Propylthiouracil

An antithyroid medication used to treat hyperthyroidism, particularly Graves' disease, and in selected cases of thyroid storm. Propylthiouracil inhibits thyroid peroxidase-mediated iodination and coupling reactions required for thyroid hormone synthesis. It also inhibits peripheral conversion of T4 to the more active T3. Because of the risk of severe hepatotoxicity and agranulocytosis, its use is generally reserved for specific clinical situations, including the first trimester of pregnancy when antithyroid treatment is necessary

CAS Number: 51-52-5

Molecular Mass: 170.23 g/mol

Formula: C₇H₁₀N₂OS

Smiles: CCCc1cc(=O)[nH]c(=S)[nH]1

Synonymes:

Propylthiouracil, propylthiouracil, 51-52-5, 6-Propyl-2-thiouracil, Propacil, Prothyran, Procasil, Propycil, Prothiurone, Thiuragyl, Prothiucil, Protiural, Prothycil, Propyl-Thiorist, Propyl-Thyracil, 6-Propylthiouracil, Thyreostat II, Propythiouracil, Propilthiouracil, 6-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one, Propyl-Thiorit, Propylthiorit, Propylthiouracile, 6-Thio-4-propyluracil, Propiltiouracilo, 4-Propyl-2-thiouracil, Propylthiouracilum, 2-Mercapto-6-propyl-4-pyrimidone, Propiltiouracile, 2-Mercapto-6-propylpyrimid-4-one, 2-Thio-6-propyl-1,3-pyrimidin-4-one, 2-Thio-4-oxo-6-propyl-1,3-pyrimidine, 2,3-Dihydro-6-propyl-2-thioxo-4(1H)-pyrimidinone, 4-Hydroxy-2-mercapto-6-propylpyrimidine, PROPYL THIOURACIL, 2-Mercapto-4-hydroxy-6-n-propylpyrimidine, 6-propyl-2-sulfanylidene-1H-pyrimidin-4-one, 6-Propyl-2-thio-2,4(1H,3H)pyrimidinedione, NSC-6498, 4(1H)-Pyrimidinone, 2,3-dihydro-6-propyl-2-thioxo-, NSC-70461, CHEBI:8502, DTXSID5021209, 721M9407IY, DTXCID101209, NSC70461, 6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one, 6 Propyl 2 Thiouracil, RefChem:55928, H03BA02, 200-103-2, 2-Mercapto-6-propylpyrimidin-4-ol, 6-N-Propylthiouracil, 6-N-Propyl-2-thiouracil, PTU (thyreostatic), 6-Propil-tiouracile, Uracil, 6-propyl-2-thio-, MFCD00006041, 500-50-5, NSC 6498, 6-propyl-2-sulfanylpyrimidin-4-ol, 2-mercapto-6-propylpyrimidin-4(3H)-one, MLS000028494, CAS-51-52-5, 6-propyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one, NCGC00022715-03, SMR000058275, Propiltiouracile [DCIT], 6-n-Propylthiouracil, 6-Propyl-2-thiouracil, PTU, WLN: T6MYMVJ BUS F3, 6-Propil-tiouracile [Italian], Propiltiouracilo [INN-Spanish], Propylthiouracile [INN-French], Propylthiouracilum [INN-Latin], 6-Propyl-2-thio-2,3H)-pyrimidinedione, CCRIS 544, HSDB 3390, SR-05000001706, 4(1H)-Pyrimidinone,3-dihydro-6-propyl-2-thioxo-, EINECS 200-103-2, 6-(n-Propyl)-2-thiouracil, AI3-25477, Propylthiouracil, 2,3-dihydro-6-propyl-2-thioxopyrimidin-4(1H)-one, UNII-721M9407IY, Propylthiouracil RS, Prestwick_810, 6-Propyl-2-thioxo-2, 3-dihydropyrimidin-4(1H)-one, Propylthiouracil CRS, Propylthiouracil [USP:INN:BAN:JAN], 6-propyl-2-thioxo-1H-pyrimidin-4-one, Spectrum_000876, Opera_ID_530, 3CJ, Prestwick0_000494, Prestwick1_000494, Prestwick2_000494, Prestwick3_000494, Spectrum2_001302, Spectrum3_001731, Spectrum4_000492, Spectrum5_001815, 6-Propyl-2-thio-2,4(1H,3H)-pyrimidinedione, Propylthiouracil (Standard), 2-THIO-4-HYDROXY-6-N-PROPYL-PYRIMIDINE, CHEMBL1518, SCHEMBL41239, BSPBio_000387, BSPBio_003402, KBioGR_001003, KBioSS_001356, PROPYLTHIOURACIL [MI], MLS002303010, MLS006011901, DivK1c_000268, PROPYLTHIOURACIL [INN], PROPYLTHIOURACIL [JAN], SPECTRUM1500515, SPBio_001363, SPBio_002308, PROPYLTHIOURACIL [HSDB], PROPYLTHIOURACIL [IARC], BPBio1_000427, GTPL6650, orb1309031, orb3140045, SCHEMBL4446870, SCHEMBL4537771, PROPYLTHIOURACIL [VANDF], PROPYLTHIOURACIL [MART.], SCHEMBL17375339, HMS500N10, HY-B0346R, KBio1_000268, KBio2_001356, KBio2_003924, KBio2_006492, KBio3_002622, MSK7141, NSC6498, PROPYLTHIOURACIL [USP-RS], PROPYLTHIOURACIL [WHO-DD], PROPYLTHIOURACIL [WHO-IP], NINDS_000268, HMS1569D09, HMS1766D22, HMS1920L22, HMS2092E03, HMS2096D09, HMS2230B22, HMS3259M04, HMS3371D17, HMS3655J07, HMS3713D09, HMS5080B13, Pharmakon1600-01500515, HY-B0346, Propylthiouracil (JP18/USP/INN), PXB42394, Tox21_110882, Tox21_201741, Tox21_300280, 2-mercapto-6-propyl-pyrimidin-4-ol, AC8761, BDBM50133597, CCG-39240, EBC-06200, EBC-11046, EBC-46021, MFCD00052385, MSK7141-100M, NSC757302, s1988, SBB003855, STL102645, PROPYLTHIOURACIL [EP IMPURITY], PROPYLTHIOURACIL [ORANGE BOOK], 6-Propyl-2-sulfanyl-4-pyrimidinol #, AKOS000120319, AKOS001053246, AKOS015892537, MSK7141-1000M, Tox21_110882_1, 2-thio-4-hydroxy-6-n-propylpyrimidine, BS-3928, DB00550, NC00533, NSC-757302, PROPYLTHIOURACIL [EP MONOGRAPH], PS-3436, 4-hydroxy-6-n-propylpyrimidine-2-thiol, IDI1_000268, PROPYLTHIOURACIL [USP MONOGRAPH], 6-Propyl-2-thiouracil, enzyme inhibitor, NCGC00016229-01, NCGC00016229-02, NCGC00016229-03, NCGC00016229-04, NCGC00016229-05, NCGC00016229-06, NCGC00016229-07, NCGC00016229-08, NCGC00016229-09, NCGC00016229-10, NCGC00016229-11, NCGC00016229-13, NCGC00016229-14, NCGC00090881-01, NCGC00090881-02, NCGC00090881-03, NCGC00178089-01, NCGC00178089-02, NCGC00183321-01, NCGC00254180-01, NCGC00259290-01, NCGC00663696-01, 2-mercapto-4-hydroxy-6-propyl pyrimidine, 6-propyl-2-sulfanyl-1H-pyrimidin-4-one, AC-10795, propylthiouracil / 6-Propyl-2-thiouracil, SMR003317355, SY038617, SBI-0051497.P003, NS00000029, P0533, ST50308196, SW196944-3, EN300-35033, C07569, D00562, 6-propyl-2-sulfanyl-3,4-dihydropyrimidin-4-one, 6-Propyl-2-thiouracil, purum, >=98.0% (T), AB00052082_05, AB00052082_06, Propylthiouracil Solution in Methanol, 100ug/mL, AS-871/40901436, F463632, Propylthiouracil Solution in Methanol, 1000ug/mL, Q377342, 6-propyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone, SR-05000001706-1, SR-05000001706-2, SR-05000001706-3, 2,3-dihydro-6-propyl-2-thioxo-Pyrimidin-4(1H)-one, BRD-K48168960-001-04-4, BRD-K48168960-001-05-1, BRD-K48168960-001-08-5, BRD-K48168960-001-18-4, BRD-K48168960-001-19-2, Z56922173, F1967-1318, F2199-0035, F3097-4245, 4(1H)-PYRIMIDINONE,6-BUTYL-2,3-DIHYDRO-2-THIOXO-, 6-Propyl-2-thiouracil, VETRANAL(TM), analytical standard, Propylthiouracil, European Pharmacopoeia (EP) Reference Standard, Propylthiouracil, United States Pharmacopeia (USP) Reference Standard, InChI=1/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11

