Photodynamic therapy (PDT) is a medical treatment using laser and photosensitizing drug taken up to destroy cancer cells. Singlet oxygen ($^1$0$_2$) generation is strongly related to this treatment. We have built a direct detection system monitoring feeble luminescence, in the near IR region, from $^1$0$_2$, We have comparatively studied the photophysical and photochemical properties in solution of a newly developed drug ATX-S10 and Photofrin already investigated clinically. We demonstrdted that ATX-S10 was capable of efficiently yielding $^1$0$_2$, which may lead to highly efficient PDT treatment. Successive laser excitation photobleached ATX -S10 readily in a dose-dependent manner. This result shows that ATX -S10 is useful in setting up suitable medical treatment conditions to minimize side effects.