I believe you would have what is considered a high risk pregnancy. We are not doctors here, so we cannot answer your question. We can offer support. You need to make an appointment with your doctor to discuss all of the risk factors and what you need to do before you try to get pregnant. For instance, if you have been on MTX, you must make sure you are off it it for quite some time before you get pregnant. This is a very serious issue, so please see a physician and find out what you need to do to ensure a safe pregnancy.
The ability to get pregnant appears to be one of the areas that RA doesn't affect. However, as V mentioned, some RA medication can be a problem. Methotrexate and Arava in particular are known to cause serious birth defects and it's important that you're off these medications for a certain length of time before you try to get pregnant. Your rheumatologist will be able to tell you more about that.
One of the great things about pregnancy as that the majority of women who have RA go into remission when they're pregnant. I once went to a terrific forum on RA where the rheumatologist giving the keynote speech jokingly recommended that all women with RA get pregnant as often as possible. Anyway, if you do go into remission during pregnancy, the RA tends to come back 6-8 weeks after giving birth. As far as I know, it is generally considered fairly safe to try to get pregnant while you are on e.g. Enbrel and may even be okay to stay on Enbrel, but it hasn't been around long enough to get really solid evidence. Usually, prednisone is the only medication that considered reasonably safe during pregnancy, so if you don't go into remission, this will probably be what keeps you going. I don't know how diabetes would impact your ability to get pregnant for your health during pregnancy, but you may be able to find information about that on our Diabetes site. As well, your PCP or nurse practitioner should be able to give you more information about diabetes and pregnancy.
We have a section on pregnancy and parenting with RA that has more information for you. It includes links to a review of a great book on pregnancy and RA and interview with this author - I highly recommend you get this book. It covers a host of issues, both the practical and emotional.
good luck! Please keep us posted on what happens.
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