Prednimustine

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MedKoo CAT#: 122755

CAS#: 29069-24-7

Description: Prednimustine is a drug used in chemotherapy. It is the ester formed from two other drugs, prednisolone and chlorambucil. Prednimustine probably kills rapidly growing cells by modifying cell's DNA with a chemical structure called an alkyl group. Thus, it is included in the group of alkylating agents. Prednimustine is a combination of two drugs joined together: chlorambucil (an alkylating agent) and methylprednisolone (a steroid).

Chemical Structure

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Prednimustine
CAS# 29069-24-7
Instruction

Theoretical Analysis

MedKoo Cat#: 122755
Name: Prednimustine
CAS#: 29069-24-7
Chemical Formula: C35H45Cl2NO6
Exact Mass: 645.26
Molecular Weight: 646.640
Elemental Analysis: C, 65.01; H, 7.01; Cl, 10.97; N, 2.17; O, 14.85

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Synonym: BRN 2826967; BRN2826967; BRN-2826967; LEO 1031; LEO1031; LEO-1031; Prednimustine.

IUPAC/Chemical Name: 2-((8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate

InChi Key: HFVNWDWLWUCIHC-GUPDPFMOSA-N

InChi Code: InChI=1S/C35H45Cl2NO6/c1-33-14-12-26(39)20-24(33)8-11-27-28-13-15-35(43,34(28,2)21-29(40)32(27)33)30(41)22-44-31(42)5-3-4-23-6-9-25(10-7-23)38(18-16-36)19-17-37/h6-7,9-10,12,14,20,27-29,32,40,43H,3-5,8,11,13,15-19,21-22H2,1-2H3/t27-,28-,29-,32+,33-,34-,35-/m0/s1

SMILES Code: O=C(OCC([C@@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=CC(C=C[C@]4(C)[C@@]3([H])[C@@H](O)C[C@]12C)=O)=O)CCCC5=CC=C(N(CCCl)CCCl)C=C5

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: >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

More Info: Prednimustine is a drug used in chemotherapy. It is the ester formed from two other drugs, prednisolone and chlorambucil. Prednimustine acts by killing quickly growing cells. Since cancerous cells are generally growing faster than normal cells, drugs that kill quickly growing cells generally affect tumors more than normal cells. However, some normal cells, such as white blood cells and platelets, also grow quickly and can be severely affected by antineoplastic drugs. Antitumor therapies create a situation in which the drug is racing to kill the tumor before it causes irreparable damage to normal tissues. The ideal situation is one in which the growth of the tumor is severely affected, but the growth of normal cells is unaffected. However, not every situation is ideal. Some patients taking antitumor drugs may have to discontinue treatment due to the severity of the drug's side effects. Prednimustine probably kills rapidly growing cells by modifying cell's DNA with a chemical structure called an alkyl group. Thus, it is included in the group of alkylating agents. Prednimustine is a combination of two drugs joined together: chlorambucil (an alkylating agent) and methylprednisolone (a steroid). Prednimustine is an investigational drug in the United States.

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 646.64 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Yau JC, Germond C, Gluck S, Cripps C, Verma S, Burns BF, Koski TM, Lister DC, Goss GD. Mitoxantrone, prednimustine, and vincristine for elderly patients with aggressive non-Hodgkin's lymphoma. Am J Hematol. 1998 Oct;59(2):156-60. PubMed PMID: 9766801.

2: Ezpeleta Echávarri D, Muñoz-Blanco JL, Diaz-Otero F, Giménez Roldán S. [Myoclonus induced by prednimustine]. Neurologia. 1998 Mar;13(3):154-5. Review. Spanish. PubMed PMID: 9608225.

3: Brice P, Bastion Y, Lepage E, Brousse N, Haïoun C, Moreau P, Straetmans N, Tilly H, Tabah I, Solal-Céligny P. Comparison in low-tumor-burden follicular lymphomas between an initial no-treatment policy, prednimustine, or interferon alfa: a randomized study from the Groupe d'Etude des Lymphomes Folliculaires. Groupe d'Etude des Lymphomes de l'Adulte. J Clin Oncol. 1997 Mar;15(3):1110-7. PubMed PMID: 9060552.

4: Barnadas A, Mendiola C, Casado A, Villar A, Jimeno J, Clerigue M, Rosell R, Diaz-Rubio E, Cortés-Funes H, García de Paredes M. Combination of oral idarubicin and prednimustine in advanced breast cancer: a phase II study. Eur J Cancer. 1997 Feb;33(2):312-5. PubMed PMID: 9135508.

5: Monnerat C, Gander M, Leyvraz S. A rare case of prednimustine-induced myoclonus. J Natl Cancer Inst. 1997 Jan 15;89(2):173-4. PubMed PMID: 8998190.

6: Braess J, Kern W, Unterhalt M, Kaufmann CC, Ramsauer B, Schüssler M, Kaeser-Fröhlich A, Hiddemann W, Schleyer E. Response to cytarabine ocfosfate (YNK01) in a patient with chronic lymphocytic leukemia refractory to treatment with chlorambucil/prednisone, fludarabine, and prednimustine/mitoxantrone. Ann Hematol. 1996 Oct;73(4):201-4. PubMed PMID: 8890711.

