Esorubicin

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MedKoo CAT#: 206064

CAS#: 63521-85-7

Description: Esorubicin 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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Chemical Structure

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Esorubicin
CAS# 63521-85-7

Theoretical Analysis

MedKoo Cat#: 206064
Name: Esorubicin
CAS#: 63521-85-7
Chemical Formula: C27H29NO10
Exact Mass: 527.17915
Molecular Weight: 527.52
Elemental Analysis: C, 61.47; H, 5.54; N, 2.66; O, 30.33

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.

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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

Preparing Stock Solutions

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.

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: 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.



Additional Information