Propylthiouracil

Modify Date: 2024-01-02 06:22:59

Propylthiouracil structure	Common Name	Propylthiouracil
	CAS Number	51-52-5	Molecular Weight	170.232
	Density	1.2±0.1 g/cm3	Boiling Point	355.2±34.0 °C at 760 mmHg
	Molecular Formula	C₇H₁₀N₂OS	Melting Point	218-220 °C(lit.)
	MSDS	Chinese USA	Flash Point	168.6±25.7 °C
	Symbol	GHS07, GHS08	Signal Word	Warning

Use of Propylthiouracil

Propylthiouracil(6-Propyl-2-thiouracil) is a thyroperoxidase and 5'-deiodinase inhibitor. Target: Thyroperoxidase (TPO)Propylthiouracil (PTU) is a thiouracil-derived drug used to treat hyperthyroidism (including Graves' disease) by decreasing the amount of thyroid hormone produced by the thyroid gland [1]. The antithyroid drug 6-propylthiouracil (PTU) was shown to have an unexpectedly prolonged inhibitory effect on iodination in the thyroid glands of rats. Eighteen hours after injection of a relatively small dose, iodination in the thyroid remained inhibited by more than 90% [2]. PTU inhibits the enzyme thyroperoxidase, which normally acts in thyroid hormone synthesis by oxidizing the anion iodide (I-) to iodine (I0), facilitating iodine's addition to tyrosine residues on the hormone precursor thyroglobulin. This is one of the essential steps in the formation of thyroxine (T4). PTU does not inhibit the action of the sodium-dependent iodide transporter located on follicular cells' basolateral membranes. Inhibition of this step requires competitive inhibitors, such as perchlorate and thiocyanate. From Wikipedia.

Name	6-propyl-2-thiouracil
Synonym	More Synonyms

Description	Propylthiouracil(6-Propyl-2-thiouracil) is a thyroperoxidase and 5'-deiodinase inhibitor. Target: Thyroperoxidase (TPO)Propylthiouracil (PTU) is a thiouracil-derived drug used to treat hyperthyroidism (including Graves' disease) by decreasing the amount of thyroid hormone produced by the thyroid gland [1]. The antithyroid drug 6-propylthiouracil (PTU) was shown to have an unexpectedly prolonged inhibitory effect on iodination in the thyroid glands of rats. Eighteen hours after injection of a relatively small dose, iodination in the thyroid remained inhibited by more than 90% [2]. PTU inhibits the enzyme thyroperoxidase, which normally acts in thyroid hormone synthesis by oxidizing the anion iodide (I-) to iodine (I0), facilitating iodine's addition to tyrosine residues on the hormone precursor thyroglobulin. This is one of the essential steps in the formation of thyroxine (T4). PTU does not inhibit the action of the sodium-dependent iodide transporter located on follicular cells' basolateral membranes. Inhibition of this step requires competitive inhibitors, such as perchlorate and thiocyanate. From Wikipedia.
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Endocrinology
References	[1]. Nakamura, H., et al., Comparison of methimazole and propylthiouracil in patients with hyperthyroidism caused by Graves' disease. J Clin Endocrinol Metab, 2007. 92(6): p. 2157-62. [2]. Taurog, A. and M.L. Dorris, A reexamination of the proposed inactivation of thyroid peroxidase in the rat thyroid by propylthiouracil. Endocrinology, 1989. 124(6): p. 3038-42.

Description

Related Catalog

Signaling Pathways >> Others >> Others

Research Areas >> Endocrinology

References

[1]. Nakamura, H., et al., Comparison of methimazole and propylthiouracil in patients with hyperthyroidism caused by Graves' disease. J Clin Endocrinol Metab, 2007. 92(6): p. 2157-62.

[2]. Taurog, A. and M.L. Dorris, A reexamination of the proposed inactivation of thyroid peroxidase in the rat thyroid by propylthiouracil. Endocrinology, 1989. 124(6): p. 3038-42.

Density	1.2±0.1 g/cm3
Boiling Point	355.2±34.0 °C at 760 mmHg
Melting Point	218-220 °C(lit.)
Molecular Formula	C₇H₁₀N₂OS
Molecular Weight	170.232
Flash Point	168.6±25.7 °C
Exact Mass	170.051376
PSA	80.74000
LogP	-0.32
Vapour Pressure	0.0±0.8 mmHg at 25°C
Index of Refraction	1.601
Storage condition	Refrigerator
Stability	Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases. Light sensitive.
Water Solubility	1.1 g/L

Propylthiouracil MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YR1400000

CHEMICAL NAME :: Uracil, 6-propyl-2-thio-

CAS REGISTRY NUMBER :: 51-52-5

LAST UPDATED :: 199706

DATA ITEMS CITED :: 40

MOLECULAR FORMULA :: C7-H10-N2-O-S

MOLECULAR WEIGHT :: 170.25

WISWESSER LINE NOTATION :: T6MYMVJ BUS F3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 42857 ug/kg/10D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - interstitial nephritis Kidney, Ureter, Bladder - urine volume decreased

