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
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(OC(=O)CC5=CC=C(C=C5)N(CCCl)CCCl)=CC=C34)[C@@H]1CC[C@@H]2OC(=O)CC6=CC=C(C=C6)N(CCCl)CCCl
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
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12830238Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12830238
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/992905 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4704108 |
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12830238
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/992905
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
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admin
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Edited
Mon Mar 31 18:10:44 GMT 2025
by
admin
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Mon Mar 31 18:10:44 GMT 2025
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| Record UNII |
GEO3F3A4K1
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C697
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DTXSID5020574
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22966-79-6
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112259
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GEO3F3A4K1
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1062
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Estradiol mustard
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31586
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C38115
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7075
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