MedKoo Cat#: 100900 | Name: Uramustine
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Description:

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

Uramustine (INN), also known as uracil mustard, is a chemotherapy drug which belongs to the class of alkylating agents. It is used in lymphatic malignancies such as non-Hodgkin's lymphoma. It works by damaging DNA, primarily in cancer cells that preferentially take up the uracil due to their need to make nucleic acids during their rapid cycles of cell division. The DNA damage leads to apoptosis of the affected cells. Bone marrow suppression and nausea are the main side effects. Chemically it is a derivative of nitrogen mustard and uracil.

Chemical Structure

Uramustine
Uramustine
CAS#66-75-1

Theoretical Analysis

MedKoo Cat#: 100900

Name: Uramustine

CAS#: 66-75-1

Chemical Formula: C8H11Cl2N3O2

Exact Mass: 251.0228

Molecular Weight: 252.10

Elemental Analysis: C, 38.11; H, 4.40; Cl, 28.13; N, 16.67; O, 12.69

Price and Availability

Size Price Availability Quantity
5mg USD 90.00 Ready to ship
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,250.00 Ready to ship
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Related CAS #
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Synonym
uracil mustard, Demethyldopan, Desmethyldopan, Uracilmostaza, Uracillost, Uramustin, Nordopan, Chlorethaminacil, Aminouracil mustard, Uramustina, Uramustinum
IUPAC/Chemical Name
5-[bis(2-chloroethyl)amino]-1H-pyrimidine-2,4-dione
InChi Key
IDPUKCWIGUEADI-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)
SMILES Code
O=C1NC(C(N(CCCl)CCCl)=CN1)=O
Appearance
White 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, not in water
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
Uramustine (INN) or uracil mustard is a chemotherapy drug which belongs to the class of alkylating agents. It is used in lymphatic malignancies such as non-Hodgkin's lymphoma. It works by damaging DNA, primarily in cancer cells that preferentially take up the uracil due to their need to make nucleic acids during their rapid cycles of cell division. The DNA damage leads to apoptosis of the affected cells. Bone marrow suppression and nausea are the main side effects. Chemically it is a derivative of nitrogen mustard and uracil.
Biological target:
N/A
In vitro activity:
N/A
In vivo activity:
N/A

