Tiopronin

HCID 5483

Basic information

CAS
1953-02-2
Standard SMILES
CC(S)C(=O)NCC(=O)O
InChIKey
YTGJWQPHMWSCST-UHFFFAOYSA-N
Molecular formula
C5H9NO3S
Average molar mass
163.2 g/mol
Monoisotopic mass
163.03031415

Overview

Tiopronin is a N-acyl-amino acid.

Names & identifiers

Preferred name
Tiopronin
IUPAC
2-(2-sulfanylpropanoylamino)acetic acid
English name
Tiopronin
Molecular formula
C5H9NO3S
Molecular weight
163.19

Names & synonyms

tiopronin1953-02-2N-(2-Mercaptopropionyl)glycineThiopronineThiolaTiopronine2-(2-sulfanylpropanoylamino)acetic acidGlycine, N-(2-mercapto-1-oxopropyl)-Thiolpropionamidoacetic acidDTXSID4023678tioproninaTioproninum
Show more names
Thiopronin2-(2-Mercaptopropanamido)acetic acidCapen2-MPGVincolSF-572ThioraEpatiol
(2-Mercaptopropionyl)glycineNSC-760416C5W04GO61STHIOLA ECDTXCID803678alpha-Mercaptopropionylglycine2 Mercaptopropionylglycine2-Mercaptopropionylglycine

Database identifiers

CAS
1953-02-2
PubChem CID
5483
DTXSID
DTXSID4023678
ChEMBL
CHEMBL1314
ChEBI
CHEBI:32229
UNII
C5W04GO61S
EC Number
217-778-4
Nikkaji
J3.692G

Properties

Computed structural properties

XLogP
-0.1
Topological polar surface area
67.4 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
10

Experimental & physicochemical properties

DrugsPharmaceuticals
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physicochemical properties

Melting point
93 · 93-98 °C
Boiling point
418.3 · 418.3±30.0 °C(Predicted)
Density
1.249 · 1.249 (estimate)
refractive index
1.5216 · 1.5216 (estimate)
storage temp.
2 · Inert atmosphere,2-8°C
solubility
DMSO (Slightly), Methanol (Slightly)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Tiopronin

Ambiguous-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
MC0596500
hs_code
2930.90.4950
Toxicity
LD50 i.v. in mice: 2.1 g/kg (Fujimura)
risk_code
22

Chemistry & industry

Pharmacology

ATC Code · 2 items

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Protein BindingTiopronin undergoes extensive protein binding in plasma. It is thought that this occurs through the formation of a disulphide bridge to the free thiol group of albumin.
Mechanism of Action · 1 item

Kidney stones form when the solubility limit is exceeded and urine becomes supersaturated with endogenous cystine. Tiopronin is an active reducing agent which undergoes a thiol-disulfide exchange with cystine to form a water-soluble mixed disulfide complex. Thus, the amount of sparingly soluble cystine is reduced. By reducing urinary cystine concentrations below the solubility limit, tiopronin helps reduce cystine stone formation.

Biological Half-LifeTiopronin has a long terminal half life of 53 hours in healthy subjects. However, the unbound drug fraction of tiopronin is eliminated much more rapidly from plasma with a calculated half life of 1.8 hours.
Metabolism/MetabolitesThe principle metabolite of tiopronin is 2-mercaptopropionic acid (2-MPA). Between 10-15% of the drug is metabolized to 2-MPA via hydrolysis.
FDA Pharmacological Classification · 6 items

C5W04GO61S

TIOPRONIN

Mechanisms of Action [MoA] - Cystine Disulfide Reduction

Chemical Structure [CS] - N-substituted Glycines

Established Pharmacologic Class [EPC] - Reducing and Complexing Thiol

Tiopronin is a Reducing and Complexing Thiol. The mechanism of action of tiopronin is as a Cystine Disulfide Reduction.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >50
Applications · 4 items

DescriptionTiopronin is a sulfiydryl derivative of N-propylglycine useful in the treatment of cystine urolithiasis in children. It is also reportedly effective in the management of rheumatoid polyarthritis, possibly due to its inhibitory effect on the free oxygen radicals produced by inflammatory macrophages and granulocytes.

DescriptionTiopronin is an antioxidant that has diverse biological activities. It reduces free radical production by murine macrophages and granulocytes in vitro in a dose-dependent manner. Tiopronin induces expression of hypoxia-inducible factor 1α (HIF-1α) and increases VEGF secretion in human colon carcinoma cells. Rectal administration (500 μL of a 10 mM solution) reduces myeloperoxidase activity and reduces pro-inflammatory cytokine production in the colon in a rat model of colitis. Tiopronin (80-320 mg/kg per day) reduces the incidence of cleft palate in fetuses born to female mice orally exposed to teratogenic methylmercury chloride. Tiopronin (100 mg/kg) reduces heme oxygenase 1 mRNA expression, lipid peroxidation, and transverse aortic constriction in a mouse model of cardiac hypertrophy. Tiopronin (20 mg/kg) is hepatoprotective, increasing activity of the antioxidant enzymes superoxide dismutase and glutathione peroxidase and reversing hepatocyte degeneration in a rat model of high-fat diet-induced non-alcoholic steatohepatitis.

UsesN-(2-Mercaptopropionyl)glycine or Tiopronin has been used:in the preparation of polyethylenimine (PEI)-coated gold microparticles (PEI-gold) for biolistic delivery of nucleic acidsto study the role of reactive oxygen species (ROS) at the reperfusion stage in in vivo isoflurane preconditioning-induced neuroprotectionas a ROS inhibitor to study its effect on lysophosphatidylcholine (LPC)-induced inflammasome activation

UsesIt is used as antidote against heavy metal poisoning; hepatoprotectant; mucolytic.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]

Additional notes

DefinitionChEBI: Tiopronin is a N-acyl-amino acid.

Related reactions

10 records

Compound notes

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