| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H12Cl2N4O |
| Molecular Weight | 335.188 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NNC(=O)C1=NN(CC2=C(Cl)C=C(Cl)C=C2)C3=CC=CC=C13
InChI
InChIKey=VENCPJAAXKBIJD-UHFFFAOYSA-N
InChI=1S/C15H12Cl2N4O/c16-10-6-5-9(12(17)7-10)8-21-13-4-2-1-3-11(13)14(20-21)15(22)19-18/h1-7H,8,18H2,(H,19,22)
| Molecular Formula | C15H12Cl2N4O |
| Molecular Weight | 335.188 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Adjudin (known as AF-2364) was developed as a male contraceptive drug, which induces reversible germ cell loss from the seminiferous epithelium by disrupting cell adhesion function between Sertoli and germ cells, in particular, elongating/elongate/round spermatids and spermatocytes but not spermatogonia. This drug was in phase II clinical trial for human. In addition was discovered, that adjudin could trigger mitochondrial dysfunction in cancer cells, apparently affecting the mitochondrial mass, inducing the loss of mitochondrial membrane potential and reducing cellular ATP levels and thus could be a potential drug for cancer therapy.
Originator
Approval Year
PubMed
Sample Use Guides
in rabbits: Animals were treated intravenously or orally with 25 mg/kg per week adjudin (1 injection each week) for 4 consecutive weeks.
Route of Administration:
Other
Adjudin inhibited cell proliferation in a dose dependent manner in SGC-7901 (human gastric adenocarcinoma cell), MDA-MB-231 (human breast adenocarcinoma cell), Smmc-7721 (human hepatoma cell) and MIA Paca-2 (human pancreatic adenocarcinoma cell) cells. The IC50 of Adjudin was determined to be 58.0 µM, 13.8 µM, 72.3 µM and 52.7 µM against SGC-7901, MDA-MB-231, Smmc-7721 and MIA Paca-2 cells, respectively, after treatment for 24 h.