Evofosfamide (TH-302)

Catalog No.S2757 Synonyms: Evofosfamide

For research use only.

Evofosfamide (TH-302) is selective hypoxia-activated prodrug targeting hypoxic regions of solid tumors with IC50 of 19 nM, demonstrates 270-fold enhanced cytotoxicity under hypoxia versus their potency under aerobic conditions, stable to cytochrome P450 metabolism.

Evofosfamide (TH-302) Chemical Structure

CAS No. 918633-87-1

Selleck's Evofosfamide (TH-302) has been cited by 2 Publications

Purity & Quality Control

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Biological Activity

Description Evofosfamide (TH-302) is selective hypoxia-activated prodrug targeting hypoxic regions of solid tumors with IC50 of 19 nM, demonstrates 270-fold enhanced cytotoxicity under hypoxia versus their potency under aerobic conditions, stable to cytochrome P450 metabolism.
In vitro

TH-302 is selectively potent under hypoxia and stable to liver microsomes. Substitution of the chlorine with bromine on the phosphorus mustard in 3b increases the potency by 10-fold and maintaines the high hypoxic selectivity [Hypoxia cytotoxicity ratio (HCR) = 270]. In both human lung cancer H460 cells and human colon cancer HT29 cells, potent cytotoxicity of TH-302 is observed under N2. TH-302 inhibits H460 cells and HT29 cells with IC90 of 0.1 μM and 0.2 μM, respectively. [1] TH-302 shows much enhanced potency in H460 spheroids compared to H460 monolayer cells under normoxia. [2] TH-302 exhibits potent cytotoxicity to MM cells with hypoxic selectivity and dose dependency. TH-302 can induce G0/G1 cell-cycle arrest under hypoxic conditions. The effect of TH-302 on cell-cycle machinery is mediated by down-regulating cyclin D1/2/3, CDK4/6, p21cip-1, p27kip-1, and pRb expression, whereas CDK2 expression remained undisturbed. TH-302 can induce dose-dependent apoptosis in both human and murine MM cells in hypoxic conditions. TH-302-activated apoptosis is mediated through down-regulating the antiapoptotic proteins BCL-2 and BCL-xL, as well as up-regulating the expression of cleaved proapoptotic protein caspase-3, -8, and -9 and poly ADP-ribose polymerase. In contrast to the hypoxia-specific toxicity, TH-302 shows very low toxicity in normoxic condition, even at high concentrations. [3]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
H460 MofDR5l1d3SxeHnjbZR6KGG|c3H5 MkPWNkBpenN? NHnI[lZEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBJPDZyIHPlcIx{KHWwZHXyJIh6eG:6aXOgZ49v\Gm2aX;uJIFnfGW{IEKgbJJ{KGK7IFHsZY1ieiCkbIXlJJN1[WmwaX7nJIF{e2G7LDDJR|UxRTBwMEG5{txONg>? MWW8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8yQDJ3N{W0OEc,OTh{NUe1OFQ9N2F-
