U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C2H7NO3S
Molecular Weight 125.1481
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAURINE

SMILES

C(CS(=O)(=O)O)N

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 125.1481
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Originator

Curator's Comment:: Taurin was first isolated from ox bile in 1827.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
406.0 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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.
Palliative
TAURINE

Approved Use

Taking 1.5-4 grams of taurine daily for up to 3 months improves liver function in people with hepatitis.
Preventing
URSA Complex

Approved Use

Taurine is a component of energy drinks used for relieving of fatigue
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Calcium-mediated transductive systems and functionally active gap junctions in astrocyte-like GL15 cells.
2001
Beneficial effects of an "energy drink" given to sleepy drivers.
2001
The influence of a taurine containing drink on cardiac parameters before and after exercise measured by echocardiography.
2001
Readiness potential in different states of physical activation and after ingestion of taurine and/or caffeine containing drinks.
2001
Changes in plasma and urinary taurine and amino acids in runners immediately and 24h after a marathon.
2001
Gene expression of the taurine transporter and taurine biosynthetic enzymes in rat kidney after antidiuresis and salt loading.
2001 Apr
Zinc and the eye.
2001 Apr
Increased taurine content in esophageal mucosa of children affected by gastroesophageal reflux.
2001 Apr
Conditioned nutritional deficiencies in the cardiomyopathic hamster heart.
2001 Apr
Dipolar coupling and ordering effects observed in magnetic resonance spectra of skeletal muscle.
2001 Apr
Killing of Schistosoma mansoni sporocysts by hemocytes from resistant Biomphalaria glabrata: role of reactive oxygen species.
2001 Apr
Cellular uptake of taurine by lactating porcine mammary tissue.
2001 Apr
Transport of L-carnitine in isolated cerebral cortex neurons.
2001 Apr
Analysis of amino acids in human serum by isocratic reversed-phase high-performance liquid chromatography with electrochemical detection.
2001 Apr 13
Fertilizability and developmental capacity of bovine oocytes cultured individually in a chemically defined maturation medium.
2001 Apr 15
Reduction of phospholemman expression decreases osmosensitive taurine efflux in astrocytes.
2001 Apr 23
Inhibition of the myeloperoxidase chlorinating activity by non-steroidal anti-inflammatory drugs investigated with a human recombinant enzyme.
2001 Apr 6
Mast cell numbers in the young rat thalamus: a search for control factors.
2001 Aug
Taurine increases rat survival and reduces striatal damage caused by 3-nitropropionic acid.
2001 Aug
Osmolytes stabilize ribonuclease S by stabilizing its fragments S protein and S peptide to compact folding-competent states.
2001 Aug 3
Effects of new taurine derivatives on primary immune response in rats.
2001 Feb
[Role of angiotensin-(1-7) in amino-acid-neurotransmitter-mediated blood pressure regulation in rat rostral ventrolateral medulla].
2001 Feb
Energy-related metabolites during and after induced myocardial infarction with special emphasis on the reperfusion injury after extracorporeal circulation.
2001 Feb
Effect of acamprosate and naltrexone, alone or in combination, on ethanol consumption.
2001 Feb
An in vivo eyecup preparation for the rat.
2001 Feb 15
Activation of an ATP-dependent K(+) conductance in Xenopus oocytes by expression of adenylate kinase cloned from renal proximal tubules.
2001 Feb 9
The protective effect of taurine against thioacetamide hepatotoxicity of rats.
2001 Jan
Dietary taurine manipulations in aged male Fischer 344 rat tissue: taurine concentration, taurine biosynthesis, and oxidative markers.
2001 Jul 1
Taurine modulates arginine vasopressin-mediated regulation of renal function.
2001 Jun
Enhanced fungicidal activity of N-chlorotaurine in nasal secretion.
2001 Jun
Occupational lead exposure and amino acid profiles and liver function tests in industrial workers.
2001 Jun
17 beta-estradiol protects neurons from ischemic damage and attenuates accumulation of extracellular excitatory amino acids.
2001 Jun
Role of taurine in preventing acetaminophen-induced hepatic injury in the rat.
2001 Jun
Bile acid hydrophobicity is correlated with induction of apoptosis and/or growth arrest in HCT116 cells.
2001 Jun 1
Swelling-activated taurine and K+ transport in human cervical cancer cells: association with cell cycle progression.
2001 Mar
Effects of acamprosate on ethanol-seeking and self-administration in the rat.
2001 Mar
A new model for diffuse brain injury by rotational acceleration: II. Effects on extracellular glutamate, intracranial pressure, and neuronal apoptosis.
2001 Mar
Evaluation of urinary carnitine and taurine excretion in 5 cystinuric dogs with carnitine and taurine deficiency.
2001 Mar-Apr
Oxidative stress and protection against reactive oxygen species in the pre-implantation embryo and its surroundings.
2001 Mar-Apr
Mechanisms of alcohol-nicotine interactions: alcoholics versus smokers.
2001 May
Pharmacological relapse prevention in alcohol dependence: from animal models to clinical trials.
2001 May
The influence of plasma on the disinfecting activity of the new antimicrobial agent N-chlorotaurine-sodium in comparison with chloramine T.
2001 May
The anti-craving compound acamprosate acts as a weak NMDA-receptor antagonist, but modulates NMDA-receptor subunit expression similar to memantine and MK-801.
2001 May
N-chlorotaurine, a novel endogenous antimicrobial agent: tolerability testing in a mouse model.
2001 May
Characterization of the mouse bile salt export pump overexpressed in the baculovirus system.
2001 May
Identification of a novel form of renal glucosuria with overexcretion of arginine, carnosine, and taurine.
2001 May
High glucose inhibits renal proximal tubule cell proliferation and involves PKC, oxidative stress, and TGF-beta 1.
2001 May
Cysteine regulates expression of cysteine dioxygenase and gamma-glutamylcysteine synthetase in cultured rat hepatocytes.
2001 May
Down-regulation of cholesterol 7alpha-hydroxylase (CYP7A1) gene expression by bile acids in primary rat hepatocytes is mediated by the c-Jun N-terminal kinase pathway.
2001 May 11
Further studies on the effects of topical lactate on amino acid efflux from the ischemic rat cortex.
2001 May 18
Patents

