Raloxifene HCl | CAS#82640-04-8 | 84449-90-1

MedKoo Cat#: 100761 | Name: Raloxifene hydrochloride

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Description:

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

Raloxifene is a selective estrogen receptor modulator with effects on bone and breast cancer and cardiovascular disease risk. It is used for breast cancer and osteoporosis research.

Chemical Structure

Raloxifene hydrochloride

CAS#82640-04-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 100761

Name: Raloxifene hydrochloride

CAS#: 82640-04-8 (HCl)

Chemical Formula: C28H28ClNO4S

Exact Mass: 0.0000

Molecular Weight: 510.05

Elemental Analysis: C, 65.94; H, 5.53; Cl, 6.95; N, 2.75; O, 12.55; S, 6.29

Price and Availability

Size	Price	Availability	Quantity
200mg	USD 150.00
500mg	USD 350.00
1g	USD 650.00
2g	USD 950.00
5g	USD 1,450.00

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Related CAS #

84449-90-1 (free base) 82640-04-8 (HCl) 84449-90-1 (HCl)

Synonym

LY-139481; LY139481; LY 139481; Raloxifene hydrochloride; US brand names: Evista; Keoxifene. Abbreviation: RALOX .

IUPAC/Chemical Name

(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl)(4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone hydrochloride

InChi Key

BKXVVCILCIUCLG-UHFFFAOYSA-N

InChi Code

InChI=1S/C28H27NO4S.ClH/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;1H

SMILES Code

O=C(C1=C(C2=CC=C(O)C=C2)SC3=CC(O)=CC=C31)C4=CC=C(OCCN5CCCCC5)C=C4.[H]Cl

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

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

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

HS Tariff Code

2934.99.9001

More Info

EVISTA (raloxifene hydrochloride) is an estrogen agonist/antagonist, commonly referred to as a selective estrogen receptor modulator (SERM) that belongs to the benzothiophene class of compounds.Raloxifene HCl is an off-white to pale-yellow solid that is very slightly soluble in water. EVISTA is supplied in a tablet dosage form for oral administration. Each EVISTA tablet contains 60 mg of raloxifene HCl, which is the molar equivalent of 55.71 mg of free base. Inactive ingredients include anhydrous lactose, carnauba wax, crospovidone, FD&C Blue No. 2 aluminum lake, hypromellose, lactose monohydrate, magnesium stearate, modified pharmaceutical glaze, polyethylene glycol, polysorbate 80, povidone, propylene glycol, and titanium dioxide. Mechanism of Action Decreases in estrogen levels after oophorectomy or menopause lead to increases in bone resorption and accelerated bone loss. Bone is initially lost rapidly because the compensatory increase in bone formation is inadequate to offset resorptive losses. In addition to loss of estrogen, this imbalance between resorption and formation may be due to age-related impairment of osteoblasts or their precursors. In some women, these changes will eventually lead to decreased bone mass, osteoporosis, and increased risk for fractures, particularly of the spine, hip, and wrist. Vertebral fractures are the most common type of osteoporotic fracture in postmenopausal women. The biological actions of raloxifene are largely mediated through binding to estrogen receptors. This binding results in activation of certain estrogenic pathways and blockade of others. Thus, raloxifene is an estrogen agonist/antagonist, commonly referred to as a selective estrogen receptor modulator (SERM). Raloxifene decreases resorption of bone and reduces biochemical markers of bone turnover to the premenopausal range. These effects on bone are manifested as reductions in the serum and urine levels of bone turnover markers, decreases in bone resorption based on radiocalcium kinetics studies, increases in bone mineral density (BMD), and decreases in incidence of fractures.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Raloxifene HCl is a selective and orally active estrogen receptor modulator (SERM), which inhibits human cytosolic aldehyde oxidase-catalyzed phthalazine oxidation activity with IC50 of 5.7 nM.

