Dr Andrew McLellan said he was "even more sad" at the physical and mental condition of prisoners at Cornton Vale than at the time of his last report in 2004.
During a follow-up inspection in February, he found 98 per cent of inmates were drug addicts, 80 per cent suffered mental health problems and 75 per cent had a history of abuse.
Dr McLellan also criticised prison authorities for failing to tackle "degrading" toilet access arrangements which meant some prisoners had to urinate in the sink of their cell.
Speaking before the publication of his follow-up inspection report today, Dr McLellan said: "When I reported last year on Cornton Vale I was extremely upset at the miserable condition of women coming into prison and the unrealistic expectation that prison could do anything very good to turn around the lives of people with such a degree of physical problems, mental problems, drug addiction and history of abuse.
"Here I am a year on, even more sad than before. I'm not saying women shouldn't be sent to prison, but I think I am being realistic enough to recognise the condition of those coming into prison makes it almost impossible for prison to do anything that will reduce criminal behaviour."
In last year's inspection Dr McLellan found "more than 90 per cent" of inmates had addiction problems and over 60 per cent had a history of abuse. He said yesterday: "The statistics were awful last year and were marginally worse this year."
His report states: "For prisoners in Younger House (which holds around 40 of the jail's inmates from a prison population of 230) the arrangements for access to toilets at night are as humiliating and degrading as they were last year."
Dr McLellan's report welcomes building work on new accommodation for at least 50 inmates, the opening of a new family centre, improved conditions at reception and the refurbishment of the jail's mother-and-baby unit.
A spokesman for the Scottish Prison Service said: "We welcome this report and have taken active steps to address many of the issues raised.
"Since the inspection we have installed CCTV cameras in the corridors, which allows prisoners to go unaccompanied to the toilet at night.
"There is a huge amount of health care provided to women in prison."
© The Scotsman