Zinostatin

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

MedKoo CAT#: 571199

CAS#: 9014-02-2

Description: Zinostatin is a cytotoxic enediyne that alkylates DNA and RNA like mitomycin does. It has antineoplastic and antibiotic properties. It is isolated from the bacterium Streptomyces carzinostaticus. It may be active against hepatocellular carcinoma.


Chemical Structure

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Zinostatin
CAS# 9014-02-2

Theoretical Analysis

MedKoo Cat#: 571199
Name: Zinostatin
CAS#: 9014-02-2
Chemical Formula: C35H35NO12
Exact Mass: 661.2159
Molecular Weight: 661.66
Elemental Analysis: C, 63.53; H, 5.33; N, 2.12; O, 29.02

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Zinostatin; Neocarcinostatin

IUPAC/Chemical Name: N/A

InChi Key: BLXZMHNVKCEIJX-LTZUVELHSA-N

InChi Code: InChI=1S/C35H35NO12/c1-16-12-19(42-4)14-22-20(16)8-9-23(37)27(22)32(40)45-24-13-18-10-11-35(26-15-43-34(41)46-26)25(48-35)7-5-6-21(18)31(24)47-33-28(36-3)30(39)29(38)17(2)44-33/h8-9,12-14,17,21,24-26,28-31,33,36-39H,6,15H2,1-4H3/t17-,21?,24-,25?,26?,28-,29+,30-,31-,33-,35+/m1/s1

SMILES Code: CC1=CC(OC)=CC2=C1C=CC(O)=C2C(O[C@@H]3C=C4C#C[C@@]5(C6COC(O6)=O)C(C#CCC4[C@H]3O[C@@H]7[C@H](NC)[C@@H](O)[C@@H](O)[C@@H](C)O7)O5)=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: >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 661.66 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

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1: Nichols JW, Bae YH. EPR: Evidence and fallacy. J Control Release. 2014 Sep 28;190:451-64. doi: 10.1016/j.jconrel.2014.03.057. Epub 2014 Apr 30. Review. PubMed PMID: 24794900.

2: Ishii H, Furuse J, Nagase M, Maru Y, Yoshino M, Hayashi T. A phase I study of hepatic arterial infusion chemotherapy with zinostatin stimalamer alone for hepatocellular carcinoma. Jpn J Clin Oncol. 2003 Nov;33(11):570-3. PubMed PMID: 14711981.

3: Okusaka T, Okada S, Ueno H, Ikeda M, Iwata R, Furukawa H, Takayasu K, Moriyama N, Sato T, Sato K. Transcatheter arterial embolization with zinostatin stimalamer for hepatocellular carcinoma. Oncology. 2002;62(3):228-33. PubMed PMID: 12065870.

4: Toge T, Jinushi K, Sawamura A, Matsuki K. [Study on the intra-tumor tissue concentration of zinostatin stimalamer in the liver following intra-arterial injection of zinostatin stimalamer (YM881) suspension]. Gan To Kagaku Ryoho. 1991 Aug;18(10):1677-80. Japanese. PubMed PMID: 1651687.

5: Sansiaume-Dagousset E, Urvoas A, Chelly K, Ghattas W, Maréchal JD, Mahy JP, Ricoux R. Neocarzinostatin-based hybrid biocatalysts for oxidation reactions. Dalton Trans. 2014 Jun 14;43(22):8344-54. doi: 10.1039/c4dt00151f. PubMed PMID: 24728274.

6: Hirashima N, Sakakibara K, Itazu I, Hirai T, Nemoto A, Matsuura H, Kumada K, Nojiri O, Kano H. Zinostatin stimalamer-transcatheter arterial embolization for hepatocellular carcinoma: a comparison with lipiodol-transcatheter arterial embolization. Semin Oncol. 1997 Apr;24(2 Suppl 6):S6-91-S6-96. PubMed PMID: 9151922.

7: Urvoas A, Ghattas W, Maréchal JD, Avenier F, Bellande F, Mao W, Ricoux R, Mahy JP. Neocarzinostatin-based hybrid biocatalysts with a RNase like activity. Bioorg Med Chem. 2014 Oct 15;22(20):5678-86. doi: 10.1016/j.bmc.2014.05.063. Epub 2014 Jun 14. PubMed PMID: 24984934.

8: Fukuhara K, Suzuki M, Unno M, Rikiyama T, Sakamoto N, Takeuchi H, Uchiyama T, Yamaki T, Iwasashi H, Kodama H, Matsuno S. [An anaphylactic shock case after hepatic arterial infusion of zinostatin stimalamer suspension improved by anti-histaminics]. Gan To Kagaku Ryoho. 1997 Jun;24(8):1023-6. Japanese. PubMed PMID: 9212813.

9: Tianqin G, Chunlei C, Jingjing W. Synergistic Anti-glioma Effects in Vitro and in Vivo of Enediyne Antibiotic Neocarzinostatin and Paclitaxel via Enhanced Growth Delay and Apoptosis-Induction. Biol Pharm Bull. 2016 Oct 1;39(10):1623-1630. Epub 2016 Jul 14. PubMed PMID: 27431785.

10: Issell BF, Ginsberg SJ, Comis RL. Zinostatin and doxorubicin. A combination phase I study. Cancer Clin Trials. 1981 Fall;4(3):323-6. PubMed PMID: 6269771.

11: Creech RH, Tritchler D, Ettinger DS, Ferraro JA, Ruckdeschel JC, Vogl SE, Woll J. Phase II study of PALA, amsacrine, teniposide, and zinostatin in small cell lung carcinoma (EST 2579). Cancer Treat Rep. 1984 Sep;68(9):1183-4. PubMed PMID: 6090017.

12: Okusaka T, Okada S, Ishii H, Ikeda M, Nakasuka H, Nagahama H, Iwata R, Furukawa H, Takayasu K, Nakanishi Y, Sakamoto M, Hirohashi S, Yoshimori M. Transarterial chemotherapy with zinostatin stimalamer for hepatocellular carcinoma. Oncology. 1998 Jul-Aug;55(4):276-83. PubMed PMID: 9663415.

13: Tanaka S, Yamamoto M, Numasaki Y. Antitumor mechanisms of zinostatin stimalamer (YM881). Res Commun Mol Pathol Pharmacol. 1996 May;92(2):165-76. PubMed PMID: 8774070.

14: Tanaka S, Numasaki Y, Maeda H. [Action mechanisms of zinostatin stimalamer (YM881)]. Gan To Kagaku Ryoho. 1991 Oct;18(13):2295-300. Japanese. PubMed PMID: 1834022.

15: Kuroiwa T, Taniguchi S, Aoki K, Hasuda K, Baba T. Potentiation of cytotoxicity of zinostatin under acidic conditions in vitro and in vivo. Cancer Treat Rep. 1987 Mar;71(3):247-51. PubMed PMID: 2949830.

16: Masuda E, Maeda H. Changes in cellular components of spleen and lymph node cells and the effector cells responsible for Meth A tumor eradication induced by zinostatin stimalamer. Cancer Res. 1996 Apr 15;56(8):1868-73. PubMed PMID: 8620506.

17: Calvo DB 3rd, Legha SS, McKelvey EM, Bodey GP, Dail DH. Zinostatin-related pulmonary toxicity. Cancer Treat Rep. 1981 Jan-Feb;65(1-2):165-7. PubMed PMID: 6452946.

18: Tanaka S, Fujihara A, Yamamoto M, Asano M, Ida H, Ohmi Y, Kitazaki T, Kikuchi Y, Yoshida S, Okamiya H, et al. [Anti-tumor activity of zinostatin stimalamer (YM 881) examined by human hepatoma cells in vitro and VX2 liver tumor in vivo]. Gan To Kagaku Ryoho. 1994 Feb;21(2):219-26. Japanese. PubMed PMID: 8311492.

19: Tanaka S, Fujihara A, Yamamoto M, Ida H, Ohmi Y, Kitazaki T, Kikuchi Y, Yoshida S, Okamiya H, Numasaki Y, Konno T. Antitumor activity of zinostatin stimalamer (YM881) in human hepatoma cell lines and VX2 liver tumor-bearing rabbits. Res Commun Mol Pathol Pharmacol. 1996 May;92(2):155-63. PubMed PMID: 8774069.

20: Saito T, Nakao I, Wakui A, Niitani H, Kurihara M, Konno T, Tsukagoshi S, Maeda H. [Early phase II study of YM 881 (zinostatin stimalamer) by intravenous injection. Research group for intravenous YM 881]. Gan To Kagaku Ryoho. 1991 Jul;18(8):1319-23. Japanese. PubMed PMID: 1829883.