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Substance Name: Propylthiouracil [USP:INN:BAN:JAN]
RN: 51-52-5
UNII: 721M9407IY
InChIKey: KNAHARQHSZJURB-UHFFFAOYSA-N

Note

  • A thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534)

Molecular Formula

  • C7-H10-N2-O-S

Molecular Weight

  • 170.235
 

Classification Codes

Classification Codes

  • Antimetabolites
  • Antithyroid Agents
  • Drug / Therapeutic Agent
  • Hormone Antagonists
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Thyroid Inhibitor
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2B
  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Name of Substance

  • Propyl thiouracil
  • Propylthiouracil
  • Propylthiouracil [USP:INN:BAN:JAN]

MeSH Heading

  • Propylthiouracil

Synonyms

  • 2,3-Dihydro-6-propyl-2-thioxo-4(1H)-pyrimidinone
  • 2-Mercapto-4-hydroxy-6-n-propylpyrimidine
  • 2-Mercapto-6-propyl-4-pyrimidone
  • 2-Thio-4-oxo-6-propyl-1,3-pyrimidine
  • 2-Thio-6-propyl-1,3-pyrimidin-4-one
  • 4(1H)-Pyrimidinone, 2,3-dihydro-6-propyl-2-thioxo-
  • 4-Propyl-2-thiouracil
  • 6-n-Propyl-2-thiouracil
  • 6-n-Propylthiouracil
  • 6-Propil-tiouracile
  • 6-Propil-tiouracile [Italian]
  • 6-Propyl-2-thio-2,4(1H,3H)pyrimidinedione
  • 6-Propyl-2-thiouracil
  • 6-Propylthiouracil
  • 6-Thio-4-propyluracil
  • AI3-25477
  • CCRIS 544
  • EINECS 200-103-2
  • HSDB 3390
  • NSC 6498
  • Procasil
  • Propacil
  • Propilthiouracil
  • Propiltiouracile
  • Propiltiouracile [DCIT]
  • Propiltiouracilo
  • Propiltiouracilo [INN-Spanish]
  • Propycil
  • Propyl-thiorist
  • Propyl-thiorit
  • Propyl-thyracil
  • Propylthiouracil
  • Propylthiouracile
  • Propylthiouracile [INN-French]
  • Propylthiouracilum
  • Propylthiouracilum [INN-Latin]
  • Propythiouracil
  • Prothiucil
  • Prothiurone
  • Prothycil
  • Prothyran
  • Protiural
  • PTU
  • PTU (thyreostatic)
  • Thiuragyl
  • Thyreostat II
  • UNII-721M9407IY
  • Uracil, 6-propyl-2-thio-

Systematic Names

  • 4(1H)-Pyrimidinone, 2,3-dihydro-6-propyl-2-thioxo-
  • Propylthiouracil
  • Uracil, 6-propyl-2-thio-

Superlist Names

  • 4(1H)-Pyrimidinone, 2,3-dihydro-6-propyl-2-thioxo-
  • Propylthiouracil

Registry Numbers

CAS Registry Number

  • 51-52-5

FDA UNII

  • 721M9407IY

Other Registry Number

  • 500-50-5

System Generated Number

  • 0000051525

Structure Descriptors

InChI

InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)

InChIKey

KNAHARQHSZJURB-UHFFFAOYSA-N

Smiles

CCCC1=CC(=O)NC(=S)N1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 165mg/kg/2W-I (165mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Drug Intelligence and Clinical Pharmacy. Vol. 19, Pg. 669, 1985.
child TDLo oral 900mg/kg/60D- (900mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"		 Annals of Internal Medicine. Vol. 82, Pg. 228, 1975.
child TDLo oral 1785mg/kg/17W (1785mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION		 Journal of Pediatric Gastroenterology and Nutrition. Vol. 7, Pg. 776, 1988.
man TDLo oral 42857ug/kg/10 (42.857mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"		 American Journal of Kidney Diseases. Vol. 24, Pg. 575, 1994.
man TDLo oral 116mg/kg/11W- (116mg/kg) LIVER: OTHER CHANGES Archives of Internal Medicine. Vol. 135, Pg. 319, 1975.
man TDLo oral 257mg/kg (257mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Postgraduate Medical Journal. Vol. 73, Pg. 445, 1997.
mouse LDLo unreported 750ug/kg (0.75mg/kg)   Drugs in Japan Vol. 6, Pg. 732, 1982.
rat LD50 oral 1250mg/kg (1250mg/kg)   Nature. Vol. 157, Pg. 659, 1946.
rat LDLo intraperitoneal 400mg/kg (400mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 97, Pg. 478, 1949.
rat LDLo unreported 750ug/kg (0.75mg/kg)   Drugs in Japan Vol. 6, Pg. 732, 1982.
women LDLo oral 84mg/kg/2W-I (84mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Archives of Internal Medicine. Vol. 142, Pg. 838, 1982.
women LDLo oral 480mg/kg/9W-I (480mg/kg) BLOOD: AGRANULOCYTOSIS

VASCULAR: OTHER CHANGES		 Southern Medical Journal. Vol. 75, Pg. 1297, 1982.
women LDLo unreported 6mg/kg (6mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

VASCULAR: SHOCK

BLOOD: CHANGES IN SPLEEN		 New England Journal of Medicine. Vol. 249, Pg. 814, 1953.
women TDLo oral 693mg/kg/11W- (693mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"		 Southern Medical Journal. Vol. 87, Pg. 943, 1994.
women TDLo oral 900mg/kg/21W- (900mg/kg) LIVER: OTHER CHANGES Archives of Internal Medicine. Vol. 140, Pg. 1184, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 219 deg C   EXP
log P (octanol-water) 0.980 (none)   EST
Water Solubility 1200 mg/L 25 EXP
Atmospheric OH Rate Constant 8.92E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.