Synonym
FK 317 dihydrobenzoxazine; FK-317 dihydrobenzoxazine; FK317 dihydrobenzoxazine; FR 073317
IUPAC/Chemical Name
(1aS,8R,9aS)-1-acetyl-8-((carbamoyloxy)methyl)-5-formyl-7-methoxy-1,1a,2,9a-tetrahydro-3,9-epoxyazirino[2,3-f]benzo[b]azocin-9(8H)-yl acetate
InChi Key
BUZDGGFWWPZBIN-DHZLCAPXSA-N
InChi Code
InChI=1S/C19H21N3O8/c1-9(24)22-14-6-21-13-4-11(7-23)5-15(27-3)16(13)12(8-28-18(20)26)19(30-21,17(14)22)29-10(2)25/h4-5,7,12,14,17H,6,8H2,1-3H3,(H2,20,26)/t12-,14-,17-,19?,22?/m0/s1
SMILES Code
COc1cc(C=O)cc2N3C[C@H]4[C@H](N4C(=O)C)C(OC(=O)C)(O3)[C@@H](COC(=O)N)c12
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
419.39
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 |
1. Naoe Y, Inami M, Matsumoto S, Takagaki S, Fujiwara T, Yamazaki S, Kawamura I, Nishigaki F, Tsujimoto S, Manda T, Shimomura K. FK317, a novel substituted dihydrobenzoxazine, exhibits potent antitumor activity against human tumor xenografts in nude mice. Jpn J Cancer Res. 1998 Dec;89(12):1306-17. doi: 10.1111/j.1349-7006.1998.tb00528.x. PMID: 10081492; PMCID: PMC5921730.
2. Beckerbauer L, Tepe JJ, Eastman RA, Mixter PF, Williams RM, Reeves R. Differential effects of FR900482 and FK317 on apoptosis, IL-2 gene expression, and induction of vascular leak syndrome. Chem Biol. 2002 Apr;9(4):427-41. doi: 10.1016/s1074-5521(02)00122-9. PMID: 11983332.
3. Naoe Y, Inami M, Kawamura I, Nishigaki F, Tsujimoto S, Matsumoto S, Manda T, Shimomura K. Cytotoxic mechanisms of FK317, a new class of bioreductive agent with potent antitumor activity. Jpn J Cancer Res. 1998 Jun;89(6):666-72. doi: 10.1111/j.1349-7006.1998.tb03269.x. PMID: 9703365; PMCID: PMC5921879.
4. Williams RM, Ducept P. Interstrand cross-linking of DNA by FK317 and its deacetylated metabolites FR70496 and FR157471. Biochemistry. 2003 Dec 16;42(49):14696-701. doi: 10.1021/bi035202x. PMID: 14661983.
