チオプロニン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/22 11:48:36」(JST)
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Tiopronin
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| Names |
| IUPAC name
2-(2-sulfanylpropanoylamino)acetic acid
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| Other names
2-mercaptopropionylglycine
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| Identifiers |
|
CAS Registry Number
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1953-02-2 Y
29335-92-0 R Y |
| ATC code |
R05CB12
QG04BC90 |
|
Beilstein Reference
|
1859822 |
| ChEMBL |
ChEMBL1314 Y |
| ChemSpider |
5283 Y
180938 R Y
643292 S Y |
| EC number |
217-778-4 |
InChI
-
InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8) Y
Key: YTGJWQPHMWSCST-UHFFFAOYSA-N Y
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| Jmol-3D images |
Image
Image |
| KEGG |
D01430 Y |
| MeSH |
Tiopronin |
| PubChem |
5483
208825 R
736152 S |
| RTECS number |
MC0596500 |
SMILES
-
CC(S)c(:[o]):[nH]Cc(:[o]):[oH]
-
CC(S)C(=O)NCC(O)=O
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| UNII |
C5W04GO61S Y |
| Properties |
|
Chemical formula
|
C5H9NO3S |
| Molar mass |
163.19 g·mol−1 |
| Appearance |
White, opaque crystals |
| Melting point |
93 to 98 °C (199 to 208 °F; 366 to 371 K) |
| log P |
−0.674 |
| Acidity (pKa) |
3.356 |
| Basicity (pKb) |
10.641 |
| Pharmacology |
| Legal status |
|
|
Pregnancy
category
|
- US: C (Risk not ruled out)
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| Hazards |
| GHS pictograms |
|
| GHS signal word |
WARNING |
|
GHS hazard statements
|
H302 |
| EU classification |
Xn |
| R-phrases |
R22 |
| S-phrases |
S36/37 |
| Lethal dose or concentration (LD, LC): |
|
LD50 (Median dose)
|
1,300 mg kg−1 (oral, rat) |
| Related compounds |
|
Related alkanoic acids
|
- Acetylcysteine
- Glycylglycine
- Iminodiacetic acid
- Nitrilotriacetic acid
- N-Oxalylglycine
- Bucillamine
- Oxalyldiaminopropionic acid
- gamma-Glutamylcysteine
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|
Related compounds
|
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
| Y verify (what is: Y/N?) |
| Infobox references |
|
|
Tiopronin (trade name Thiola) is a prescription thiol drug used to control the rate of cystine precipitation and excretion in the disease cystinuria.[1][2] Due to the rarity of the disorder, tiopronin falls under the classification of an orphan drug.
Contents
- 1 Uses
- 2 Side effects
- 3 References
- 4 External links
Uses
Tiopronin is used primarily for cystinuria and is well known in the cystinuric community. Depending on the severity of a person's cystinuria, tiopronin may be taken for life, possibly starting in early childhood.
It may also be used for Wilson's disease (an overload of copper in the body), and certain rare types of arthritis, though tiopronin is not an anti-inflammatory.
Tiopronin is also sometimes used as a stabilizing agent for metal nanoparticles. The thiol group binds to the nanoparticles, preventing coagulation.[3]
Side effects
Tiopronin may present a wide variety of side effects, but side effects are usually limited and subside over time with continued usage. Due to the rarity of the disease cystinuria, tiopronin has not been studied substantially.
References
- ^ Lindell, Å.; Denneberg, T.; Hellgren, E.; Jeppsson, J. -O.; Tiselius, H. -G. "Clinical course and cystine stone formation during tiopronin treatment". Urological Research 23 (2): 111–117. doi:10.1007/BF00307941.
- ^ Coe, Fredric L.; Parks, Joan H.; Asplin, John R. (15 October 1992). "The Pathogenesis and Treatment of Kidney Stones". New England Journal of Medicine 327 (16): 1141–1152. doi:10.1056/NEJM199210153271607.
- ^ Jennifer A. Dahl, Bettye L. S. Maddux, and James E. Hutchison (2007). "Toward Greener Nanosynthesis". Chemical Reviews 107 (6): 2228–2269. doi:10.1021/cr050943k. PMID 17564480.
