Levormeloxifene is a selective estrogen receptor modulator (SERM) that is being investigated for its potential therapeutic applications in various areas, including cancer, osteoporosis, and neurodegenerative diseases. It is a chiral molecule, with only the levorotatory enantiomer exhibiting significant biological activity. Levormeloxifene has shown promising preclinical results in various studies. For example, it has demonstrated antitumor activity in breast cancer cell lines and has been shown to reduce bone loss in animal models of osteoporosis. Research efforts are ongoing to explore the safety and efficacy of levormeloxifene in clinical trials for these conditions. Levormeloxifene's unique pharmacological properties, including its selective estrogen receptor modulation, make it a promising candidate for therapeutic development.'
levormeloxifene: RN refers to (trans)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 35805 |
| CHEMBL ID | 301327 |
| SCHEMBL ID | 107914 |
| MeSH ID | M0281301 |
| Synonym |
|---|
| trans-1-(2-(p-(7-methoxy-2,2-dimethyl-3-phenyl-4-chromanyl)phenoxy)ethyl)pyrrolidine |
| brn 6075092 |
| 3,4-trans-2,2-dimethyl-3-phenyl-4-(p-(beta-pyrrolidinoethoxy)-phenyl)-7-methoxychroman |
| pyrrolidine, 1-(2-(4-(3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2h-1-benzopyran-4-yl)phenoxy)ethyl)-, (3r-trans)- |
| 1-(2-(p-(trans-7-methoxy-2,2-dimethyl-3-phenyl-4-chromanyl)phenoxy)ethyl)pyrrolidine |
| 3,4-trans-2,2-dimethyl-3-phenyl-4-(p-(beta-pyrrolidinoethoxy)phenyl)-7-methoxychroman |
| trans-2,2-dimethyl-3-phenyl-4-(p-(beta-pyrrolidinoethoxy)phenyl)-7-methoxychroman |
| compound 67/20 |
| pyrrolidine, 1-(2-(p-(7-methoxy-2,2-dimethyl-3-phenyl-4-chromanyl)phenoxy)ethyl)-, trans- |
| pyrrolidine, 1-(2-(4-(3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2h-1-benzopyran-4-yl)phenoxy)ethyl)-, trans- |
| (-)-1-(2-(4-((3r,4r)-7-methoxy-2,2-dimethyl-3-phenyl-4-chromanyl)phenoxy)ethyl)pyrrolidine |
| 9512ukz352 , |
| levormeloxifene [inn] |
| unii-9512ukz352 |
| centron |
| 6720-cdri |
| choice 7 |
| saheli |
| centchroman-l |
| nnc-46-0020 |
| 78994-23-7 |
| levormeloxifene |
| trans-centchroman |
| (-)-centchroman |
| CHEMBL301327 |
| centchroman (-)-form |
| l-centchroman |
| 1-[2-[4-[(3r,4r)-7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydrochromen-4-yl]phenoxy]ethyl]pyrrolidine |
| 78994-24-8 |
| (- )-1-(2-(p-(trans-7-methoxy-2,2-dimethyl-3-phenyl-4-chromanyl)phenoxy)ethyl)pyrrolidine |
| ormeloxifene [inn] |
| 44axy5ve90 , |
| unii-44axy5ve90 |
| (+/-)-1-(2-(p-(trans-7-methoxy-2,2-dimethyl-3-phenyl-4-chromanyl)phenoxy)ethyl)pyrrolidine |
| ormeloxifene [mart.] |
| centchroman [mi] |
| ormeloxifene [who-dd] |
| levormeloxifene [who-dd] |
| centchroman (-)-form [mi] |
| SCHEMBL107914 |
| AKOS032953987 |
| DB13310 |
| Q6535824 |
| 1-(2-(4-((3r,4r)-7-methoxy-2,2-dimethyl-3-phenylchroman-4-yl)phenoxy)ethyl)pyrrolidine |
| bdbm50219398 |
| DTXSID301317017 |
Levormeloxifene is a selective estrogen receptor modulator. It was developed as an alternative to estrogen replacement therapy for the treatment and prevention of postmenopausal bone loss.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Levormeloxifene is a selective estrogen receptor modulator that was developed for the purpose of the treatment and prevention of postmenopausal osteoporosis." | ( Adverse events that are associated with the selective estrogen receptor modulator levormeloxifene in an aborted phase III osteoporosis treatment study. Goldstein, SR; Nanavati, N, 2002) | 1.26 |
| "Levormeloxifene is a selective estrogen receptor modulator (SERM). " | ( Adverse effects of a SERM (Levormeloxifene). Safety parameters and bone mineral density 12 months after treatment withdrawal. Christiansen, C; Christoffersen, C; Delmas, PD; Riis, BJ; Stakkestad, JA; Warming, L, 2003) | 2.06 |
| "Levormeloxifene is a selective estrogen receptor modulator that was developed as an alternative to estrogen replacement therapy for the treatment and prevention of postmenopausal bone loss. " | ( What can be learned from the levormeloxifene experience? Christiansen, C; Nielsen, TF; Ravn, P, 2006) | 2.07 |
levormeloxifene has oestrogen-like bone preserving and antiatherogenic effects. Short-term administration of the drug in postmenopausal women was well-tolerated.
