MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 530348 | Name: Thiohydantoin
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Thiohydantoin, also known as 2-Thiohydantoin and NSC 11772, is a potent inhibitors of mutant IDH1. Thiohydantoin can decrease the cellular concentration of D2HG, reduce the levels of histone methylation, and suppress the proliferation of stem-like cancer cells in BT142 glioma with IDH1 R132H mutation. Somatic mutations of isocitrate dehydrogenase 1 (IDH1) at R132 are frequently found in certain cancers such as glioma. With losing the activity of wild-type IDH1, the R132H and R132C mutant proteins can reduce α-ketoglutaric acid (α-KG) to d-2-hydroxyglutaric acid (D2HG).

Chemical Structure

Thiohydantoin
Thiohydantoin
CAS# 503-87-7

Theoretical Analysis

MedKoo Cat#: 530348

Name: Thiohydantoin

CAS#: 503-87-7

Chemical Formula: C3H4N2OS

Exact Mass: 116.0044

Molecular Weight: 116.14

Elemental Analysis: C, 31.03; H, 3.47; N, 24.12; O, 13.78; S, 27.61

Price and Availability

Size Price Availability Quantity
2g USD 150.00
5g USD 250.00
10g USD 350.00
20g USD 550.00
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Thiohydantoin; 2-Thiohydantoin; NSC 11772; NSC11772; NSC-11772.
IUPAC/Chemical Name
2-Thioxo-4-imidazolidinone
InChi Key
UGWULZWUXSCWPX-UHFFFAOYSA-N
InChi Code
InChI=1S/C3H4N2OS/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)
SMILES Code
O=C(CN1)NC1=S
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 116.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wu F, Jiang H, Zheng B, Kogiso M, Yao Y, Zhou C, Li XN, Song Y. Inhibition of Cancer-Associated Mutant Isocitrate Dehydrogenases by 2-Thiohydantoin Compounds. J Med Chem. 2015 Sep 10;58(17):6899-908. doi: 10.1021/acs.jmedchem.5b00684. PubMed PMID: 26280302; PubMed Central PMCID: PMC4567406. 2: Deval V, Kumar A, Gupta V, Sharma A, Gupta A, Tandon P, Kunimoto KK. Molecular structure (monomeric and dimeric) and hydrogen bonds in 5-benzyl 2-thiohydantoin studied by FT-IR and FT-Raman spectroscopy and DFT calculations. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Nov 11;132:15-26. doi: 10.1016/j.saa.2014.04.101. PubMed PMID: 24845873. 3: Sharma A, Gupta V, Tandon P, Rawat P, Maeda S, Kunimoto KK. Experimental (FT-IR, FT-Raman, NMR) and theoretical spectroscopic properties of intermolecular hydrogen bonded 1-acetyl-2-thiohydantoin polymorphs. Spectrochim Acta A Mol Biomol Spectrosc. 2012 May;90:141-51. doi: 10.1016/j.saa.2012.01.033. PubMed PMID: 22336046. 4: Kumar R, Khan S, Chauhan PM. 2-Aminoimidazole, glycociamidine and 2-thiohydantoin-marine alkaloids as molecular inspirations for the development of lead structures. Curr Drug Targets. 2011 Oct;12(11):1689-708. Review. PubMed PMID: 21561428. 5: Lee TS, Chen LC, Liu Y, Wu J, Liang YC, Lee WS. 5,5-Diphenyl-2-thiohydantoin-N10 (DPTH-N10) suppresses proliferation of cultured colon cancer cell line COLO-205 by inhibiting DNA synthesis and activating apoptosis. Naunyn Schmiedebergs Arch Pharmacol. 2010 Jul;382(1):43-50. doi: 10.1007/s00210-010-0519-4. PubMed PMID: 20449574. 6: Liu Y, Wu J, Ho PY, Chen LC, Chen CT, Liang YC, Cheng CK, Lee WS. Anti-angiogenic action of 5,5-diphenyl-2-thiohydantoin-N10 (DPTH-N10). Cancer Lett. 2008 Nov 28;271(2):294-305. doi: 10.1016/j.canlet.2008.06.016. PubMed PMID: 18649995. 