The nearly two-minute web ad
by former U.S. Attorney Conner Eldridge pieces together clips from Trump's long history of inflammatory remarks about women, including going back to old Howard Stern radio shows and footage from "The Apprentice" of Trump dissecting women's attractiveness.
The provocative ad overlays text of a dictionary definition of harassment as it plays footage and audio of Trump saying things such as describing a woman who "ate like a pig," that flat-chested women rarely can be a "10" and ends with him unwilling to say he respects women.
It also uses statements from this election cycle, including his comment that Fox News anchor Megyn Kelly had "blood coming out of her ... wherever."
Eldridge then ties Trump to his opponent, Arkansas Republican Sen. John Boozman, playing a clip of Boozman saying he'd support the eventual Republican nominee for president, even if it was Trump.
The ad, which the campaign says will run on Facebook, also highlights Eldridge's background as a prosecutor and says he fought domestic violence cases.
Eldridge's campaign did not release whether the ad was a paid Facebook buy or how much was behind it. Campaigns often release low-budget digital videos to get extra ad time through media coverage.
Boozman's campaign did not immediately respond to a request for comment.
Trump, for his part, has maintained that he is well-liked among women, saying he cherishes them.
"I cherish women. And will protect women. And take care of women. And I have great respect for women," Trump said
after a dust-up with GOP candidate Carly Fiorina last fall.
Republicans have feared that the GOP front-runner could harm vulnerable Senate incumbents from battleground states this November, while Democrats have looked to capitalize on the polarizing mogul's statements.
Trump has struggled among women voters. In a March CNN/ORC poll, 73% of women viewed him negatively.