H460 NIPabHhEgXSxdH;4bYNqfHliYYPzZZk> MljUNkBpenN? NEfHVIpEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBJPDZyIHPlcIx{KHWwZHXyJIh6eG:6aXOgZ49v\Gm2aX;uJIFnfGW{IEKgbJJ{KGK7IHPsc45w\2WwaXOgZZN{[XluIFnDPVA:OC5zzszNMi=> MV28ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8yQDJ3N{W0OEc,OTh{NUe1OFQ9N2F-
HT29 NV\POXlMS3m2b4TvfIlkcXS7IHHzd4F6 MXGyJIhzew>? NHrLRmpEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBJXDJ7IHPlcIx{KHWwZHXyJIh6eG:6aXOgZ49v\Gm2aX;uJIFnfGW{IEKgbJJ{KGK7IHPsc45w\2WwaXOgZZN{[XluIFnDPVA:OC5{zszNMi=> M1\HT|xiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF6MkW3OVQ1Lz5zOEK1O|U1PDxxYU6=
H460 M4fEZ2N6fG:2b4jpZ4l1gSCjc4PhfS=> MlnJNkBpenN? NWfqTJI4S3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hUDR4MDDj[YxteyC3bnTldkBvd3Kvb4jpZ{Bkd26maYTpc44h[W[2ZYKgNkBpenNiYomgRYxidWG{IHLseYUhe3SjaX7pcoch[XO|YYmsJGlEPTB;NT6x{txONg>? M2PtO|xiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF6MkW3OVQ1Lz5zOEK1O|U1PDxxYU6=
H460 NUnIXXpvS3m2b4TvfIlkcXS7IHHzd4F6 MVGyJIhzew>? M2LFN2N6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGg1PjBiY3XscJMhfW6mZYKgco9zdW:6aXOgZ49v\Gm2aX;uJIFnfGW{IEKgbJJ{KGK7IHPsc45w\2WwaXOgZZN{[XluIFnDPVA:OzEQvF2u M{HHe|xiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF6MkW3OVQ1Lz5zOEK1O|U1PDxxYU6=
HT29 M3:yUGN6fG:2b4jpZ4l1gSCjc4PhfS=> NH;VV2kzKGi{cx?= MlPuR5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gTHQzQSClZXzsd{B2dmSncjDuc5Jud3irYzDjc45lcXSrb36gZYZ1\XJiMjDodpMh[nliY3zvco9o\W6rYzDhd5NigSxiSVO5NF01OM7:TT6= NEfiW4g9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9zOEK1O|U1PCd-MUiyOVc2PDR:L3G+
NCI-H460 NFX4R|hEgXSxdH;4bYNqfHliYYPzZZk> NWTLTpdMOjRiaILz NELBSppEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBPS0lvSES2NEBk\WyuczDwdoV1emWjdHXkJIZweiB{NDDodpMhfW6mZYKgbJlxd3irYzDjc45lcXSrb36g[o9tdG:5ZXSgZpkh[2:vcH;1coQhf2G|aH;1eEBu\WG|dYLl[EBi\nSncjC3NkBpenNiYomgUXRVKGG|c3H5MEBKSzVyPUmuNFjPxE1w NHXSZnY9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{OEO1NFk6Pyd-MkizOVA6QTd:L3G+
HT-29 NHXQNFZEgXSxdH;4bYNqfHliYYPzZZk> Mln0NlQhcHK| NX;xPVFJS3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hUFRvMkmgZ4VtdHNicILleJJm[XSnZDDmc5IhOjRiaILzJJVv\GW{IHj5dI95cWNiY3;u[Il1cW:wIH\vcIxwf2WmIHL5JINwdXCxdX7kJJdie2ixdYSgcYVie3W{ZXSgZYZ1\XJiN{KgbJJ{KGK7IF3UWEBie3OjeTygTWM2OD12OT61Ne69VS5? MnizQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOjh|NUC5PVcoRjJ6M{WwPVk4RC:jPh?=
NCI-H460 NFHE[GREgXSxdH;4bYNqfHliYYPzZZk> NIn3dWYzPCCqcoO= NXXFd5ZSS3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hVkOLLVi0OlAh[2WubIOgZYZ1\XJiMkSgbJJ{KHWwZHXyJIh6eG:6aXOgZ49v\Gm2aX;uJIJ6KGy3bXnu[ZNk\W6lZT3iZZNm\CCFZXzsMXRqfGW{IFfsc{Bie3OjeTygTWM2OD1yLkCwPVPPxE1w NX\6VnhqRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMkmwO|k1PzRpPkK5NFc6PDd2PD;hQi=>