7: Cheng CK, Wu J, Liu Y, Lee TS, Kang SJ, Sheu MT, Lee WS. Structure and anti-proliferation function of 5,5-diphenyl-2-thiohydantoin (DPTH) derivatives in vascular endothelial cells. Vascul Pharmacol. 2008 Feb-Mar;48(2-3):138-42. doi: 10.1016/j.vph.2008.01.007. PubMed PMID: 18295547. 8: Gregg BT, Golden KC, Quinn JF, Tymoshenko DO, Earley WG, Maynard DA, Razzano DA, Rennells WM, Butcher J. Expedient Lewis acid catalyzed synthesis of a 3-substituted 5-arylidene-1-methyl-2-thiohydantoin Library. J Comb Chem. 2007 Nov-Dec;9(6):1036-40. PubMed PMID: 17867645. 9: Incesu Z, Benkli K, Akalin G, Kaplancikli ZA. Modification of intracellular free calcium in cultured F2408 embryo fibroblasts by 3-substituted-2-thiohydantoin derivatives. Cell Biol Int. 2004;28(4):267-72. PubMed PMID: 15109982. 10: Shih CR, Wu J, Liu Y, Liang YC, Lin SY, Sheu MT, Lee WS. Anti-proliferation effect of 5,5-diphenyl-2-thiohydantoin (DPTH) in human vascular endothelial cells. Biochem Pharmacol. 2004 Jan 1;67(1):67-75. PubMed PMID: 14667929. 11: Khodair AI. Glycosylation of 2-thiohydantoin derivatives. Synthesis of some novel S-alkylated and S-glucosylated hydantoins. Carbohydr Res. 2001 Apr 23;331(4):445-53. PubMed PMID: 11398987. 12: Suzen S, Buyukbingol E. Evaluation of anti-HIV activity of 5-(2-phenyl-3'-indolal)-2-thiohydantoin. Farmaco. 1998 Jul 30;53(7):525-7. PubMed PMID: 9836465. 13: Khodair AI, el-Subbagh HI, el-Emam AA. Synthesis of certain 5-substituted 2-thiohydantoin derivatives as potential cytotoxic and antiviral agents. Boll Chim Farm. 1997 Sep;136(8):561-7. PubMed PMID: 9440349. 14: Kiec-Kononowicz K, Karolak-Wojciechowska J, Robak J. Fused 2-thiohydantoin derivatives: evaluation as potential antioxidants. Arch Pharm (Weinheim). 1997 Apr;330(4):85-90. PubMed PMID: 9230525. 15: al-Obaid AM, el-Subbagh HI, Khodair AI, Elmazar MM. 5-substituted-2-thiohydantoin analogs as a novel class of antitumor agents. Anticancer Drugs. 1996 Nov;7(8):873-80. PubMed PMID: 8991192. 16: Büyükbingöl E, Süzen S, Klopman G. Studies on the synthesis and structure-activity relationships of 5-(3'-indolal)-2-thiohydantoin derivatives as aldose reductase enzyme inhibitors. Farmaco. 1994 Jun;49(6):443-7. PubMed PMID: 8074787. 17: Nomoto Y, Takai H, Hirata T, Teranishi M, Ohno T, Kubo K. Studies on cardiotonic agents. IV. Synthesis of novel 1-(6,7-dimethoxy-4-quinazolinyl)piperidine derivatives carrying substituted hydantoin and 2-thiohydantoin rings. Chem Pharm Bull (Tokyo). 1990 Nov;38(11):3014-9. PubMed PMID: 2085880. 18: Kleinrok Z, Sermak W, Chodkowska A, Kozicka M. 5-Nitrobenzylidene derivatives or 3-benzoyl-2-thiohydantoin and their pharmacological properties. Ann Univ Mariae Curie Sklodowska Med. 1990;45:173-80. PubMed PMID: 1670022. 19: Rydzik E, Szadowska A, Kiełek MB. [Synthesis and testing of anticonvulsant properties of 5-benzylidene derivatives of 3-o-, 3-m- I 3-p-chlorophenyl-2-thiohydantoin]. Acta Pol Pharm. 1990;47(5-6):27-30. Polish. PubMed PMID: 1669328. 20: Kleinrok Z, Sermak W, Kozicka M. Synthesis and search for anticonvulsive and hypoglycemic properties of novel 5-benzylidene derivatives of 3-o-chloro- and 3-o-methylbenzoyl-2-thiohydantoin. Pol J Pharmacol Pharm. 1987 May-Jun;39(3):237-44. PubMed PMID: 3438210.