Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H31Cl2NO3 |
Molecular Weight | 440.403 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@H](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=FRPJXPJMRWBBIH-RBRWEJTLSA-N
InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
Molecular Formula | C23H31Cl2NO3 |
Molecular Weight | 440.403 |
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 |
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Target ID: CHEMBL206 Sources: http://www.drugbank.ca/drugs/DB01196 |
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Target ID: P78559 Gene ID: 4130.0 Gene Symbol: MAP1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1647395 |
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Target ID: CHEMBL2390810 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1599956 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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Treatment options in hormone-refractory prostate cancer: current and future approaches. | 2001 |
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Docetaxel, estramustine, plus trastuzumab in patients with metastatic androgen-independent prostate cancer. | 2001 Aug |
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Docetaxel, estramustine, and short-term androgen withdrawal for patients with biochemical failure after definitive local therapy for prostate cancer. | 2001 Aug |
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Treatment of hormone refractory prostate cancer. | 2001 Aug |
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[A male case of primary bilateral breast cancers during estrogen therapy for prostate cancer]. | 2001 Nov |
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Differential effect of vinorelbine versus paclitaxel on ERK2 kinase activity during apoptosis in MCF-7 cells. | 2001 Nov 2 |
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Single-agent estramustine phosphate (EMP) is active in advanced breast cancer after failure with anthracyclines and taxanes. | 2001 Sep |
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Phase I trial of oral estramustine and 3-hr infusional paclitaxel for the treatment of hormone refractory prostate cancer. | 2002 |
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Controversies in chemotherapy of prostate cancer. | 2002 |
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Editorial: the coming revolution in the treatment of prostate cancer patients. | 2002 Aug |
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Hypertriglyceridemia and pancreatitis associated with estramustine phosphate. | 2002 Aug |
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[Therapy for hormone-refractory prostate cancer]. | 2002 Dec |
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[Chemotherapy for prostate cancers]. | 2002 Dec |
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Fatal respiratory failure associated with treatment of prostate cancer using docetaxel and estramustine. | 2002 Dec |
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An active regimen of weekly paclitaxel and estramustine in metastatic androgen-independent prostate cancer. | 2002 Dec |
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Editorial: States and state transitions are all that really matter. | 2002 Dec |
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Combination chemotherapy with paclitaxel, estramustine and carboplatin for hormone refractory prostate cancer. | 2002 Dec |
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EMP combination chemotherapy and low-dose monotherapy in advanced prostate cancer. | 2002 Feb |
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The flare in alkaline phosphatase activity post-orchidectomy predicts which patient may benefit from early chemotherapy in metastatic prostate cancer. | 2002 Feb 1 |
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Mechanism of action of antitumor drugs that interact with microtubules and tubulin. | 2002 Jan |
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The antimicrotubule drug estramustine but not irradiation induces apoptosis in malignant glioma involving AKT and caspase pathways. | 2002 Jan |
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Docetaxel in the integrated management of prostate cancer. Current applications and future promise. | 2002 Jun |
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Effects of docetaxel on pain due to metastatic androgen-independent prostate cancer. | 2002 Jun |
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Acute estramustine-induced hypocalcemia unmasking severe vitamin D deficiency. | 2002 Jun 1 |
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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 |
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Estramustine phosphate enhances the effects of hyperthermia and induces the small heat shock protein HSP27 in the human prostate carcinoma cell line PC-3. | 2002 May |
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[Hormonal chemotherapy for hormone-refractory prostate cancer]. | 2002 Nov |
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Pattern of somatic androgen receptor gene mutations in patients with hormone-refractory prostate cancer. | 2002 Nov |
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Penile metastasis of prostatic adenocarcinoma. | 2002 Oct |
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Drug resistance in prostate cancer cell lines is influenced by androgen dependence and p53 status. | 2002 Oct |
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Chemotherapy for prostate cancer. | 2002 Sep |
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Role of chemotherapy in hormone-refractory prostate cancer. Old issues, recent advances and new perspectives. | 2003 |
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[Prostatic cancer in the young adult]. | 2003 Apr |
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Neoadjuvant docetaxel and estramustine chemotherapy in high-risk/locallyadvanced prostate cancer. | 2003 Apr |
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A phase II trial of docetaxel and estramustine in patients with refractory metastatic breast carcinoma. | 2003 Feb 1 |
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Estimating survival benefit in castrate metastatic prostate cancer: decision making in proceeding to a definitive phase III trial. | 2003 Jan |
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A phase I study of paclitaxel, estramustine phosphate and vinorelbine (Pacl-E-Vin) in advanced malignancies: triple tubulin targeting. | 2003 Jan |
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Bisphosphonate therapy for hormone refractory prostate cancer with bone metastasis. | 2003 Jan |
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Docetaxel (taxotere) in the treatment of prostate cancer. | 2003 Jun |
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The combination of estramustine and mitoxantrone in hormone-refractory prostate cancer: a phase II feasibility study conducted by the Hellenic Cooperative Oncology Group. | 2003 Jun |
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Dose escalation study of intravenous estramustine phosphate in combination with Paclitaxel and Carboplatin in patients with advanced prostate cancer. | 2003 Jun |
|
Current strategies in the management of hormone refractory prostate cancer. | 2003 Jun |
|
[Malignant priapism as a sign of a recurrent prostate cancer. Differential diagnosis of induratio penis plastica]. | 2003 Jun |
|
Chemotherapy of prostate cancer: present and future. | 2003 Jun |
|
Randomized, multicenter, phase II trial of two multicomponent regimens in androgen-independent prostate cancer. | 2003 Mar 1 |
|
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
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admin
on
Edited
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on
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Record UNII |
35LT29625A
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000007246
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L01XX11
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N0000175558
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N0000007246
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NCI_THESAURUS |
C697
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C25974
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N0000007659
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QL01XX11
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N0000000236
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D004961
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m5031
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ESTRAMUSTINE
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4089
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DB01196
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C479
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35LT29625A
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Metabolite produced by hydrolysis. Estramustine,s primary mechanism of antineoplastic action is inhibition of mitosis.
PLASMA
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PRODRUG -> METABOLITE ACTIVE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |