Raloxifene | CAS#84449-90-1 | Estrogen receptor modulator

MedKoo Cat#: 558343 | Name: Raloxifene

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Raloxifene is a selective estrogen receptor modulator and a SERM antimicrobial adjuvant. Raloxifene increases lumbar spine bone mineral density (BMD) and lowers vertebral fracture risk in patients with osteoporosis.

Chemical Structure

Raloxifene

CAS#84449-90-1

Theoretical Analysis

MedKoo Cat#: 558343

Name: Raloxifene

CAS#: 84449-90-1

Chemical Formula: C28H27NO4S

Exact Mass: 473.1661

Molecular Weight: 473.59

Elemental Analysis: C, 71.01; H, 5.75; N, 2.96; O, 13.51; S, 6.77

Price and Availability

Size	Price	Availability	Quantity
200mg	USD 510.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Raloxifene; Pharoxifene; Raloxifenum;

IUPAC/Chemical Name

Methanone, (6-hydroxy-2-(4-hydroxyphenyl)benzo(b)thien-3-yl)(4-(2-(1-piperidinyl)ethoxy)phenyl)-

InChi Key

GZUITABIAKMVPG-UHFFFAOYSA-N

InChi Code

InChI=1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2

SMILES Code

O=C(C1=C(C2=CC=C(O)C=C2)SC3=CC(O)=CC=C31)C4=CC=C(OCCN5CCCCC5)C=C4

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO and ethanol

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO and ethanol

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Raloxifene is a benzothiophene-derived selective estrogen receptor modulator. Raloxifene has estrogen-agonistic effects on bone and lipids and estrogen-antagonistic effects on the breast and uterus.

In vitro activity:

The combined treatment of raloxifene and gefitinib decreased the ability of neovascularization as assessed by tube formation of endothelial cells. These results suggested the potential of the combination of raloxifene and gefitinib for the prevention of triple-negative breast cancer growth and the appearance of metastatic events. Reference: Med Oncol. 2022 Dec 9;40(1):45. https://pubmed.ncbi.nlm.nih.gov/36494506/

In vivo activity:

This study showed that raloxifene decreased depression, fearfulness, and anxiety after focal cranial blast traumatic brain injury in mice, using standard assays of these behavioral end-points. These results indicate that raloxifene could be used to treat deficits after mild traumatic brain injury. Reference: Neurotrauma Rep. 2022 Nov 24;3(1):534-544. https://pubmed.ncbi.nlm.nih.gov/36479361/

	Solvent	mg/mL	mM
Solubility
	DMSO	95.0	200.60
	Ethanol	10.0	21.12

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 473.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Narendra G, Raju B, Verma H, Kumar M, Jain SK, Tung GK, Thakur S, Kaur R, Kaur S, Sapra B, Singh PK, Silakari O. Raloxifene and bazedoxifene as selective ALDH1A1 inhibitors to ameliorate cyclophosphamide resistance: A drug repurposing approach. Int J Biol Macromol. 2023 Jul 1;242(Pt 1):124749. doi: 10.1016/j.ijbiomac.2023.124749. Epub 2023 May 7. PMID: 37160174. 2. Taurin S, Rosengren RJ. Raloxifene potentiates the effect of gefitinib in triple-negative breast cancer cell lines. Med Oncol. 2022 Dec 9;40(1):45. doi: 10.1007/s12032-022-01909-3. PMID: 36494506. 3. Hering NA, Günzler E, Arndt M, Zibell M, Lauscher JC, Kreis ME, Beyer K, Seeliger H, Pozios I. Targeting Interleukin-6/Glycoprotein-130 Signaling by Raloxifene or SC144 Enhances Paclitaxel Efficacy in Pancreatic Cancer. Cancers (Basel). 2023 Jan 11;15(2):456. doi: 10.3390/cancers15020456. PMID: 36672405; PMCID: PMC9856922. 4. Honig MG, Del Mar NA, Moore BM, Reiner A. Raloxifene Mitigates Emotional Deficits after Mild Traumatic Brain Injury in Mice. Neurotrauma Rep. 2022 Nov 24;3(1):534-544. doi: 10.1089/neur.2022.0052. PMID: 36479361; PMCID: PMC9718433.

In vitro protocol:

In vivo protocol:

1. Hering NA, Günzler E, Arndt M, Zibell M, Lauscher JC, Kreis ME, Beyer K, Seeliger H, Pozios I. Targeting Interleukin-6/Glycoprotein-130 Signaling by Raloxifene or SC144 Enhances Paclitaxel Efficacy in Pancreatic Cancer. Cancers (Basel). 2023 Jan 11;15(2):456. doi: 10.3390/cancers15020456. PMID: 36672405; PMCID: PMC9856922. 2. Honig MG, Del Mar NA, Moore BM, Reiner A. Raloxifene Mitigates Emotional Deficits after Mild Traumatic Brain Injury in Mice. Neurotrauma Rep. 2022 Nov 24;3(1):534-544. doi: 10.1089/neur.2022.0052. PMID: 36479361; PMCID: PMC9718433.

1: Lušin TT, Mrhar A, Marc J, Trontelj J, Zavratnik A, Zegura B, Pfeifer M, Ostanek B. Inverse correlation of carotid intima-media thickness with raloxifene serum levels in osteoporosis. Wien Klin Wochenschr. 2014 Jul;126(13-14):403-8. doi: 10.1007/s00508-014-0551-3. Epub 2014 May 20. PubMed PMID: 24842749. 2: Gufford BT, Chen G, Vergara AG, Lazarus P, Oberlies NH, Paine MF. Milk Thistle Constituents Inhibit Raloxifene Intestinal Glucuronidation: A Potential Clinically Relevant Natural Product-Drug Interaction. Drug Metab Dispos. 2015 Sep;43(9):1353-9. doi: 10.1124/dmd.115.065086. Epub 2015 Jun 12. PubMed PMID: 26070840; PubMed Central PMCID: PMC4538855. 3: Gizzo S, Saccardi C, Patrelli TS, Berretta R, Capobianco G, Di Gangi S, Vacilotto A, Bertocco A, Noventa M, Ancona E, D'Antona D, Nardelli GB. Update on raloxifene: mechanism of action, clinical efficacy, adverse effects, and contraindications. Obstet Gynecol Surv. 2013 Jun;68(6):467-81. doi: 10.1097/OGX.0b013e31828baef9. Review. PubMed PMID: 23942473. 4: Kim K, Svedbom A, Luo X, Sutradhar S, Kanis JA. Comparative cost-effectiveness of bazedoxifene and raloxifene in the treatment of postmenopausal osteoporosis in Europe, using the FRAX algorithm. Osteoporos Int. 2014 Jan;25(1):325-37. doi: 10.1007/s00198-013-2521-4. Epub 2013 Oct 10. PubMed PMID: 24114398. 5: Nagatoya K, Nishimoto K, Shibahara N, Takahashi T, Kanehara H, Ueno N, Yasuda H, Okada S, Ueda H, Hirai K, Inoue T; Hokusetsu Renal Osteodystrophy Study Group. Effects of raloxifene on bone metabolism in postmenopausal women on chronic hemodialysis. Clin Exp Nephrol. 2015 Oct;19(5):939-46. doi: 10.1007/s10157-014-1065-z. Epub 2014 Dec 11. PubMed PMID: 25504368. 6: Khodaie-Ardakani MR, Khosravi M, Zarinfard R, Nejati S, Mohsenian A, Tabrizi M, Akhondzadeh S. A Placebo-Controlled Study of Raloxifene Added to Risperidone in Men with Chronic Schizophrenia. Acta Med Iran. 2015;53(6):337-45. PubMed PMID: 26069170. 7: Su FM, Chen YC, Cheng TT, Lin WC, Lui CC. Is raloxifene associated with lower risk of mortality in postmenopausal women with vertebral fractures after vertebroplasty?: a hospital-based analysis. BMC Musculoskelet Disord. 2015 Aug 19;16:209. doi: 10.1186/s12891-015-0670-7. PubMed PMID: 26286481; PubMed Central PMCID: PMC4545327. 8: Mencej-Bedrač S, Zupan J, Mlakar SJ, Zavratnik A, Preželj J, Marc J. Raloxifene pharmacodynamics is influenced by genetic variants in the RANKL/RANK/OPG system and in the Wnt signaling pathway. Drug Metabol Drug Interact. 2014;29(2):111-4. doi: 10.1515/dmdi-2013-0066. PubMed PMID: 24615483. 9: Sun D, Jones NR, Manni A, Lazarus P. Characterization of raloxifene glucuronidation: potential role of UGT1A8 genotype on raloxifene metabolism in vivo. Cancer Prev Res (Phila). 