Centchroman: A non-steroidal anti-fertility agent with anti-hormonal properties. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 154413 |
| CHEMBL ID | 284200 |
| SCHEMBL ID | 6863582 |
| MeSH ID | M0003797 |
| Synonym |
|---|
| ormeloxifene |
| centchroman |
| NCGC00181100-01 |
| 9032-43-3 |
| 31477-60-8 |
| rel-ormeloxifene |
| CHEMBL284200 |
| 1-[2-[4-[(3s,4s)-7-methoxy-2,2-dimethyl-3-phenyl-3,4-dihydrochromen-4-yl]phenoxy]ethyl]pyrrolidine |
| D08301 |
| centron (tn) |
| 78994-25-9 |
| pyrrolidine, 1-(2-(4-((3s,4s)-3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2h-1-benzopyran-4-yl)phenoxy)ethyl)- |
| v994wjy688 , |
| unii-v994wjy688 |
| ormeloxifene, (+)- |
| dtxcid901473968 |
| tox21_112716 |
| cas-31477-60-8 |
| dtxsid6046844 , |
| cellulose sulfate gel |
| SCHEMBL6863582 |
| pyrrolidine, 1-(2-(4-(3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2h-1-benzopyran-4-yl)phenoxy)ethyl)-, (3s-trans)- |
| 1-(2-(4-((3s,4s)-3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2h-1-benzopyran-4-yl)phenoxy)ethyl)pyrrolidine |
| (+)-centchroman |
| d-centchroman |
| Q7103387 |
| AKOS040745284 |
Centchroman is a safe nonsteroidal drug for the treatment of mastalgia and fibroadenoma. It has been found to be a candidate drug for breast cancer exhibiting partial to complete remission of lesions in 40.5% of breast cancer patients.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Centchroman is a non-steroidal oral contraceptive and has been found to be a candidate drug for breast cancer exhibiting partial to complete remission of lesions in 40.5% of breast cancer patients. " | ( Therapeutic effect of centchroman alone and in combination with glycine soya on 7,12-dimethylbenz[alpha]anthracene-induced breast tumor in rat. Bhadauria, S; Mishra, J; Mishra, R; Murthy, PK; Murthy, PS; Tiwari, A, 2010) | 2.12 |
| "Centchroman is a safe nonsteroidal drug for the treatment of mastalgia and fibroadenoma. " | ( Role of centchroman in regression of mastalgia and fibroadenoma. Dhar, A; Srivastava, A, 2007) | 2.22 |
| "Centchroman is a non-steroidal once a week oral contraceptive." | ( Binding of centchroman with human serum as determined by charcoal adsorption method. Gupta, RC; Kamboj, VP; Khurana, M; Paliwal, JK, 1999) | 1.41 |
Centchroman (CC) has been established as a potent antineoplastic agent in MCF-7 (ER+ve) and MDA MB-231 (ER-ve) Human Breast Cancer Cells. Centchroman has been reported to induce only minimal side effects and no hormonal imbalance.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Centchroman (CC) has been established as a potent antineoplastic agent in MCF-7 (ER+ve) and MDA MB-231 (ER-ve) Human Breast Cancer Cells (HBCCs) previously by us. " | ( Centchroman mediated apoptosis involves cross-talk between extrinsic/intrinsic pathways and oxidative regulation. Balapure, AK; Gupta, DK; Nigam, D; Nigam, M; Ranjan, V; Sharma, R; Singh, N; Sundaram, S; Zaidi, D, 2010) | 3.25 |
| "Centchroman has been reported to induce only minimal side effects and no hormonal imbalance." | ( Centchroman: is unsupervised long-term use warranted? Case report. Bhatia, A; Malhotra, KP; Sherpa, M, 2011) | 2.53 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Centchroman did not produce any deleterious effect on embryos which survived until Day 19 of pregnancy in foster mothers." | ( Viability and development of 'tube-locked' mouse embryos. Kamboj, VP; Sethi, N; Singh, MM; Wadhwa, V, 1983) | 0.99 |
Centchroman (3,4-trans-2,2-dimethyl-3-phenyl-4-p-(beta-pyrrolidinoethoxy) phenyl-7-methoxy chroman) has been evaluated in 4 male and 75 female patients. Treatment did not demonstrate any consistent pattern of stimulation or inhibition in any of the estrogen-sensitive biochemical parameters.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Centchroman treatment did not demonstrate any consistent pattern of stimulation or inhibition in any of the estrogen-sensitive biochemical parameters." | ( Effect of long-term centchroman treatment on some estrogen-sensitive biochemical constituents in the genital organs of female rhesus monkeys (Macaca mulatta). Chandra, H; Kamboj, VP; Nigam, PK, 1985) | 1.31 |