Bioactivity: Antithyroid agent (thionamide); thyroid peroxidase (TPO) inhibitor; inhibitor of peripheral thyroxine (T4) to triiodothyronine (T3) conversion

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Propanol	278.15	-	5.015	[107]
1-Propanol	278.15	-	5.707	[108]
1-Propanol	283.15	-	6.014	[107]
1-Propanol	283.15	-	6.538	[108]
1-Propanol	288.15	-	7.161	[107]
1-Propanol	288.15	-	7.306	[108]
1-Propanol	293.15	-	8.482	[107]
1-Propanol	293.15	-	8.258	[108]
1-Propanol	298.15	-	9.994	[107]
1-Propanol	298.15	-	9.514	[108]
1-Propanol	303.15	-	11.71	[107]
1-Propanol	303.15	-	11.17	[108]
1-Propanol	308.15	-	13.66	[107]
1-Propanol	308.15	-	13.1	[108]
1-Propanol	313.15	-	15.86	[107]
1-Propanol	313.15	-	15.43	[108]
1-Propanol	318.15	-	18.33	[107]
1-Propanol	318.15	-	17.78	[108]
1-Propanol	323.15	-	21.1	[107]
1-Propanol	323.15	-	20.43	[108]
1-Propanol	328.15	-	24.19	[107]
1-Propanol	333.15	-	27.63	[107]
Dimethyl sulfoxide	293.15	-	480.7	[109]
Dimethyl sulfoxide	298.15	-	562.8	[109]
Dimethyl sulfoxide	303.15	-	665.5	[109]
Dimethyl sulfoxide	308.15	-	782.9	[109]
Dimethyl sulfoxide	313.15	-	930.5	[109]
Dimethyl sulfoxide	318.15	-	1098.1	[109]
Dimethyl sulfoxide	323.15	-	1308.5	[109]
Dimethyl sulfoxide	328.15	-	1569.6	[109]
Dimethyl sulfoxide	333.15	-	1904.9	[109]
Dimethylformamide	278.15	-	219.3	[108]
Dimethylformamide	283.15	-	255.4	[108]
Dimethylformamide	288.15	-	288.7	[108]
Dimethylformamide	293.15	-	331.6	[108]
Dimethylformamide	293.15	-	311.6	[109]
Dimethylformamide	298.15	-	369.6	[108]
Dimethylformamide	298.15	-	389.1	[109]
Dimethylformamide	303.15	-	401.9	[108]
Dimethylformamide	303.15	-	478.7	[109]
Dimethylformamide	308.15	-	593.8	[109]
Dimethylformamide	313.15	-	742.4	[109]
Dimethylformamide	318.15	-	941.4	[109]
Dimethylformamide	323.15	-	1202.8	[109]
Dimethylformamide	328.15	-	1557.0	[109]
Dimethylformamide	333.15	-	2066.2	[109]
Ethanol	278.15	-	7.436	[107]
Ethanol	278.15	-	9.288	[108]
Ethanol	283.15	-	8.842	[107]
Ethanol	283.15	-	10.79	[108]
Ethanol	288.15	-	10.46	[107]
Ethanol	288.15	-	12.33	[108]
Ethanol	293.15	-	12.31	[107]
Ethanol	293.15	-	14.1	[108]
Ethanol	298.15	-	14.41	[107]
Ethanol	298.15	-	15.34	[108]
Ethanol	303.15	-	16.78	[107]
Ethanol	303.15	-	17.2	[108]
Ethanol	308.15	-	19.44	[107]
Ethanol	308.15	-	20.3	[108]
Ethanol	313.15	-	22.58	[107]
Ethanol	313.15	-	23.17	[108]
Ethanol	318.15	-	26.22	[107]
Ethanol	318.15	-	26.7	[108]
Ethanol	323.15	-	30.07	[107]
Ethanol	323.15	-	31.48	[108]
Ethanol	328.15	-	34.53	[107]
Ethanol	333.15	-	39.7	[107]
Ethylene Glycol	293.15	-	22.34	[109]
Ethylene Glycol	298.15	-	25.88	[109]
