URACIL MUSTARD

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H11Cl2N3O2
Molecular Weight	252.098
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClCCN(CCCl)C1=CNC(=O)NC1=O

InChI

InChIKey=IDPUKCWIGUEADI-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C8H11Cl2N3O2
Molecular Weight	252.098
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/012892Orig1s015s016lbl.pdf

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. Uracil Mustard selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Uracil Mustard-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. After activation, it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function. The DNA damage leads to apoptosis of the affected cells. Chemically it is a derivative of nitrogen mustard and uracil.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/012892Orig1s015s016lbl.pdf	Interacts 323

Conditions

Condition	Modality	Highest Phase	Product
Chronic lymphocytic leukemia 59 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/012892Orig1s015s016lbl.pdf	Palliative	Approved 8583	URACIL MUSTARD Approved Use URACIL MUSTARD is used in the palliative treatment of symptomatic Chronic Lymphocytic leukemia
Non-Hodgkin's lymphoma 81 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/012892Orig1s015s016lbl.pdf	Palliative	Approved 8583	URACIL MUSTARD Approved Use URACIL MUSTARD is effective for palliative treatment of Lymphomas of the histiocytic or lymphocytic type
Chronic myelogenous leukemia 21 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/012892Orig1s015s016lbl.pdf	Palliative	Approved 8583	URACIL MUSTARD Approved Use URACIL MUSTARD is used in the palliative treatment of patients with chronic myelogenous leukemia

F_unbound

Value	Dose	Co-administered	Analyte	Population
95% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14088966/	single		URACIL MUSTARD plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-067847	http://www.3bsc.com/index/pro_info.php?id=107217
AA Blocks	AA00FB2C	https://www.aablocks.com/goods/Goods/detail?id=AA00FB2C
abcr GmbH	AB336380	http://www.abcr.com/shop/en/AB336380
Acadechem	ACDC-030845	http://acadechemical.com/product/2410
Achemtek	0102-012548	http://www.achemtek.com/66-75-1
Acorn PharmaTech	ACN-039812	http://www.acornpharmatech.com/
Adooq BioScience	A13473	https://www.adooq.com/uramustine.html
AHH Chemical co.,ltd	MT-02231	http://www.ahhchemical.com/product/MT-02231.html
AK Scientific, Inc. (AKSCI)	66996	http://www.aksci.com/item_detail.php?cat=66996
Ambinter	Amb21520296	http://www.ambinter.com/reference/21520296
Aurora Fine Chemicals LLC	A17.996.900	http://online.aurorafinechemicals.com/info?ID=A17.996.900
BioChemPartner	BCP27982	http://www.biochempartner.com/66-75-1-BCP27982
Chem Scene	CS-5184	http://www.chemscene.com/66-75-1.html
ChemMol	44014512	http://www.chemmol.com/chemmol/44014512.html
ChemMol	51501343	http://www.chemmol.com/chemmol/51501343.html
ChemMol	99122214	http://www.chemmol.com/chemmol/99122214.html
Chemspace	CSSB00000058676	https://chem-space.com/CSSB00000058676
DC Chemicals	DC7524	http://www.dcchemicals.com/product_show-Uramustine.html
Debye Scientific	DB-005369	http://www.debyesci.com/DB-005369.html
eNovation Chemicals	D371839	http://www.enovationchem.com/productDetails.asp?productID=D371839
Finetech	FT-0602268	http://www.finetechnology-ind.com/prod/detail/pub/66-75-1.html
iChemical	EBD51823	http://www.ichemical.com/chemicals/cas-66-75-1
mcule	MCULE-1273389092	https://mcule.com/MCULE-1273389092/
MedChem Express	HY-13544	https://www.medchemexpress.com/Uramustine.html
MuseChem	I004511	https://www.musechem.com/product/I004511.html
Parchem	30247	http://www.parchem.com/chemical-supplier-distributor/Uramustine-020247.aspx
Sigma-Aldrich	S375063_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/s375063
Smolecule	S546432	http://www.smolecule.com/products/s546432
Synchem UG and Co KG	66608	http://www.synchem.de/chemical_2,6-Dihydroxy-5-bis[2-chloroethyl]aminopyrimidine.html
THE BioTek	bt-285380	https://www.thebiotek.com/product/inhibitors/bt-285380

PubMed

Title	Date	PubMed
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.	2010-07-23	20550100
Design, synthesis, and analysis of minor groove binder pyrrolepolyamide-2'-deoxyguanosine hybrids.	2010	20700414
Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design.	2009-04	19235683
Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida.	2009-01	18941821
A new tyrosinase inhibitor from Crinum yemense as potential treatment for hyperpigmentation.	2008-05	18557429
Alkaloid variability in Leucojum aestivum from wild populations.	2007-12-12	18069233
Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids.	2007-04	17331551
Analysis of Amaryllidaceae alkaloids from Narcissus by GC-MS and capillary electrophoresis.	2006-09-11	16460902
Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids.	2004-09	15386196
Alkaloids in Bulgarian Pancratium maritimum L.	2004-03-17	15018055
Intraspecific variability in the alkaloid metabolism of Galanthus elwesii.	2004-03	15003421
Galanthamine pattern in Narcissus confusus plants.	2003-12	14750039
Antimalarial activity screening of some alkaloids and the plant extracts from Amaryllidaceae.	2003-12	14669261
Solid-phase extraction and reversed-phase high-performance liquid chromatography of the five major alkaloids in Narcissus confusus.	2002-12-24	12494748
Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A.	2002-08-15	12166936
Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis.	2002-05	12058326
Uracil mustard revisited.	1999-05-15	10326707
Acute leukemia following treatment of polycythemia vera and essential thrombocythemia with uracil mustard.	1988-05	3369437

Patents

Sample Use Guides

In Vivo Use Guide

adult: a single weekly dose of 0.15 mg/kg bw for 4 weeks children: a single weekly dose of 0.30 mg/kg bw for 4 weeks

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:41 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:41 GMT 2025`
Record UNII	W7KQ46GJ8U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

URACIL MUSTARD

Official Name

English

URAMUSTINE

Preferred Name

English

5-[Bis(2-chloroethyl)amino]uracil

Systematic Name

English

URACIL MUSTARD [HSDB]

Common Name

English

URACIL MUSTARD [USAN]

Common Name

English

URACIL MUSTARD [IARC]

Common Name

English

NSC-34462

Code

English

U-8344

Code

English

URACIL MUSTARD [MI]

Common Name

English

URACIL MUSTARD [ORANGE BOOK]

Common Name

English

URACIL MUSTARD [VANDF]

Common Name

English

URAMUSTINE [MART.]

Common Name

English

Uramustine [WHO-DD]

Common Name

English

2,4(1H,3H)-PYRIMIDINEDIONE, 5-(BIS(2-CHLOROETHYL)AMINO)-

Systematic Name

English

uramustine [INN]

Common Name

English

Classification Tree Code System Code

IARC

Uracil mustard

NCI_THESAURUS

C697