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Revision as of 13:35, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470437647 of page Tiopronin for the Chem/Drugbox validation project (updated: '').		Latest revision as of 04:36, 20 March 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,153 edits →External links: remove section head
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			{{chembox
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			| Watchedfields = changed
	{{Chembox
			| verifiedrevid = 470610633
	| ImageFile = Tiopronin.svg		| ImageFile = Tiopronin.svg
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageName = Skeletal formula of tiopronin		| ImageName = Skeletal formula of tiopronin
			| IUPACName = ''N''-(2-Sulfanylpropanoyl)glycine
	| IUPACName = acetic acid{{Citation needed|date=January 2012}}
			| SystematicName = (2-Sulfanylpropanamido)acetic acid
	| OtherNames = Thiopronine{{Citation needed|date=January 2012}}
			| OtherNames = 2-mercaptopropionylglycine<br />Acadione
	| Section1 = {{Chembox Identifiers
			|Section1={{Chembox Identifiers
	| CASNo = 1953-02-2
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo = 1953-02-2
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo1 = 29335-92-0		| CASNo1 = 29335-92-0
	| CASNo1_Ref = {{cascite|correct|??}}		| CASNo1_Ref = {{cascite|correct|CAS}}
	| CASNo1_Comment = <small>''R''</small>		| CASNo1_Comment = <small>''R''</small>
	| PubChem = 5483		| PubChem = 5483
			| PubChem1 = 208825
	| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
			| PubChem1_Comment = <small>''R''</small>
	| PubChem1 = 208825
			| PubChem2 = 736152
	| PubChem1_Ref = {{Pubchemcite|correct|Pubchem}}
	| PubChem1_Comment = <small>''R''</small>		| PubChem2_Comment = <small>''S''</small>
	| PubChem2 = 736152		| ChemSpiderID = 5283
	| PubChem2_Ref = {{Pubchemcite|correct|Pubchem}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID1 = 180938
	| PubChem2_Comment = <small>''S''</small>
			| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 5283
			| ChemSpiderID1_Comment = <small>''R''</small>
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID2 = 643292
	| ChemSpiderID1 = 180938
	| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID1_Comment = <small>''R''</small>		| ChemSpiderID2_Comment = <small>''S''</small>
			| UNII = C5W04GO61S
	| ChemSpiderID2 = 643292
	| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}		| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII1_Ref = {{fdacite|correct|FDA}}
	| ChemSpiderID2_Comment = <small>''S''</small>
	| UNII = C5W04GO61S		| UNII1 = X294K8K2PF
			| UNII1_Comment = <small>''R''</small>
	| UNII_Ref = {{fdacite|correct|FDA}}
	| EINECS = 217-778-4		| EINECS = 217-778-4
	| KEGG = D01430		| KEGG = D01430
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| MeSHName = Tiopronin		| MeSHName = Tiopronin
	| ChEMBL = 1314		| ChEMBL = 1314
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| RTECS = MC0596500		| RTECS = MC0596500
			| Beilstein = 1859822
	| ATCCode_prefix = R05
			| SMILES = CC(S)C(=O)NCC(O)=O
	| ATCCode_suffix = CB12
			| StdInChI = 1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
	| ATC_Supplemental = {{ATCvet|G04|BC90}}
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| Beilstein = 1859822
			| StdInChIKey = YTGJWQPHMWSCST-UHFFFAOYSA-N
	| SMILES = CC(S)C(=O)NCC(O)=O
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = YTGJWQPHMWSCST-UHFFFAOYSA-N
