Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H27FO2 |
| Molecular Weight | 306.4149 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](C[C@H](F)C4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O
InChI
InChIKey=GGQPTOITOZXLBE-QXROXWLYSA-N
InChI=1S/C19H27FO2/c1-18-7-5-11(21)9-15(18)16(20)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16-17,22H,3-8,10H2,1-2H3/t12-,13-,14-,16-,17-,18+,19-/m0/s1
| Molecular Formula | C19H27FO2 |
| Molecular Weight | 306.4149 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
6α-fluorotestosterone (6α-fluoro T) acts as a competitive inhibitor of aromatase cytochrome P450. The mechanism by which substitution of a fluorine at the 6 alpha-position interferes with the aromatization reaction remains to be determined, but the inhibitory action on estrogen formation may potentiate the androgenic properties of 6 alpha-fluorotestosterone in vivo due to a lowering of estrogen levels. Besides, 6α-fluoroT promotes male sex behavior, it does not promote mating by unassisted estrogen receptor binding and it does not promote mating via metabolism to another androgen.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Two aromatase inhibitors inhibit the ability of a third to promote mating in male rats. | 2015-09 |
|
| 6 alpha-fluorotestosterone: a nonaromatizable androgen inhibitor of aromatase cytochrome P450. | 1990-05 |
|
| Activation and differentiation of sexual behavior and translocation of hypothalamic estrogen receptors in rats by 6 alpha-fluorotestosterone. | 1981-06 |
Sample Use Guides
how mating induced in castrated male rats by 6α-fluorotestosterone: starting the day after castration, one set was injected sc daily with 6α-fluorotestosterone (6α-fluoroTP) at a dose of 25 μg/day. That was increased to 50 μg after week 5, 100 μg after week 6, 200 μg 4 days after week 7, and 400 μg after week 8.
Route of Administration:
Other
In Vitro Use Guide
Curator's Comment: Under conditions in which testosterone was readily aromatized, no aromatization of 6 alpha-fluorotestosterone was observed using either fluorescence detection of dansyl-estrogens separated by high-performance liquid chromatography or estrogen radioimmunoassay methods. The lack of aromatization is not due to failure of 6 alpha-fluorotestosterone to bind to P450arom because 6 alpha-fluorotestosterone acts as a competitive inhibitor of the enzyme, and it exhibits a binding affinity similar to that of testosterone. Moreover, the addition of 6 alpha-fluorotestosterone to human placental microsomes elicits a spectral shift indicative of conversion of the heme from a low to a high spin state as observed for androgen substrates, consistent with its binding to the substrate site.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:36:03 GMT 2025
by
admin
on
Mon Mar 31 20:36:03 GMT 2025
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| Record UNII |
O9R6BZK55Y
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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NCI_THESAURUS |
C243
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10357822
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O9R6BZK55Y
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1597-68-8
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C29043
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DTXSID70873369
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ACTIVE MOIETY |
