MedKoo Cat#: 592519 | Name: Alestramustine

Description:

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

Alestramustine is a cytostatic antineoplastic agent. It is the L-alanine ester of estramustine, which is a combination of the nitrogen mustard normustine coupled via a carbamate to the estrogen estradiol.Alestramustine acts as a prodrug to estramustine, and also forms estradiol as a byproduct.The drug, via its active metabolites, binds to microtubule-associated proteins and β-tubulin and interferes with microtubule function, thereby inhibiting cell division. Due to its estrogen moiety, alestramustine is selectively concentrated in estrogen receptor-positive cells such as prostate and breast.

Chemical Structure

Alestramustine
Alestramustine
CAS#139402-18-9

Theoretical Analysis

MedKoo Cat#: 592519

Name: Alestramustine

CAS#: 139402-18-9

Chemical Formula: C26H36Cl2N2O4

Exact Mass: 510.2052

Molecular Weight: 511.48

Elemental Analysis: C, 61.05; H, 7.09; Cl, 13.86; N, 5.48; O, 12.51

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 #
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Synonym
Alestramustine
IUPAC/Chemical Name
Estradiol 3-(bis(2-chloroethyl)carbamate), 17-ester with L-alanine
InChi Key
NRUFLTXGIPFVSH-KBVRNWHJSA-N
InChi Code
InChI=1S/C26H36Cl2N2O4/c1-16(29)24(31)34-23-8-7-22-21-5-3-17-15-18(33-25(32)30(13-11-27)14-12-28)4-6-19(17)20(21)9-10-26(22,23)2/h4,6,15-16,20-23H,3,5,7-14,29H2,1-2H3/t16-,20+,21+,22-,23-,26-/m0/s1
SMILES Code
C[C@H](N)C(O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]3[C@H]2CCc4cc(OC(N(CCCl)CCCl)=O)ccc43)=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 511.48 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: Wong YN, Manola J, Hudes GR, Roth BJ, Moul JW, Barsevick AM, Scher RM, Volk MJ, Vaughn DJ, Williams SD, Fisch MJ, Cella D, Carducci MA, Wilding G. Phase 2 Study of Weekly Paclitaxel Plus Estramustine in Metastatic Hormone-Refractory Prostate Carcinoma: ECOG-ACRIN Cancer Research Group (E1898) Trial. Clin Genitourin Cancer. 2018 Apr;16(2):e315-e322. doi: 10.1016/j.clgc.2017.10.001. Epub 2017 Oct 16. PubMed PMID: 29173976; PubMed Central PMCID: PMC5975965. 2: Qin Z, Li X, Zhang J, Tang J, Han P, Xu Z, Yu Y, Yang C, Wang C, Xu T, Xu Z, Zou Q. Chemotherapy with or without estramustine for treatment of castration-resistant prostate cancer: A systematic review and meta-analysis. Medicine (Baltimore). 2016 Sep;95(39):e4801. doi: 10.1097/MD.0000000000004801. Review. PubMed PMID: 27684806; PubMed Central PMCID: PMC5265899.