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 278 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 8429	URACIL MUSTARD Approved Use URACIL MUSTARD is used in the palliative treatment of symptomatic Chronic Lymphocytic leukemia
Non-Hodgkin's lymphoma 79 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/012892Orig1s015s016lbl.pdf	Palliative	Approved 8429	URACIL MUSTARD Approved Use URACIL MUSTARD is effective for palliative treatment of Lymphomas of the histiocytic or lymphocytic type
Chronic myelogenous leukemia 22 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/012892Orig1s015s016lbl.pdf	Palliative	Approved 8429	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
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
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
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
Finetech	FT-0602268	http://www.finetechnology-ind.com/prod/detail/pub/66-75-1.html
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
abcr GmbH	AB336380	http://www.abcr.com/shop/en/AB336380
eNovation Chemicals	D371839	http://www.enovationchem.com/productDetails.asp?productID=D371839
iChemical	EBD51823	http://www.ichemical.com/chemicals/cas-66-75-1
mcule	MCULE-1273389092	https://mcule.com/MCULE-1273389092/

PubMed

Title	Date	PubMed
Acute leukemia following treatment of polycythemia vera and essential thrombocythemia with uracil mustard.	1988 May	3369437
Uracil mustard revisited.	1999 May 15	10326707
Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A.	2002 Aug 15	12166936
Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis.	2002 May	12058326
Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids.	2004 Sep	15386196
Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids.	2007 Apr	17331551
Alkaloid variability in Leucojum aestivum from wild populations.	2007 Sep-Oct	18069233
A new tyrosinase inhibitor from Crinum yemense as potential treatment for hyperpigmentation.	2008 May	18557429
Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design.	2009 Apr	19235683
Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida.	2009 Jan	18941821
Design, synthesis, and analysis of minor groove binder pyrrolepolyamide-2'-deoxyguanosine hybrids.	2010	20700414
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.	2010 Jul 23	20550100

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 `Fri Dec 15 15:29:06 UTC 2023` Edited by `admin` on `Fri Dec 15 15:29:06 UTC 2023`
Record UNII	W7KQ46GJ8U
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

URACIL MUSTARD

Official 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

Official Name

English

uramustine [INN]

Common Name

English

Classification Tree Code System Code

IARC

Uracil mustard

NCI_THESAURUS

C697