Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H35NO3 |
Molecular Weight | 457.6038 |
Optical Activity | ( - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C2[C@H]([C@H](C3=CC=CC=C3)C(C)(C)OC2=C1)C4=CC=C(OCCN5CCCC5)C=C4
InChI
InChIKey=XZEUAXYWNKYKPL-WDYNHAJCSA-N
InChI=1S/C30H35NO3/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/h4-6,9-16,21,28-29H,7-8,17-20H2,1-3H3/t28-,29+/m1/s1
Molecular Formula | C30H35NO3 |
Molecular Weight | 457.6038 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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Primary | Unknown Approved UseUnknown |
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Primary | SEVISTA Approved UseDysfunctional uterine bleeding Launch Date6.9422403E11 |
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Preventing | SEVISTA Approved UseContraceptive Launch Date6.9422403E11 |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Optimization of contraceptive dosage regimen of Centchroman. | 2001 Jan |
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Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders. | 2001 Jul |
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Evaluation of interaction potential of certain concurrently administered drugs with pharmacological and pharmacokinetic profile of centchroman in rats. | 2002 Jul |
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Effects of 3-phenyl-4-[[4-[2-(1-piperidinyl)ethoxy]phenyl]methyl]- 2H-1-benzopyran-7-ol (CHF 4056), a novel nonsteroidal estrogen agonist/antagonist, on reproductive and nonreproductive tissue. | 2002 Mar |
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Differential effects of estrogen and raloxifene on messenger RNA and matrix metalloproteinase 2 activity in the rat uterus. | 2005 Apr |
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Clinical pharmacokinetics and interaction of centchroman--a mini review. | 2010 Apr |
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Effects of estrogen, raloxifene, and levormeloxifene on the expression of Rho-kinase signaling molecules in urethral smooth muscle cells. | 2010 Dec |
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The effect of long-term hormonal treatment on voiding patterns during filling cystometry and on urethral histology in a postpartum, ovariectomized female rat. | 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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:06:07 UTC 2023
by
admin
on
Fri Dec 15 16:06:07 UTC 2023
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Record UNII |
9512UKZ352
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1821
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CHEMBL301327
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C82904
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7357
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C108255
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100000082283
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m3242
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35805
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LEVORMELOXIFENE
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SUB08489MIG
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78994-23-7
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DTXSID301317017
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9512UKZ352
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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ENANTIOMER -> ENANTIOMER |
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RACEMATE -> ENANTIOMER |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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