WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H206064
CAS#: 63521-85-7 (free base)
Description: Esorubicin, also known as 4'-deoxydoxorubicin, and NSC 267469, is a synthetic derivative of the anthracycline antineoplastic antibiotic doxorubicin with potential antineoplastic activity. Esorubicin intercalates into DNA and inhibits topoisomerase II, thereby inhibiting DNA replication and ultimately, interfering with RNA and protein synthesis. This agent exhibits less cardiotoxicity than the parent antibiotic doxorubicin, but may cause more severe myelosupression compared to other compounds within the anthracycline class. Esorubicin was being clinically tested for the treatment of solid tumors as well as lymphomas an leukemias. Esorubicin development has been discontinued.
Hodoodo Cat#: H206064
Name: Esorubicin free base
CAS#: 63521-85-7 (free base)
Chemical Formula: C27H29NO10
Exact Mass: 527.18
Molecular Weight: 527.520
Elemental Analysis: C, 61.47; H, 5.54; N, 2.66; O, 30.33
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Related CAS #: 63521-85-7 (free base) 63950-06-1 (HCl)
Synonym: Esorubicin; deoxyadriamycin; deoxyadriamycin hydrochloride; deoxydoxorubicin. Code name: IMI58.
IUPAC/Chemical Name: (8S,10S)-10-(((2S,4R,6S)-4-amino-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
InChi Key: ITSGNOIFAJAQHJ-BMFNZSJVSA-N
InChi Code: InChI=1S/C27H29NO10/c1-11-6-12(28)7-18(37-11)38-16-9-27(35,17(30)10-29)8-14-20(16)26(34)22-21(24(14)32)23(31)13-4-3-5-15(36-2)19(13)25(22)33/h3-5,11-12,16,18,29,32,34-35H,6-10,28H2,1-2H3/t11-,12+,16-,18-,27-/m0/s1
SMILES Code: C[C@@H]1O[C@@H](O[C@@H](C2)C3=C(O)C(C4=O)=C(C(C5=C4C(OC)=CC=C5)=O)C(O)=C3C[C@@]2(O)C(CO)=O)C[C@H](N)C1
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, not in water
Shelf Life: >5 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
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 527.52 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Alberts DS, Mason-Liddil N, Stock-Novack D, O'Toole RV, Abbott TM, Salmon SE. A phase II evaluation of esorubicin in ovarian cancer. A Southwest Oncology Group study. Am J Clin Oncol. 1992 Apr;15(2):146-9. PubMed PMID: 1553903.
2: Miller TP, Dahlberg S, Salmon SE, Williamson SK, Belt RJ, Dana BW, Fisher RI. Activity of esorubicin in recurrent malignant lymphoma: a Southwest Oncology Group study. J Clin Oncol. 1991 Jul;9(7):1204-9. PubMed PMID: 2045860.
3: Green JB 3rd, Green S, O'Toole RV, Alberts DS, Nahhas WA, Wallace DL. Esorubicin in advanced endometrial cancer: an ineffective and potentially toxic therapy. A Southwest Oncology Group study. Invest New Drugs. 1991 May;9(2):191-3. PubMed PMID: 1874602.
4: Rigas JR, Kris MG, Gralla RJ, Heelan RT, Marks LD. Phase II trial of esorubicin (4'deoxydoxorubicin, DxDx) in patients with small cell lung cancer. Invest New Drugs. 1991 May;9(2):187-90. PubMed PMID: 1651908.
5: Somlo G, Doroshow J, Akman S, Leong L, Margolin K, McNamara M, Multhauf P, Blayney D, Morgan R, Raschko J. Phase II study of 4'-deoxydoxorubicin (esorubicin) in advanced or metastatic adenocarcinoma of the stomach. Invest New Drugs. 1991 Feb;9(1):83-5. PubMed PMID: 2026486.
6: Green MD, Speyer JL, Wernz JC, Colombo N, Beller U, Muggia FM, Beckman EM. Phase II study of esorubicin (4'deoxydoxorubicin) in anthracycline naive patients with ovarian cancer. Invest New Drugs. 1990 Aug;8(3):333-6. PubMed PMID: 2272774.
7: Hochster H, Hunt M, Green M, Parkinson D, Smith T. Esorubicin (deoxydoxorubicin) has low grade activity in malignant melanoma. Results of an Eastern Cooperative Oncology Group study (EST 2685). Invest New Drugs. 1990 Aug;8(3):329-32. PubMed PMID: 2272773.
8: Muss HB, Van Echo D, Korzun AH, Henderson IC, Campbell T, Vogelzang NJ, Rice MA, Wood W. Esorubicin (4'-deoxydoxorubicin, NSC 267469) in advanced breast cancer. A phase II study of the CALGB. Am J Clin Oncol. 1990 Jun;13(3):233-7. PubMed PMID: 2346128.
9: Ringenberg QS, Propert KJ, Muss HB, Weiss RB, Schilsky RL, Modeas C, Perry MC, Norton L, Green M. Clinical cardiotoxicity of esorubicin (4'-deoxydoxorubicin,DxDx): prospective studies with serial gated heart scans and reports of selected cases. A Cancer and Leukemia Group B report. Invest New Drugs. 1990 May;8(2):221-6. PubMed PMID: 2166722.
10: Vaughn CB, Salmon SE, Fleming TR. Phase II evaluation of esorubicin (4'deoxydoxorubicin) in pancreatic adenocarcinoma: a Southwest Oncology Group study. Invest New Drugs. 1990 Feb;8(1):81-5. PubMed PMID: 2188929.