NCI-H460 NVfVfpVpS3m2b4TvfIlkcXS7IHHzd4F6 NEX3OVMzPCCqcoO= MnS2R5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gUmNKNUh2NkCgZ4VtdHNiYX\0[ZIhOjRiaILzJJVv\GW{IH7vdo1wgGmlIHPvcoRqfGmxbjDifUBtfW2rbnXzZ4Vv[2VvYnHz[YQhS2WubD3UbZRmeiCJbH:gZZN{[XluIFnDOVA:Pi54Nd88UU4> NH64Zmo9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{OUC3PVQ4PCd-MkmwO|k1PzR:L3G+
DU145 M2qzZ2N6fG:2b4jpZ4l1gSCjc4PhfS=> NWLuVmw2OiCqcoO= MWfDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDEWVE1PSClZXzsd{BqdmO3YnH0[YQh\m:{IEKgbJJ{KHWwZHXyJIh6eG:6aXOgZ49v\Gm2aX;uJI1m[XO3cnXkJIFnfGW{IEeyJIhzeyCkeTDBcIFu[XJiYnz1[UBie3OjeTygTWM2OD12LkG0{txONg>? MYW8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zQTJ3OUe0Okc,Ojl{NUm3OFY9N2F-
PC3 NU[1NmRIS3m2b4TvfIlkcXS7IHHzd4F6 M133c|IhcHK| M3;SXWN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJHBEOyClZXzsd{BqdmO3YnH0[YQh\m:{IEKgbJJ{KHWwZHXyJIh6eG:6aXOgZ49v\Gm2aX;uJI1m[XO3cnXkJIFnfGW{IEeyJIhzeyCkeTDBcIFu[XJiYnz1[UBie3OjeTygTWM2OD14LkS5{txONg>? NE\acoU9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9{OUK1PVc1Pid-MkmyOVk4PDZ:L3G+
HEMC-SS MYDBcpRqeHKxbHnm[ZJifGm4ZTDhd5NigQ>? M4HwO|I1KGi{cx?= MX3BcpRqeHKxbHnm[ZJifGm4ZTDhZ5Rqfmm2eTDh[4FqdnO2IHj1cYFvKEiHTVOtV3Mh[2WubIOgeJJm[XSnZDDmc5IhOjRiaILzJJVv\GW{IHj5dI95cWNiY3;u[Il1cW:wIH\vcIxwf2WmIHL5JINwdXCxdX7kJJdie2hvb4X0JIFv\CCrbnP1ZoF1\WRidX7k[ZIhdm:{bX;4bYMh[2:wZHn0bY9vKG[xcjC0PEBpenNiYomgZYxidWG{IHLseYUh[XO|YYmsJGlEPTB;MD6xN:69VS5? M2LJcFxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzNyMUm5O|A2Lz5|MEG5PVcxPTxxYU6=
HEMC-SS MmrORY51cXC{b3zp[oVz[XSrdnWgZZN{[Xl? Ml\sNlQhcHK| M3XURWFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4SgbJVu[W5iSFXNR{1UWyClZXzsd{B1emWjdHXkJIZweiB{NDDodpMhfW6mZYKgco9zdW:6aXOgZ49v\Gm2aX;uJIZwdGyxd3XkJIJ6KGOxbYDveY5lKHejc3itc5V1KGGwZDDpcoN2[mG2ZXSgeY5l\XJibn;ycY95cWNiY3;u[Il1cW:wIH\vdkA1QCCqcoOgZpkh[WyjbXHyJIJtfWViYYPzZZktKEmFNUC9Nk46|ryPLh?= NHy4Tpk9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9|MEG5PVcxPSd-M{CxPVk4ODV:L3G+
NCI-H460 NFzYfG9CdnSrcILvcIln\XKjdHn2[UBie3OjeR?= MX\BcpRqeHKxbHnm[ZJifGm4ZTDhZ5Rqfmm2eTDh[4FqdnO2IHj1cYFvKE6FST3IOFYxKGOnbHzzJIlvKHC{ZYPlcoNmKG:oIF6yMEBKSzVyPUNOwG0v MVG8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8{ODJ7NUS3O{c,OzB{OUW0O|c9N2F-
NCI-H460 NH7HTYpCdnSrcILvcIln\XKjdHn2[UBie3OjeR?= MYXBcpRqeHKxbHnm[ZJifGm4ZTDhZ5Rqfmm2eTDh[4FqdnO2IHj1cYFvKE6FST3IOFYxKGOnbHzzJIlvKHC{ZYPlcoNmKG:oIF:yMEBKSzVyPUK1{txONg>? NIHZTZc9[SC2YYLn[ZQ:L1:kbHHub{chcHKnZk2nbJR1eHN8Lz;weYJu\WRwbnPibU5vdG1wbnnoModwfi9|MEK5OVQ4Pyd-M{CyPVU1Pzd:L3G+