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=5|H=9|N=1|S=1|O=2		| C=5 | H=9 | N=1 | S=1 | O=3
			| Appearance = White, opaque crystals
	| ExactMass = 163.030313849 g mol<sup>−1</sup>
			| MeltingPtC = 93 to 98
	| Appearance = White, opaque crystals
			| LogP = −0.674
	| MeltingPtCL = 93
	| MeltingPtCH = 98		| pKa = 3.356
	| LogP = −0.674		| pKb = 10.641
	| pKa = 3.356
	| pKb = 10.641
	}}		}}
	| Section3 = {{Chembox Pharmacology		| Section6 = {{Chembox Pharmacology
	| Legal_US = Rx		| Pharmacology_ref =
	| PregCat_US = C		| ATCCode_prefix = G04
			| ATCCode_suffix = BX16
			| ATC_Supplemental = {{ATCvet|G04|BX16}}
			| ATCvet =
			| Licence_EU =
			| INN =
			| INN_EMA =
			| Licence_US =
			| Legal_status =
			| Legal_AU =
			| Legal_AU_comment =
			| Legal_CA =
			| Legal_CA_comment =
			| Legal_NZ =
			| Legal_NZ_comment =
			| Legal_UK =
			| Legal_UK_comment =
			| Legal_US = Rx-only
			| Legal_US_comment = <ref name="Thiola FDA label">{{cite web | title=Thiola- tiopronin tablet, sugar coated | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=494a714e-923c-cd57-df6c-12886afb265a | access-date=18 June 2021}}</ref><ref name="Thiola EC FDA label">{{cite web | title=Thiola EC- tiopronin tablet, delayed release | website=DailyMed | date=15 March 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=20298a52-a194-a161-8632-d84b6f26e23c | access-date=6 March 2023}}</ref>
			| Legal_EU =
			| Legal_EU_comment =
			| Legal_UN =
			| Legal_UN_comment =
			| Pregnancy_category =
			| Pregnancy_AU =
			| Pregnancy_AU_comment =
			| Dependence_liability =
			| AdminRoutes = ]
			| Bioavail =
			| ProteinBound =
			| Metabolism =
			| Metabolites =
			| OnsetOfAction =
			| HalfLife =
			| DurationOfAction =
			| Excretion =
			}}
			|Section7={{Chembox Hazards
			| GHSPictograms = {{gHS exclamation mark}}
			| GHSSignalWord = '''WARNING'''
			| HPhrases = {{h-phrases|302}}
			| LD50 = 1,300 mg kg<sup>−1</sup> <small>(oral, rat)</small>
	}}		}}
	| Section4 = {{Chembox Hazards		|Section8={{Chembox Related
			| OtherFunction_label = alkanoic acids
	| GHSPictograms = {{GHS exclamation mark}}
			| OtherFunction = {{unbulleted list|]|]|]|]|]|]|]|]}}
	| GHSSignalWord = '''WARNING'''
			| OtherCompounds = {{unbulleted list|]}}
	| HPhrases = {{H-phrases|302}}
	| EUClass = {{Hazchem Xn}}
	| RPhrases = {{R22}}
	| SPhrases = {{S36/37}}
	| LD50 = 1.300 mg kg<sup>−1</sup> (oral, rat)
	}}		}}
	| Section5 = {{Chembox Related
	| OtherCpds = {{Unbulleted list|]|]}}
	}}		}}
			{{Infobox drug
			| drug_name =
			| INN =
			| type = <!-- empty -->
			| image =
			| width =
			| alt =
			| caption =
			<!-- Clinical data -->
			| pronounce =
			| tradename = Thiola
			| Drugs.com =
			| MedlinePlus =
			| licence_EU = <!-- EMA uses INN (or special INN_EMA) -->
			| DailyMedID = Tiopronin
			| licence_US = <!-- FDA may use generic or brand name (generic name preferred) -->
			| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
			| pregnancy_AU_comment =
			| pregnancy_category=
			| dependency_liability =
			| class =
			| ATCvet =
			| ATC_prefix = <!-- 'none' if uncategorised -->
			| ATC_suffix =
			| ATC_supplemental =
			<!-- Legal status -->
			| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
			| legal_AU_comment =
			| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
			| legal_BR_comment =
			| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
			| legal_CA_comment =
			| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
			| legal_DE_comment =
			| legal_NZ = <!-- Class A, B, C -->
			| legal_NZ_comment =
			| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
			| legal_UK_comment =
			| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
			| legal_US_comment =
			| legal_EU =
			| legal_EU_comment =
			| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
			| legal_UN_comment =
			| legal_status = <!-- For countries not listed above -->
			<!-- Pharmacokinetic data -->
			| bioavailability =
			| protein_bound =
			| metabolism =
			| metabolites =
			| onset =
			| elimination_half-life =
			| duration_of_action =
			| excretion =
			<!-- Identifiers -->
			| CAS_number_Ref =
			| CAS_number =
			| CAS_supplemental =
			| PubChem =
			| IUPHAR_ligand =
			| DrugBank_Ref =
			| DrugBank = DB06823
			| ChemSpiderID_Ref =
			| ChemSpiderID =
			| UNII_Ref =
			| UNII =
			| KEGG_Ref =
			| KEGG =
			| KEGG2_Ref =
			| KEGG2 =
			| ChEBI_Ref =
			| ChEBI = 32229
			| ChEMBL_Ref =
			| ChEMBL =
			| NIAID_ChemDB =
			| PDB_ligand =
			| synonyms =
			<!-- Chemical and physical data -->
			| IUPAC_name =
			| chemical_formula_ref =
			| chemical_formula =
			| C= | H= | Ag= | Al= | As= | Au= | B= | Bi= | Br= | Ca= | Cl= | Co= | F= | Fe= | Gd= | I=
			| K= | Li= | Mg= | Mn= | N= | Na= | O= | P= | Pt= | S= | Sb= | Se= | Sr= | Tc= | Zn= | charge=
			| molecular_weight =
			| molecular_weight_comment =
			| SMILES =
			| StdInChI =
			| StdInChI_comment =
			| StdInChIKey =
			| density =
			| density_notes =
			| melting_point =
			| melting_high =
			| melting_notes =
			| boiling_point =
			| boiling_notes =
			| solubility =
			| sol_units =
			| specific_rotation =
	}}		}}
			'''Tiopronin''', sold under the brand name '''Thiola''', is a ] used to control the rate of ] precipitation and excretion in the disease ].<ref>{{cite journal | vauthors = Lindell A, Denneberg T, Hellgren E, Jeppsson JO, Tiselius HG | title = Clinical course and cystine stone formation during tiopronin treatment | journal = Urological Research | volume = 23 | issue = 2 | pages = 111–7 | year = 1995 | pmid = 7676533 | doi = 10.1007/BF00307941 | s2cid = 34308815 }}</ref><ref>{{cite journal | vauthors = Coe FL, Parks JH, Asplin JR | title = The pathogenesis and treatment of kidney stones | journal = The New England Journal of Medicine | volume = 327 | issue = 16 | pages = 1141–52 | date = October 1992 | pmid = 1528210 | doi = 10.1056/NEJM199210153271607 }}</ref>
			It is available as a ].<ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref><ref>{{cite web | title=First Generic Drug Approvals 2023 | website=U.S. ] (FDA) | date=30 May 2023 | url=https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/first-generic-drug-approvals | archive-url=https://web.archive.org/web/20230630003621/https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/first-generic-drug-approvals | archive-date=30 June 2023 | url-status=live | access-date=30 June 2023}}</ref>
			==Medical uses==
			Tiopronin is ], in combination with high fluid intake, alkali, and diet modification, for the prevention of cystine stone formation in people {{convert|20|kg|lb}} and greater with severe homozygous cystinuria, who are not responsive to these measures alone.<ref name="Thiola FDA label" /><ref name="Thiola EC FDA label" />
			==Side effects==
