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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H50Cl4N2O4
Molecular Weight 788.669
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL MUSTARD

SMILES

[H][C@@]12CC[C@H](OC(=O)CC3=CC=C(C=C3)N(CCCl)CCCl)[C@@]1(C)CC[C@]4([H])C5=C(CC[C@@]24[H])C=C(OC(=O)CC6=CC=C(C=C6)N(CCCl)CCCl)C=C5

InChI

InChIKey=LRSFXIJGHRPOQQ-VZRQQIPSSA-N
InChI=1S/C42H50Cl4N2O4/c1-42-17-16-36-35-13-11-34(51-40(49)26-29-2-7-32(8-3-29)47(22-18-43)23-19-44)28-31(35)6-12-37(36)38(42)14-15-39(42)52-41(50)27-30-4-9-33(10-5-30)48(24-20-45)25-21-46/h2-5,7-11,13,28,36-39H,6,12,14-27H2,1H3/t36-,37-,38+,39+,42+/m1/s1

HIDE SMILES / InChI

Molecular Formula C42H50Cl4N2O4
Molecular Weight 788.669
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/4704108 | https://www.ncbi.nlm.nih.gov/pubmed/4370003 | https://www.ncbi.nlm.nih.gov/pubmed/992905 | https://www.ncbi.nlm.nih.gov/pubmed/4751260

Estradiol mustard (developmental code name NSC-112259), also known as chlorphenacyl estradiol diester, as well as estradiol 3,17β-bis(4-(bis(2-chloroethyl)amino)phenyl)acetate, is a synthetic, steroidal estrogen and alkylating antineoplastic agent and a nitrogen mustard-coupled estrogen ester that was never marketed.[1] It is selectively distributed into estrogen receptor (ER)-positive tissues such as ER-expressing tumors like those seen in breast and prostate cancers. For this reason, estradiol mustard and other cytostatic-linked estrogens like estramustine phosphate have reduced toxicity relative to non-linked nitrogen mustard alkylating antineoplastic agents. However, they may stimulate breast tumor growth due to their inherent estrogenic activity and are said to be devoid of major therapeutic efficacy in breast cancer,[3] although estramustine phosphate has been approved for and is used (almost exclusively) in the treatment of prostate cancer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

Groups of 35 Sprague-Dawley rats and 34-36 B6C3F1 mice of each sex were administered estradiol mustard at one of the following doses, either 0.62 or 1.25 mg/kg body weight for rats and either 15 or 30 mg/kg body weight for mice. The vehicle used for the test chemical consisted of 0.05% polysorbate 80 in phosphate-buffered saline. The rats and mice were dosed three times per week for 52 weeks, then observed for an additional 30-34 weeks.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Aliquots of 100 mkl of cytosol were mixed with an equal volume of homogenization buffer containing 3H-E2, at a final concentration of 5 x 10^-9 The tubes were incubated at 18C or 30 C for 30 min. Following incubation, 250mkl of a suspension of dextran-coated charcoal (DCC) was added (0.005 % dextran4.5 % charcoal in the homogenization buffer). EM (Estradiol mustard ) was dissolved in pure dimethylsulfoxide (DMSO). Aliquots were added to the incubation mixtures of the 3H-E2 binding assay. The final concentration of DMSO was 20% in each tube, including the control tubes.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:50:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:50:48 GMT 2023
Record UNII
GEO3F3A4K1
Record Status Validated (UNII)
Record Version
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Name Type Language
ESTRADIOL MUSTARD
Common Name English
OESTRADIOL MUSTARD [IARC]
Common Name English
ESTRADIOL 3,17-MUSTARD
Common Name English
NSC-112259
Code English
NCI-C01570
Code English
OESTRADIOL MUSTARD
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,17-DIOL (17.BETA.)-, 3,17-BIS(4-(BIS(2-CHLOROETHYL)AMINO)BENZENEACETATE)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C697
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID5020574
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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CAS
22966-79-6
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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NSC
112259
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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FDA UNII
GEO3F3A4K1
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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DRUG CENTRAL
1062
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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WIKIPEDIA
Estradiol mustard
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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PUBCHEM
31586
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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NCI_THESAURUS
C38115
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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HSDB
7075
Created by admin on Fri Dec 15 15:50:48 GMT 2023 , Edited by admin on Fri Dec 15 15:50:48 GMT 2023
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