Ethylene Glycol	303.15	-	30.52	[109]
Ethylene Glycol	308.15	-	36.08	[109]
Ethylene Glycol	313.15	-	42.09	[109]
Ethylene Glycol	318.15	-	49.05	[109]
Ethylene Glycol	323.15	-	57.01	[109]
Ethylene Glycol	328.15	-	66.69	[109]
Ethylene Glycol	333.15	-	77.79	[109]
Isopropanol	278.15	-	3.51	[107]
Isopropanol	283.15	-	4.231	[107]
Isopropanol	288.15	-	5.066	[107]
Isopropanol	293.15	-	6.031	[107]
Isopropanol	298.15	-	7.138	[107]
Isopropanol	303.15	-	8.408	[107]
Isopropanol	308.15	-	9.853	[107]
Isopropanol	313.15	-	11.48	[107]
Isopropanol	318.15	-	13.33	[107]
Isopropanol	323.15	-	15.4	[107]
Isopropanol	328.15	-	17.74	[107]
Isopropanol	333.15	-	20.35	[107]
Methanol	278.15	-	13.4	[107]
Methanol	278.15	-	24.55	[108]
Methanol	283.15	-	15.88	[107]
Methanol	283.15	-	28.82	[108]
Methanol	288.15	-	18.72	[107]
Methanol	288.15	-	32.49	[108]
Methanol	293.15	-	22.15	[107]
Methanol	293.15	-	37.01	[108]
Methanol	298.15	-	25.97	[107]
Methanol	298.15	-	39.23	[108]
Methanol	303.15	-	30.23	[107]
Methanol	303.15	-	45.25	[108]
Methanol	308.15	-	35.17	[107]
Methanol	308.15	-	52.25	[108]
Methanol	313.15	-	40.36	[107]
Methanol	313.15	-	57.91	[108]
Methanol	318.15	-	45.84	[107]
Methanol	318.15	-	66.59	[108]
Methanol	323.15	-	52.61	[107]
Methanol	323.15	-	75.06	[108]
Methanol	328.15	-	59.52	[107]
Methanol	333.15	-	67.13	[107]
N-Methyl-2-pyrrolidone	293.15	-	162.6	[109]
N-Methyl-2-pyrrolidone	298.15	-	190.0	[109]
N-Methyl-2-pyrrolidone	303.15	-	226.6	[109]
N-Methyl-2-pyrrolidone	308.15	-	266.7	[109]
N-Methyl-2-pyrrolidone	313.15	-	315.5	[109]
N-Methyl-2-pyrrolidone	318.15	-	371.4	[109]
N-Methyl-2-pyrrolidone	323.15	-	442.4	[109]
N-Methyl-2-pyrrolidone	328.15	-	522.8	[109]
N-Methyl-2-pyrrolidone	333.15	-	626.0	[109]
Water	278.15	-	0.453	[107]
Water	278.15	-	0.747	[108]
Water	283.15	-	0.5888	[107]
Water	283.15	-	0.8994	[108]
Water	288.15	-	0.7402	[107]
Water	288.15	-	1.04	[108]
Water	293.15	-	0.9303	[107]
Water	293.15	-	1.179	[108]
Water	298.15	-	1.19	[107]
Water	298.15	-	1.366	[108]
Water	303.15	-	1.472	[107]
Water	303.15	-	1.562	[108]
Water	308.15	-	1.788	[107]
Water	308.15	-	1.804	[108]
Water	313.15	-	2.181	[107]
Water	313.15	-	2.06	[108]
Water	318.15	-	2.679	[107]
Water	318.15	-	2.415	[108]
Water	323.15	-	3.231	[107]
Water	323.15	-	2.755	[108]
Water	328.15	-	3.846	[107]
Water	333.15	-	4.669	[107]

Molecule 3D descriptors

Descriptor	Value
PMI1	338.2443
PMI2	950.5874
PMI3	1279.3727
NPR1	0.2644
NPR2	0.7430
RadiusOfGyration	2.7465
InertialShapeFactor	0.0022
Eccentricity	0.9644
Asphericity	0.4151
SpherocityIndex	0.0800
PBF	0.2527