| Excerpt | Reference | Relevance |
|---|---|---|
| " In a separate pharmacokinetic study, plasma C(max) was generally observed 6 h after dose administration and the half-life of elimination was long (24 h) and a doubling in dose resulted in an approximate doubling in exposure." | ( Metabolism, disposition, excretion, and pharmacokinetics of levormeloxifene, a selective estrogen receptor modulator, in the rat. John, BA; Kiehr, B; Mountfield, RJ, 2000) | 0.55 |
| "The possibility of age dependence in the pharmacokinetic behavior and tolerability of levormeloxifene was investigated in a single-center, open-label study." | ( Pharmacokinetics of levormeloxifene in young versus elderly postmenopausal women. Kiehr, B; Müller, M; Pedersen, PC; Skrumsager, BK, 2001) | 0.86 |
| " Peak plasma concentration, time to maximum plasma concentration, area under the plasma concentration-time curves from zero to the last quantifiable value and to infinity, and terminal half-life were calculated for levormeloxifene and compared between age groups." | ( Pharmacokinetics of levormeloxifene in young versus elderly postmenopausal women. Kiehr, B; Müller, M; Pedersen, PC; Skrumsager, BK, 2001) | 0.82 |
| " However, no statistically significant differences were observed between groups in any of the pharmacokinetic parameters, except for the elimination rate constant." | ( Pharmacokinetics of levormeloxifene in young versus elderly postmenopausal women. Kiehr, B; Müller, M; Pedersen, PC; Skrumsager, BK, 2001) | 0.63 |
| " The pharmacodynamic properties were investigated after multiple dosing by assessment of the short-term effects on bone and lipid metabolism and on the hypothalamic-pituitary axis." | ( Levormeloxifene: safety, pharmacodynamics and pharmacokinetics in healthy postmenopausal women following single and multiple doses of a new selective oestrogen receptor modulator. Bjarnason, K; Gerrits, M; Kiehr, B; Pedersen, PC; Skrumsager, BK; Watson, N, 2002) | 1.76 |
| "Short-term administration of levormeloxifene in postmenopausal women was well-tolerated at doses that elicited a favourable pharmacodynamic response suggesting oestrogen-like bone preserving and antiatherogenic effects." | ( Levormeloxifene: safety, pharmacodynamics and pharmacokinetics in healthy postmenopausal women following single and multiple doses of a new selective oestrogen receptor modulator. Bjarnason, K; Gerrits, M; Kiehr, B; Pedersen, PC; Skrumsager, BK; Watson, N, 2002) | 2.05 |
| " Allometric scaling was used to predict human pharmacokinetic parameters and the performance of the approach was evaluated." | ( Pharmacokinetics and allometric scaling of levormeloxifene, a selective oestrogen receptor modulator. Erichsen, L; Ingwersen, SH; Kiehr, B; Poulsen, HE; Østerberg, O, 2003) | 0.58 |
levormeloxifene, a selective oestrogen receptor modulator (SERM), was investigated in postmenopausal women following single doses and multiple dosing once daily up to 56 days. Serum CrossLaps decreased by about 50% with no dose-response effect.
