기본 정보
- 표준 SMILES
CC(S)C(=O)NCC(=O)O- InChIKey
YTGJWQPHMWSCST-UHFFFAOYSA-N- 분자식
- C5H9NO3S
- 평균 분자량
- 163.2 g/mol
- 단동위원소 질량
- 163.03031415
개요
Tiopronin is a N-acyl-amino acid.
이름 및 식별자
- 우선 이름
- Tiopronin
- IUPAC
- 2-(2-sulfanylpropanoylamino)acetic acid
- 현지명
- 티오프로닌
- 영어명
- Tiopronin
- 분자식
- C5H9NO3S
- 분자량
- 163.19
이름 및 동의어
tiopronin1953-02-2N-(2-Mercaptopropionyl)glycineThiopronineThiolaTiopronine2-(2-sulfanylpropanoylamino)acetic acidGlycine, N-(2-mercapto-1-oxopropyl)-Thiolpropionamidoacetic acidDTXSID4023678tioproninaTioproninum
이름 더 보기
티오프로닌Thiopronin2-(2-Mercaptopropanamido)acetic acidCapen2-MPGVincolSF-572ThioraEpatiol
(2-Mercaptopropionyl)glycineNSC-760416C5W04GO61STHIOLA ECDTXCID803678alpha-Mercaptopropionylglycine2 Mercaptopropionylglycine2-Mercaptopropionylglycine
데이터베이스 식별자
- CAS
1953-02-2- PubChem CID
- 5483
- DTXSID
DTXSID4023678- ChEMBL
CHEMBL1314- ChEBI
CHEBI:32229- UNII
- C5W04GO61S
- EC Number
- 217-778-4
- Nikkaji
- J3.692G
물성
구조 계산 물성
- XLogP
- -0.1
- 극성 표면적
- 67.4 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 10
- 형식 전하
- 0
- 복잡도
- 148
실험 및 물리화학적 성질
DrugsPharmaceuticals
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
물리화학적 성질
- 녹는점
- 93 · 93-98 °C
- 끓는 점
- 418.3 · 418.3±30.0 °C(Predicted)
- 밀도
- 1.249 · 1.249 (estimate)
- 굴절률
- 1.5216 · 1.5216 (estimate)
- 저장 조건
- 2 · Inert atmosphere,2-8°C
- 용해도
- DMSO(약간 용해됨), 메탄올(약간 용해됨)
- 산도 계수 (pKa)
- 3.36 · 3.36±0.10(Predicted)
- 물리적 상태
- 고체
- 색상
- 하얀색
- Merck
- 14 · 14,9453
- BRN
- 1859822 · 1859822
- 주요 응용
- 세포 분석펩타이드 합성
- 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
화학적 성질
White Solid
안전 및 규제
GHS 분류
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.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (100%)
독성 정보
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
안전 데이터
- wgk
- 3
- rtecs
- MC0596500
- 독성
- LD50 i.v. in mice: 2.1 g/kg (Fujimura)
- HS 번호
- 2930.90.4950
- risk_code
- 22
- hazard_code
- Xn
- safety_code
- 36/37
- 기존화학 물질
- KE-23100
- Hazard Classifications
- Acute Tox. 4 Oral
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
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.
용도 및 제조
UsesUse (kg; approx.) in Germany (2009): >50
응용 분야
개요Tiopronin 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.
용도N-(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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