MDA-MB-468 M{jSZmN6fG:2b4jpZ4l1gSCjc4PhfS=> MWi0JIhzew>? M{f3OmN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJG1FSS2PQj20Olgh[2WubIOgbY5kfWKjdHXkJIZweiB2IHjyd{B2dmSncjDofZBwgGmlIHPvcoRqfGmxbjDmc4xtd3enZDDifUBkd22yb4Xu[EB4[XOqb4X0JIFv\CCvZXHzeZJm\CCjZoTldkA2KGSjeYOgZpkhW1KEIHHzd4F6NCCLQ{WwQVAvODB4Mt88UU4> MYS8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8{ODh6NU[4NEc,OzB6OEW2PFA9N2F-
SW620 NF\pXHJEgXSxdH;4bYNqfHliYYPzZZk> M{[4XVQhcHK| NWOyTmRoS3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hW1d4MkCgZ4VtdHNiaX7jeYJifGWmIH\vdkA1KGi{czD1coRmeiCqeYDvfIlkKGOxbnTpeIlwdiCob3zsc5dm\CCkeTDjc41xd3WwZDD3ZZNpd3W2IHHu[EBu\WG|dYLl[EBi\nSncjC1JIRigXNiYomgV3JDKGG|c3H5MEBKSzVyPUCuNFUz|ryPLh?= Mn3BQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOzB6OEW2PFAoRjNyOEi1OlgxRC:jPh?=
MDA-MB-468 NF\6dnJEgXSxdH;4bYNqfHliYYPzZZk> MVu0JIhzew>? NFzodZNEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBOTEFvTVKtOFY5KGOnbHzzJIlv[3WkYYTl[EBnd3JiNDDodpMhfW6mZYKgZYVzd2KrYzDjc45lcXSrb36g[o9tdG:5ZXSgZpkh[2:vcH;1coQhf2G|aH;1eEBidmRibXXhd5Vz\WRiYX\0[ZIhPSCmYYnzJIJ6KFOUQjDhd5NigSxiSVO1NF01NjRyM988UU4> MWi8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8{ODh6NU[4NEc,OzB6OEW2PFA9N2F-
SW620 NU[5NHpCS3m2b4TvfIlkcXS7IHHzd4F6 MkDTOEBpenN? MVzDfZRwfG:6aXPpeJkh[WejaX7zeEBpfW2jbjDTW|YzOCClZXzsd{BqdmO3YnH0[YQh\m:{IESgbJJ{KHWwZHXyJIFmem:kaXOgZ49v\Gm2aX;uJIZwdGyxd3XkJIJ6KGOxbYDveY5lKHejc3jveZQh[W6mIH3lZZN2emWmIHHmeIVzKDViZHH5d{BjgSCVUlKgZZN{[XluIFnDOVA:OjBwNt88UU4> MoXBQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOzB6OEW2PFAoRjNyOEi1OlgxRC:jPh?=
In vivo TH302 inhibits primary tumor growth by 41% on day 25 after implantation, whereas TH302 plus gemcitabine (a nucleoside analog) inhibits primary tumor growth by 96% on day 25. [1] When TH-302 is administered at 6.25, 12.5, 25, or 50 mg/kg in the H460 NSCLC xenograft model QD × 5/wk × 2 wks (once a day for 5 days per week for 2 weeks) i.p., the tumor growth inhibition at Day 22 is 43%, 51%, 75%, and 89%, respectively. TH-302 at 100 mg/kg shows a decrease in blood cell counts 3 days after treatment end, but is totally recovered 7 days post-treatment. TH-302 under all tested regimens exhibits efficacy metrics ranging from 58% to 89% tumor growth inhibition. TH-302 induced cell killing is breathing oxygen concentration dependent, with the greatest cytotoxicity occurring when the tumor-bearing mice are exposed to low oxygen concentrations. Tumor growth is significantly reduced by TH-302 in animals breathing 10% O2 compared with 95% O2 breathing. After TH-302 treatment, the pimonidazole-positive area is significantly decreased at 48 hours after dosing (6.3 % in vehicle vs. 1.8 % in the TH-302 treatment group). [4]

