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）』「2013/10/29 10:53:17」(JST)
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| Tiopronin |
|
| Identifiers |
| CAS number |
1953-02-2 Y, 29335-92-0 R Y |
| PubChem |
5483, 208825 R, 736152 S |
| ChemSpider |
5283 Y, 180938 R Y, 643292 S Y |
| UNII |
C5W04GO61S Y |
| EC number |
217-778-4 |
| KEGG |
D01430 Y |
| MeSH |
Tiopronin |
| ChEMBL |
CHEMBL1314 Y |
| RTECS number |
MC0596500 |
| ATC code |
R05CB12,QG04BC90 |
| Beilstein Reference |
1859822 |
| Jmol-3D images |
Image 1
Image 2 |
-
CC(S)c(:[o]):[nH]Cc(:[o]):[oH]
CC(S)C(=O)NCC(O)=O
|
-
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
|
| Properties |
| Molecular formula |
C5H9NO3S |
| Molar mass |
163.19 g mol−1 |
| Appearance |
White, opaque crystals |
| Melting point |
93-98 °C, 366-371 K, 199-208 °F
|
| log P |
−0.674 |
| Acidity (pKa) |
3.356 |
| Basicity (pKb) |
10.641 |
| Pharmacology |
| Legal status |
℞-only(US)
|
Pregnancy
category |
C(US) |
| Hazards |
| GHS pictograms |
|
| GHS signal word |
WARNING |
| GHS hazard statements |
H302 |
| EU classification |
Xn |
| R-phrases |
R22 |
| S-phrases |
S36/37 |
| LD50 |
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
|
| Related compounds |
|
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| 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. Due to the rarity of the disorder, tioronin falls under the classification of an orphan drug.
Contents
- 1 Uses
- 2 Side effects
- 3 References
- 4 External links
Uses[edit]
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 types of rare 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.[1]
Side effects[edit]
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[edit]
- ^ 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[edit]
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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
- Codeine
- Dextromethorphan
- Diacetylmorphine
- Dihydrocodeine
- Dimemorfan
- Droxypropine
- Ethylmorphine
- Hydrocodone
- Hydromorphone
- 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
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anat (n, x, l, c)/phys/devp
|
noco (c, p)/cong/tumr, sysi/epon, injr
|
proc, drug (R1/2/3/5/6/7)
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English Journal
- Influence of tiopronin, captopril and levamisole therapeutics on the oxidative degradation of hyaluronan.
- Valachová K1, Baňasová M1, Topoľská D1, Sasinková V2, Juránek I1, Collins MN3, Šoltés L1.
- Carbohydrate polymers.Carbohydr Polym.2015 Dec 10;134:516-23. doi: 10.1016/j.carbpol.2015.07.029. Epub 2015 Jul 19.
- The ability to protect hyaluronic acid (HA) from oxidative degradation by cupric ions and ascorbate (production of OH and peroxy-type radicals) during acute phase joint inflammation has been investigated using the following drugs: tiopronin, captopril, and levamisole. Radical scavenging activity, i.
- PMID 26428153
- Prospective analysis of tiopronin in prevention of sorafenib and antiviral therapy inducing liver toxicity in advanced hepatitis B virus-related hepatocellular carcinoma.
- Li J1, Qiu X, Guo W, Yan B, Zhang S.
- Medical oncology (Northwood, London, England).Med Oncol.2015 Oct;32(10):684. doi: 10.1007/s12032-015-0684-x. Epub 2015 Sep 2.
- Hepatotoxicity induced by sorafenib and antiviral therapy is a limitation for its continuation treatment for patients with advanced hepatitis B virus-related hepatocellular carcinoma (HCC). This prospective study determined the efficacy of tiopronin in hepatotoxicity prevention of HBV-related HCC tr
- PMID 26330362
- Determination of biodistribution of ultrasmall, near-infrared emitting gold nanoparticles by photoacoustic and fluorescence imaging.
- Poon W1, Heinmiller A2, Zhang X3, Nadeau JL3.
- Journal of biomedical optics.J Biomed Opt.2015 Jun;20(6):066007. doi: 10.1117/1.JBO.20.6.066007.
- This study compares fluorescence and photoacoustic (PA) imaging of ex vivo tumors and organs from tumor-bearing mice injected intravenously with ultrasmall (<3 nm ) tiopronin-capped Au nanoparticles and compares the data with inductively coupled plasma mass spectrometry (ICP-MS). Good agreem
- PMID 26102572
Japanese Journal
- 高度の小葉間胆管消失像を示したチオプロニン起因性肝障害の1男性例
- Thiopronine-induced herpetiform pemphigus : report of a case studied by immunoelectron microscopy and immunoblot analysis
Related Links
- Thiopronine information including symptoms, causes, diseases, symptoms, treatments, and other medical and health issues. ... Introduction: Thiopronine Description of Thiopronine Thiopronine: Sulfhydryl acylated derivative of ...
- The liver therapeutic, thiopronine (2-mercaptopropionylglycine, MPG), was administered to ketotic cows. When 50-100mlof NPG was initravenously administered alone or in combination with some other therapeutics to these cows ...
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