A derivative of estradiol that destabilizes microtubules
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Estramustine Phosphate (sodium salt)

Item No. 23126

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
estra-1,3,5(10)-triene-3,17-diol (17β)-3-[N,N-bis(2-chloroethyl)carbamate] 17-(dihydrogen phosphate), disodium salt
CAS Number
52205-73-9
Synonyms
  • Ro 21-8837/001
Molecular Formula
C23H30Cl2NO6P • 2Na
Formula Weight
564.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.25 mg/mlDMSO: 0.25 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
204, 269 nm
SMILES
[O-]P(O[C@H]1CC[C@@]2([H])[C@]3([H])CCC4=CC(OC(N(CCCl)CCCl)=O)=CC=C4[C@@]3([H])CC[C@@]21C)([O-])=O.[Na+].[Na+]
InChi Code
InChI=1S/C23H32Cl2NO6P.2Na/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);;/q;2*+1/p-2/t18-,19-,20+,21+,23+;;/m1../s1
InChi Key
IIUMCNJTGSMNRO-VVSKJQCTSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $32

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    50 mg

    $120

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    100 mg

    $176

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    250 mg

    $400

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    Cayman Chemical
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    Product Description

    Estramustine phosphate is a derivative of estradiol (Item Nos. 20776 | 10006315) that contains a nor-nitrogen mustard group. Estramustine phosphate destabilizes microtubules by binding to microtubule-associated proteins (MAPs) with Kd values of 10 and 15 µM for MAP-1 and MAP-2, respectively.1 Estramustine induces cell cycle arrest in mitosis at the metaphase stage in DU145 and PC3 prostate cancer cells and induces apoptosis in U87MG human malignant glioma cells.2,3 The metabolites of estramustine phosphate have anti-androgenic effects.4 Formulations containing estramustine phosphate are used in the palliative treatment of prostate cancer.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tew, K.D., and Stearns, M.E. Estramustine--a nitrogen mustard/steroid with antimicrotubule activity. Pharmacol. Ther. 43(3), 299-319 (1989).

    2. Hartley-Asp, B. Estramustine-induced mitotic arrest in two human prostatic carcinoma cell lines DU 145 and PC-3. Prostate 5(1), 93-100 (1984).

    3. Yoshida, D., Hoshino, S., Shimura, T., et al. Drug-induced apoptosis by anti-microtubule agent, estramustine phosphate on human malignant glioma cell line, U87MG; in vitro study. J. Neurooncol. 47(2), 133-140 (2000).

    4. Wang, L.G., Liu, X.M., Kreis, W., et al. Androgen antagonistic effect of estramustine phosphate (EMP) metabolites on wild-type and mutated androgen receptor. Biochem. Pharmacol. 55(9), 1427-1433 (1998).