基本情報
- 標準SMILES
CC(S)C(=O)NCC(=O)O- InChIKey
YTGJWQPHMWSCST-UHFFFAOYSA-N- 分子式
- C5H9NO3S
- 平均分子量
- 163.2 g/mol
- 単同位体質量
- 163.03031415
概要
Tiopronin is a N-acyl-amino acid.
名称と識別子
- 優先名称
- Tiopronin
- IUPAC
- 2-(2-sulfanylpropanoylamino)acetic acid
- 現地名
- チオプロニン
- 英語名
- Tiopronin
- 分子式
- C5H9NO3S
- 分子量
- 163.19
名称と別名
tiopronin1953-02-2N-(2-Mercaptopropionyl)glycineThiopronineThiolaTiopronine2-(2-sulfanylpropanoylamino)acetic acidGlycine, N-(2-mercapto-1-oxopropyl)-Thiolpropionamidoacetic acidDTXSID4023678tioproninaTioproninum
名称をさらに表示
ムコリシンN-(2-メルカプト-1-オキソプロピル)グリシンビンコールメルカプトプロピオニルグリシンN-(1-オキソ-2-メルカプトプロピル)グリシンエパチオール[(2-メルカプトプロピオニル)アミノ]酢酸N-(α-メルカプトプロピオニル)グリシンN-(2-メルカプトプロピオニル)グリシンメルカミズムチオラメプリンチオプロニンデルターチオリドンチオグリシントN-(2-メルカプトプロパノイル)グリシンチオプロニン標準品Ｎ（αメルカプトプロピオニル）グリシンチオプロニン (JAN)2-(2-スルファニルプロパンアミド)酢酸Thiopronin2-(2-Mercaptopropanamido)acetic acidCapen2-MPGVincolSF-572ThioraEpatiol
(2-Mercaptopropionyl)glycineNSC-760416C5W04GO61STHIOLA ECDTXCID803678alpha-Mercaptopropionylglycine2 Mercaptopropionylglycine2-Mercaptopropionylglycine
データベース識別子
- CAS
1953-02-2- PubChem CID
- 5483
- DTXSID
DTXSID4023678- ChEMBL
CHEMBL1314- ChEBI
CHEBI:32229- UNII
- C5W04GO61S
- EC Number
- 217-778-4
- Nikkaji
- J3.692G
物性
構造計算による物性
- XLogP
- -0.1
- 極性表面積
- 67.4 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 4
- 回転可能結合数
- 3
- 重原子数
- 10
- 形式電荷
- 0
- 複雑度
- 148
実験および物理化学的性質
DrugsPharmaceuticals
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
物理化学的性質
- 融点
- 93 · 93-98 °C
- 沸点
- 418.3 · 418.3±30.0 °C(Predicted)
- 比重(密度)
- 1.249 · 1.249 (estimate)
- 屈折率
- 1.5216 · 1.5216 (estimate)
- 貯蔵温度
- 2 · Inert atmosphere,2-8°C
- 溶解性
- DMSO（微量）、メタノール（微量）
- 酸解離定数(Pka)
- 3.36 · 3.36±0.10(Predicted)
- 外見
- 個体
- 色
- 白い
- Merck
- 14 · 14,9453
- BRN
- 1859822 · 1859822
- 主な用途
- 細胞分析ペプチド合成
- 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 データベース
- 1953 · 1953-02-2(CAS DataBase Reference)
化学的性質
化学的特性White Solid
安全と法規制
GHS分類
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.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
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
安全データ
- wgk
- 3
- rtecs
- MC0596500
- 毒性
- LD50 i.v. in mice: 2.1 g/kg (Fujimura)
- hs_code
- 2930.90.4950
- risk_code
- 22
- 化審法
- (2)-1207, (9)-1423
- hazard_code
- Xn
- safety_code
- 36/37
- Hazard Classifications
- Acute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
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
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
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.
用途と製造
UsesUse (kg; approx.) in Germany (2009): >50
応用分野
説明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.
使用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
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