| "Treatment with Centchroman (3,4-trans-2,2-dimethyl-3-phenyl-4-p-(beta-pyrrolidinoethoxy) phenyl-7-methoxy chroman) has been evaluated in 4 male and 75 female patients with advanced breast cancer. " | ( Centchroman--a non-steroidal anti-cancer agent for advanced breast cancer: phase-II study. Agarwal, AK; Gupta, R; Kamboj, VP; Misra, NC; Nigam, PK, 1989) | 2.07 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Adverse effects included ovarian cyst (7." | ( Efficacy and safety of ormeloxifene in management of menorrhagia: a pilot study. Agarwal, N; Kriplani, A; Kulshrestha, V, 2009) | 0.35 |
| "Ormeloxifene is an effective and safe therapeutic option for the medical management of menorrhagia." | ( Efficacy and safety of ormeloxifene in management of menorrhagia: a pilot study. Agarwal, N; Kriplani, A; Kulshrestha, V, 2009) | 0.35 |
| "Background and objectives: Abnormal uterine bleeding is a significant clinical and gynaecological concern that necessitates its safe and effective treatment." | ( Evaluation of the Safety and Efficacy of Ormeloxifene, a Selective Estrogen Receptor Modulator and Medroxyprogesterone Acetate in Women with Non-Structural Abnormal Uterine Bleeding: A Randomized Clinical Trial. Ali, T; Almuqbil, M; Alshehri, AM; Alshehri, S; Amin, F; Ara, R; Bader, GN; Hamid, L; Malik, A; Mir, SA; Shakeel, F; Wani, SUD, 2022) | 0.72 |
Study reports assay methodology, tissue distribution, and the basic pharmacokinetic behavior of centchroman and its 7-desmethyl metabolite. Pharmacokinetic parameters of cent chroman were determined after a single oral dose of 60 mg (2 x 30-mg tablets) in two healthy female volunteers.
| Excerpt | Reference | Relevance |
|---|---|---|
| " Pharmacokinetic parameters of centchroman were determined after a single oral dose of 60 mg (2 x 30-mg tablets) in two healthy female volunteers." | ( High performance liquid chromatographic (HPLC) determination of centchroman in human serum and application to single-dose pharmacokinetics. Asthana, OP; Grover, PK; Gupta, RC; NityaNand, S; Paliwal, JK; Srivastava, JS, 1989) | 0.8 |
| " The mean terminal elimination half-life (t1/2) was 165 (s." | ( Pharmacokinetics of centchroman in healthy female subjects after oral administration. Asthana, OP; Gupta, RC; Lal, J; Nityanand, S, 1995) | 0.61 |
| "This study reports assay methodology, tissue distribution, and the basic pharmacokinetic behavior of centchroman and its 7-desmethyl metabolite [7-desmethyl centchroman (DMC)] after a single 12." | ( Tissue distribution and pharmacokinetics of centchroman. A new nonsteroidal postcoital contraceptive agent and its 7-desmethyl metabolite in female rats after a single oral dose. Gupta, RC; Paliwal, JK, 1996) | 0.77 |
| " In view of its vast clinical application and the interaction of steroidal oral contraceptives with certain commonly used therapeutic agents, evaluation of interaction of certain concomitantly administered therapeutic agents (ibuprofen, rifampicin, diazepam, salbutamol, nifedipine, paracetamol, haloperidol, and tetracycline), in terms of both the postcoital contraceptive efficacy and pharmacokinetic profile, with centchroman was undertaken in female Sprague-Dawley rats." | ( Evaluation of interaction potential of certain concurrently administered drugs with pharmacological and pharmacokinetic profile of centchroman in rats. Gupta, RC; Kamboj, VP; Khurana, M; Lal, J; Paliwal, JK; Singh, MM, 2002) | 0.68 |
| " The pharmacokinetic parameters were compared with the control data reported previously from this laboratory." | ( Pharmacokinetic interaction of tetracycline with centchroman in healthy female volunteers. Gupta, RC; Kamboj, VP; Khurana, M; Lal, J; Nityanand, S, 2003) | 0.57 |
