Tiopronin

Tiopronin
Clinical data
Trade names	Thiola
License data	US DailyMed: Tiopronin;
Identifiers
DrugBank	DB06823;
ChEBI	CHEBI:32229;
CompTox Dashboard (EPA)	DTXSID4023678 ;
ECHA InfoCard	100.016.163

Tiopronin
Names
	IUPAC name N-(2-Sulfanylpropanoyl)glycine
	Systematic IUPAC name (2-Sulfanylpropanamido)acetic acid
	Other names 2-mercaptopropionylglycine; Acadione
Identifiers
CAS Number	1953-02-2 ; 29335-92-0 R ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1859822
ChEMBL	ChEMBL1314 ;
ChemSpider	5283 ; 180938 R ; 643292 S ;
ECHA InfoCard	100.016.163
EC Number	217-778-4;
KEGG	D01430 ;
MeSH	Tiopronin
PubChem CID	5483; 208825 R; 736152 S;
RTECS number	MC0596500;
UNII	C5W04GO61S ; X294K8K2PF R ;
CompTox Dashboard (EPA)	DTXSID4023678 ;
	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−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
ATC code	G04BX16 (WHO) QG04BX16 (WHO)
Routes of; administration	By mouth
Legal status	US: ℞-only;
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
	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;
Related compounds	N-Acetylglycinamide;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Tiopronin, sold under the brand name Thiola, is a medication used to control the rate of cystine precipitation and excretion in the disease cystinuria.^[3]^[4]

It is available as a generic medication.^[5]^[6]

^ "Thiola- tiopronin tablet, sugar coated". DailyMed. Retrieved 18 June 2021.
^ "Thiola EC- tiopronin tablet, delayed release". DailyMed. 15 March 2021. Retrieved 6 March 2023.
^ 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.
^ 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.
^ "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.
^ "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.

[Thiola_FDA_label-1] "Thiola- tiopronin tablet, sugar coated". DailyMed. Retrieved 18 June 2021.

[Thiola_EC_FDA_label-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.

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Names

IUPAC name N-(2-Sulfanylpropanoyl)glycine
Systematic IUPAC name (2-Sulfanylpropanamido)acetic acid
Other names 2-mercaptopropionylglycine Acadione
Identifiers
CAS Number	1953-02-2^Y 29335-92-0 R^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1859822
ChEMBL	ChEMBL1314^Y
ChemSpider	5283^Y 180938 R^Y 643292 S^Y
ECHA InfoCard	100.016.163
EC Number	217-778-4
KEGG	D01430^Y
MeSH	Tiopronin
PubChem CID	5483 208825 R 736152 S
RTECS number	MC0596500
UNII	C5W04GO61S^Y X294K8K2PF R^Y
CompTox Dashboard (EPA)	DTXSID4023678
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
SMILES CC(S)C(=O)NCC(O)=O
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 (pK_a)	3.356
Basicity (pK_b)	10.641
Pharmacology
ATC code	G04BX16 (WHO) QG04BX16 (WHO)
Routes of administration	By mouth
Legal status	US: ℞-only^[1]^[2]
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
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
Related compounds	N-Acetylglycinamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Tiopronin

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