Sample Use Guides

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 Jun 25 20:59:26 UTC 2021
Edited
by admin
on Fri Jun 25 20:59:26 UTC 2021
Record UNII
1EQV5MLY3D
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
TAURINE
FHFI   INCI   INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INCI   INN  
Official 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
JAN  
Systematic Name English
AMINOETHYLSULFONIC ACID [JAN]
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 [WHO-DD]
Common Name English
TAURINE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
LOINC 26896-1
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LOINC 15208-2
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LOINC 56985-5
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NCI_THESAURUS C45564
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LOINC 2981-9
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LOINC 15140-7
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LOINC 25985-3
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LOINC 20657-3
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JECFA EVALUATION TAURINE
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LOINC 30563-1
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LOINC 17679-2
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LOINC 2979-3
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NCI_THESAURUS C68442
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DSLD 2060 (Number of products:2643)
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LOINC 2980-1
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LOINC 13415-5
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FDA ORPHAN DRUG 298709
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LOINC 17678-4
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LOINC 44411-7
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LOINC 28595-7
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LOINC 27310-2
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LOINC 13814-9
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LOINC 25138-9
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LOINC 26614-8
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LOINC 2982-7
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LOINC 25533-1
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LOINC 15136-5
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CFR 21 CFR 573.980
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DSLD 504 (Number of products:17)
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LOINC 33214-8
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LOINC 32271-9
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LOINC 47782-8
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LOINC 9324-5
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Code System Code Type Description
HSDB
8167
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
DRUG BANK
DB01956
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
CAS
107-35-7
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
ECHA (EC/EINECS)
203-483-8
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
FDA UNII
1EQV5MLY3D
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
WIKIPEDIA
TAURINE
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
RXCUI
10337
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY RxNorm
RXCUI
1431306
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
EPA CompTox
107-35-7
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
ChEMBL
CHEMBL239243
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
PUBCHEM
1123
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
EVMPD
SUB10836MIG
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
USP_CATALOG
1643361
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
4486
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
MERCK INDEX
M10481
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C61962
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
INN
6171
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
MESH
D013654
Created by admin on Fri Jun 25 20:59:26 UTC 2021 , Edited by admin on Fri Jun 25 20:59:26 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SUB_CONCEPT->SUBSTANCE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY