Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H32O2 |
| Molecular Weight | 328.4883 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCOC1=CC2=C(C=C1)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC2)OC
InChI
InChIKey=IUWKNLFTJBHTSD-AANPDWTMSA-N
InChI=1S/C22H32O2/c1-4-13-24-16-6-8-17-15(14-16)5-7-19-18(17)11-12-22(2)20(19)9-10-21(22)23-3/h6,8,14,18-21H,4-5,7,9-13H2,1-3H3/t18-,19-,20+,21+,22+/m1/s1
| Molecular Formula | C22H32O2 |
| Molecular Weight | 328.4883 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Promestriene (3-propyl ethyl, 17B-methyl estradiol) is a synthetic estrogen analog, which is used in topical estrogen therapy. Promestriene’s potential for treating vaginal atrophy symptoms associated with aromatase inhibitor treatment would be precluded if its minimal absorption leads to estrogen-like effects on cell proliferation and estrogen-responsive gene expression. The concern with absorbed vaginal estrogens or estrogen analogs is that they activate occult sites of residual breast cancer or negate the tumor suppressive effects of aromatase inhibitor adjuvant therapy. Promestriene has been studied in phase IV of the clinical trial on improvement of hormonal cytology, local and systemic climacteric complaints, as well as its endometrial security in patients with vaginitis atrophic pelvic; organ prolapse and endometrial hyperplasia. It has been also studied in phase III of the clinical trial in the post-operative patients with hypospadias. In addition, promestriene was in phase IV of the clinical trial to study its treatment of patients with vaginosis, bacterial, but that studied was terminated.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Urogenital disorders associated with oestrogen deficiency: the role of promestriene as topical oestrogen therapy. | 2010-09 |
|
| [Safety of promestriene capsule used in postmenopausal atrophic vaginitis]. | 2009-08 |
|
| Estrogen therapy influence on periurethral vessels in postmenopausal incontinent women using Dopplervelocimetry analysis. | 2008-11-20 |
|
| Atypical squamous cells and low squamous intraepithelial lesions in postmenopausal women: implications for management. | 2008-10 |
|
| Presurgical promestriene therapy in postmenopausal women with stress urinary incontinence. | 2007 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20003787
Promestriene was given by continuous therapy for 20 days, then maintenance therapy for 8 weeks (1 pill two times per week used). The level of follicle stimulation hormone (FSH) and estradiol (E(2)) in serum was and thickness of endometrium was detected before and after treatment.
Route of Administration:
Vaginal
In Vitro Use Guide
Sources: http://file.scirp.org/pdf/JCT_2015082416065374.pdf
In estrogen sufficient cultures, promestriene exhibited no cell proliferative properties on MCF-7, BT-474, or T47-D tumor cells, even at very high concentrations (up to 100000 pg/mL). However, in estrogen deprivation conditions, low dose promestriene (2 - 10 pg/ml) stimulated GREB1 expression in all cell lines tested to levels equal to or greater than estrogen. In both estrogen replete and depleted cultures of MCF7 cells, 2 pg/ml promestriene stimulated GREB1 expression significantly greater than that seen with estradiol. For BT-474 cells, there was no significant difference in the GREB1 expression stimulated by 2 pg/ml promestriene compared to that induced by estradiol in either estrogen-replete or depleted conditions.
| Substance Class |
Chemical
Created
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| Record UNII |
GXM4PER6WZ
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Validated (UNII)
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WHO-VATC |
QG03CA09
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WHO-ATC |
G03CA09
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C483
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100000081126
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PROMESTRIENE
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34625
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254-361-6
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4023
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DB12487
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CHEMBL2105394
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C013657
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C76998
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9883915
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