TAURINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C2H7NO3S
Molecular Weight	125.147
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCS(O)(=O)=O

InChI

InChIKey=XOAAWQZATWQOTB-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C2H7NO3S
Molecular Weight	125.147
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://doi.org/10.1016/S0378-1097(03)00611-6
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3676193 | http://www.medscape.com/viewarticle/804080 | https://www.ncbi.nlm.nih.gov/pubmed/21334852 | https://www.ncbi.nlm.nih.gov/pubmed/26208967

Taurine is a semi-essential amino acid and is not incorporated into proteins. Taurine is considered conditionally essential because it cannot be synthesized by infants younger than 4-6 weeks, and it may not be adequately synthesized in patients receiving long-term parenteral nutrition and patients with short-term hypermetabolic conditions. In mammalian tissues, taurine is ubiquitous and is the most abundant free amino acid in the heart, retina, skeletal muscle, brain, and leukocytes. Taurin occurs naturally in fish and meat. The mean daily intake from omnivore diets was determined to be around 58 mg. Taurine is a component of energy drinks, with many contain 1000 mg per serving. In medicine, taurine supplementation demonstrated efficacy in relieving symptoms of heart failure, hepatitis, hypertension and psychotic disorder. Taurine exerts many physiological functions, including membrane stabilization, osmoregulation and cytoprotective effects, antioxidant and anti-inflammatory actions as well as modulation of intracellular calcium concentration and ion channel function. In addition taurine may control muscle metabolism and gene expression, through yet unclear mechanisms. The cellular and biochemical mechanisms mediating the actions of taurine are not fully known.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL1907607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23637894	Agonist 2678
Glycine receptor 13 Target ID: CHEMBL3392921 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9279812	Agonist 2678		406.0 µM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Congestive heart failure 54 Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-1024-taurine.aspx?activeingredientid=1024	Primary	Approved 8429	TAURINE Approved Use Taking 2-3 grams of taurine by mouth one to two times daily for 6-8 weeks seems to improve heart function and symptoms in patients with moderate heart failure to severe heart failure. Some patients with severe heart failure rapidly improve from NYHA class IV to II after 4-8 weeks of treatment. Improvement seems to continue for as long as taurine treatment is continued, up to one year.
Hepatitis 8 Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-1024-taurine.aspx?activeingredientid=1024	Palliative	Approved 8429	TAURINE Approved Use Taking 1.5-4 grams of taurine daily for up to 3 months improves liver function in people with hepatitis.
Fatigue 46 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26830981	Preventing	Approved 8429	URSA Complex Approved Use Taurine is a component of energy drinks used for relieving of fatigue
Prehypertension 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26781281	Primary	Phase III 656	Unknown Approved Use Unknown
Psychotic disorder 26 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27835719	Primary	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Calcium-mediated transductive systems and functionally active gap junctions in astrocyte-like GL15 cells.	2001	11384510
Beneficial effects of an "energy drink" given to sleepy drivers.	2001	11310933
The influence of a taurine containing drink on cardiac parameters before and after exercise measured by echocardiography.	2001	11310932
Changes in plasma and urinary taurine and amino acids in runners immediately and 24h after a marathon.	2001	11310927
Isolation and characterization of an alpha 2-type zebrafish glycine receptor subunit.	2001	11274795
New developments in the pharmacotherapy of alcohol dependence.	2001	11268820
Oxygen metabolites in immune- stimulated ion transport in rat colon: modulation by taurine.	2001	11244251
Gene expression of the taurine transporter and taurine biosynthetic enzymes in rat kidney after antidiuresis and salt loading.	2001 Apr	11374073
Zinc and the eye.	2001 Apr	11349933
Increased taurine content in esophageal mucosa of children affected by gastroesophageal reflux.	2001 Apr	11330417
Conditioned nutritional deficiencies in the cardiomyopathic hamster heart.	2001 Apr	11329545
Dipolar coupling and ordering effects observed in magnetic resonance spectra of skeletal muscle.	2001 Apr	11320539
Killing of Schistosoma mansoni sporocysts by hemocytes from resistant Biomphalaria glabrata: role of reactive oxygen species.	2001 Apr	11318558
Cellular uptake of taurine by lactating porcine mammary tissue.	2001 Apr	11290448
Analysis of amino acids in human serum by isocratic reversed-phase high-performance liquid chromatography with electrochemical detection.	2001 Apr 13	11355826
Fertilizability and developmental capacity of bovine oocytes cultured individually in a chemically defined maturation medium.	2001 Apr 15	11354704
Endogenous glutamate-taurine interaction in striatum and nucleus accumbens of the freely moving rat: studies during the normal process of aging.	2001 Apr 15	11240162
Reduction of phospholemman expression decreases osmosensitive taurine efflux in astrocytes.	2001 Apr 23	11336802
Mast cell numbers in the young rat thalamus: a search for control factors.	2001 Aug	11328703
Taurine increases rat survival and reduces striatal damage caused by 3-nitropropionic acid.	2001 Aug	11328702
Osmolytes stabilize ribonuclease S by stabilizing its fragments S protein and S peptide to compact folding-competent states.	2001 Aug 3	11373282
Effects of new taurine derivatives on primary immune response in rats.	2001 Feb	11391397
Effect of acamprosate and naltrexone, alone or in combination, on ethanol consumption.	2001 Feb	11331108
Taurine - monograph.	2001 Feb	11207458
Can this pill stop you from hitting the bottle?	2001 Feb 12	11246723
Activation of an ATP-dependent K(+) conductance in Xenopus oocytes by expression of adenylate kinase cloned from renal proximal tubules.	2001 Feb 9	11342145
The protective effect of taurine against thioacetamide hepatotoxicity of rats.	2001 Jan	11339621
Effects of methionine loading on plasma and erythrocyte sulphur amino acids and sulph-hydryls before and after co-factor supplementation in haemodialysis patients.	2001 Jan	11209001
Determination of bile acids in biological fluids by liquid chromatography-electrospray tandem mass spectrometry.	2001 Jan	11160372
Dietary taurine manipulations in aged male Fischer 344 rat tissue: taurine concentration, taurine biosynthesis, and oxidative markers.	2001 Jul 1	11377394
Taurine modulates arginine vasopressin-mediated regulation of renal function.	2001 Jun	11392471
Enhanced fungicidal activity of N-chlorotaurine in nasal secretion.	2001 Jun	11389121
Occupational lead exposure and amino acid profiles and liver function tests in industrial workers.	2001 Jun	11382350
17 beta-estradiol protects neurons from ischemic damage and attenuates accumulation of extracellular excitatory amino acids.	2001 Jun	11375837
Swelling-activated taurine and K+ transport in human cervical cancer cells: association with cell cycle progression.	2001 Mar	11316262
Two-voxel localization sequence for in vivo two-dimensional homonuclear correlation spectroscopy.	2001 Mar	11273760
Reactive nitrogen oxygen species metabolize N-acetylbenzidine.	2001 Mar	11258981
Hypocholesterolemic effect of bile acid sulfonate analogs in hamsters.	2001 Mar	11256473
Effect of starvation on free histidine and amino acids in white muscle of milkfish Chanos chanos.	2001 Mar	11250545
Alteration of excitation-contraction coupling mechanism in extensor digitorum longus muscle fibres of dystrophic mdx mouse and potential efficacy of taurine.	2001 Mar	11226135
Relative reactivities of N-chloramines and hypochlorous acid with human plasma constituents.	2001 Mar 1	11182523
Intrathecal magnesium sulfate attenuates algogenic behavior and spinal amino acids release after kainic acid receptor activation in rats.	2001 Mar 30	11248436
Evaluation of urinary carnitine and taurine excretion in 5 cystinuric dogs with carnitine and taurine deficiency.	2001 Mar-Apr	11300604
Mechanisms of alcohol-nicotine interactions: alcoholics versus smokers.	2001 May	11391065
Pharmacological relapse prevention in alcohol dependence: from animal models to clinical trials.	2001 May	11391061
The influence of plasma on the disinfecting activity of the new antimicrobial agent N-chlorotaurine-sodium in comparison with chloramine T.	2001 May	11370708
N-chlorotaurine, a novel endogenous antimicrobial agent: tolerability testing in a mouse model.	2001 May	11346428
Characterization of the mouse bile salt export pump overexpressed in the baculovirus system.	2001 May	11343252
Identification of a novel form of renal glucosuria with overexcretion of arginine, carnosine, and taurine.	2001 May	11325687
Further studies on the effects of topical lactate on amino acid efflux from the ischemic rat cortex.	2001 May 18	11368947

