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And the fifth angel poured out his vial upon the seat of the beast; and his kingdom was full of darkness; and they gnawed their tongues for pain, and blasphemed the God of heaven because of their pains and their sores, and repented not of their deeds. (Revelation 16:10-11)
The fifth angel pours out his bowl and a great darkness covers the kingdom of the antichrist, including his ten-nation kingdom. It is also stated that they gnawed their tongues because of the pain. It’s not apparent what part of this fifth bowl judgment has caused this pain, but it very well could have been from the previous plagues. Although, it is more likely that God has intensified their sores from the first bowl judgment. Either way their pain was very severe. Refusing to repent, they blasphemed God.