External links
|
Cough and cold preparations (R05)
|
|
| Expectorants |
- Althea root
- Antimony pentasulfide
- Creosote
- Guaiacolsulfonate
- Guaifenesin
- Ipecacuanha (Syrup of ipecac)
- Levoverbenone
- Potassium iodide
- Senega
- Tyloxapol
- Ammonium Chloride
|
|
| Mucolytics |
- Acetylcysteine
- Ambroxol
- Bromhexine
- Carbocisteine
- Domiodol
- Dornase alfa
- Eprazinone
- Erdosteine
- Letosteine
- Mannitol
- Mesna
- Neltenexine
- Sobrerol
- Stepronin
- Tiopronin
|
|
| Cough suppressants |
Opium alkaloids,
opioids,
and derivatives |
- Acetyldihydrocodeine
- Benzylmorphine
- Butorphanol
- Codeine
- Dextromethorphan
- Dihydrocodeine
- Dimemorfan
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- Heroin
- Hydrocodone
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- Isoaminile
- Laudanum
- Levomethadone
- Levopropoxyphene
- Methadone
- Nicocodeine
- Nicodicodeine
- Normethadone
- Noscapine
- Pholcodine
- Thebacon
- Tipepidine
|
|
| Other |
- Benzonatate
- Benproperine
- Bibenzonium bromide
- Butamirate
- Clobutinol
- Clofedanol
- Cloperastine
- Diphenhydramine
- Dibunate
- Dimethoxanate
- Dropropizine
- Fedrilate
- Glaucine
- Levodropropizine
- Meprotixol
- Morclofone
- Nepinalone
- Oxolamine
- Oxeladin
- Pentoxyverine
- Pipazetate
- Prenoxdiazine
- Piperidione
- Zipeprol
|
|
|
|
Index of the respiratory system
|
|
| Description |
- Anatomy
- Physiology
- Development
|
|
| Disease |
- Congenital
- Neoplasms and cancer
- Chest trauma
- Infection
- common cold
- pneumonia
- tuberculosis
- Other
- Symptoms and signs
|
|
| Treatment |
- Procedures
- Drugs
- nasal
- throat
- obstructive airway diseases
- cough and cold
- histaminergics
- pulmonary arterial hypertension
- other
- Surgery
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|
UpToDate Contents
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English Journal
- Hypoxia and reoxygenation modulate the arrhythmogenic activity of the pulmonary vein and atrium.
- Lin YK, Lai MS, Chen YC, Cheng CC, Huang JH, Chen SA, Chen YJ, Lin CI.SourceDivision of Cardiovascular Medicine, Taipei Medical University, Wan Fang Hospital, Taiwan.
- Clinical science (London, England : 1979).Clin Sci (Lond).2012 Feb;122(3):121-32.
- Ischaemia and reperfusion contribute to the genesis of AF (atrial fibrillation). PVs (pulmonary veins) and the atria are important foci for AF initiation and maintenance. However, the effect of ischaemia and reperfusion on PVs and the atria has not yet been fully elucidated. In the present study, co
- PMID 21880017
- A role for metalloendopeptidases in the breakdown of the gut hormone, PYY 3-36.
- Addison ML, Minnion JS, Shillito JC, Suzuki K, Tan TM, Field BC, Germain-Zito N, Becker-Pauly C, Ghatei MA, Bloom SR, Murphy KG.SourceSection of Investigative Medicine, Imperial College London, Commonwealth Building, Du Cane Road, London W12 0NN, United Kingdom.
- Endocrinology.Endocrinology.2011 Dec;152(12):4630-40. Epub 2011 Sep 27.
- Peptide YY(3-36) (PYY(3-36)) is a gut hormone that acts on Y2 receptors to reduce appetite. Obese humans are sensitive to the anorectic effects of PYY(3-36) and display a blunted postprandial rise in PYY(3-36). Bariatric surgery results in increased circulating PYY-immunoreactivity, which appears to
- PMID 21952244
Japanese Journal
- Spectrophotometric Determination of Tiopronin Using Its Catalytic Reaction between Sodium 1,2-Naphthoquinone-4-sulfonate and Hydroxyl Ion
- Li Quanmin,Gao Linxiao
- Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 25(1), 89-93, 2009-01-10
- NAID 10025209592
- Spectrophotometric Determination of Tiopronin Using Its Catalytic Reaction between Sodium 1,2-Naphthoquinone-4-sulfonate and Hydroxyl Ion
- LI Quanmin,GAO Linxiao
- Analytical Sciences 25(1), 89-93, 2009
- … A novel and simple spectrophotometric method for the determination of tiopronin with sodium 1,2-naphthoquinone-4-sulfonate (NQS) is established in this paper. … It is based on the fact that tiopronin can catalyze the reaction between sodium 1,2-naphthoquinone-4-sulfonate and hydroxyl ion to form 2-hydroxy-1,4-naphthoquinone in a buffer solution of pH 13.00 at the maximal absorption wavelength of 445 nm. …
- NAID 130004441753
Related Links
- Tiopronin (trade name Thiola) is a prescription thiol drug used to control the rate of cystine precipitation and excretion in the disease cystinuria. Due to the rarity of the disorder, tioronin falls under the classification of an orphan drug.
- [Tiopronin] [1953-02-2] | 価格や在庫、物性値などの詳細情報ページです。
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