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
Show more names
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
- Formal charge
- 0
- Complexity
- 148
Experimental & physicochemical properties
Human Drugs
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)
- pka
- 3.36 · 3.36±0.10(Predicted)
- form
- solid
- color
- White
- Merck
- 14 · 14,9453
- BRN
- 1859822 · 1859822
- Major Application
- cell analysispeptide synthesis
- InChI
- InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
- InChIKey
- YTGJWQPHMWSCST-UHFFFAOYSA-N
- SMILES
- C(O)(=O)CNC(=O)C(S)C
- CAS DataBase Reference
- 1953 · 1953-02-2(CAS DataBase Reference)
- FDA UNII
- 5 W04GO61S · C5W04GO61S
- ATC code
- 4 BX16 · G04BX16
- UNSPSC Code
- 12352209 · 12352209
- NACRES
- 26 · NA.26
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- 36 · 36/37
- WGK Germany
- 3 · 3
- RTECS
- 596500 · MC0596500
- HS Code
- 2930.9 · 2930.90.4950
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 i.v · LD50 i.v. in mice: 2.1 g/kg (Fujimura)
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Drug Induced Liver Injury
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Pharmacology
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Mechanism of Action
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.
FDA Pharmacological Classification
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.
Absorption, Distribution and Excretion
Tiopronin undergoes slow absorption, reaching peak plasma concentration 3-6 hours after ingestion. In a study of healthy subjects, the bioavailability of total and unbound tiopronin was found to be 63% and 40%, respectively.
Tiopronin is 100% excreted in urine.
The volume of distribution of tiopronin is high at 455 L, indicating that a large portion of the drug is bound to tissues outside plasma.
Total renal clearance for the total and unbound fractions of tiopronin were found to be 3.3 and 13.3 L/h respectively.
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Additional notes
DefinitionChEBI: Tiopronin is a N-acyl-amino acid.
Related reactions
Compound notes
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