re = /^(-?(?=\d{1,15}(?:[.,]0+)?0*$|(?:(?=[,.\d]{1,16}0*$)(?:\d+[.,]\d{1,2}$))).{1,16}).*$/m
str = '// PASS
0
0.12
1
-1
1.23456789012345
10.2345678901234
12.3456789012345
-123.4
-12.34
-1,33
-1.33
-1.333
-1234567.12
-1234567890123450
-12345678901234.50
12345678901234.50
123456789012345.00
// FAIL
-1234567890123456
-12345678901234.56
12345678901234.56
123456789012345.60
1.234567890123456
12.34567890123456
123456789012340.6
123456789012300.67
123456789012300000000000.67
10000000000010000000001000010000000001.22'
subst = '$1'
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html