5 occurrences across the corpus

King James Version

Psalms 73:16

When I thought to know this, it was too painful for me;

KJV Apocrypha (Catholic Deuterocanon)

2 Maccabees 2:26

Therefore to us, that have taken upon us this painful labour of abridging, it was not easy, but a matter of sweat and watching;

KJV Apocrypha (Eastern Orthodox Additions)

2 Esdras 7:12

Then were the entrances of this world made narrow, full of sorrow and travail: they are but few and evil, full of perils,: and very painful.

OT Pseudepigrapha

The Letter of Aristeas 4:21

For they all work spontaneously, though it entails much painful exertion, and each one has a special task allotted to him.

The Letter of Aristeas 6:60

Then I said 'I suppose you mean the informers, for he constantly exposes them to tortures and to painful forms of death.'