. Mfcd00008197

55. Taurine (8ci)

56. 2-aminoethylsulfonate

57. 2-aminoethyl Sulfonate

58. Beta-aminoethylsulfonate

59. Taurine-[13c2]

60. Tocris-0209

61. Taurine [vandf]

62. 2aminoethanesulfonic Acid

63. Taurine [fhfi]

64. Taurine [inci]

65. Taurine, >=99%

66. B-aminoethylsulfonic Acid

67. Taurine [jan]

68. Taurine [mi]

69. Taurine [mart.]

70. Lopac-t-0625

71. Taurine [usp-rs]

72. Taurine [who-dd]

73. Wln: Z2swq

74. 1-aminoethane-2-sulfonate

75. Bmse000120

76. Bmse000805

77. Bmse000863

78. Ec 203-483-8

79. 2-aminoethanesulfonic Acid.

80. Lopac0_001134

81. Schembl23068

82. Taurine, >=98%, Fg

83. Mls000859681

84. Mls001332383

85. Mls001332384

86. Taurine (jp17/usp/inn)

87. Chembl239243

88. Gtpl2379

89. Taurine [usp Monograph]

90. Dtxsid3021304

91. Taurine, >=99.0% (t)

92. Hms2093l13

93. Hms2233d19

94. Hms3263d09

95. Hms3370j18

96. Pharmakon1600-01505463

97. Hy-b0351

98. Rkl10149

99. Taurine; 2-aminoethanesulfonic Acid

100. Zinc3809490

101. Tox21_110277

102. Tox21_202520

103. Tox21_501134

104. Bdbm50357220

105. Nsc759150

106. S2008

107. Stl197941

108. Akos005208848

109. Tox21_110277_1

110. Ccg-205208

111. Db01956

112. Ethanesulfonic Acid, 2-amino- (9ci)

113. Lp01134

114. Nsc-759150

115. Sdccgsbi-0051101.p003

116. Taurine, Bioultra, >=99.5% (t)

117. Taurine, Saj First Grade, >=98.5%

118. Ncgc00015997-01

119. Ncgc00015997-02

120. Ncgc00015997-03

121. Ncgc00015997-04

122. Ncgc00015997-05

123. Ncgc00015997-07

124. Ncgc00015997-08

125. Ncgc00015997-10

126. Ncgc00015997-20

127. Ncgc00024497-01

128. Ncgc00024497-02

129. Ncgc00024497-03

130. Ncgc00024497-04

131. Ncgc00024497-05

132. Ncgc00260069-01

133. Ncgc00261819-01

134. As-13587

135. Nci60_002814

136. Sbi-0051101.p002

137. Taurine, Vetec(tm) Reagent Grade, >=99%

138. A0295

139. Am20080018

140. B1846

141. Eu-0101134

142. Ft-0611241

143. T-130

144. C00245

145. D00047

146. D78121

147. T 0625

148. Ab00443712-07

149. Ab00443712_09

150. Ab00443712_10

151. Q207051

152. J-508042

153. Sr-01000076144-1

154. Sr-01000076144-3

155. Sr-01000076144-5

156. Taurine, Certified Reference Material, Tracecert(r)

157. F2191-0280

158. Z1317839154

159. Taurine, Cell Culture Tested, Meets Usp Testing Specifications

160. Taurine, United States Pharmacopeia (usp) Reference Standard

161. Taurine, Pharmaceutical Secondary Standard; Certified Reference Material

162. Taurine, Pharmagrade, Ajinomoto, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 125.15 g/mol
Molecular Formula C2H7NO3S
XLogP3-4.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass125.01466426 g/mol
Monoisotopic Mass125.01466426 g/mol
Topological Polar Surface Area88.8 Ų
Heavy Atom Count7
Formal Charge0
Complexity120
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

Taurine may be helpful in some with congestive heart failure and hypertension. It has demonstrated some antiatherogenic effects in both animal and human studies.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 607


THERAPEUTIC CATEGORY (VETERINARY): In preventation of retinal degeneration and in prevention and treatment of taurine-deficiency cardiomyopathy in cats

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1679


Taurine has been added to most human infant formulas since the mid-1980s.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 607


4.2 Drug Warning

Pregnant women and nursing mothers should avoid taurine supplements unless recommended by their physicians. Those with congestive heart failure should only use taurine under medical supervision.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 609


Taurine is contraindicated in those hypersensitive to any component of a taurine-containing nutritional supplement.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 609


4.3 Drug Indication

The use of diet supplements containing taurine is indicated for the nutritional support of infants and young pediatric patients requiring total parenteral nutrition via central or peripheral routes. The usage of diet supplements containing taurine prevents nitrogen and weight loss or to treat negative nitrogen balance in pediatric patients where the alimentary tract cannot be done through oral, gastrostomy or jejunostomy administration, there is impaired gastrointestinal absorption or protein requirements are substantially increased.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

The diet supplements containing taurine are formulated as a well-tolerated nitrogen source for nutritional support. Administration of diet supplements regulates the level of plasma amino acid concentration, nitrogen balance, weight and serum protein concentration to reach normal values, thus improving the nutritional status.


