A controversial bailout package was passed with 229 votes, 64 votes against it and six abstentions.
Ex-finance minister Yanis Varoufakis and the current Energy Minister Panagiotis Lafazanis, Deputy Labour Minister Dimitris Stratoulis and speaker of parliament Zoe Constantopoulou all voted against the deal.
The Greek Parliament has approved a package of bailout measures following a vote by the country's MPs.
Greece' Prime Minister has made a last ditch appeal to parliament asking for support of the tough package of bailout measures imposed by European partners.
Alexis Tsipras told lawmakers there was no alternative, even though he disagreed with the measures.
"We don't believe in it, but we are forced to adopt it," he said.
Greek Prime Minister Alexis Tsipras has told MPs that they are called on to take a decision with responsibility in address to parliament.
New footage shows protesters hurling petrol bombs at riot police outside the Greek parliament in Athens.
The clashes come as MPs inside the building prepare to vote on a bailout package that would see the country forced to impose a new range of austerity measures.
Police responded with tear gas, sending hundreds of people running from the square and ending the brief violence.
At least 31 protesters have been detained following the clashes, while there are no reports of any serious injuries.
Protesters have been involved in violent clashes with police as a debate on a controversial bailout package gets underway - watch live footage from outside the Greek Parliament:
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Riot police have been pictured tackling petrol bombs thrown at them by protesters as violence erupted outside the Greek parliament.
Protesters and riot police have clashed in a square outside Greece's parliament ahead of a debate on a bailout package for the country.
Petrol bombs were thrown at officers by a small number of anti-austerity demonstrators, while tear gas appeared to fired in an effort to disperse crowds.
The clashes follow peaceful protests earlier in the day over the additional austerity measures due to be included in the deal with Greece's international creditors.
Greece's proposed bailout deal is like the Versailles treaty which led to the rise of Adolf Hitler, former finance minister Yanis Varoufakis has claimed.
Varoufakis, who resigned last week citing complaints from European creditors over his combative style of negotiation, quoted a famous British economist in a statement to MPs that was met by heckling from some areas of the room.
"'The powerful demanded that the losers accept terms they had no right to demand. The losers accepted commitments they had no right to accept'.
"These were the words of John Maynard Keynes on the Versailles Treaty. What we are confronted with is a new Versailles Treaty."
However, he did not say whether he would vote against the proposed agreement, or even if he would attend.
In the 1919 Treaty of Versailles, Germany was forced to pay crippling reparations as the price of defeat in World War One - a factor historians attribute to the rise of Hitler's Nazi party.
Asked earlier this week whether she thought there were similarities between the Greek deal and Versailles, German Chancellor said she would not take part in historical comparisons "especially when I didn't make them myself".