Israel has struck the infamous Evin Prison in Tehran, Israeli officials confirmed to The Jerusalem Post on Monday.
Footage from the attack shows one strike hitting the entrance gate to the prison.
Iran's judiciary confirmed the prison had been hit but said the situation was under control, according to Iranian media.
The strike was deliberately targeted at the entrance gate so as to avoid hitting the inmate housing, Iran International reported.
Evin Prison played a role in the 1979 Revolution
Evin Prison holds many Iranian political prisoners and is where many of the anti-regime protesters are sent following arrest.
It has become infamous due to allegations of torture and sexual abuse perpetrated by prison guards, with many of the 2009 protesters in Iran directly accusing prison officials of raping male and female prisoners.
Rape has featured prominently in the Islamic Republic's prisons dating back to the 1980s, with anti-regime protesters describing it as routine. The Islamic Republic's theological view is that rape victims cannot enter Heaven.
The prison dates back to the time of the Shah's regime, where it was notably smaller but served the same purpose of holding and torturing political prisoners and was run by the SAVAK secret police.
The prison played an important part in the 1979 Iranian Revolution, when its storming led to the release of thousands of anti-Shah dissidents, fueling the ongoing revolution.
Israeli strikes on the Basiji headquarters in Tehran
Strikes also targeted the Basiji headquarters in Tehran. The Organization for Mobilization of the Oppressed (Basiji) functions as the Islamic Republic's paramilitary volunteer militia. It acts to suppress opposition to the regime, often violently.
The Basiji are officially the paramilitary wing of the Islamic Revolutionary Guard Corps and are allegedly run directly by Ayatollah Ali Khamenei's son and possible successor, Mojtaba Khamenei.