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{{Chembox {{chembox
| Watchedfields = changed
| 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
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| PubChem1_Comment = <small>''R''</small>
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| PubChem2 = 736152
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| 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}}
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| 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 =
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| 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 =
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| Metabolites =
| OnsetOfAction =
| HalfLife =
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}}
|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
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{{Infobox drug
| drug_name =
| INN =
| type = <!-- empty -->
| image =
| width =
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| 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 =
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<!-- 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 =
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}} }}
'''Tiopronin''' (trade name '''Thiola''') is a prescription ] drug used to control the rate of ] precipitation and excretion in the disease ]. Due to the rarity of the disorder, tioronin falls under the classification of an ].
==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.


'''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 may also be used for ] (an overload of ] in the body), and certain types of rare ]. It should be mentioned though, that tiopronin is not an ].

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" />


Tiopronin is also sometimes used as a stabilizing agent for metal ]. The thiol group binds to the nanoparticles, preventing coagulation.<ref>{{cite journal | author = Jennifer A. Dahl, Bettye L. S. Maddux, and James E. Hutchison | title = Toward Greener Nanosynthesis | journal = Chemical Reviews | volume = 107 | issue = 6 | pages = 2228–2269 | year = 2007 | doi = 10.1021/cr050943k | pmid = 17564480}}</ref>
==Side effects== ==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" />
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==
== Pharmacology ==
{{Reflist}}
=== Mechanism of action ===
==External links==
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>
*

{{Cough and cold preparations}}
==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}}

]
]
] ]
] ]
] ]
]
]

Latest revision as of 04:36, 20 March 2024

Tiopronin
Skeletal formula of tiopronin
Names
IUPAC name N-(2-Sulfanylpropanoyl)glycine
Systematic IUPAC name (2-Sulfanylpropanamido)acetic acid
Other names 2-mercaptopropionylglycine
Acadione
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1859822
ChEMBL
ChemSpider
ECHA InfoCard 100.016.163 Edit this at Wikidata
EC Number
  • 217-778-4
KEGG
MeSH Tiopronin
PubChem CID
RTECS number
  • MC0596500
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)Key: YTGJWQPHMWSCST-UHFFFAOYSA-N
SMILES
  • CC(S)C(=O)NCC(O)=O
Properties
Chemical formula C5H9NO3S
Molar mass 163.19 g·mol
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
ATC code G04BX16 (WHO) QG04BX16 (WHO)
Routes of
administration 		By mouth
Legal status
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1,300 mg kg (oral, rat)
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound Pharmaceutical compound
Tiopronin
Clinical data
Trade namesThiola
License data
Identifiers
DrugBank
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.016.163 Edit this at Wikidata

Tiopronin, sold under the brand name Thiola, is a medication used to control the rate of cystine precipitation and excretion in the disease cystinuria.

It is available as a generic medication.

Medical uses

Tiopronin is indicated, in combination with high fluid intake, alkali, and diet modification, for the prevention of cystine stone formation in people 20 kilograms (44 lb) and greater with severe homozygous cystinuria, who are not responsive to these measures alone.

Side effects

Tiopronin may present a variety of side effects, which are broadly similar to those of D-penicillamine and other compounds containing active sulfhydryl groups. Its pharmacokinetics have been studied.

Pharmacology

Mechanism of action

Tiopronin works by reacting with urinary cysteine to form a more soluble, disulfide linked, tiopronin-cysteine complex.

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 Martin Shkreli, and the price increased to $30 per pill for a 100 mg capsule.

In 2016 Imprimis Pharmaceuticals introduced a lower cost version marketed as a compounded drug.

Research

It may also be used for Wilson's disease (an overload of copper in the body), and has also been investigated for the treatment 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.

References

  1. ^ "Thiola- tiopronin tablet, sugar coated". DailyMed. Retrieved 18 June 2021.
  2. ^ "Thiola EC- tiopronin tablet, delayed release". DailyMed. 15 March 2021. Retrieved 6 March 2023.
  3. Lindell A, Denneberg T, Hellgren E, Jeppsson JO, Tiselius HG (1995). "Clinical course and cystine stone formation during tiopronin treatment". Urological Research. 23 (2): 111–7. doi:10.1007/BF00307941. PMID 7676533. S2CID 34308815.
  4. Coe FL, Parks JH, Asplin JR (October 1992). "The pathogenesis and treatment of kidney stones". The New England Journal of Medicine. 327 (16): 1141–52. doi:10.1056/NEJM199210153271607. PMID 1528210.
  5. "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  6. "First Generic Drug Approvals 2023". U.S. Food and Drug Administration (FDA). 30 May 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
  7. Jaffe IA (March 1986). "Adverse effects profile of sulfhydryl compounds in man". The American Journal of Medicine. 80 (3): 471–6. doi:10.1016/0002-9343(86)90722-9. PMID 2937293.
  8. ^ Carlsson MS, Denneberg T, Emanuelsson BM, Kågedal B, Lindgren S (August 1993). "Pharmacokinetics of oral tiopronin". European Journal of Clinical Pharmacology. 45 (1): 79–84. doi:10.1007/BF00315354. PMID 8405034. S2CID 8879752.
  9. Lowe D (11 September 2014). "The Most Unconscionable Drug Price Hike I Have Yet Seen". In the Pipeline.
  10. Carroll J (September 20, 2015). "Why would Martin Shkreli hike an old drug price by 5000%? Only a 'moron' would ask". FierceBiotech.
  11. Elvidge S (September 29, 2016). "Imprimis shuts down Texas plant, axes 8% of jobs". BioPharma Dive.
  12. Delecoeuillerie G (April 1989). "". Revue du Rhumatisme et des Maladies Osteo-Articulaires. 56 (5 Pt 2): 38–42. PMID 2740804.
  13. Pasero G, Pellegrini P, Ambanelli U, Ciompi ML, Colamussi V, Ferraccioli G, et al. (August 1982). "Controlled multicenter trial of tiopronin and d-penicillamine for rheumatoid arthritis". Arthritis and Rheumatism. 25 (8): 923–9. doi:10.1002/art.1780250803. PMID 7115451.
  14. Dahl JA, Maddux BL, Hutchison JE (June 2007). "Toward greener nanosynthesis". Chemical Reviews. 107 (6): 2228–69. CiteSeerX 10.1.1.454.2724. doi:10.1021/cr050943k. PMID 17564480.
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