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estramustine

Trade name: emcyt

Small moleculeapproved

Approved

Dec 24, 1981

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. — NCATS

Clinical trial activity

51 trials · 49 clinical orgs · 1 marketing orgs

Phase 1
12
Phase 2
47
Phase 3
8
Phase 4
0

Earliest trial started Mar 1, 1995 (NCT00002721)

Timeline

1980s

  1. Dec 24, 1981

    Pharmacia & Upjohn — Earliest FDA Approval

  2. Dec 24, 1981

    Pharmacia & Upjohn — NDA Organization

  3. Dec 24, 1981

    Pharmacia & Upjohn — NDA Secondary Org

1990s

  1. Jan 1, 1995

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 1996

    Earliest Phase 2 Sponsor(trial)

  3. Jan 1, 1996

    Earliest Phase 3 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedDec 24, 1981

Chemistry & pharmacology

Loading structure…

SMILES

C[C@]12CC[C@@H]3c4ccc(OC(=O)N(CCCl)CCCl)cc4CC[C@H]3[C@@H]1CC[C@@H]2OP(=O)(O)O
Mol. weight
520.39 g/mol
Lipinski Ro5
2 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Discontinued

Oral

Yes

Parenteral

No

Topical

No

Prodrug

Sources

Also known as

  • 17beta-estradiol 3-(bis(2-chloroethyl)carbamate)
  • 17beta-estradiol 3-(bis(2-chloroethyl)carbamate)
  • 17β-estradiol 3-(bis(2-chloroethyl)carbamate)
  • 17β-estradiol 3-(bis(2-chloroethyl)carbamate)
  • emcyt
  • emcyt
  • emcyt
  • estracty
  • estracyt
  • estracyt
  • estradiol 3-(n,n-bis(2-chloroethyl)carbamate)
  • estradiol 3-(n,n-bis(2-chloroethyl)carbamate)
  • estramustina
  • estramustina
  • estramustine
  • estramustine
  • estramustine
  • estramustine
  • estramustine
  • estramustine
  • estramustine
  • estramustine
  • estramustine
  • estramustine
  • estramustine phosphate
  • estramustine phosphate
  • estramustine phosphate
  • estramustine phosphate
  • estramustine phosphate
  • estramustine phosphate sodium
  • estramustine phosphate sodium
  • estramustine phosphate sodium
  • estramustine phosphate sodium
  • estramustinum
  • estramustinum
  • ro-218837001
  • ro-218837001
  • ro-218837-001
  • ro-218837-001
  • ro-222296000
  • ro-222296000
  • ro-22-2296000
  • ro-22-2296000

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT02853071Phase 2Jan 1, 2017University of Franche-Comté
NCT02560051Phase 2Nov 1, 2015University of Texas at Houston
NCT02494713Phase 2Oct 1, 2015University of Texas at Houston
NCT02866955Phase 2Jun 1, 2011Institut de Cancérologie de Lorraine
NCT00705822Phase 3Aug 1, 2006Sanofi
NCT00193271Phase 2Aug 1, 2004Aventis, SCRI Development Innovations
NCT00165399Phase 2Mar 1, 2004Harvard University
NCT00083005Phase 2Mar 1, 2004Eastchester Center for Cancer Care, National Cancer Institute (NCI), National Institutes of Health (NIH)
NCT00541281Phase 2Dec 1, 2003CHU Mont-Godinne, Sanofi, Université catholique de Louvain
NCT00132756Phase 1/Phase 2 (Phase 2)Dec 1, 2003Morton Plant Mease Health Care, Ortho Biotech, Inc.
NCT00084565Phase 2Nov 1, 2003Temple University
NCT00027859Phase 3May 1, 2003Cancer and Leukemia Group B (CALGB), Deaconess Medical Center, Spokane, Washington, Department of Veteran Affairs, Eastern Cooperative Oncology Group, Johns Hopkins University, National Cancer Institute (NCI), Southwest Oncology Group
NCT00176527Phase 2Nov 1, 2002National Cancer Institute (NCI), Rutgers University, University of Medicine and Dentistry of New Jersey
NCT00052845Phase 2Nov 1, 2002National Cancer Institute (NCI), University of Maryland
NCT00055731Phase 3Nov 1, 2002Institut Gustave Roussy, UNICANCER
NCT00030654Phase 3Oct 1, 2002Cancer and Leukemia Group B (CALGB), Deaconess Medical Center, Spokane, Washington, Eastern Cooperative Oncology Group, National Cancer Institute (NCI), NRG Oncology, Radiation Therapy Oncology Group, Southwest Oncology Group, Temple University, University of California, Davis, University of Maryland, University of Michigan
NCT00218205Phase 2Jul 1, 2002Department of Veteran Affairs, Pfizer
NCT00151073Phase 2Apr 1, 2002Aventis, Novartis, University of Michigan
NCT00024167Phase 3Apr 1, 2002National Cancer Institute (NCI), University of Texas at Houston
NCT00151086Phase 1/Phase 2 (Phase 2)Dec 1, 2001GlaxoSmithKline, University of Michigan
Showing 20 of 51 trials
Page 1 / 3

Organizations

Research & Development (49)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Cancer Institute (NCI)Government23431996
University of Texas at HoustonAcademic/Hospital7721996
University of MichiganAcademic/Hospital6321998
Cancer and Leukemia Group B (CALGB)Academic/Hospital4021999
Eastern Cooperative Oncology GroupAcademic/Hospital4321998
Harvard UniversityAcademic/Hospital4321999
Herbert Irving Comprehensive Cancer CenterAcademic/Hospital4331997
Southwest Oncology GroupAcademic/Hospital4221999
Temple UniversityAcademic/Hospital4221996
AventisFor profit3012001
Cornell UniversityAcademic/Hospital3311998
Deaconess Medical Center, Spokane, WashingtonAcademic/Hospital2012002
Department of Veteran AffairsGovernment2122002
New York UniversityAcademic/Hospital2221997
Radiation Therapy Oncology GroupAcademic/Hospital2212000
Rutgers UniversityAcademic/Hospital2012001
SanofiFor profit2122003
SCRI Development InnovationsFor profit2212000
University of MarylandAcademic/Hospital2022002
University of New MexicoAcademic/Hospital2221995
49 organizations
Page 1 / 3

Marketing (2)

OrganizationOrg typeRelationshipDate
Pharmacia & UpjohnFor profitNDADec 24, 1981
Pharmacia & UpjohnFor profitNDA2Dec 24, 1981