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Estrogen receptor | Homo sapiens (human) | IC50 (µMol) | 0.0730 | 0.0000 | 0.7237 | 32.7000 | AID69240 |
| Estrogen receptor beta | Homo sapiens (human) | IC50 (µMol) | 0.0730 | 0.0001 | 0.5294 | 32.7000 | AID69240 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID67812 | Percent stimulation of alkaline phosphatase activity in Ishikawa human endometrial adenocarcinoma cells relative to moxestrol | 2002 | Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1 | Synthesis and biological evaluation of novel thio-substituted chromanes as high-affinity partial agonists for the estrogen receptor. |
| AID1144744 | Estrogenic activity in immature female rat assessed as mixture of leukocytes,epithelial cells and estrus smear with cornified cells at 10 mg/kg, po bid for 3 days | 1976 | Journal of medicinal chemistry, Feb, Volume: 19, Issue:2 | Antifertility agents. 12. Structure-activity relationship of 3,4-diphenylchromenes and -chromans. |
| AID1144730 | Antifertility activity in po dosed pregnant female albino rat assessed as absence of implantation in both uterine horns on day 10 of pregnancy compound administered for 5 days | 1976 | Journal of medicinal chemistry, Feb, Volume: 19, Issue:2 | Antifertility agents. 12. Structure-activity relationship of 3,4-diphenylchromenes and -chromans. |
| AID187626 | Relative uterotrophic activity in immature female Sprague-Dawley rats | 1994 | Journal of medicinal chemistry, Mar-04, Volume: 37, Issue:5 | An X-ray crystallographic study of the nonsteroidal contraceptive agent centchroman. |
| AID1283253 | Inhibition of Dhcr24 in Dhcr7-deficient mouse Neuro2a cells assessed as increase in 7-dehydrodesmosterol levels at 1 uM by LC-MS/GC-MS analysis | 2016 | Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3 | The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts. |
| AID1283262 | Inhibition of DR24 in human SLOS fibroblasts assessed as decrease in 7-DHC levels at 10 nM after 5 days by LC-MS/GC-MS analysis | 2016 | Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3 | The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts. |
| AID69364 | Percent affinity for estrogen receptor binding relative to d-estradiol | 1994 | Journal of medicinal chemistry, Mar-04, Volume: 37, Issue:5 | An X-ray crystallographic study of the nonsteroidal contraceptive agent centchroman. |
| AID69240 | Displacement of [3H]17-beta-estradiol from Estrogen receptor of rabbit uterine tissue | 2002 | Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1 | Synthesis and biological evaluation of novel thio-substituted chromanes as high-affinity partial agonists for the estrogen receptor. |
| AID1283267 | Cytotoxicity against human SLOS fibroblasts at 5 uM after 5 days by Cell Titer assay | 2016 | Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3 | The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts. |
| AID1283269 | Inhibition of DR24 in Dhcr7-deficient mouse Neuro2a cells assessed as decrease in 7-DHC levels at 1 uM by LC-MS/GC-MS analysis | 2016 | Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3 | The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts. |
| AID1283273 | Decrease in cholesterol levels in human SLOS fibroblasts at 10 nM after 5 days by LC-MS/GC-MS analysis | 2016 | Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3 | The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts. |
| AID1144736 | Estrogenic activity in immature female rat assessed as vaginal opening at 10 mg/kg, po bid for 3 days | 1976 | Journal of medicinal chemistry, Feb, Volume: 19, Issue:2 | Antifertility agents. 12. Structure-activity relationship of 3,4-diphenylchromenes and -chromans. |
| AID1283252 | Inhibition of C-24 reductase in Dhcr7-deficient mouse Neuro2a cells assessed as increase in desmosterol levels at 1 uM by LC-MS/GC-MS analysis | 2016 | Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3 | The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts. |
| AID1283264 | Inhibition of delta 8-7 isomerase in human SLOS fibroblasts assessed as decrease in 7-DHC levels at 10 nM after 5 days by LC-MS/GC-MS analysis | 2016 | Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3 | The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts. |
| AID67813 | Stimulation of alkaline phosphatase activity in Ishikawa human endometrial adenocarcinoma cells | 2002 | Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1 | Synthesis and biological evaluation of novel thio-substituted chromanes as high-affinity partial agonists for the estrogen receptor. |
| AID1283268 | Inhibition of delta 8-7 isomerase in Dhcr7-deficient mouse Neuro2a cells assessed as decrease in 7-DHC levels at 1 uM by LC-MS/GC-MS analysis | 2016 | Journal of medicinal chemistry, Feb-11, Volume: 59, Issue:3 | The Effect of Small Molecules on Sterol Homeostasis: Measuring 7-Dehydrocholesterol in Dhcr7-Deficient Neuro2a Cells and Human Fibroblasts. |
| AID1144733 | Estrogenic activity in immature female rat assessed as uterine weight on day 4 at 10 mg/kg, po bid for 3 days (Rvb = 13.6 +/- 0.8 mg) | 1976 | Journal of medicinal chemistry, Feb, Volume: 19, Issue:2 | Antifertility agents. 12. Structure-activity relationship of 3,4-diphenylchromenes and -chromans. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (3.33) | 18.7374 |
| 1990's | 6 (20.00) | 18.2507 |
| 2000's | 18 (60.00) | 29.6817 |
| 2010's | 5 (16.67) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (24.91) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 8 (25.00%) | 5.53% |
| Reviews | 2 (6.25%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 22 (68.75%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||