Protocol (from reference)

Cell Research:[1]
  • Cell lines: Human H460 or HT29 cells
  • Concentrations: 0.01 -1 μM
  • Incubation Time: 2 hours
  • Method: Exponentially growing human H460 or HT29 cells are seeded into 60 mm notched glass plates at 3 × 105 cells per plate and grown in RPMI medium supplemented with 10% fetal bovine serum for 2 days prior to initiating treatment. On the day of the test, TH-302 stocks of known concentrations are prepared in complete medium and 2 mL of the desired stock is added to each plate. The plates are placed in either an anaerobic chamber or a standard tissue-culture incubator. The anaerobic chamber is evacuated and gassed with the anaerobic gas mixture (90% N2/5% CO2/5% H2) to create a hypoxic environment. Cells are then incubated with TH-302 for 2 hours at 37 °C. At the end of treatment, plates are removed from each vessel and washed with phosphate-buffered saline and a solution of trypsin-EDTA and then trypsinized for 5 min at 37 °C. Detached cells are neutralized with medium plus serum and spun for 5 min at 100g. Cells are resuspended at approximately 1 × 106 cells/mL and diluted 10-fold for plating. The exact concentration of each stock is determined. Known numbers of cells are plated and placed undisturbed in an incubator for between 9 and 13 days. Colonies are fixed and stained with a solution of 95% ethanol with 0.25% crystal violet stain. Colonies of greater than 50 cells are counted, and the surviving fraction is determined. Plating efficiencies (PEs) are determined by dividing the number of colonies by the actual number of cells plated. Surviving fractions are calculated by dividing the PEs of treated cells by the PEs of untreate
Animal Research:[4]
  • Animal Models: H460, Calu-6, PC-3, H82, A375, Stew2, 786-O, PLC/PRF/5, Hs766t, BxPC-3, and SU.86.86 xenografts are established in NCI SCID female mice.
  • Dosages: 50 mg/kg
  • Administration: Intraperitoneally

Solubility (25°C)

In vitro

In vivo

Add solvents to the product individually and in order
(Data is from Selleck tests instead of citations):
30% propylene glycol, 5% Tween 80, 65% D5W
For best results, use promptly after mixing.

30 mg/mL

Chemical Information

Molecular Weight 449.04
Formula

C9H16Br2N5O4P

CAS No. 918633-87-1
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CN1C(=CN=C1[N+](=O)[O-])COP(=O)(NCCBr)NCCBr

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Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02020226 Unknown status Drug: TH-302 Solid Tumors Threshold Pharmaceuticals November 2013 Phase 1
NCT01833546 Completed Drug: Evofosfamide|Drug: Gemcitabine Solid Tumor|Pancreatic Cancer Merck KGaA Darmstadt Germany|Threshold Pharmaceuticals April 18 2013 Phase 1

(data from https://clinicaltrials.gov, updated on 2022-01-17)

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