7: Tirelli U, Errante D, Spina M, Gastaldi R, Nigra E, Nosari AM, Magnani G, Vaccher E. Second-line chemotherapy in human immunodeficiency virus-related non-Hodgkin's lymphoma: evidence of activity of a combination of etoposide, mitoxantrone, and prednimustine in relapsed patients. Cancer. 1996 May 15;77(10):2127-31. PubMed PMID: 8640681.

8: Unterhalt M, Herrmann R, Tiemann M, Parwaresch R, Stein H, Trümper L, Nahler M, Reuss-Borst M, Tirier C, Neubauer A, Freund M, Kreuser ED, Dietzfelbinger H, Bodenstein H, Engert A, Stauder R, Eimermacher H, Landys K, Hiddemann W. Prednimustine, mitoxantrone (PmM) vs cyclophosphamide, vincristine, prednisone (COP) for the treatment of advanced low-grade non-Hodgkin's lymphoma. German Low-Grade Lymphoma Study Group. Leukemia. 1996 May;10(5):836-43. PubMed PMID: 8656680.

9: Zinzani PL, Barbieri E, Bendandi M, Perini F, Gherlinzoni F, Neri S, Ammendolia I, Salvucci M, Babini L, Fiacchini M, et al. CEP regimen (CCNU, etoposide, prednimustine) for relapsed/refractory Hodgkin's disease. Tumori. 1994 Dec 31;80(6):438-42. PubMed PMID: 7900233.

10: Roncadin M, Arcicasa M, Zagonel V, Bortolus R, Valeri P, Pinto A, De Paoli A, Franchin G, Carbone A, Trovò MG. Total body irradiation and prednimustine in chronic lymphocytic leukemia and low grade non-Hodgkin's lymphomas. A 9-year experience at a single institution. Cancer. 1994 Aug 1;74(3):978-84. PubMed PMID: 8039128.

11: Illés A, Bányai A, Szegedi G. [Treatment of advanced stage Hodgkin disease with CCNU, etoposide and prednimustine (CEP)]. Orv Hetil. 1994 May 29;135(22):1187-90. Review. Hungarian. PubMed PMID: 8015814.

12: Hiddemann W, Unterhalt M, Koch P, Nahler M, Herrmann R. New aspects in the treatment of advanced low-grade non-Hodgkin's lymphomas: prednimustine/mitoxantrone versus cyclophosphamide/vincristine/prednisone followed by interferon alfa versus observation only--a preliminary update of the German Low-Grade Lymphoma Study Group. Semin Hematol. 1994 Apr;31(2 Suppl 3):32-5. PubMed PMID: 8073307.

13: Tirelli U, Zagonel V, Sorio R, Errante D, Talamini R, Carbone A, Monfardini S. Mitoxantrone in combination with etoposide and prednimustine in patients older than 70 years with unfavorable non-Hodgkin's lymphoma: a prospective study in 52 patients. Semin Hematol. 1994 Apr;31(2 Suppl 3):13-22. PubMed PMID: 8073302.

14: Martin M, Diaz-Rubio E, Casado A, Valverde JJ, Garcia Urra D, López-Martin JA, Rodriguez-Lescure A. Prednimustine-induced myoclonus--a report of three cases. Acta Oncol. 1994;33(1):81-2. PubMed PMID: 8142134.

15: Alberto P. Phase II study of an oral combination of doxifluridine, prednimustine and idarubicin (FUPRIDA) for first line treatment of advanced breast cancer. Ann Oncol. 1993 May;4(5):423-5. PubMed PMID: 8353076.

16: Yosef H, Slater A, Keen CW, Bunting JS, Hope-Stone H, Parmar H, Roberts JT, Termander B, Nilsson B. Prednimustine (Sterecyt) versus cyclophosphamide both in combination with methotrexate and 5-fluorouracil in the treatment of advanced breast cancer. Eur J Cancer. 1993;29A(8):1100-5. PubMed PMID: 8518020.

17: Hatschek T, Baldetorp L, Carstensen J, Håkansson L, Möller T, Nilsson B, Termander B. Continuous versus intermittent prednimustine treatment of non-Hodgkin's lymphoma. Med Oncol Tumor Pharmacother. 1993;10(4):159-66. PubMed PMID: 8164452.

18: Freund M, Wunsch-Zeddies S, Schäfers M, Wysk J, Seidel I, Hiddemann W, Hanauske AR, Link H, Schmoll HJ, Poliwoda H. Prednimustine and mitoxantrone (PmM) in patients with low-grade malignant non-Hodgkin's lymphoma (NHL), chronic lymphocytic leukemia (CLL), and prolymphocytic leukemia (PLL). Ann Hematol. 1992 Feb;64(2):83-7. PubMed PMID: 1554799.

19: Lundberg B. Assembly of prednimustine low-density-lipoprotein complexes and their cytotoxic activity in tissue culture. Cancer Chemother Pharmacol. 1992;29(3):241-7. PubMed PMID: 1733558.

20: Musch E, Malek M, Peter-Katalinic J, Egge H, Rink H, Lathan B, Riedel E. Cellular kinetics of prednimustine versus chlorambucil plus prednisolone in vitro. Cancer Chemother Pharmacol. 1992;29(4):297-304. PubMed PMID: 1537076.