Grundinformationen
- Standard-SMILES
CC(S)C(=O)NCC(=O)O- InChIKey
YTGJWQPHMWSCST-UHFFFAOYSA-N- Summenformel
- C5H9NO3S
- Durchschnittliche Molmasse
- 163,2 g/mol
- Monoisotopische Masse
- 163,03031415
Überblick
Tiopronin is a N-acyl-amino acid.
Namen und Bezeichner
- Bevorzugter Name
- Tiopronin
- IUPAC
- 2-(2-sulfanylpropanoylamino)acetic acid
- Lokaler Name
- Tiopronin
- Englischer Name
- Tiopronin
- Summenformel
- C5H9NO3S
- Molmasse
- 163.19
Namen und Synonyme
tiopronin1953-02-2N-(2-Mercaptopropionyl)glycineThiopronineThiolaTiopronine2-(2-sulfanylpropanoylamino)acetic acidGlycine, N-(2-mercapto-1-oxopropyl)-Thiolpropionamidoacetic acidDTXSID4023678tioproninaTioproninum
Weitere Namen anzeigen
Thiopronin2-(2-Mercaptopropanamido)acetic acidCapen2-MPGVincolSF-572ThioraEpatiol
(2-Mercaptopropionyl)glycineNSC-760416C5W04GO61STHIOLA ECDTXCID803678alpha-Mercaptopropionylglycine2 Mercaptopropionylglycine2-Mercaptopropionylglycine
Datenbank-Bezeichner
- CAS
1953-02-2- PubChem CID
- 5483
- DTXSID
DTXSID4023678- ChEMBL
CHEMBL1314- ChEBI
CHEBI:32229- UNII
- C5W04GO61S
- EC Number
- 217-778-4
- Nikkaji
- J3.692G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,1
- Polarare Oberfläche (TPSA)
- 67,4 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 10
- Formalladung
- 0
- Komplexität
- 148
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Schmelzpunkt
- 93 · 93-98 °C
- Siedepunkt
- 418.3 · 418.3±30.0 °C(Predicted)
- Dichte
- 1.249 · 1.249 (estimate)
- Brechungsindex
- 1.5216 · 1.5216 (estimate)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- pka
- 3.36 · 3.36±0.10(Predicted)
- Aggregatzustand
- solid
- Farbe
- 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 Datenbank
- 1953 · 1953-02-2(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxikologische Informationen
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
Sicherheitsdaten
- wgk
- 3
- hs_code
- 2930.90.4950
- RTECS-Nr.
- MC0596500
- risk_code
- 22
- Toxizität
- LD50 i.v. in mice: 2.1 g/kg (Fujimura)
- hazard_code
- Xn
- safety_code
- 36/37
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
UsesUse (kg; approx.) in Germany (2009): >50
Anwendungen
BeschreibungTiopronin 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.
VerwendenN-(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
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
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]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海诺宝化工有限公司+86(0)21 60484900
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
重庆普瑞生物医药科技有限公司023-89130144 18523560356 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
武汉励合化学新材料有限公司027-88395709
上海嵩爰化工科技有限公司010-1234567 18521000990 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
大连韦德生化科技有限公司0411-88165855 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技（武汉）有限公司027-59207879 1972026995 18140587686 · [email protected]
武汉森威尔世纪化工有限公司027-86652399 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
成都赛诺宁科技有限公司28-87999436 02887999436 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学（上海）科技有限公司4009209199 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
西安天广源生物科技有限公司+86-029-86333380 +86-18829239519 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
Zugehörige Reaktionen
10
Verknüpfte Notizen
Wird geladen…