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 480 mg/kg/9W-I

TOXIC EFFECTS :: Vascular - other changes Blood - agranulocytosis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 900 mg/kg/60D-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), diffuse Liver - jaundice, other or unclassified

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 900 mg/kg/21W-I

TOXIC EFFECTS :: Liver - other changes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 165 mg/kg/2W-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), diffuse

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 84 mg/kg/2W-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), diffuse

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 116 mg/kg/11W-I

TOXIC EFFECTS :: Liver - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 750 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 750 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 910 mg/kg/13W-I

TOXIC EFFECTS :: Endocrine - changes in thyroid weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 18200 mg/kg/2W-I

TOXIC EFFECTS :: Endocrine - other changes Endocrine - changes in thyroid weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 1974 mg/kg/25W-I

TOXIC EFFECTS :: Blood - other changes Immunological Including Allergic - uncharacterized Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 600 gm/kg/73W-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 37 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Endocrine - thyroid tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 653 gm/kg/70W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Endocrine - thyroid tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1818 mg/kg

SEX/DURATION :: female 33 day(s) pre-mating female 1-39 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Effects on Newborn - other neonatal measures or effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1092 mg/kg

SEX/DURATION :: female 14-40 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Effects on Newborn - other neonatal measures or effects

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4600 mg/kg

SEX/DURATION :: female 70 day(s) pre-mating female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 400 mg/kg

SEX/DURATION :: female 20-21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - endocrine system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 240 mg/kg

SEX/DURATION :: female 10-21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 500 mg/kg

SEX/DURATION :: female 18-22 day(s) after conception lactating female 20 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1050 mg/kg

SEX/DURATION :: lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 mL/kg

SEX/DURATION :: lactating female 25 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - other effects on male Endocrine - evidence of thyroid hyperfunction

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 330 mg/kg

SEX/DURATION :: female 11-25 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - endocrine system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1470 mg/kg

SEX/DURATION :: female 38-58 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Specific Developmental Abnormalities - endocrine system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

DOSE :: 615 ug/kg

SEX/DURATION :: female 29-32 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - endocrine system

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 100 mg/L

REFERENCE :: JCEMAZ Journal of Clinical Endocrinology and Metabolism. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.12- 1952- Volume(issue)/page/year: 43,1406,1976 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 7,67,1974 IARC Cancer Review:Human Inadequate Evidence IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,329,1987 IARC Cancer Review:Group 2B IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,329,1987 TOXICOLOGY REVIEW PCNAA8 Pediatric Clinics of North America. (W.B. Saunders Co., W. Washington Sq., Philadelphia, PA 19105) V.1- 1954- Volume(issue)/page/year: 8,413,1961 TOXICOLOGY REVIEW NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 304,538,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83947 No. of Facilities: 33 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 297 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83947 No. of Facilities: 330 (estimated) No. of Industries: 6 No. of Occupations: 12 No. of Employees: 3331 (estimated) No. of Female Employees: 1666 (estimated)

Symbol	GHS07, GHS08
Signal Word	Warning
Hazard Statements	H302-H351
Precautionary Statements	P281
Personal Protective Equipment	Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes	Xn:Harmful
Risk Phrases	R22;R40
Safety Phrases	S36/37-S45
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	YR1400000
HS Code	2933599090

thiourea

CAS#:17356-08-0

Methyl 3-oxohex...

CAS#:30414-54-1

~79%

Propylthiouracil

CAS#:51-52-5

Literature: PROGENICS PHARMACEUTICALS, INC.; HAN, Amy, Qi; WANG, Eric; GAUSS, Carla; XIE, Walter; COBURN, Glen; DEMUYS, Jean-Marc Patent: WO2010/118367 A2, 2010 ; Location in patent: Page/Page column 51 ;

Ethyl 3-oxohexanoate

CAS#:3249-68-1

thiourea

CAS#:17356-08-0

Propylthiouracil

CAS#:51-52-5

Literature: Brown; Blakemore; Durant; Emmett; Ganellin; Parsons; Rawlings; Walker European Journal of Medicinal Chemistry, 1988 , vol. 23, # 1 p. 53 - 62

Precursor 2
CAS#:30414-54-1 Methyl 3-oxohex... CAS#:3249-68-1 Ethyl 3-oxohexanoate
DownStream 7
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HS Code	2933599090
Summary	2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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6-Propyl-2-thiouracil

T 72

PROTHYRAN

Propylthiouracil [BAN:INN:JAN]

4-propyl-2-thiouracil

EINECS 200-103-2

6-n-propyl-2-thiouracil

6-propyl-2-sulfanylpyrimidin-4-ol

Prothycil

6-Propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-on

2,3-Dihydro-6-propyl-2-thioxo-4(1H)-pyrimidinone,4-Hydroxy-2-mercapto-6-propylpyrimidine

Thiuragyl

6-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

MFCD00006041

6-Propyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone

PROPACIL

6-n-propylthiouracil

6-propylthiouracil

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

propylthiouracil

Protiural

PROPYCIL

2-mercapto-6-propylpyrimidin-4-ol

4-Hydroxy-2-mercapto-6-propylpyrimidine

PROIL

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