Preparing Stock Solutions

The following data is based on the product molecular weight 252.10 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
Formulation protocol:
N/A
In vitro protocol:
N/A
In vivo protocol:
N/A
1: Min L, Liang W, Bajsa-Hirschel J, Ye P, Wang Q, Sun X, Cantrell CL, Han L, Sun N, Duke SO, Liu X. Synthesis, Herbicidal Activity, Mode of Action, and In Silico Analysis of Novel Pyrido[2,3-d]pyrimidine Compounds. Molecules. 2023 Oct 31;28(21):7363. doi: 10.3390/molecules28217363. PMID: 37959782; PMCID: PMC10647610. 2: Elzupir AO. Molecular Docking and Dynamics Investigations for Identifying Potential Inhibitors of the 3-Chymotrypsin-like Protease of SARS-CoV-2: Repurposing of Approved Pyrimidonic Pharmaceuticals for COVID-19 Treatment. Molecules. 2021 Dec 9;26(24):7458. doi: 10.3390/molecules26247458. PMID: 34946540; PMCID: PMC8707611. 3: M-Hamvas M, Ajtay K, Beyer D, Jámbrik K, Vasas G, Surányi G, Máthé C. Cylindrospermopsin induces biochemical changes leading to programmed cell death in plants. Apoptosis. 2017 Feb;22(2):254-264. doi: 10.1007/s10495-016-1322-6. PMID: 27787653. 4: Lambert JM. Antibody-Drug Conjugates (ADCs): Magic Bullets at Last! Mol Pharm. 2015 Jun 1;12(6):1701-2. doi: 10.1021/acs.molpharmaceut.5b00302. PMID: 26027696. 5: Kittler K, Hoffmann H, Lindemann F, Koch M, Rohn S, Maul R. Biosynthesis of 15N-labeled cylindrospermopsin and its application as internal standard in stable isotope dilution analysis. Anal Bioanal Chem. 2014 Sep;406(24):5765-74. doi: 10.1007/s00216-014-8026-y. Epub 2014 Jul 27. PMID: 25064600. 6: Kohorn EI. Uracil mustard and 5-fluorouracil combination chemotherapy: a historic record. Conn Med. 2013 Aug;77(7):433-6. PMID: 24195184. 7: Máthé C, Vasas G, Borbély G, Erdődi F, Beyer D, Kiss A, Surányi G, Gonda S, Jámbrik K, M-Hamvas M. Histological, cytological and biochemical alterations induced by microcystin-LR and cylindrospermopsin in white mustard (Sinapis alba L.) seedlings. Acta Biol Hung. 2013 Mar;64(1):71-85. doi: 10.1556/ABiol.64.2013.1.7. PMID: 23567832. 8: Li YQ, Chai XY, Sun JF, Liu YH. [Study on the chemical constituents qf Spongilla Wagner]. Zhong Yao Cai. 2010 Jan;33(1):60-1. Chinese. PMID: 20518307. 9: M-Hamvas M, Máthé C, Vasas G, Jámbrik K, Papp M, Beyer D, Mészáros I, Borbély G. Cylindrospermopsin and microcystin-LR alter the growth, development and peroxidase enzyme activity of white mustard (Sinapis alba L.) seedlings, a comparative analysis. Acta Biol Hung. 2010;61 Suppl:35-48. doi: 10.1556/ABiol.61.2010.Suppl.5. PMID: 21565763. 10: Vlasakova K, Skopek TR, Glaab WE. Induced mutation spectra at the upp locus in Salmonella typhimurium: response of the target gene in the FU assay to mechanistically different mutagens. Mutat Res. 2005 Oct 15;578(1-2):225-37. doi: 10.1016/j.mrfmmm.2005.05.022. PMID: 16143350. 11: Baraldi PG, Romagnoli R, Guadix AE, Pineda de las Infantas MJ, Gallo MA, Espinosa A, Martinez A, Bingham JP, Hartley JA. Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A. J Med Chem. 2002 Aug 15;45(17):3630-8. doi: 10.1021/jm011113b. PMID: 12166936. 12: Herrlinger U, Jacobs A, Aghi M, Schuback DE, Breakefield XO. HSV-1 Vectors for Gene Therapy of Experimental CNS Tumors. Methods Mol Med. 2000;35:287-312. doi: 10.1385/1-59259-086-1:287. PMID: 21390812. 13: Kennedy BJ, Torkelson JL, Torlakovic E. Uracil mustard revisited. Cancer. 1999 May 15;85(10):2265-72. PMID: 10326707. 14: Bulygin KN, Matasova NB, Graifer DM, Veniyaminova AG, Yamkovoy VI, Stahl J, Karpova GG. Protein environment of mRNA at the decoding site of 80S ribosomes from human placenta as revealed from affinity labeling with mRNA analogs-- derivatives of oligoribonucleotides. Biochim Biophys Acta. 1997 Apr 10;1351(3):325-32. doi: 10.1016/s0167-4781(96)00224-2. PMID: 9130596. 15: Mattes WB, Lee CS, Laval J, O'Connor TR. Excision of DNA adducts of nitrogen mustards by bacterial and mammalian 3-methyladenine-DNA glycosylases. Carcinogenesis. 1996 Apr;17(4):643-8. doi: 10.1093/carcin/17.4.643. PMID: 8625472. 16: Emilia G, Sacchi S, Temperani P, Longo R, Vecchi A. Progression of essential thrombocythemia to blastic crisis via idiopathic myelofibrosis. Leuk Lymphoma. 1993 Mar;9(4-5):423-6. doi: 10.3109/10428199309148545. PMID: 8348078. 17: Coley HM, Mongelli N, D'Incalci M. The effects of a benzoic acid mustard derivative of distamycin A (FCE 24517) and related minor groove-binding distamycin analogues on the activity of major groove-binding alkylating agents. Biochem Pharmacol. 1993 Feb 9;45(3):619-26. doi: 10.1016/0006-2952(93)90135-j. PMID: 8442762. 18: Doweyko AM, Mattes WB. An application of 3D-QSAR to the analysis of the sequence specificity of DNA alkylation by uracil mustard. Biochemistry. 1992 Oct 6;31(39):9388-92. doi: 10.1021/bi00154a009. PMID: 1327114. 19: Bulygin KN, Graĭfer DM, Zenkova MA, Malygin AA, Iamkovoĭ VI, Karpova GG. Affinnaia modifikatsiia 80S ribosom iz platsenty cheloveka analogami mRNK-- proizvodnymi oligouridilatov s alkiliruiushcheĭ gruppoĭ na 3'-kontse [Affinity modification of 80S ribosomes from human placenta with mRNA analogs--derivatives of oligouridylates with alkylating groups at the 3'-end]. Mol Biol (Mosk). 1992 Jul-Aug;26(4):821-8. Russian. PMID: 1435775. 20: Hartley JA, Bingham JP, Souhami RL. DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards is preserved in intact cells. Nucleic Acids Res. 1992 Jun 25;20(12):3175-8. doi: 10.1093/nar/20.12.3175. PMID: 1620613; PMCID: PMC312455.