Anisindione

C16H12O3, Mr = 252.3, orthorhombic, Pna21, a = 6.633 (3), b = 13.367 (2), c = 14.056 (2) A, V = 1246.3 (9) A3, Z = 4, Dx = 1.344 g cm-3, lambda (Cu K alpha) = 1.54184 A, mu = 7.17 cm-1, F(000) = 528, T = 296 K, R = 0.027 for 2337 observations (of 2508 unique date). The average deviation from planarity is 0.013 (1) A with a maximum of 0.028 (1) A for the fused-rings system, and 0.003 (1) A with a maximum of 0.005 (1) A for the methoxyphenyl ring. The dihedral angle between the two systems is 4.7 (3) degrees. The methoxyphenyl ring is pushed away from the vinyl proton and towards the endocyclic O atom; the bond angles are 130.13 (9) and 110.13 (8) degrees, respectively.

Coumarin derivatives are the anticoagulants most widely used in the United States. These agents are relatively contraindicated during pregnancy, and the use of these drugs in breast-feeding women remains controversial. Much of the confusion regarding the passage of these agents into breast milk might stem from the fact that different agents possess significantly different chemical properties. A review of the chemical structure of different coumarin derivatives, as well as available clinical evidence, suggests that warfarin sodium is not excreted into breast milk, and can be safely given to women requiring therapeutic anticoagulation postpartum. For the rare patient who cannot tolerate warfarin sodium, the use of dicumarol, rather than anisindione, is preferred.

Patients who require oral anticoagulation usually receive warfarin. We used an indanedione drug, anisindione, in two patients who were intolerant of warfarin but who needed long-term oral anticoagulation. The use of this alternative oral anticoagulant is reviewed.