			Tiopronin may present a variety of side effects, which are broadly similar to those of ] and other compounds containing active sulfhydryl groups.<ref>{{cite journal | vauthors = Jaffe IA | title = Adverse effects profile of sulfhydryl compounds in man | journal = The American Journal of Medicine | volume = 80 | issue = 3 | pages = 471–6 | date = March 1986 | pmid = 2937293 | doi = 10.1016/0002-9343(86)90722-9 }}</ref> Its ] have been studied.<ref name="Carlsson" />
			== Pharmacology ==
			=== Mechanism of action ===
			Tiopronin works by reacting with urinary ] to form a more soluble, ] linked, tiopronin-cysteine complex.<ref name="Carlsson">{{cite journal | vauthors = Carlsson MS, Denneberg T, Emanuelsson BM, Kågedal B, Lindgren S | title = Pharmacokinetics of oral tiopronin | journal = European Journal of Clinical Pharmacology | volume = 45 | issue = 1 | pages = 79–84 | date = August 1993 | pmid = 8405034 | doi = 10.1007/BF00315354 | s2cid = 8879752 }}</ref>
			==Society and culture==
			In the U.S., the drug was marketed by Mission Pharmacal at $1.50 per pill, but in 2014 the rights were bought by Retrophin, owned by ], and the price increased to $30 per pill for a 100&nbsp;mg capsule.<ref>{{cite news| vauthors = Lowe D |title=The Most Unconscionable Drug Price Hike I Have Yet Seen|url=https://www.science.org/content/blog-post/most-unconscionable-drug-price-hike-i-have-yet-seen|work=In the Pipeline|date=11 September 2014}}</ref><ref>{{cite web|url=http://www.fiercebiotech.com/story/why-would-martin-shkreli-hike-old-drug-price-5000-only-moron-would-ask/2015-09-20|title=Why would Martin Shkreli hike an old drug price by 5000%? Only a 'moron' would ask|work=FierceBiotech | vauthors = Carroll J |date=September 20, 2015}}</ref>
			In 2016 ] introduced a lower cost version marketed as a ].<ref>{{cite news| vauthors = Elvidge S |title=Imprimis shuts down Texas plant, axes 8% of jobs|url=https://www.biopharmadive.com/news/imprimis-shuts-down-texas-plant-axes-8-of-jobs/427296/|work=BioPharma Dive|date=September 29, 2016}}</ref>
			== Research ==
			It may also be used for ] (an overload of ] in the body), and has also been investigated for the treatment of ],<ref>{{cite journal | vauthors = Delecoeuillerie G | title = | journal = Revue du Rhumatisme et des Maladies Osteo-Articulaires | volume = 56 | issue = 5 Pt 2 | pages = 38–42 | date = April 1989 | pmid = 2740804 }}</ref><ref>{{cite journal | vauthors = Pasero G, Pellegrini P, Ambanelli U, Ciompi ML, Colamussi V, Ferraccioli G, Barbieri P, Mazzoni MR, Menegale G, Trippi D | display-authors = 6 | title = Controlled multicenter trial of tiopronin and d-penicillamine for rheumatoid arthritis | journal = Arthritis and Rheumatism | volume = 25 | issue = 8 | pages = 923–9 | date = August 1982 | pmid = 7115451 | doi = 10.1002/art.1780250803 | doi-access = }}</ref> though tiopronin is not an ].{{citation needed|date=June 2021}}
			Tiopronin is also sometimes used as a stabilizing agent for metal ]. The thiol group binds to the nanoparticles, preventing coagulation.<ref>{{cite journal | vauthors = Dahl JA, Maddux BL, Hutchison JE | title = Toward greener nanosynthesis | journal = Chemical Reviews | volume = 107 | issue = 6 | pages = 2228–69 | date = June 2007 | pmid = 17564480 | doi = 10.1021/cr050943k | name-list-style = amp | citeseerx = 10.1.1.454.2724 }}</ref>
			== References ==
			{{reflist}}
			{{Urologicals, including antispasmodics}}
			{{Portal bar | Medicine}}
			]
			]
			]
			]
			]