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MedKoo Cat#: 598582 | Name: Estromustine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Estromustine is a major active metabolite of the cystotatic estrogen and nitrogen mustard alkylating antineoplastic agent estramustine phosphate, a medication used in the treatment of prostate cancer.

Chemical Structure

Estromustine
Estromustine
CAS#62899-40-5

Theoretical Analysis

MedKoo Cat#: 598582

Name: Estromustine

CAS#: 62899-40-5

Chemical Formula: C23H29Cl2NO3

Exact Mass: 437.1524

Molecular Weight: 438.38

Elemental Analysis: C, 63.02; H, 6.67; Cl, 16.17; N, 3.20; O, 10.95

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Leo 271 f; Leo-271 f; Leo271 f; Estromustine;
IUPAC/Chemical Name
(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl bis(2-chloroethyl)carbamate
InChi Key
AXWYROHIFVWHMR-UGTOYMOASA-N
InChi Code
InChI=1S/C23H29Cl2NO3/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/h3,5,14,18-20H,2,4,6-13H2,1H3/t18-,19-,20+,23+/m1/s1
SMILES Code
C[C@]1([C@](CC2)([H])[C@]3([H])CCC4=C(C=CC(OC(N(CCCl)CCCl)=O)=C4)[C@@]3([H])CC1)C2=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 438.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Daehlin L, Damber JE, Selstam G, Bergman B. Effects of human chorionic gonadotrophin, oestradiol and estromustine on testicular blood flow in hypophysectomized rats. Int J Androl. 1985 Feb;8(1):58-68. PubMed PMID: 3997272. 2: Gunnarsson PO, Andersson SB, Sandberg AA, Ellman M. Accumulation of estramustine and estromustine in adipose tissue of rats and humans. Cancer Chemother Pharmacol. 1991;28(5):361-4. PubMed PMID: 1914079. 3: Edman K, Svensson L, Eriksson B, Gunnarsson PO. Determination of estramustine phosphate and its metabolites estromustine, estramustine, estrone and estradiol in human plasma by liquid chromatography with fluorescence detection and gas chromatography with nitrogen-phosphorus and mass spectrometric detection. J Chromatogr B Biomed Sci Appl. 2000 Feb 11;738(2):267-79. PubMed PMID: 10718645. 4: Norlén BJ, Andersson SB, Björk P, Gunnarsson PO, Fritjofsson A. Uptake of estramustine phosphate (estracyt) metabolites in prostatic cancer. J Urol. 1988 Nov;140(5):1058-62. PubMed PMID: 3172360. 5: Daehlin L. On the effects of oestrogen in the male. Some effects of different oestrogenic substances in rats and men with prostatic carcinoma. Scand J Urol Nephrol Suppl. 1985;91:1-44. PubMed PMID: 3868029. 6: Gunnarsson PO, Davidsson T, Andersson SB, Backman C, Johansson SA. Impairment of estramustine phosphate absorption by concurrent intake of milk and food. Eur J Clin Pharmacol. 1990;38(2):189-93. PubMed PMID: 2338118. 7: Breda M, Basileo G, James CA. Simultaneous determination of estramustine phosphate and its four metabolites in human plasma by liquid chromatography-ionspray mass spectrometry. Biomed Chromatogr. 2004 Jun;18(5):293-301. PubMed PMID: 15236437. 8: Gunnarsson PO, Andersson SB, Johansson SA, Nilsson T, Plym-Forshell G. Pharmacokinetics of estramustine phosphate (Estracyt) in prostatic cancer patients. Eur J Clin Pharmacol. 1984;26(1):113-9. PubMed PMID: 6714283. 9: Wang LG, Liu XM, Kreis W, Budman DR. Androgen antagonistic effect of estramustine phosphate (EMP) metabolites on wild-type and mutated androgen receptor. Biochem Pharmacol. 1998 May 1;55(9):1427-33. PubMed PMID: 10076535. 10: Yamanaka H, Imai K, Suzuki T, Yuasa H, Takahashi E. [Estracyt (estradiol-nitrogen mustard complex)--estramustine binding protein and its specificity]. Gan To Kagaku Ryoho. 1984 Oct;11(10):2106-14. Japanese. PubMed PMID: 6486830. 11: Daehlin L, Södergård R, Damber JE. Relative affinities of estramustine phosphate metabolites to the cytosol oestrogen receptor of rat testis. Scand J Clin Lab Invest. 1986 Apr;46(2):159-62. PubMed PMID: 3715367. 12: Björk P, Borg A, Fernö M, Nilsson S. Expression and partial characterization of estramustine-binding protein (EMBP) in human breast cancer and malignant melanoma. Anticancer Res. 1991 May-Jun;11(3):1173-82. PubMed PMID: 1888147. 13: Björk P, Jönsson U, Andrén-Sandberg A. Binding sites for the cytotoxic metabolites of estramustine phosphate (Estracyt) in rat and human pancreas that are distinct from pancreatic estrogen-binding protein. Pancreas. 1991 Jan;6(1):77-89. PubMed PMID: 1994382. 14: Dixon R, Brooks M, Gill G. Estramustine phosphate: plasma concentrations of its metabolites following oral administration to man, rat and dog. Res Commun Chem Pathol Pharmacol. 1980 Jan;27(1):17-29. PubMed PMID: 7360997. 15: Batra S, Karlsson R, Witt L. Potentiation by estramustine of the cytotoxic effect of vinblastine and doxorubicin in prostatic tumor cells. Int J Cancer. 1996 Nov 27;68(5):644-9. PubMed PMID: 8938148. 16: Bergenheim AT, Gunnarsson PO, Edman K, von Schoultz E, Hariz MI, Henriksson R. Uptake and retention of estramustine and the presence of estramustine binding protein in malignant brain tumours in humans. Br J Cancer. 1993 Feb;67(2):358-61. PubMed PMID: 8431366; PubMed Central PMCID: PMC1968176. 17: Yamanaka H, Shida K. [Pharmacology and metabolism of a new therapeutic drug for prostatic cancer "Estracyt"]. Gan To Kagaku Ryoho. 1984 Mar;11(3):537-44. Japanese. PubMed PMID: 6422861. 18: Forsgren B, Björk P, Carlström K, Gustafsson JA, Pousette A, Högberg B. The presence in rat and human prostate of proteins that bind steroid-cytostatic complexes. Prog Clin Biol Res. 1981;75A:391-407. PubMed PMID: 7339627. 19: Punzi JS, Duax WL, Strong P, Griffin JF, Flocco MM, Zacharias DE, Carrell HL, Tew KD, Glusker JP. Molecular conformation of estramustine and two analogues. Mol Pharmacol. 1992 Mar;41(3):569-76. PubMed PMID: 1545778. 20: Björk P, Isaacs JT, Hartley-Asp B. Estramustine binding protein (EMBP) in rat R3327 Dunning tumors: partial characterization and effect of hormonal withdrawal, hormonal replacement, and cytotoxic treatment on its expression. Prostate. 1991;18(3):181-200. PubMed PMID: 2020618.

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