2013 Jul;6(7):719-30. doi: 10.1158/1940-6207.CAPR-12-0448. Epub 2013 May 16. PubMed PMID: 23682072; PubMed Central PMCID: PMC4057281. 10: Lewiecki EM, Miller PD, Harris ST, Bauer DC, Davison KS, Dian L, Hanley DA, McClung MR, Yuen CK, Kendler DL. Understanding and communicating the benefits and risks of denosumab, raloxifene, and teriparatide for the treatment of osteoporosis. J Clin Densitom. 2014 Oct-Dec;17(4):490-5. doi: 10.1016/j.jocd.2013.09.018. Epub 2013 Oct 25. Review. PubMed PMID: 24206867. 11: Meme L, Santarelli A, Marzo G, Emanuelli M, Nocini PF, Bertossi D, Putignano A, Dioguardi M, Lo Muzio L, Bambini F. Novel hydroxyapatite biomaterial covalently linked to raloxifene. Int J Immunopathol Pharmacol. 2014 Jul-Sep;27(3):437-44. PubMed PMID: 25280036. 12: Battani S, Pawar H, Suresh S. Evaluation of oral bioavailability and anticancer potential of raloxifene solid lipid nanoparticles. J Nanosci Nanotechnol. 2014 Aug;14(8):5638-45. PubMed PMID: 25935981. 13: O'Donnell EF, Koch DC, Bisson WH, Jang HS, Kolluri SK. The aryl hydrocarbon receptor mediates raloxifene-induced apoptosis in estrogen receptor-negative hepatoma and breast cancer cells. Cell Death Dis. 2014 Jan 30;5:e1038. doi: 10.1038/cddis.2013.549. PubMed PMID: 24481452; PubMed Central PMCID: PMC4040680. 14: Mahmood S, Taher M, Mandal UK. Experimental design and optimization of raloxifene hydrochloride loaded nanotransfersomes for transdermal application. Int J Nanomedicine. 2014 Sep 12;9:4331-46. doi: 10.2147/IJN.S65408. eCollection 2014. PubMed PMID: 25246789; PubMed Central PMCID: PMC4168883. 15: Haghverdi F, Farbodara T, Mortaji S, Soltani P, Saidi N. Effect of raloxifene on parathyroid hormone in osteopenic and osteoporotic postmenopausal women with chronic kidney disease stage 5. Iran J Kidney Dis. 2014 Nov;8(6):461-6. Erratum in: Iran J Kidney Dis. 2015 Jan;9(1):76. PubMed PMID: 25362221. 16: Anwar MJ, Radhakrishna KV, Sharma A, Vohora D. Raloxifene preserves phenytoin and sodium valproate induced bone loss by modulating serum estradiol and TGF-β3 content in bone of female mice. Eur J Pharm Sci. 2014 Oct 1;62:219-26. doi: 10.1016/j.ejps.2014.05.018. Epub 2014 May 28. PubMed PMID: 24880111. 17: Bal UA, Atar İ, Öktem M, Zeyneloğlu HB, Yıldırır A, Kuşcu E, Müderrisoğlu H. The effect of raloxifene on left ventricular hypertrophy in postmenopausal women: A prospective, randomized, and controlled study. Anatol J Cardiol. 2015 Jun;15(6):480-4. doi: 10.5152/akd.2014.5473. Epub 2014 Jun 3. PubMed PMID: 25430415; PubMed Central PMCID: PMC5779141. 18: Sameena Y, Sudha N, Chandrasekaran S, Enoch IV. The role of encapsulation by β-cyclodextrin in the interaction of raloxifene with macromolecular targets: a study by spectroscopy and molecular modeling. J Biol Phys. 2014 Sep;40(4):347-67. doi: 10.1007/s10867-014-9355-y. Epub 2014 Jul 30. PubMed PMID: 25073419; PubMed Central PMCID: PMC4119190. 19: Arsenyan P, Paegle E, Domracheva I, Gulbe A, Kanepe-Lapsa I, Shestakova I. Selenium analogues of raloxifene as promising antiproliferative agents in treatment of breast cancer. Eur J Med Chem. 2014 Nov 24;87:471-83. doi: 10.1016/j.ejmech.2014.09.088. Epub 2014 Sep 30. PubMed PMID: 25282270. 20: Kumar P, Song ZH. Identification of raloxifene as a novel CB2 inverse agonist. Biochem Biophys Res Commun. 2013 May 24;435(1):76-81. doi: 10.1016/j.bbrc.2013.04.040. Epub 2013 Apr 20. PubMed PMID: 23611779; PubMed Central PMCID: PMC5084446.