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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H32Cl2NO6P
Molecular Weight 520.383
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRAMUSTINE PHOSPHATE

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(OC(=O)N(CCCl)CCCl)=CC=C34)[C@@H]1CC[C@@H]2OP(O)(O)=O

InChI

InChIKey=ADFOJJHRTBFFOF-RBRWEJTLSA-N
InChI=1S/C23H32Cl2NO6P/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/h3,5,14,18-21H,2,4,6-13H2,1H3,(H2,28,29,30)/t18-,19-,20+,21+,23+/m1/s1

HIDE SMILES / InChI
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

Description
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

Originator

Approval Year

1981
142
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 4.5 µM [IC50]
Modulator
846
Agonist
2752
Microtubule-associated protein 1A
6
Target ID: P78559
Gene ID: 4130.0
Gene Symbol: MAP1A
Target Organism: Homo sapiens (Human)
Antagonist
2849
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
Emcyt

Approved Use

EMCYT Capsules are indicated in the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate.

Launch Date

1991
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/7736407
ESTRAMUSTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/11844837
unhealthy, 66
Health Status: unhealthy
Age Group: 66
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/11844837
DLT: Malaise and fatigue, Hypotension...
Dose limiting toxicities:
Malaise and fatigue (grade 3, 75%)
Hypotension (grade 3, 25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11844837
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:
https://pubmed.ncbi.nlm.nih.gov/11844837
unhealthy, 66
Health Status: unhealthy
Age Group: 66
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/11844837
DLT: Malaise and fatigue...
Dose limiting toxicities:
Malaise and fatigue (grade 3, 40%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11844837
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/11844837
unhealthy, 66
Health Status: unhealthy
Age Group: 66
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/11844837
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:
https://pubmed.ncbi.nlm.nih.gov/11844837
unhealthy, 66
Health Status: unhealthy
Age Group: 66
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/11844837
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:
https://pubmed.ncbi.nlm.nih.gov/11844837
unhealthy, 66
Health Status: unhealthy
Age Group: 66
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/11844837
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1741
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1932
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:4868
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4868
ChemicalBook
CB9127416
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9127416
eMolecules
30151822
https://www.emolecules.com/cgi-bin/more?vid=30151822
MolPort
MolPort-006-114-857
https://www.molport.com/shop/molecule-link/MolPort-006-114-857
ZINC
ZINC000004099032
http://zinc15.docking.org/substances/ZINC000004099032
PubMed

