Appears 4 times in the Quran.
11:77 وَلَمَّا جَآءَتْ رُسُلُنَا لُوطًا سِىٓءَ بِهِمْ وَضَاقَ بِهِمْ ذَرْعًا وَقَالَ هَٰذَا يَوْمٌ عَصِيبٌ
And when Our messengers came to Lut, he was grieved for them, and he lacked strength to protect them, and said: This is a hard day.
18:18 وَتَحْسَبُهُمْ أَيْقَاظًا وَهُمْ رُقُودٌ وَنُقَلِّبُهُمْ ذَاتَ ٱلْيَمِينِ وَذَاتَ ٱلشِّمَالِ وَكَلْبُهُم بَٰسِطٌ ذِرَاعَيْهِ بِٱلْوَصِيدِ لَوِ ٱطَّلَعْتَ عَلَيْهِمْ لَوَلَّيْتَ مِنْهُمْ فِرَارًا وَلَمُلِئْتَ مِنْهُمْ رُعْبًا
And you might think them awake while they were asleep and We turned them about to the right and to the left, while their dog (lay) outstretching its paws at the entrance; if you looked at them you would certainly turn back from them in flight, and you would certainly be filled with awe because of them.
29:33 وَلَمَّآ أَن جَآءَتْ رُسُلُنَا لُوطًا سِىٓءَ بِهِمْ وَضَاقَ بِهِمْ ذَرْعًا وَقَالُوا۟ لَا تَخَفْ وَلَا تَحْزَنْ إِنَّا مُنَجُّوكَ وَأَهْلَكَ إِلَّا ٱمْرَأَتَكَ كَانَتْ مِنَ ٱلْغَٰبِرِينَ
And when Our messengers came to Lut he was grieved on account of them, and he felt powerless (to protect) them; and they said: Fear not, nor grieve; surely we will deliver you and your followers, except your wife; she shall be of those who remain behind.
Then thrust him into a chain the length of which is seventy cubits.