1953-02-2 Usage
Description
Different sources of media describe the Description of 1953-02-2 differently. You can refer to the following data:
1. 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.
2. Tiopronin 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.
Chemical Properties
White Solid
Originator
Roussel-Uclaf (Japan)
Uses
Different sources of media describe the Uses of 1953-02-2 differently. You can refer to the following data:
1. It is used as antidote against heavy metal poisoning; hepatoprotectant; mucolytic.
2. N-(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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 1953-02-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,5 and 3 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1953-02:
(6*1)+(5*9)+(4*5)+(3*3)+(2*0)+(1*2)=82
82 % 10 = 2
So 1953-02-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
1953-02-2Relevant articles and documents
Light-Induced Formation/Scission of C-N, C-O, and C-S Bonds Enables Switchable Stability/Degradability in Covalent Systems
Hai, Yu,Li, Ziyi,Lu, Hanwei,Ye, Hebo,You, Lei,Zou, Hanxun
supporting information, p. 20368 - 20376 (2021/12/03)
The manipulation of covalent bonds could be directed toward degradable, recyclable, and sustainable materials. However, there is an intrinsic conflict between properties of stability and degradability. Here we report light-controlled formation/scission of three types of covalent bonds (C-N, C-O, and C-S) through photoswitching between equilibrium and nonequilibrium states of dynamic covalent systems, achieving dual benefits of photoaddressable stability and cleavability. The photocyclization of dithienylethene fused aldehyde ring-chain tautomers turns on the reactivity, incorporating/releasing amines, alcohols, and thiols reversibly with high efficiency, respectively. Upon photocycloreversion the system is shifted to kinetically locked out-of-equilibrium form, enabling remarkable robustness of covalent assemblies. Reaction coupling allows remote and directional control of a diverse range of equilibria and further broadens the scope. Through locking and unlocking covalent linkages with light when needed, the utility is demonstrated with capture/release of bioactive molecules, modification of surfaces, and creation of polymers exhibiting tailored stability and degradability/recyclability. The versatile toolbox for photoswitchable dynamic covalent reactions to toggle matters on and off should be appealing to many endeavors.
Preparation methods of tiopronin and zinc complex of tiopronin
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Paragraph 0038; 0039, (2017/02/24)
The invention discloses preparation methods of tiopronin and zinc complex of tiopronin and belongs to the technical field of a medicine compound for relieving acute/chronic liver diseases. The technical scheme is characterized in that the formula is shown in the specification. The operation is simple, the cost of raw materials is low, the repeatability of experimental results of a process route is higher, and the production cost can be remarkably reduced.
Carotenoid analogs or derivatives for controlling C-reactive protein levels
-
, (2008/06/13)
A method of controlling (e.g., influencing or affecting) C-reactive protein levels in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include an acyclic alkene including at least one substituent and/or a cyclic ring including at least one substituent. In some embodiments, a carotenoid analog or derivative may include at least one substituent.