| " In view of the vast clinical applications and interactions of steroidal oral contraceptives with commonly used therapeutic agents, the interaction potential of certain concomitantly administered therapeutic agents was investigated in terms of postcoital contraceptive efficacy (pharmacological) and the pharmacokinetic profile of centchroman in female Sprague-Dawley rats." | ( Effect of concurrently coadministered drugs on the pharmacokinetic/pharmacodynamic profile of centchroman, a nonsteroidal oral contraceptive, in rats. Gupta, RC; Kumar, V; Lal, J; Singh, MM, 2006) | 0.73 |
| " Pharmacokinetic interaction was studied in normal female rats with or without coadministered drugs." | ( Effect of concurrently coadministered drugs on the pharmacokinetic/pharmacodynamic profile of centchroman, a nonsteroidal oral contraceptive, in rats. Gupta, RC; Kumar, V; Lal, J; Singh, MM, 2006) | 0.55 |
| " In pharmacokinetic interaction studies, most of the therapeutic agents affected the rate and extent of absorption of centchroman." | ( Effect of concurrently coadministered drugs on the pharmacokinetic/pharmacodynamic profile of centchroman, a nonsteroidal oral contraceptive, in rats. Gupta, RC; Kumar, V; Lal, J; Singh, MM, 2006) | 0.76 |
| " The assay was successfully applied to determine the pharmacokinetic parameters in Sprague-Dawley rats after an oral administration of centchroman at 20mg/kg." | ( Development and validation of a rapid, sensitive liquid chromatography-tandem mass spectrometry method using electrospray ionization for quantitation of centchroman in rat plasma and its application to preclinical pharmacokinetic study. Jain, GK; Singh, RS; Singh, SP, 2008) | 0.75 |
| "The study was intended to investigate the effect of concomitant administration of antimalarial drug (pyrimethamine or arteether) on pharmacokinetic and post coitus contraceptive efficacy of ormeloxifene in female Sprague-Dawley rats." | ( Effect of arteether and pyrimethamine coadministration on the pharmacokinetic and pharmacodynamic profile of ormeloxifene. Jaiswal, S; Lal, J; Sharma, A; Shukla, M, 2017) | 0.46 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Findings suggest that interference with anti-implantation action of ormeloxifene by tetracycline might be due primarily to the almost complete abolition of its estrogen antagonistic activity at the uterine level, effected by decreased bioavailability of ormeloxifene and/or its active metabolite(s) by altered enterohepatic recirculation because of the effect on gut microflora." | ( Interaction with anti-implantation and estrogen antagonistic activities of dl-ormeloxifene, a selective estrogen receptor modulator, by tetracycline in female Sprague-Dawley rats. Ghosh, R; Kamboj, VP; Singh, MM, 2001) | 0.31 |
| " It reduced the bioavailability of centchroman and its active metabolite by increasing their excretion through bile and feces." | ( Evaluation of interaction potential of certain concurrently administered drugs with pharmacological and pharmacokinetic profile of centchroman in rats. Gupta, RC; Kamboj, VP; Khurana, M; Lal, J; Paliwal, JK; Singh, MM, 2002) | 0.8 |
| " This might be related to its estrogen antagonistic activity and/or decreased bioavailability of estradiol at a cellular level due to its increased metabolism to biologically less-active estrone via activation of estradiol-17 beta-hydroxysteroid dehydrogenase and suppression of estrone-17 beta-hydroxysteroid dehydrogenase." | ( Antioxidant defense system during endometrial receptivity in the guinea pig: effect of ormeloxifene, a selective estrogen receptor modulator. Bansode, FW; Makker, A; Singh, MM; Srivastava, VM, 2006) | 0.33 |
| " In other pharmacokinetic parameters, clearance (CL) remained unchanged; however, there was decrease in bioavailability (F) and volume of distribution (V(d)) in some situations." | ( Effect of concurrently coadministered drugs on the pharmacokinetic/pharmacodynamic profile of centchroman, a nonsteroidal oral contraceptive, in rats. Gupta, RC; Kumar, V; Lal, J; Singh, MM, 2006) | 0.55 |
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " There was no significant increase in centchroman concentrations in milk after multiple dosing (group II)." | ( Centchroman: a new non-steroidal oral contraceptive in human milk. Asthana, OP; Gupta, RC; Lal, J; Nityanand, S; Paliwal, JK, 1995) | 2 |
