Protons | Rofecoxib | Rofecoxib-3′,4′-dihydrodiol3-b | 4′-Hydroxyrofecoxib-O-β-d-glucuronide3-c | 5-Hydroxyrofecoxib-O-β-d-glucuronide3-c | |
---|---|---|---|---|---|
Major Isomer | Minor Isomer | ||||
a | 7.93 (AA′XX′, 2H,J = 8.6) | 7.96 (AA′XX′, 2H, J = 8.5) | 7.96 (AA′XX′, 2H, J = 8.5) | 7.87 (AA′XX′, 2H, J = 8.5) | 7.86 (AA′XX′, 2H, J = 8.5) |
b | 7.62 (AA′XX′, 2H, J = 8.6) | 7.66 (AA′XX′, 2H, J = 8.5) | 7.64 (AA′XX′, 2H, J = 8.5) | 7.69 (AA′XX′, 2H, J = 8.5) | 7.82 (AA′XX′, 2H,J = 8.5) |
c | 7.39 (m, 5H) | 6.20 (t, 1H, J= 2.0) | 7.27 (AA′XX′, 2H, J = 8.7) | 7.45, 7.33 (m, 5H) | 7.43, 7.36 (m, 5H) |
c′ | 5.85 (dd, 1H, J = 9.9, 2.4) | 7.04 (AA′XX′, 2H, J = 8.7) | |||
c′′ | 5.54 (dt, 1H, J = 9.9, 2.0) | ||||
c′′′ | 4.39 (m, 2H, J = 11.3) | ||||
d | 5.34 (s, 2H) | 5.17, 5.06 (AB, 2H,J = 17.3) | 5.36 (AB, 2H, J = 17.8) | 6.88 (s, 1H) | 6.83 (s, 1H) |
d′ | |||||
e | 3.12 (s, 3H) | 3.08 (s, 3H) | 3.24 (s, 3H) | 3.24 (s, 3H) | 3.22 (s, 3H) |
f | 4.85 (d, 1H, J = 7.3) | 4.77 (d, 1H,J = 7.8) | 4.62 (d, 1H, J = 7.8) | ||
g | 3.36 (d, 1H, J = 10.0) | ||||
h | 3.09, 3.2 (m, 3H) | 3.0–3.7 (m, 4H) | 3.0–3.7 (m, 4H) | ||
i | |||||
j |
Protons | 5-Hydroxyrofecoxib | Rofecoxib-erythro-3,4-dihydrohydroxy acid3-c3-d | cis-3,4-Dihydrorofecoxib | trans-3,4-Dihydrorofecoxib |
---|---|---|---|---|
a | 7.92 (AA′XX′, 2H,J = 8.6) | 7.91 (AA′XX′, 2H, J = 8.2) | 7.69 (AA′XX′, 2H, J = 8.4) | 7.90 (AA′XX′, 2H,J = 8.4) |
b | 7.67 (AA′XX′, 2H, J = 8.6) | 7.69 (AA′XX′, 2H, J = 8.2) | 7.17 (AA′XX′, 2H,J = 8.4) | 7.60 (AA′XX′, 2H, J = 8.4) |
c | 7.39 (m, 5H) | 7.53 (m, 2H) | 6.87 (m, 2H) | 7.22 (m, 2H) |
c′ | 7.39 (m, 2H) | 7.11 (m, 2H) | 7.31 (m, 2H) | |
c′′ | 7.33 (m, 1H) | 7.11 (m, 1H) | 7.27 (m, 1H) | |
c′′′ | ||||
d | 6.59 (s, 1H) | 3.43 (dd, 1H,J = 3.3, 10.9) | 4.82 (dd, 1H, J = 9.7, 6.5) | 4.76 (dd, 1H, J = 8.4, 8.7) |
d′ | 3.50 (dd, 1H, J = 7.4, 10.9) | 4.77 (dd, 1H, J = 9.7, 3.8) | 4.41 (dd, 1H, J = 10.6, 8.7) | |
e | 3.12 (s, 3H) | 3.12 (s, 3H) | 3.01 (s, 3H) | 3.08 (s, 3H) |
f | ||||
g | ||||
h | ||||
i | 4.10 (d, 1H, J = 11.5) | 4.57 (d, 1H, J = 8.8) | 4.26 (d, 1H, J = 12.4) | |
j | 3.56 (ddd, 1H,J = 11.5, 3.3, 7.4) | 4.26 (ddd, 1H, J = 8.8, 6.5, 3.8) | 4.12 (ddd, 1H, J = 12.4, 10.6, 8.4) |
↵3-a Splitting patterns: s = singlet, d = doublet, t = triplet, dd = doublet of doublets, ddd = doublet of doublet of doublets, dt = doublet of triplets, m = multiplet, AA′XX′ = multiplet, characteristic ofpara-substituted benzene ring. Coupling constants (J) are expressed in Hz.
↵3-b Spectrum recorded in CD3CN.
↵3-c Metabolite dissolved in DMSO-d6.
↵3-d Data reported for protons Hd, Hd′, and Hj were obtained from analysis of synthetic standard; these signals in the human urine sample were obscured by impurities.