| Identification | More | [Name]
Tiopronin | [CAS]
1953-02-2 | [Synonyms]
ALPHA-MERCAPTO PROPIONYL GLYCINE
A-MERCAPTOPROPIONYL GLYCINE
LABOTEST-BB LT00451995
N-(2-MERCAPTOPROPIONYL)GLYCINE
TIOPRONIN
Tiopronin, Vetranal
N-(2-MERCAPTOPROPIONYL)GLYCINE 99%
TOPRONIN
(2-Mercaptopropionamido)acetic acid
(2-Mercaptopropionyl)glycine
Acadione
a-Mercaptopropionyglycine
BRN 1859822
Capen
Captimer
CCRIS 1935
DL-(a-Mercaptopropionyl)glycine
Epatiol
Glycine, N-(2-mercapto-1-oxopropyl)-(9CI)
Glycine, N-(2-mercaptopropionyl)-(7CI, 8CI) | [EINECS(EC#)]
217-778-4 | [Molecular Formula]
C5H9NO3S | [MDL Number]
MFCD00004861 | [Molecular Weight]
163.19 | [MOL File]
1953-02-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
93-98 °C
| [Boiling point ]
418.3±30.0 °C(Predicted) | [density ]
1.249 (estimate) | [refractive index ]
1.5216 (estimate) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
solid | [pka]
3.36±0.10(Predicted) | [color ]
White | [Merck ]
13,9532 | [BRN ]
1859822 | [CAS DataBase Reference]
1953-02-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [RTECS ]
MC0596500
| [HS Code ]
2930.90.4950 | [Toxicity]
LD50 i.v. in mice: 2.1 g/kg (Fujimura) |
| Hazard Information | Back Directory | [Description]
Tiopronin 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. | [Chemical Properties]
White Solid | [Originator]
Roussel-Uclaf (Japan) | [Uses]
It is used as antidote against heavy metal poisoning; hepatoprotectant; mucolytic. | [Definition]
ChEBI: Tiopronin is a N-acyl-amino acid. | [Manufacturing Process]
α-Benzylmercaptopropionic acid (melting point 76°C to 78°C; 100 g) prepared
by condensation of α-mercaptopropionic acid with benzyl chloride is allowed to
stand overnight with 80 g of thionyl chloride. After removal of excess thionyl
chloride distillation in vacuo gives 70 g of α-benzylmercaptopropionic acid
chloride of boiling point 138°C to 139°C/7 to 8 mm Hg.
Then, 25 g of glycine is dissolved in 165 ml of 2 N sodium hydroxide solution
and 70 g of α-benzylmercaptopropionic acid chloride and 100 ml of 2 N
sodium hydroxide solution are dropped thereinto simultaneously at 3°C to
5°C. The solution is then stirred at room temperature for 3 to 4 hours to
complete the reaction, the reaction solution is washed with ether, the aqueous
layer is acidified with hydrochloric acid, and the resulting crystals are collected
by filtration. These are recrystallized from a mixture of methanol and ethyl
acetate to give 60 g of α-benzylmercaptopropionylglycine of melting point
133°C to 134°C.
This α-benzylmercaptopropionylglycine (60 g) is dissolved in 400 ml of liquid
ammonia, kept at about -50°C, and 12 g of sodium metal is gradually added
thereto. After the reaction, excess ammonia is removed therefrom, the
residue is dissolved in water, washed with ether and the residual aqueous
layer is adjusted to pH 1 with hydrochloric acid and concentrated in vacuo in a
stream of hydrogen sulfide. The crystalline residue is dried and recrystallized
from ethyl acetate to give 25 g of α-mercaptopropionylglycine of melting point
95°C to 97°C. | [Brand name]
Thiola | [Therapeutic Function]
Antidote (heavy metal) | [Biochem/physiol Actions]
N-(2-Mercaptopropionyl)glycine (NMPG) is a thiol compound associated with autoimmune hypoglycemia. It is a diffusible antioxidant and reduces the severity of colonic injury. NMPG also relieves myeloperoxidase activity and stimulates hypoxia-inducible factor-1 (HIF-1) - vascular endothelial growth factor (VEGF) pathway for ulcer healing. | [Veterinary Drugs and Treatments]
Tiopronin is indicated for the prevention of cystine urolithiasis in
patients where dietary therapy combined with urinary alkalinization
is not completely effective. It may also be useful in combination
with urine alkalinization to dissolve stones. | [storage]
Store at -20°C |
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