U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of URACIL MUSTARD

SMILES

C(CN(CCCl)c1cnc(nc1O)O)Cl

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
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
URACIL MUSTARD

Approved Use

URACIL MUSTARD is used in the palliative treatment of symptomatic Chronic Lymphocytic leukemia
Palliative
URACIL MUSTARD

Approved Use

URACIL MUSTARD is effective for palliative treatment of Lymphomas of the histiocytic or lymphocytic type
Palliative
URACIL MUSTARD

Approved Use

URACIL MUSTARD is used in the palliative treatment of patients with chronic myelogenous leukemia
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
95%
single
URACIL MUSTARD plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Acute leukemia following treatment of polycythemia vera and essential thrombocythemia with uracil mustard.
1988 May
Uracil mustard revisited.
1999 May 15
Design, synthesis, and biological activity of hybrid compounds between uramustine and DNA minor groove binder distamycin A.
2002 Aug 15
Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis.
2002 May
Solid-phase extraction and reversed-phase high-performance liquid chromatography of the five major alkaloids in Narcissus confusus.
2002 Nov-Dec
Galanthamine pattern in Narcissus confusus plants.
2003 Dec
Antimalarial activity screening of some alkaloids and the plant extracts from Amaryllidaceae.
2003 Dec
Alkaloids in Bulgarian Pancratium maritimum L.
2004 Jan-Feb
Intraspecific variability in the alkaloid metabolism of Galanthus elwesii.
2004 Mar
Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids.
2004 Sep
Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design.
2009 Apr
Two novel ceramides with a phytosphingolipid and a tertiary amide structure from Zephyranthes candida.
2009 Jan
Design, synthesis, and analysis of minor groove binder pyrrolepolyamide-2'-deoxyguanosine hybrids.
2010
Amaryllidaceae alkaloids belonging to different structural subgroups display activity against apoptosis-resistant cancer cells.
2010 Jul 23
Patents

Sample Use Guides

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
Name Type Language
URACIL MUSTARD
HSDB   MI   ORANGE BOOK   USAN   VANDF  
USAN  
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
URAMUSTINE [WHO-DD]
Common Name 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
2,4(1H,3H)-PYRIMIDINEDIONE, 5-(BIS(2-CHLOROETHYL)AMINO)-
Systematic Name English
URAMUSTINE
INN   MART.   WHO-DD  
INN  
Official Name English
URAMUSTINE [INN]
Common Name English
Classification Tree Code System Code
IARC Uracil mustard
NCI_THESAURUS C697
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
WHO-ATC L01AD08
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
Code System Code Type Description
FDA UNII
W7KQ46GJ8U
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
RXCUI
10996
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
200-631-3
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
INN
1351
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
NCI_THESAURUS
C918
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
DRUG BANK
DB00791
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
MERCK INDEX
M11306
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PRIMARY Merck Index
EVMPD
SUB11383MIG
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
CAS
66-75-1
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
WIKIPEDIA
URAMUSTINE
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
DRUG CENTRAL
2795
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
IUPHAR
7621
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
MESH
D014499
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL1488
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
EPA CompTox
66-75-1
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
HSDB
3261
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY
PUBCHEM
6194
Created by admin on Sat Jun 26 11:18:10 UTC 2021 , Edited by admin on Sat Jun 26 11:18:10 UTC 2021
PRIMARY