Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H32Cl2NO6P.C7H17NO5 |
Molecular Weight | 715.597 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.[H][C@@]12CC[C@H](OP(O)(O)=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OC(=O)N(CCCl)CCCl)C=C4
InChI
InChIKey=XCRFEYAXJYXVHT-HLZMRHSNSA-N
InChI=1S/C23H32Cl2NO6P.C7H17NO5/c1-23-9-8-18-17-5-3-16(31-22(27)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)32-33(28,29)30;1-8-2-4(10)6(12)7(13)5(11)3-9/h3,5,14,18-21H,2,4,6-13H2,1H3,(H2,28,29,30);4-13H,2-3H2,1H3/t18-,19-,20+,21+,23+;4-,5+,6+,7+/m10/s1
Molecular Formula | C7H17NO5 |
Molecular Weight | 195.2136 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C23H32Cl2NO6P |
Molecular Weight | 520.383 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB01196Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/018045s023lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01196
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/018045s023lbl.pdf
Estramustine is an antineoplastic agent indicated in the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate. Estramustine is a combination of estradiol with nitrogen mustard. In vivo, the nitrogen-mustard moiety becomes active and participates in alkylation of DNA or other cellular components. This causes DNA damage in rapidly dividing cancerous cells leading to cell death and ideally, tumor shrinkage. Also, due to the drugs estrogen component, it can bind more selectively to active estrogen receptors. Used for the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0001935 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17851838 |
4.5 µM [IC50] | ||
Target ID: CHEMBL242 Sources: http://www.drugbank.ca/drugs/DB01196 |
|||
Target ID: CHEMBL206 Sources: http://www.drugbank.ca/drugs/DB01196 |
|||
Target ID: P78559 Gene ID: 4130.0 Gene Symbol: MAP1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1647395 |
|||
Target ID: CHEMBL2390810 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1599956 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Emcyt Approved UseEMCYT Capsules are indicated in the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate. Launch Date1991 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
362 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6714283 |
140 mg single, oral dose: 140 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESTRAMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.88 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6714283 |
140 mg single, oral dose: 140 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESTRAMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED |
|
972 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16568471 |
280 mg 3 times / day multiple, oral dose: 280 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ESTRAMUSTINE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6714283 |
140 mg single, oral dose: 140 mg route of administration: Oral experiment type: SINGLE co-administered: |
ESTRAMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7736407 |
ESTRAMUSTINE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3000 mg/m2 1 times / week multiple, intravenous Highest studied dose Dose: 3000 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 3000 mg/m2, 1 times / week Sources: Page: p.1118 |
unhealthy, 66 n = 4 Health Status: unhealthy Condition: Prostate cancer Age Group: 66 Sex: M Population Size: 4 Sources: Page: p.1118 |
DLT: Malaise and fatigue, Hypotension... Dose limiting toxicities: Malaise and fatigue (grade 3, 75%) Sources: Page: p.1118Hypotension (grade 3, 25%) |
2500 mg/m2 1 times / week multiple, intravenous MTD Dose: 2500 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2500 mg/m2, 1 times / week Sources: Page: p.1119, 1124 |
unhealthy, 66 n = 6 Health Status: unhealthy Condition: Prostate cancer Age Group: 66 Sex: M Population Size: 6 Sources: Page: p.1119, 1124 |
DLT: Malaise and fatigue... Dose limiting toxicities: Malaise and fatigue (grade 3, 40%) Sources: Page: p.1119, 1124 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypotension | grade 3, 25% DLT |
3000 mg/m2 1 times / week multiple, intravenous Highest studied dose Dose: 3000 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 3000 mg/m2, 1 times / week Sources: Page: p.1118 |
unhealthy, 66 n = 4 Health Status: unhealthy Condition: Prostate cancer Age Group: 66 Sex: M Population Size: 4 Sources: Page: p.1118 |
Malaise and fatigue | grade 3, 75% DLT |
3000 mg/m2 1 times / week multiple, intravenous Highest studied dose Dose: 3000 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 3000 mg/m2, 1 times / week Sources: Page: p.1118 |
unhealthy, 66 n = 4 Health Status: unhealthy Condition: Prostate cancer Age Group: 66 Sex: M Population Size: 4 Sources: Page: p.1118 |
Malaise and fatigue | grade 3, 40% DLT |
2500 mg/m2 1 times / week multiple, intravenous MTD Dose: 2500 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2500 mg/m2, 1 times / week Sources: Page: p.1119, 1124 |
unhealthy, 66 n = 6 Health Status: unhealthy Condition: Prostate cancer Age Group: 66 Sex: M Population Size: 6 Sources: Page: p.1119, 1124 |
PubMed
Title | Date | PubMed |
---|---|---|
Regulation of Cyp1a1 induction by dioxin as a function of cell cycle phase. | 2001 Nov |
|
Combination therapy in hormone-refractory prostate cancer. | 2001 Sep |
|
Editorial: the coming revolution in the treatment of prostate cancer patients. | 2002 Aug |
|
EMP combination chemotherapy and low-dose monotherapy in advanced prostate cancer. | 2002 Feb |
|
The flare in alkaline phosphatase activity post-orchidectomy predicts which patient may benefit from early chemotherapy in metastatic prostate cancer. | 2002 Feb 1 |
|
Phase I clinical and pharmacologic trial of intravenous estramustine phosphate. | 2002 Feb 15 |
|
Mechanism of action of antitumor drugs that interact with microtubules and tubulin. | 2002 Jan |
|
High activity Rhenium-186 HEDP with autologous peripheral blood stem cell rescue: a phase I study in progressive hormone refractory prostate cancer metastatic to bone. | 2002 Jun 5 |
|
Docetaxel (taxotere) in the treatment of prostate cancer. | 2003 Jun |
|
Activity of docetaxel with or without estramustine phosphate versus mitoxantrone in androgen dependent and independent human prostate cancer xenografts. | 2003 May |
|
Physician attitudes toward cytotoxic chemotherapy use in patients with advanced prostate carcinoma. | 2003 May 1 |
|
Characterization of the MRP4- and MRP5-mediated transport of cyclic nucleotides from intact cells. | 2003 May 16 |
|
Neoadjuvant therapy before radical prostatectomy in high-risk localized prostate cancer: defining appropriate endpoints. | 2003 May-Jun |
|
High-risk localized prostate cancer: primary surgery and adjuvant therapy. | 2003 May-Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/emcyt.html
The recommended daily dose is 14 mg per kg of body weight (ie, one 140 mg capsule for each 10 kg or 22 lb of body weight), given in 3 or 4 divided doses. Most patients in studies in the United States have been treated at a dosage range of 10 to 16 mg per kg per day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17851838
Estramustine inhibited human endothelial cell proliferation with an IC50 of 4.5 uM and was active at 10-33% of the maximum tolerated dose (MTD) from clinical schedules
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 14:32:21 GMT 2023
by
admin
on
Sat Dec 16 14:32:21 GMT 2023
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Record UNII |
C89YOK4N2S
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Record Status |
Validated (UNII)
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Record Version |
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