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Headache disorders are extraordinarily common and disproportionately impact women of childbearing age. This article reviews the importance of proper diagnosis, natural history, and management of headache disorders in pregnant and postpartum women.Red flags for secondary headache specifically among pregnant women include elevated blood pressure and lack of a previous headache history, as well as a prolonged duration of the headache attack in those with a prior history of migraine. Migraine improvement is typical for most pregnant women, but the prognosis for women who have migraine with aura or chronic migraine is less predictable. Migraine is now an established risk factor for the development of preeclampsia. Recent data suggest hazards for compounds containing butalbital and possibly a better safety profile for triptans than previously believed during pregnancy. Peripheral nerve blocks and noninvasive neurostimulation devices are procedural and emerging therapies that have promising safety profiles for pregnant women with headache disorders.Acute headache occurring in pregnancy and the postpartum period is a red flag requiring diagnostic vigilance. Migraine frequency in women typically improves during pregnancy, although this trend is less certain when aura is present and after delivery. Acute and preventive treatment plans during pregnancy and lactation are plausible but may require shifts in therapeutic hierarchy. Relatively safe oral, parenteral, and procedural therapies are available for pregnant women. Noninvasive neuromodulation devices are already available and will likely play a greater role in the coming years. Migraine is associated with medical and obstetrical complications during pregnancy, and women with frequent migraine attacks may need to be considered high risk.