UPDATE: Frank Artiles resigned his Florida Senate seat Friday morning, unable to recover from a flurry of insenstive remarks directed at fellow lawmakers and lobbyists. 

"It is clear to me my recent actions and words that I spoke fell far short of what I expect for myself, and for this I am very sorry," Artiles wrote in his resignation letter. "I apologize to my family and friends and I apologize to all of my fellow Senators and lawmakers. To the people of my district and all of Miami-Dade, I am sorry I have let you down and ask for your forgiveness."

Artiles apologized Wednesday for derogatory comments about two colleagues but it was not enough. In his resignation letter, Artiles recognized his behavior had become too big a distraction from important matters of government. 

"My actions and my presence in government is now a distraction to my colleagues, the legislative process, and the citizens of our great State," Artiles wrote.

Artiles, a Miami Republican, reportedly referred to fellow Senators as “niggas” during a round of drinks at the Governor’s Club earlier this week in Tallahassee. He also called Senate President Joe Negron a "pussy," sources say. 

In a three minute statement inside the Senate chamber, Artiles attempted to correct course, offering “a heartfelt apology to my colleagues and to all of those I have offended. My harsh words have adversely reflected more on me than they could ever on anyone else.”

A Cuban-American who has served in the U.S. Marine Corps, Artiles is no stranger to controversy. As a member of the Florida House, Artiles introduced the notorious “bathroom bill” targeting transgender people and, in a separate incident, was accused of punching a man in the face at a Tallahassee bar. 

Representative Carlos Guillermo Smith (D-Orlando) was one of the first to call for Artiles' resignation. Smith, Florida’s first LGBT Latino legislator, said Artiles also owes transgender Floridians an apology. 

“After apologizing for his racist comments, he should apologize to the transgender community for his bigotry + transphobia,” Smith tweeted. 

The Miami Herald reports Artiles called members of his own party “niggas” and then hurled inflammatory comments at Sen. Audrey Gibson, a Jacksonville Democrat. Artiles reportedly called Gibson a “bitch” among other things.

The incident occurred at a private club steps away from the state capitol building in Tallahassee. SAVE, a South Florida human rights organization, sent out an email on Wednesday citing a St. Petersburg blog's report that Artiles called two lobbyists "faggots" after leaving the club. Before his apology on Wednesday, Artiles was removed as chairman of the Senate’s communications, energy and public utilities committee. 

Senator Perry Thurston (D-Plantation) said Artiles’ apology was “too little, too late." Speaking at Florida Legislature Black Caucus press conference, Thurston said Artiles had failed to learn "the values of respect and dignity owed to members of which he serves."

Artiles represented western parts of Miami-Dade County in the Florida Senate. He is a licensed general contractor, public adjuster and military veteran who saw action in the 2003 Operation Iraqi Freedom campaign.