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History
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1) a hard, painful and poisoned swelling under the skin (boil)

2) a sudden and painful tightening of the muscles, usually caused by cold or overwork, making movement difficult (cramp)

3) strong, cold and painful (cutting)

4) a painful disease of the bowels which produces mucus and blood (dysentery)

5) the painless killing of people suffering from incurable painful diseases (euthanasia)

6) a disease causing painful swellings in joints, especially toes, knees and fingers (gout)

7) that cannot be tolerated because too strong, painful etc (intolerable)

8) any severe or painful test of character or endurance (ordeal)

9) a painful squeeze using the fingers and thumb; an amount which can be taken up with the thumb finger (pinch)

10) (of smells, tastes) very strong, sharp; (of remarks) very painful (pungent)

Synonyms
UK
US
Meaning:
arduous

needing and using much energy and thought

difficult, hard to endure

cruel

(of a person) taking pleasure in causing pain to, watching the suffering of, others

vicious, pitiless; causing pain

difficult

requiring much effort, strength, skill or ability

hard on someone; hard to do

doleful

sad, depressed

depressing

harrowing

causing distress

dangerous, frightening

insufferable

unbearable

horrible, intolerable

intolerable

that cannot be tolerated because too strong, painful etc

unacceptable; beyond bearing

onerous

needing much effort

difficult; requiring hard labor

sore

(of a part of the body) painful; hurting when touched or used; filled with sorrow; sad

hurt physically

tragic

of tragedy; very sad or unfortunate

catastrophic, very bad

troublesome

causing worry, unhappiness, difficulty

bothersome, worrisome

upstream

(moving) in the opposite direction to the stream or current

hard on someone; hard to do

PAINFUL as in Wiktionary
PAINFUL as in Wikipedia