Chemical structures, Rf values and mass spectrometric data for deramciclane and its metabolites produced by hepatocytes from various species
Metabolitea | Formed by the Hepatocytes (%) | Rf b | Molecular Ionc | Fragment Ions | |
|---|---|---|---|---|---|
| Deramciclane (FAB, MS/MS) | Rat | 8.67 ± 1.59d | 0.200 | 302(MH+) | 213, 90 |
| Mouse | 37.82 ± 2.49 | |||
| Rabbit | 4.51 ± 1.91 | ||||
| Dog | 47.67 ± 10.57 | ||||
| Human | 64.73 ± 0.164 | ||||
| N-Desmethyl deramciclane (FAB, MS/MS) | Rat | 18.15 ± 3.82 | 0.370 | 288(MH+) | 213 |
| Mouse | 24.50 ± 4.28 | |||
| Rabbit | 7.00 ± 0.554 | ||||
| Dog | 27.12 ± 7.66 | ||||
| Human | 4.55 ± 4.83 | ||||
| 9-Hydroxy-deramciclane (FAB, MS/MS) | Rat | 28.44 ± 3.57 (3:1)e | 0.059 | 318(MH+) | 229, 211, 185, 171, 143, 90 |
| Mouse | 10.92 ± 3.73 | |||
| Rabbit | 24.25 ± 3.74 (2:3) | ||||
| Dog | 0.57 ± 0.519 | ||||
| 8-Hydroxy-deramciclane (FAB, MS/MS) | Rat | <2.00 | 0.135 | 318(MH+) | 229, 211, 185, 171, 143, 90 |
| |||||
| Hydroxy-deramciclane IIa (FAB, MS/MS) | Rat | 6.10 ± 1.74 | 0.088 | 318(MH+) | 229, 169, 156, 90 |
| Mouse | 1.65 ± 1.06 | ||||
| Rabbit | 12.54 ± 0.57 (1:0) | ||||
| Dog | 3.67 ± 2.09 (1:1) | ||||
| Human | 1.16 ± 0.39 | 0.115 | 318(MH+) | 229, 169, 156, 90 | |
| Hydroxy-deramciclane IIb (FAB, MS/MS) | Rat | <2.00 | |||
| |||||
| 1′-Hydroxy-deramciclane (FAB, MS/MS) | Rat | 1.71 ± 0.70 | 0.200 | 318(MH+) | 213, 106 |
| Human | 1.71 ± 0.67 | |||
| Deramciclane N-oxide (FAB, MS/MS) | Rat | 4.42 ± 2.53 | 0.338 | 318(MH+) | 213, 157, 106 |
| Human | 1.23 ± 0.59 | |||
| N-Desmethyl 9-hydroxy-deramciclane (FAB, MS/MS) | Rat | 5.57 ± 3.05 (3:2) | 0.115 | 304(MH+) | 229, 211, 185, 171, 143, 76 |
| Mouse | 1.92 ± 0.72 | |||
| Rabbit | 23.09 ± 3.33 (2:3) | ||||
| N-Desmethyl 8 hydroxy-deramciclane (FAB, MS/MS) | Rat | <2.00 | 0.262 | 304(MH+) | 229, 211, 185, 171, 143, 76 |
| Rabbit | <2.00 | |||
| N-Desmethyl hydroxy-deramciclane II (GC-MS) | Rat | 1.66 ± 1.78 | 303(M+) | 229, 211, 58, 44 | |
| Mouse | 1.77 ± 1.21 | |||
| Rabbit | 8.03 ± 3.04 (2:3) | ||||
| Dog | 1.16 ± 0.32 | ||||
| Human | <2.00 | ||||
| Dihydroxy-deramciclane A (FAB, MS/MS) | Rabbit | <2.00 | 0.115 | 334(MH+) | 229, 211, 106 |
| Dihydroxy-deramciclane B (FAB, MS/MS) | Rat | <2.00 | 0.241 | 334(MH+) | 229, 211, 106 |
| Rabbit | <2.00 | |||
| Dog | <2.00 | ||||
| Carboxy-deramciclane A (FAB, MS/MS) | Rat | <2.00 | 0.200 | 332(MH+) | 243, 197, 90 |
| Human | <2.00 | ||||
| Carboxy-deramciclane B (FAB, MS/MS) | Rat | <2.00 | 0.241 | 332(MH+) | 243, 197, 90 |
| Rabbit | <2.00 | |||
| N-Desmethyl carboxy-deramciclane (FAB, MS/MS) | Rat | <2.00 | 0.294 | 318(MH+) | 243, 197, 76 |
| Rabbit | <2.00 | |||
| Phenylborneol (GC-MS) | Rat | 3.66 ± 3.72 (3:2) | 0.720 | 230(M+)f | 197, 184, 169 |
| Mouse | 1.30 ± 1.04 | |||
| Rabbit | 7.76 ± 3.92 (2:3) | ||||
| Dog | 1.91 ± 0.21 (4:1) | ||||
| Human | 0.97 ± 0.22 | ||||
| Hydroxy-phenylborneol (GC-MS) | Rat | <2.00 | 0.720 | 244(M+)g | 197, 169 |
|
|
|
|
|
|
-
↵ a The method of identification is given in parenthesees: FAB, MS/MS (CID), or GC-MS (electron impact ionization).
-
↵ b Rf values on thin layer developed in butanol/acetic acid/water (4:1:1 v/v).
-
↵ c Molecular ion: MH+ in FAB and M+ in GC-MS measurements.
-
↵ d The values represent the amount of parent compound remained unchanged during the 24-h incubation period and the relative amounts of metabolite formed in 24 h. They are expressed as mean ± S.D. (n = 3).
-
↵ e The values in parentheses represent the ratio of glucuronide conjugate and phase I metabolite.
-
↵ f Phenylcamphene and phenylbornylene (M+ = 212) were identified by GC-MS instead of phenylborneol (M+ = 230).
-
↵ g Hydroxy-phenylcamphene and hydroxy-phenylbornylene (M+ = 228) were identified by GC-MS instead of hydroxy-phenylborneol (M+ = 244).