5.2 Absorption, Distribution and Excretion

Absorption

Oral administration of taurine was studied and it reported dose-dependent values of AUC, Cmax and tmax wherein a dose of 1-30 mg/kg ranged from 89-3452 mcg min/L, 2-15.7 mcg min/ml and 15 min respectively. Further studies in healthy individuals gave an AUC, Cmax and tmax in the range of 116-284.5 mg h/L, 59-112.6 mg/L and 1-2.5 h.


Route of Elimination

Taurine flows and gets distributed in veins and arteries and reports have observed the presence of a significant released of taurine in portally drained viscera, thus suggesting that the main elimination route of taurine is by the gut. This elimination route may be explained by the enterohepatic cycle of taurine.


Volume of Distribution

The distribution of taurine was studied under the two-compartment model and each one of the compartments gave a range for the volume of distribution of 299-353 ml/kg in compartment 1 and 4608-8374 ml/kg in compartment 2 in mice. Further studies in healthy indivudals gave a volume of distribution that ranged from 19.8 to 40.7 L.


Clearance

The clearance rate of orally administered taurine was reported to be dose-dependent wherein a dose of 1 mg/kg it presents a clearance rate of 11.7 ml min/kg, 10 mg/kg generates a clearance rate of 18.7 ml min/kg and a dose of 30 mg/kg reports a clearance rate of 9.4 ml min/kg. Further studies in healthy individuals generate a clearance rate that ranged from 14 to 34.4 L/h.


Taurine is not usually completely reabsorbed from the kidneys, and some fraction of an ingested dose of taurine is excreted in the urine.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 608


Following ingestion, taurine is absorbed from the small intestine via the beta-amino acid or taurine transport system... Tautine is transported to the liver via the portal circulation, where much of it forms conjugates with bile acids... The taurine conjugates are excreted via the biliary route. Taurine that is not conjugated in the liver is distributed via the systemic circulation to various tissues in the body.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 608


Taurine is present in high amounts in the brain, retina, myocardium, skeletal and smoth muscle, platelets and neutrophils.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 607


Human studies showed significant increases in plasma taurine 90 minutes after consumption of a taurine-rich meal with levels declining to background within 180-270 minutes...

European Food Safety Authority (EFSA); EFSA Journal 935: 1-31 (2009). Available from, as of August 19, 2014: https://www.efsa.europa.eu/en/efsajournal/doc/935.pdf


For more Absorption, Distribution and Excretion (Complete) data for Taurine (7 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

Taurine can be metabolized by diverse organisms to form different types of metabolites derived from the original form of taurine. In the human, the pathways that form the metabolism of taurine are divided in the formation of 5-glutamyl-taurine by the action of the enzyme gamma-glutamyltransferase 6 or the formation of taurocholate by the action of the bile acid-CoA:amino acid N-acyltransferase.


There are two sources of taurine in the body: dietary and endogenous. In mammals, taurine is synthesised in many tissues; the main sites are liver, brain and pancreas, predominantly in alpha-islets. Taurine is synthesised from cysteine and methionine in a few steps, one of which requires pyridoxal-5-phosphate (vitamin B6) as coenzyme of cysteine sulphinate decarboxylase. In species other than mammals, the biosynthesis of taurine has been poorly studied. The extent of synthesis varies widely between species. An adult rat consuming standard laboratory food produces about 80 % of its total body taurine and obtains the remainder from the diet. However, if required, rats can obtain all body taurine from biosynthesis, since rats fed taurine-free diets for extended periods do not exhibit any decrease in tissue taurine concentrations. Cats have low levels of activity of cysteine sulphinate decarboxylase, the rate-limiting enzyme for taurine biosynthesis, and are, therefore, dependent on a dietary source to maintain their body pool of this amino acid. Thus, taurine is an essential nutrient in cats.

European Food Safety Authority (EFSA); EFSA Journal 10 (6): 2736 (2012). Available from, as of August 19, 2014: https://www.efsa.europa.eu/en/efsajournal/doc/2736.pdf


Taurocholate, the bile salt conjugate of taurine and cholic acid, is the principal conjugate formed via the action of the enzyme choloyl-CoA N-acyltransferase.

PDR for Nutritional Supplements 2nd ed. Thomson Reuters, Montvale, NJ 2008, p. 608


In all vertebrates except mammals, taurine is the sole amino acid conjugated to form bile salts. Among the mammals, carnivores also tend to be conjugators of taurine only, whereas other species tend to conjugate both taurine and glycine. High concentrations of taurine are present in retina, liver, pancreas, central nervous system and white blood cells. The largest pools of taurine are found in skeletal and cardiac muscles, where it regulates intracellular Ca2+ concentration...

European Food Safety Authority (EFSA); EFSA Journal 10 (6): 2736 (2012). Available from, as of August 19, 2014: https://www.efsa.europa.eu/en/efsajournal/doc/2736.pdf


5.4 Biological Half-Life

Oral administration of taurine in healthy individuals gave a plasma elimination half-life that ranged from 0.7-1.4 h.


5.5 Mechanism of Action

The diet supplements containing taurine function by replacing the missing nutriments in the body. Taurine, as a single agent, presents different functions like substrate for formation of bile salts, cell volume regulation, modulation of intracellular calcium, cytoprotection of central nervous system, etc.


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06-Jan-2021
27-Aug-2024
KGS
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