PubMed

TitleDatePubMed
Estramustine plus a taxane for advanced prostate cancer: the new standard therapy?
2002
Phase I trial of oral estramustine and 3-hr infusional paclitaxel for the treatment of hormone refractory prostate cancer.
2002
Controversies in chemotherapy of prostate cancer.
2002
[Second cancer after starting treatment for prostate cancer].
2002 Aug
Ondansetron but not granisetron affect cell volume regulation and potassium ion transport of glioma cells treated with estramustine phosphate.
2002 Aug
Chemotherapy for androgen-independent prostate cancer.
2002 Aug
Editorial: the coming revolution in the treatment of prostate cancer patients.
2002 Aug
Hypertriglyceridemia and pancreatitis associated with estramustine phosphate.
2002 Aug
[Therapy for hormone-refractory prostate cancer].
2002 Dec
[Chemotherapy for prostate cancers].
2002 Dec
Fatal respiratory failure associated with treatment of prostate cancer using docetaxel and estramustine.
2002 Dec
An active regimen of weekly paclitaxel and estramustine in metastatic androgen-independent prostate cancer.
2002 Dec
Editorial: States and state transitions are all that really matter.
2002 Dec
Combination chemotherapy with paclitaxel, estramustine and carboplatin for hormone refractory prostate cancer.
2002 Dec
EMP combination chemotherapy and low-dose monotherapy in advanced prostate cancer.
2002 Feb
Higher doses of mitoxantrone among men with hormone-refractory prostate carcinoma: a Cancer and Leukemia Group B study.
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
The role of chemotherapy in advanced prostate cancer.
2002 Jun
Docetaxel in the integrated management of prostate cancer. Current applications and future promise.
2002 Jun
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
A phase II Hoosier Oncology Group study of vinorelbine and estramustine phosphate in hormone-refractory prostate cancer.
2002 Mar
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
Estramustine phosphate combined with orchidectomy as first-line therapy in patients with prostate carcinoma. Effect of age on survival.
2002 May 15
[Hormonal chemotherapy for hormone-refractory prostate cancer].
2002 Nov
Pattern of somatic androgen receptor gene mutations in patients with hormone-refractory prostate cancer.
2002 Nov
Penile metastasis of prostatic adenocarcinoma.
2002 Oct
Drug resistance in prostate cancer cell lines is influenced by androgen dependence and p53 status.
2002 Oct
Combined anti-microtubule therapy: a phase II study of weekly docetaxel plus estramustine in patients with metastatic breast cancer.
2002 Oct
Chemotherapy for prostate cancer.
2002 Sep
Weekly epirubicin in patients with hormone-resistant prostate cancer.
2002 Sep 23
Role of chemotherapy in hormone-refractory prostate cancer. Old issues, recent advances and new perspectives.
2003
[Prostatic cancer in the young adult].
2003 Apr
Neoadjuvant docetaxel and estramustine chemotherapy in high-risk/locallyadvanced prostate cancer.
2003 Apr
A phase II trial of docetaxel and estramustine in patients with refractory metastatic breast carcinoma.
2003 Feb 1
Estimating survival benefit in castrate metastatic prostate cancer: decision making in proceeding to a definitive phase III trial.
2003 Jan
A phase I study of paclitaxel, estramustine phosphate and vinorelbine (Pacl-E-Vin) in advanced malignancies: triple tubulin targeting.
2003 Jan
Bisphosphonate therapy for hormone refractory prostate cancer with bone metastasis.
2003 Jan
Docetaxel (taxotere) in the treatment of prostate cancer.
2003 Jun
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
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
Patents

Patents

05036062
6
20050222431
14
20070037988
12
20070116729
163
20070244331
14
JP2002511777A
420
JP2003529540A
50
JP2005519871A
30
JP2005520795A
26
JP2007538099A
19
JP2009513567A
66
JP2011522802A
31
JP2011524416A
146
JPS61189214A
7

Sample Use Guides

In Vivo Use Guide
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
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 Mon Mar 31 18:12:57 GMT 2025
Edited
by admin
on Mon Mar 31 18:12:57 GMT 2025
Record UNII
MUZ9585Y7B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRAMUSTINE 17-(DIHYDROGEN PHOSPHATE)
MI  
Preferred Name English
ESTRAMUSTINE PHOSPHATE
WHO-DD  
Common Name English
ESTRAMUSTINE 17-(DIHYDROGEN PHOSPHATE) [MI]
Common Name English
LS 299
Common Name English
LS-299
Common Name English
ESTRADIOL, 3-(BIS(2-CHLOROETHYL)CARBAMATE) DIHYDROGEN PHOSPHATE
Common Name English
ESTRACYT
Brand Name English
NSC-89199
Code English
Estramustine phosphate [WHO-DD]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID7048667
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
CHEBI
31562
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
ECHA (EC/EINECS)
225-512-3
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
FDA UNII
MUZ9585Y7B
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
SMS_ID
100000092342
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
CAS
4891-15-0
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
DRUG BANK
DB14674
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
NSC
89199
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
PUBCHEM
259329
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
RXCUI
105556
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m5031
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY Merck Index
DRUG CENTRAL
1066
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
WIKIPEDIA
Estramustine phosphate
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
CHEBI
68643
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
EVMPD
SUB01969MIG
Created by admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
PRIMARY
Related Record Type Details
Structure of ESTRAMUSTINE PHOSPHATE MEGLUMINE
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SALT/SOLVATE -> PARENT
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Structure of ESTROMUSTINE
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