Tiopronin

A thiol-containing drug used for the prevention of cystine kidney stones in patients with cystinuria. Tiopronin undergoes thiol-disulfide exchange with cystine to form more soluble mixed disulfides, thereby reducing urinary cystine concentration and preventing cystine stone formation. It has also been investigated for antioxidant and mucolytic activities

CAS Number: 1953-02-2

Molecular Mass: 163.2 g/mol

Formula: C₅H₉NO₃S

Smiles: CC(S)C(=O)NCC(=O)O

Synonymes:

Tiopronin, tiopronin, 1953-02-2, N-(2-Mercaptopropionyl)glycine, Thiopronine, Thiola, Tiopronine, 2-(2-sulfanylpropanoylamino)acetic acid, Glycine, N-(2-mercapto-1-oxopropyl)-, Thiolpropionamidoacetic acid, tiopronina, Tioproninum, DTXSID4023678, (2-Mercaptopropionyl)glycine, NSC-760416, C5W04GO61S, THIOLA EC, DTXCID803678, alpha-Mercaptopropionylglycine, 2 Mercaptopropionylglycine, 2-Mercaptopropionylglycine, alpha Mercaptopropionylglycine, 2 Thiolpropionamidoacetic Acid, 2-Thiolpropionamidoacetic Acid, Tiopronin Base, Acid, 2-Thiolpropionamidoacetic, 2 Thiol propionamido acetic Acid, 2-Thiol-propionamido-acetic Acid, Acid, 2-Thiol-propionamido-acetic, VENXXIVA, RefChem:56132, G04BX16, 217-778-4, Mercaptopropionylglycine, Acadione, Captimer, Mucolysin, Epatiol, Capen, Tiopronin (Thiola), Thiosol, 2-(2-Mercaptopropanamido)acetic acid, MFCD00004861, alpha-mercaptopropionyl glycine, Thiopronin, 2-(2-sulfanylpropanamido)acetic acid, CHEMBL1314, N-(2-mercaptopropanoyl)glycine, N-(2-Sulfanylpropanoyl)glycine, NCGC00159422-02, NCGC00159422-04, Sutilan, Vincol, N-(2-Mercapto-1-oxopropyl)glycine, Tioglis, CAS-1953-02-2, Meprin (detoxicant), A-MERCAPTOPROPIONYL GLYCINE, Tiopronine [INN-French], Tioproninum [INN-Latin], Tiopronino [INN-Spanish], Tiopronin [INN:DCF:JAN], Tiopronino, CCRIS 1935, MFCD30157366, EINECS 217-778-4, Thiola (TN), BRN 1859822, Tiopronin (JAN/INN), TIOPRONIN [INN], TIOPRONIN [JAN], TIOPRONIN [MI], GLYCINE, N-(2-MERCAPTOPROPIONYL)-, TIOPRONIN [VANDF], 2-mercapto-propionylglycine, TIOPRONIN [MART.], Glycine, N-(2-mercapto-1-oxopropyl)- (9CI), TIOPRONIN [WHO-DD], (2-mercaptopropanoyl)glycine, UNII-C5W04GO61S, SCHEMBL19989, MLS006010632, MERCAPTOPROPIONYLGLYCINE-, orb1307968, TIOPRONIN [ORANGE BOOK], n-(2-mercaptopropionyl) glycine, CHEBI:32229, N-(2-mercaptopropanoyl) glycine, (+)-(2-Mercaptopropanoyl)glycine, (-)-(2-Mercaptopropanoyl)glycine, GLXC-22196, HMS3264B11, HMS3655L15, HMS5080E04, Pharmakon1600-01506190, HY-B0373, MSK10365, 2-(2-Mercaptopropanamido)aceticacid, Tox21_111654, BDBM50020805, EBC-26113, NSC760416, s2062, SBB057668, (2-Mercaptopropionylamino)acetic acid, AKOS015895408, N-(2-Mercaptopropionyl)glycine, 99%, Tox21_111654_1, AC-2087, CCG-214007, DB06823, FM28287, NSC 760416, (2-Mercapto-propionylamino)-acetic acid, NCGC00159422-03, 1939-02-2, AS-12522, SMR001550282, SY107319, DB-352240, NS00005173, ST51006782, SW219206-1, Tiopronin, VETRANAL(TM), analytical standard, C73708, D01430, SBI-0653504.0001, AB00376096_02, EN300-7408657, F099155, Q414456, SR-01000942263, SR-01000942263-1, BRD-A85295731-001-02-3, BRD-A85295731-001-03-1, BRD-A85295731-001-04-9, BRD-A85295731-001-05-6, BRD-A85295731-001-06-4, Z2681891170, TIOPRONIN, Dextiopronin, Tiopronin (n-2-mercaptopropionyl glycine), 2254742-22-6, 2254742-23-7

Bioactivity: Thiol drug; cystine-binding and reducing agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	273.15	-	46.8	[492]
1-Butanol	278.15	-	58.03	[492]
1-Butanol	283.15	-	70.89	[492]
1-Butanol	288.15	-	84.61	[492]
1-Butanol	293.15	-	99.57	[492]
1-Butanol	298.15	-	116.1	[492]
1-Butanol	303.15	-	134.8	[492]
1-Butanol	308.15	-	155.1	[492]
1-Butanol	313.15	-	176.7	[492]
1-Butanol	318.15	-	199.9	[492]
Acetonitrile	273.15	-	30.54	[492]
Acetonitrile	278.15	-	33.63	[492]
Acetonitrile	283.15	-	36.69	[492]
Acetonitrile	288.15	-	40.06	[492]
Acetonitrile	293.15	-	43.65	[492]
Acetonitrile	298.15	-	47.38	[492]
Acetonitrile	303.15	-	51.41	[492]
Acetonitrile	308.15	-	55.87	[492]
Acetonitrile	313.15	-	60.31	[492]
Acetonitrile	318.15	-	64.99	[492]
Isobutanol	273.15	-	21.75	[492]
Isobutanol	278.15	-	25.57	[492]
Isobutanol	283.15	-	30.17	[492]
Isobutanol	288.15	-	34.47	[492]
Isobutanol	293.15	-	39.09	[492]
Isobutanol	298.15	-	44.47	[492]
Isobutanol	303.15	-	50.63	[492]
Isobutanol	308.15	-	57.62	[492]
Isobutanol	313.15	-	65.62	[492]
Isobutanol	318.15	-	74.16	[492]
Toluene	273.15	-	0.518	[492]
Toluene	278.15	-	0.578	[492]
Toluene	283.15	-	0.637	[492]
Toluene	288.15	-	0.695	[492]
Toluene	293.15	-	0.77	[492]
Toluene	298.15	-	0.856	[492]
Toluene	303.15	-	0.942	[492]
Toluene	308.15	-	1.04	[492]
Toluene	313.15	-	1.16	[492]
Toluene	318.15	-	1.301	[492]

Molecule 3D descriptors

Descriptor	Value
PMI1	178.0251
PMI2	1123.6112
PMI3	1198.5083
NPR1	0.1485
NPR2	0.9375
RadiusOfGyration	2.7676
InertialShapeFactor	0.0053
Eccentricity	0.9889
Asphericity	0.6211
SpherocityIndex	0.2143
PBF	0.5930