Patents

Sample Use Guides

In Vivo Use Guide

Taurin occurs naturally in fish and meat. The mean daily intake from omnivore diets was determined to be around 58 mg.

Route of Administration: Oral

In Vitro Use Guide

Agonist properties of taurine on glycine receptor of supraoptic magnocellular neurones acutely dissociated from adult rats, using whole-cell voltage clamp. Responses to 1 mM taurine were blocked by strychnine but not by gabazine and showed no additivity with glycine-induced currents, indicating selective activation of glycine receptors.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 14:58:08 GMT 2023` Edited by `admin` on `Fri Dec 15 14:58:08 GMT 2023`
Record UNII	1EQV5MLY3D
Record Status	`Validated (UNII)`
Record Version

Download

Related Record	Type

Name

Type

Language

TAURINE

Official Name

English

TAURINE [JAN]

Common Name

English

TAURINE [MI]

Common Name

English

taurine [INN]

Common Name

English

TAURINE [USP-RS]

Common Name

English

TAURINE [FHFI]

Common Name

English

AMINOETHYLSULFONIC ACID

Systematic Name

English

AMINOETHYLSULFONIC ACID [JAN]

Common Name

English

Taurine [WHO-DD]

Common Name

English

NSC-32428

Code

English

TAURINE [MART.]

Common Name

English

Ethanesulfonic acid, 2-amino-

Common Name

English

FEMA NO. 3813

Code

English

TAURINE [INCI]

Common Name

English

TAURINE [VANDF]

Common Name

English

TAURINE [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

LOINC

26896-1