Synonym
Zindoxifene; D 16726
IUPAC/Chemical Name
1-Ethyl-2-(p-hydroxyphenyl)-3-methylindol-5-ol diacetate (ester)
InChi Key
KSZGVNZSUJHOJA-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H21NO4/c1-5-22-20-11-10-18(26-15(4)24)12-19(20)13(2)21(22)16-6-8-17(9-7-16)25-14(3)23/h6-12H,5H2,1-4H3
SMILES Code
CC1=C(C2=CC=C(OC(C)=O)C=C2)N(CC)C3=C1C=C(OC(C)=O)C=C3
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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
351.40
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.
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: Stein RC, Dowsett M, Cunningham DC, Davenport J, Ford HT, Gazet JC, von Angerer E, Coombes RC. Phase I/II study of the anti-oestrogen zindoxifene (D16726) in the treatment of advanced breast cancer. A Cancer Research Campaign Phase I/II Clinical Trials Committee study. Br J Cancer. 1990 Mar;61(3):451-3. PubMed PMID: 2328214; PubMed Central PMCID: PMC1971274.
2: Schneider MR, Schiller CD, Humm A, von Angerer E. Effect of zindoxifene on experimental prostatic tumours of the rat. J Cancer Res Clin Oncol. 1991;117(1):33-6. PubMed PMID: 1997466.
3: von Angerer E, Prekajac J, Berger M. The inhibitory effect of 5-acetoxy-2-(4-acetoxyphenyl)-1-ethyl-3-methylindole (D 16726) on estrogen-dependent mammary tumors. Eur J Cancer Clin Oncol. 1985 Apr;21(4):531-7. PubMed PMID: 3924626.
4: von Angerer E, Birnböck H, Kager M, Maucher A. The effect of a combination of zindoxifene and cisplatin on Dunning R3327-G prostatic carcinomas of the rat. J Cancer Res Clin Oncol. 1992;118(5):339-43. PubMed PMID: 1583065.
5: Alba E, Ragonesi G, Colla F, Mazzoleni A, Farina C. [Antiestrogen therapy in the treatment of breast neoplasms]. Minerva Ginecol. 2002 Jun;54(3):245-51. Review. Italian. PubMed PMID: 12063440.
6: Schneider MR, von Angerer E, Höhn W, Sinowatz F. Antitumor activity of antiestrogenic phenylindoles on experimental prostate tumors. Eur J Cancer Clin Oncol. 1987 Jul;23(7):1005-15. PubMed PMID: 3665986.
7: Csapo Z, Brand K, Schrott KM, Schwindl B. Prostatic acid phosphatase in the serially transplantable human prostatic tumor lines PC-82 and PC-EW. Urol Res. 1990;18(2):137-42. PubMed PMID: 2339482.
8: Jordan VC, Tormey DC. Antiestrogen therapy for breast cancer: current strategies and future prospects. Cancer Treat Res. 1988;39:97-110. Review. PubMed PMID: 2908611.
9: von Angerer E. Development of new drugs for endocrine tumour chemotherapy. Cancer Treat Rev. 1984 Mar;11 Suppl A:147-53. PubMed PMID: 6547370.
10: Hilgard P, Pohl J, Engel J. The development of alkylphosphocholines as signal transduction inhibitors: experimental and clinical challenges. J Cancer Res Clin Oncol. 1997;123(5):286-7. PubMed PMID: 9201252.
11: Birnböck H, Ringshandl R, von Angerer E. Chromatographic analysis of the new antiestrogen zindoxifene and its metabolites in biological material. J Chromatogr. 1987 Feb 20;414(1):235-41. PubMed PMID: 3571389.
12: Schiller CD, von Angerer E, Schneider MR. 6,7-Dihydro-4H-indolones: synthesis and biological properties. Arch Pharm (Weinheim). 1991 Oct;324(10):767-71. PubMed PMID: 1805709.
13: Robinson SP, Koch R, Jordan VC. In vitro estrogenic actions in rat and human cells of hydroxylated derivatives of D16726 (zindoxifene), an agent with known antimammary cancer activity in vivo. Cancer Res. 1988 Feb 15;48(4):784-7. PubMed PMID: 3338076.