Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H35NO3.C4H4O4 |
Molecular Weight | 573.676 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C(O)=O.COC1=CC2=C(C=C1)[C@H]([C@H](C3=CC=CC=C3)C(C)(C)O2)C4=CC=C(OCCN5CCCC5)C=C4
InChI
InChIKey=CKDZFQCZLXNLRD-JJGRXVLVSA-N
InChI=1S/C30H35NO3.C4H4O4/c1-30(2)29(23-9-5-4-6-10-23)28(26-16-15-25(32-3)21-27(26)34-30)22-11-13-24(14-12-22)33-20-19-31-17-7-8-18-31;5-3(6)1-2-4(7)8/h4-6,9-16,21,28-29H,7-8,17-20H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t28-,29+;/m1./s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12841887https://www.ncbi.nlm.nih.gov/pubmed/23895678 | http://adisinsight.springer.com/drugs/800009670 | https://www.ncbi.nlm.nih.gov/pubmed/25619124 | http://www.drugsupdate.com/generic/view/367/OrmeloxifeneCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24468615 | https://www.ncbi.nlm.nih.gov/pubmed/11738564
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12841887https://www.ncbi.nlm.nih.gov/pubmed/23895678 | http://adisinsight.springer.com/drugs/800009670 | https://www.ncbi.nlm.nih.gov/pubmed/25619124 | http://www.drugsupdate.com/generic/view/367/Ormeloxifene
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24468615 | https://www.ncbi.nlm.nih.gov/pubmed/11738564
Ormeloxifene (also known as centchroman) is a selective estrogen receptor modulator. It is a once-a-week non-steroidal oral contraceptive agent marketed in India and other countries under the brand names Novex-DS, Centron, and Sevista. Ormeloxifene has been investigated in the management of benign breast diseases such as mastalgia. The l-isomer, levormeloxifene, which has oestrogenic effects, has been investigated in the management of postmenopausal osteoporosis, but development appears to have been discontinued because of adverse effects. Recent studies have shown Ormeloxifene`s potent anti-cancer activities in breast, head and neck, and chronic myeloid leukemia cells. Several in vivo and clinical studies have reported that ormeloxifene possesses an excellent therapeutic index and has been well-tolerated, without any haematological, biochemical or histopathological toxicity, even with chronic administration. In India, ormeloxifene has been available as birth control since the early 1990s, and it is currently marketed there under the trade name Saheli. Ormeloxifene has also been licensed under the trade names Centron and Sevista. Ormeloxifene acts on oestrogen receptors. It has a weak estrogenic and potent antiestrogenic actions. It is expected to exert a contraceptive effect and normalise the bleeding from uterine cavity by regularising the expression of oestrogen receptors on the endometrium. As a contraceptive, it prevents proliferation and decidualisation of the endometrium, enhances blastocyst formation and slightly increases embryo transport through the oviducts.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11738564 |
13.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | SEVISTA Approved UseDysfunctional uterine bleeding Launch Date1992 |
|||
Preventing | SEVISTA Approved UseContraceptive Launch Date1992 |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Optimization of contraceptive dosage regimen of Centchroman. | 2001 Jan |
|
Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders. | 2001 Jul |
|
Interaction with anti-implantation and estrogen antagonistic activities of dl-ormeloxifene, a selective estrogen receptor modulator, by tetracycline in female Sprague-Dawley rats. | 2001 Oct |
|
Evaluation of interaction potential of certain concurrently administered drugs with pharmacological and pharmacokinetic profile of centchroman in rats. | 2002 Jul |
|
Modulation of estrogen action during preimplantation period and in immature estradiol-primed rat uterus by anti-implantation agent, ormeloxifene. | 2005 Jun |
|
Effect of ormeloxifene on ovariectomy-induced bone resorption, osteoclast differentiation and apoptosis and TGF beta-3 expression. | 2006 Aug |
|
Modulation of AP-1 mediated estrogenic response by ormeloxifene in rat uterus. | 2007 May |
|
Efficacy and safety of ormeloxifene in management of menorrhagia: a pilot study. | 2009 Aug |
|
Clinical pharmacokinetics and interaction of centchroman--a mini review. | 2010 Apr |
|
Long-term progestin contraceptives (LTPOC) induce aberrant angiogenesis, oxidative stress and apoptosis in the guinea pig uterus: A model for abnormal uterine bleeding in humans. | 2010 Apr 27 |
|
Effects of estrogen, raloxifene, and levormeloxifene on the expression of Rho-kinase signaling molecules in urethral smooth muscle cells. | 2010 Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12841887
The participants were randomly assigned to double-blind therapy with levormeloxifene1.25, 5.00, 10.00 or 20.00 mg/day or placebo for 12 months.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11738564
The Ishikawa cell line is grown in DMEM+10% FCS. Cells are plated in microtiter plates (1x10^5 cells/mL) in stimulation medium (DMEM+5% dextran-coated charcoal treated FSC and a total of 4.5 g/L d-glucose) and incubated for 1 day at 37 C and 5% CO2. The medium is changed and the Levormeloxifene is added in a total volume of 150 mL. The cells are incubated for another 3 days. The increased level of the alkaline phosphatase enzyme is measured as described in Littlefield et al. using pnitrophenyl phosphate as a substrate. All compounds are tested in dose–response curves from 10^6 to 10^14 M, maximal effect was achieved using 10 nM moxestrol.
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
9938031
Created by
admin on Fri Dec 15 19:19:40 GMT 2023 , Edited by admin on Fri Dec 15 19:19:40 GMT 2023
|
PRIMARY | |||
|
2XFK7X56Q3
Created by
admin on Fri Dec 15 19:19:40 GMT 2023 , Edited by admin on Fri Dec 15 19:19:40 GMT 2023
|
PRIMARY | |||
|
199583-01-2
Created by
admin on Fri Dec 15 19:19:40 GMT 2023 , Edited by admin on Fri Dec 15 19:19:40 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD