Sulfur-containing amino acid

In the brain and spinal cord, white blood cells, heart and muscle cells, retina, and almost all other tissues, taurine is one of the most prevalent amino acids [1]. In addition to controlling intracellular calcium concentration and avoiding ischemia-reperfusion injury, taurine also possesses anti-atherosclerotic, hypotensive, and antioxidant properties [2].

Taurine (2-aminoethanesulphonic acid), a sulphur-containing amino acid, is found in most mammalian tissues. Although it can be synthesized endogenously, the major source of taurine is from the diet. Taurine was found to exhibit diverse biological actions, including protection against ischemia-reperfusion injury, modulation of intracellular calcium concentration, and antioxidant, antiatherogenic and blood pressure-lowering effects. The present review will address the potential beneficial actions of taurine in congestive heart failure, hypertension, ischemic heart disease, atherosclerosis and diabetic cardiomyopathy. There is a wealth of experimental information and some clinical evidence available in the literature suggesting that taurine could be of benefit in cardiovascular disease of different etiologies. However, double-blind long-term clinical trials need to be conducted before taurine can be unequivocally recommended as a nutritional intervention for the prevention and/or treatment of cardiovascular disease[2].

Alterations in adipocyte characteristics are highly implicated in the pathology of obesity. In a recent article, we demonstrated that high-fat diet-induced obesity impairs lysosomal function, thereby suppressing autophagy in mice white adipose tissue. Taurine, an amino acid naturally contained in the normal diet and existing ubiquitously in tissues, has been reported to improve insulin resistance and chronic inflammation in animal models, but underlying mechanisms remain unclear. From these findings, we hypothesized that improvement of obese pathology by taurine may be mediated through recovery of autophagy. In matured 3T3-L1 mouse adipocytes, treatment with taurine-promoted autophagy. Moreover, taurine-induced nuclear translocation of transcription factor EB (TFEB), a master regulator of autophagy- and lysosome-related factors. As this translocation is regulated by several kinase pathways, including extracellular signal-related kinase 1 and 2 (ERK1/2) and mechanistic target of rapamycin protein kinase complex 1 (MTORC1), we examined related signaling elements. Consequently, taurine-reduced phosphorylation levels of ERK1/2 but did not alter the phosphorylation of MTORC1 pathway-associated adenosine monophosphate-activated protein kinase or ribosomal protein S6 kinase. Taken together, these results suggest that taurine may enhance TFEB nuclear translocation through ERK1/2 to accelerate autophagy. The effect discovered in this study may represent a novel mechanism for the improvement of obesity-related pathology by taurine[3].

Absorption, Distribution and Excretion
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.
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.
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.
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.
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.
Taurine is present in high amounts in the brain, retina, myocardium, skeletal and smoth muscle, platelets and neutrophils.
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...
For more Absorption, Distribution and Excretion (Complete) data for Taurine (7 total), please visit the HSDB record page.

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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.
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.
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...

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

Protein Binding
Taurine is highly bound to plasma proteins and retained in the plasma fraction.

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Interactions
It prevented the development of ethanol-induced hypertension in rats.
In animal studies, taurine was found to ameliorate the pulmonary side effects (pulmonary fibrosis) of bleomycin.
...Three fatalities occurred after "energy" drinks had been consumed in combination with alcohol, whereby the forensic examinations including autopsy yielded negative results concerning medicaments and drugs, values between 0.59 and 0.87 parts per thousand of ethanol in blood samples, but no clear causes of death.
...Severe adverse effects arose after consumption of an "energy" drink in combination with physical efforts: A 31-year old regularly trained man consumed 750 mL of an "energy" drink while taking part in a 3,000 m competition. He developed a poor general condition with a rhabdomyolysis and acute kidney failure with tubular necrosis diagnosed one week after the competition.
For more Interactions (Complete) data for Taurine (10 total), please visit the HSDB record page.

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Non-Human Toxicity Values
LD50 Rats oral >7000 mg/kg bw
LD50 Mice sc 6000 mg/kg

[1]. Ripps H, Shen W. Review: taurine: a "very essential" amino acid. Mol Vis. 2012;18:2673-2686.

[2]. The potential health benefits of taurine in cardiovascular disease. Exp Clin Cardiol. 2008;13(2):57-65.

[3]. Taurine is an amino acid with the ability to activate autophagy in adipocytes. Amino Acids. 2018;50(5):527-535.

Large white crystals or white powder.
Taurine is an amino sulfonic acid that is the 2-amino derivative of ethanesulfonic acid. It is a naturally occurring amino acid derived from methionine and cysteine metabolism. An abundant component of fish- and meat-based foods, it has been used as an oral supplement in the treatment of disorders such as cystic fibrosis and hypertension. It has a role as a human metabolite, an antioxidant, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a glycine receptor agonist, a nutrient and a radical scavenger. It is a conjugate acid of a 2-aminoethanesulfonate. It is a tautomer of a taurine zwitterion.
Taurine, whose chemical name is 2-aminoethanesulfonic acid, is one of the most abundant amino acids in several organs. It plays important role in essential biological processes. This conditional amino acid can be either be manufactured by the body or obtained in the diet mainly by the consumption of fish and meat. The supplements containing taurine were FDA approved by 1984 and they are hypertonic injections composed by cristalline amino acids.
Taurine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Taurine has been reported in Sargassum fulvellum, Drosophila melanogaster, and other organisms with data available.
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.
See also: Sodium Taurate (is active moiety of); Potassium Taurate (is active moiety of); Sodium taurine laurate (is active moiety of) ... View More ...

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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

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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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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.
THERAPEUTIC CATEGORY (VETERINARY): In preventation of retinal degeneration and in prevention and treatment of taurine-deficiency cardiomyopathy in cats
Taurine has been added to most human infant formulas since the mid-1980s.

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

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Pharmacodynamics
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.

C2H7NO3S

125.1469

125.014

C, 19.20; H, 5.64; N, 11.19; O, 38.35; S, 25.62

107-35-7

Taurine-d4;342611-14-7;Taurine-13C2;70155-54-3;Taurine-13C2,15N;2483830-42-6

1123

White to off-white solid powder

1.5±0.1 g/cm3

>300 °C(lit.)

1.515

-2.46

2

4

2

7

120

0

XOAAWQZATWQOTB-UHFFFAOYSA-N

InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)

2-amino-ethanesulfonic acid

NSC-32428; β-Aminoethylsulfonic Acid; NSC 32428

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

H2O : ~25 mg/mL (~199.76 mM)
DMSO : ~1 mg/mL (~7.99 mM)

Solubility in Formulation 1: 12.5 mg/mL (99.88 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

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 (Please use freshly prepared in vivo formulations for optimal results.)