Synonym
Bromofosfamide; KM 135; KM-135; KM135;
IUPAC/Chemical Name
2-((2-bromoethyl)amino)-3-(2-chloroethyl)-1,3,2-oxazaphosphinane 2-oxide
InChi Key
ZJVAVRRLTFVZIP-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H15BrClN2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)
SMILES Code
C1CN(P(=O)(OC1)NCCBr)CCCl
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Biological target:
Bromofosfamide, also known KM-135, is an alkylating agent with antitumor activity.
In vitro activity:
Combination of CY or CBM-11 with 6-7 p.t. injections of IL-2-secreting cells resulted in potentiation of the therapeutic effects: TGD and ILS values were considerably increased and long-lasting CRs were observed. The overall incidence of CR after combined treatment was ca 16% and 42% for CY and CBM-11, respectively (P=0.049).
Reference: Med Oncol. 1999 Dec;16(4):267-78. https://pubmed.ncbi.nlm.nih.gov/10618690/
In vivo activity:
(S)-(-)-Bromofosfamide (CBM-11), an enantiomerically pure bromo analog of ifosfamide, was found to be potent against several model tumors in mice. Therapeutic indices of CBM-11 were more favorable as compared to those received for ifosfamide.
Reference: Anticancer Drugs. 2001 Jun;12(5):453-8. https://pubmed.ncbi.nlm.nih.gov/11505792/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
305.54
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:
1. Kusnierczyk H, Pajtasz-Piasecka E, Radzikowski C. Synergistic antitumour effects of chemo-immunotherapy with an oxazaphosphorine drug and IL-2-secreting cells in a mouse colon cancer model. Med Oncol. 1999 Dec;16(4):267-78. doi: 10.1007/BF02785873. PMID: 10618690.
2. Misiura K, Kinas RW, Kuśnierczyk H, Radzikowski C, Stec WJ. (S)-(-)-Bromofosfamide (CBM-11): synthesis and antitumor activity and toxicity in mice. Anticancer Drugs. 2001 Jun;12(5):453-8. doi: 10.1097/00001813-200106000-00006. PMID: 11395573.
In vitro protocol:
1. Kusnierczyk H, Pajtasz-Piasecka E, Radzikowski C. Synergistic antitumour effects of chemo-immunotherapy with an oxazaphosphorine drug and IL-2-secreting cells in a mouse colon cancer model. Med Oncol. 1999 Dec;16(4):267-78. doi: 10.1007/BF02785873. PMID: 10618690.
In vivo protocol:
1. Misiura K, Kinas RW, Kuśnierczyk H, Radzikowski C, Stec WJ. (S)-(-)-Bromofosfamide (CBM-11): synthesis and antitumor activity and toxicity in mice. Anticancer Drugs. 2001 Jun;12(5):453-8. doi: 10.1097/00001813-200106000-00006. PMID: 11395573.
1: Liang J, Huang M, Duan W, Yu XQ, Zhou S. Design of new oxazaphosphorine anticancer drugs. Curr Pharm Des. 2007;13(9):963-78. doi: 10.2174/138161207780414296. PMID: 17430192.
2: Misiura K. Leki oksazafosforinanowe. Poszukiwanie nowych pochodnych, badania metabolizmu i stosowanie nowych strategii terapeutycznych terapeutycznych [Oxazaphosphorinane drugs. New analogues, metabolic studies, and therapeutic approaches]. Postepy Hig Med Dosw (Online). 2004;58:463-71. Polish. PMID: 15599340.
3: Misiura K. Synthesis of potential metabolites of (S)-(-)-bromofosfamide. Pharmazie. 2004 Sep;59(9):668-72. PMID: 15497745.
4: Kobylińska K, Koralewski P, Sobik B, Gasiorek M, Kobylińska M. Pharmacokinetics and toxicity of oral (-)-(S)-bromofosfamide in lung cancer patients. Arzneimittelforschung. 2001;51(7):600-3. doi: 10.1055/s-0031-1300086. PMID: 11505793.
5: Kobylińska K, Kobylińska M, Sobik B. Pharmacokinetics of (-)-(S)-bromofosfamide after intravenous and oral administration in mice. Arzneimittelforschung. 2001;51(7):596-9. doi: 10.1055/s-0031-1300085. PMID: 11505792.
6: Misiura K, Kinas RW, Kuśnierczyk H, Radzikowski C, Stec WJ. (S)-(-)-Bromofosfamide (CBM-11): synthesis and antitumor activity and toxicity in mice. Anticancer Drugs. 2001 Jun;12(5):453-8. doi: 10.1097/00001813-200106000-00006. PMID: 11395573.
7: Kusnierczyk H, Pajtasz-Piasecka E, Radzikowski C. Synergistic antitumour effects of chemo-immunotherapy with an oxazaphosphorine drug and IL-2-secreting cells in a mouse colon cancer model. Med Oncol. 1999 Dec;16(4):267-78. doi: 10.1007/BF02785873. PMID: 10618690.
8: Sloderbach A, Hładoń B, Sochacki M, Kinas R, Kuśnierczyk H, Laskowska H. Pharmacokinetic-stereoselective differentiation of some isomeric analogues of ifosfamide. Pol J Pharmacol. 1997 Nov-Dec;49(6):463-9. PMID: 9566050.
9: Kuśnierczyk H, Konarski L, Kowalski P, Radzikowski C. Influence of mesna on urotoxic effects of selected bromosubstituted analogs of ifosfamide. Arch Immunol Ther Exp (Warsz). 1997;45(1):79-85. PMID: 9090445.
10: Sloderbach A, Hładoń B, Laskowska H. Pharmacokinetics and bioavailability of stereoisomeric analogues of ifosfamide. Acta Physiol Hung. 1996;84(4):459-60. PMID: 9328631.
11: Studzian K, Kinas R, Ciesielska E, Szmigiero L. Effects of alkylating metabolites of ifosfamide and its bromo analogues on DNA of HeLa cells. Biochem Pharmacol. 1992 Mar 3;43(5):937-43. doi: 10.1016/0006-2952(92)90596-b. PMID: 1554391.