| " The present study was undertaken to simplify the dosing schedule without sacrificing the purpose of twice a week dosing regimen, using modeling and measurement approaches." | ( Optimization of contraceptive dosage regimen of Centchroman. Asthana, OP; Gupta, RC; Lal, J; Nagaraja, NV; Nitynand, S, 2001) | 0.57 |
| " This was prevented by ormeloxifene and the effect, though apparently more in females supplemented with higher dose of ormeloxifene, was not always significantly different and clear dose-response was not evident until BMD data was evaluated on T-/Z-score basis." | ( In vitro anti-resorptive activity and prevention of ovariectomy-induced osteoporosis in female Sprague-Dawley rats by ormeloxifene, a selective estrogen receptor modulator. Arshad, M; Ghosh, R; Sawlani, V; Sengupta, S; Sharma, S; Singh, MM, 2004) | 0.32 |
| "Ormeloxifene with its convenient twice-weekly dosage schedule was effective in treating AUB-L, with 72% of patients responding to 6-month treatment compared with 8% with COC, even though leiomyoma volume increased insignificantly with both ormeloxifene and COCs." | ( Efficacy of ormeloxifene versus oral contraceptive in the management of abnormal uterine bleeding due to uterine leiomyoma. Agarwal, N; Bhatla, N; Hari, S; Kachhawa, G; Kriplani, A; Kulshrestha, V; Srivastava, A, 2016) | 0.43 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| TDP1 protein | Homo sapiens (human) | Potency | 23.8723 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| AR protein | Homo sapiens (human) | Potency | 28.5518 | 0.0002 | 21.2231 | 8,912.5098 | AID743035; AID743042; AID743053 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 26.6261 | 0.0002 | 14.3764 | 60.0339 | AID720691; AID720692; AID720719 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 15.8489 | 0.0054 | 28.0263 | 1,258.9301 | AID1346985 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 26.3881 | 0.0002 | 29.3054 | 16,493.5996 | AID743069; AID743075; AID743078; AID743079 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 21.3138 | 0.0010 | 19.4141 | 70.9645 | AID743094 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 13.3332 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| potassium voltage-gated channel subfamily H member 2 isoform d | Homo sapiens (human) | Potency | 10.0000 | 0.0178 | 9.6374 | 44.6684 | AID588834 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 9.7188 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 31.6704 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID720552 |
| ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 23.7101 | 0.0119 | 17.9420 | 71.5630 | AID651632 |
| Ataxin-2 | Homo sapiens (human) | Potency | 23.7101 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID69512 | Relative binding affinity(RBA) against Estrogen receptor in rat liver | 1992 | Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8 | Synthesis of 2-(p-chlorobenzyl)-3-aryl-6-methoxybenzofurans as selective ligands for antiestrogen-binding sites. Effects on cell proliferation and cholesterol synthesis. |
| AID38618 | Relative binding affinity(RBA) against AEBS (Antiestrogen binding site) in rat liver | 1992 | Journal of medicinal chemistry, Apr-17, Volume: 35, Issue:8 | Synthesis of 2-(p-chlorobenzyl)-3-aryl-6-methoxybenzofurans as selective ligands for antiestrogen-binding sites. Effects on cell proliferation and cholesterol synthesis. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 46 (31.08) | 18.7374 |
| 1990's | 28 (18.92) | 18.2507 |
| 2000's | 24 (16.22) | 29.6817 |
| 2010's | 42 (28.38) | 24.3611 |
| 2020's | 8 (5.41) | 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 very strong demand-to-supply ratio for research on this compound.
| This Compound (61.54) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 12 (7.64%) | 5.53% |
| Reviews | 7 (4.46%) | 6.00% |
| Case Studies | 1 (0.64%) | 4.05% |
| Observational | 1 (0.64%) | 0.25% |
| Other | 136 (86.62%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||