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	102.0	199.98

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 510.05 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: Lee J, Kim J, Jeong C, Baek KH, Ha J. Beyond breast cancer: role of selective estrogen receptor modulators in reducing systemic malignancies: evidence from population-based data. Curr Med Res Opin. 2024 Sep;40(9):1589-1596. doi: 10.1080/03007995.2024.2390649. Epub 2024 Aug 18. PMID: 39115280. 2: Yamada Y, Kurokawa R, Kurokawa M, Tsujimoto R, Shimura A, Maki H, Kondo A, Abe O. Longitudinal CT, MRI, and 18F-FDG PET/CT Imaging Findings of Peliosis Hepatis: A Case Report. Cureus. 2024 Jun 23;16(6):e62997. doi: 10.7759/cureus.62997. PMID: 39050295; PMCID: PMC11266828. 3: Kandel SE, Tooker BC, Lampe JN. Drug metabolism of ciprofloxacin, ivacaftor, and raloxifene by Pseudomonas aeruginosa cytochrome P450 CYP107S1. J Biol Chem. 2024 Aug;300(8):107594. doi: 10.1016/j.jbc.2024.107594. Epub 2024 Jul 18. PMID: 39032655; PMCID: PMC11382314. 4: Demirbaş AE, Mohsen F, Topan C, Karakaya M, Kütük N, Alkan A. The Combined Therapy of Teriparatide and Raloxifene Improves Osseointegration of Dental Implants in the Osteoporotic Rabbit Model. Int J Oral Maxillofac Implants. 2024 Jun 21;(3):435-445. doi: 10.11607/jomi.10040. PMID: 38905118. 5: Kher JD, Sorathia K. Bioavailability Enhancement of BCS Class II Raloxifene Hydrochloride by Inclusion Complex and Solid Dispersion Techniques. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2024 Jun 12;40:e20240002. doi: 10.62958/j.cjap.2024.002. PMID: 38862271. 6: Moreira GG, Taveira SF, Martins FT, Wagner KG, Marreto RN. Multivariate Analysis of Solubility Parameters for Drug-Polymer Miscibility Assessment in Preparing Raloxifene Hydrochloride Amorphous Solid Dispersions. AAPS PharmSciTech. 2024 Jun 6;25(5):127. doi: 10.1208/s12249-024-02844-4. PMID: 38844724. 7: Wang Y, Sauvage M, Diennet M, Weber S, Mader S, Gleason JL. Design, synthesis and antiproliferative activity of raloxifene/histone deacetylase inhibitor hybrids in breast cancer. Eur J Med Chem. 2024 Aug 5;274:116533. doi: 10.1016/j.ejmech.2024.116533. Epub 2024 May 24. PMID: 38838548. 8: Knight KJ, Fordham RJ, Crabtree NJ, Knapp KM. Evaluating the impact of COVID-19 on DXA waiting lists and osteoporosis prescription trends in England 2019-2023. Osteoporos Int. 2024 Aug;35(8):1451-1460. doi: 10.1007/s00198-024-07120-6. Epub 2024 May 25. PMID: 38795142. 9: He W, Zhang S, Qi Z, Liu W. Unveiling the potential of estrogen: Exploring its role in neuropsychiatric disorders and exercise intervention. Pharmacol Res. 2024 Jun;204:107201. doi: 10.1016/j.phrs.2024.107201. Epub 2024 May 3. PMID: 38704108. 10: Otake H, Nagai N. [Development of Transdermal Formulation Based on Nanotechnology and Elucidation of Its Drug Delivery Pathways]. Yakugaku Zasshi. 2024;144(5):505-510. Japanese. doi: 10.1248/yakushi.23-00178-1. PMID: 38692925. 11: Gogos A, Sbisa A, van den Buuse M. Disruption of NMDA receptor-mediated regulation of PPI in the maternal immune activation model of schizophrenia is restored by 17β-estradiol and raloxifene. Schizophr Res. 2024 May;267:432-440. doi: 10.1016/j.schres.2024.04.008. Epub 2024 Apr 19. PMID: 38642484. 12: Kazimir A, Götze T, Lönnecke P, Murganić B, Mijatović S, Maksimović-Ivanić D, Hey-Hawkins E. Exploring Raloxifene-Based Metallodrugs: A Versatile Vector Combined with Platinum(II), Palladium(II) and Nickel(II) Dichlorides and Carborates against Triple-Negative Breast Cancer. ChemMedChem. 2024 Jul 15;19(14):e202400006. doi: 10.1002/cmdc.202400006. Epub 2024 Jun 5. PMID: 38642018. 13: Creecy A, Segvich D, Metzger C, Kohler R, Wallace JM. Combining anabolic loading and raloxifene improves bone quantity and some quality measures in a mouse model of osteogenesis imperfecta. Bone. 2024 Jul;184:117106. doi: 10.1016/j.bone.2024.117106. Epub 2024 Apr 17. PMID: 38641232; PMCID: PMC11130993. 14: Chauhan D, Maity D, Yadav PK, Vishwakarma S, Agarwal A, Chourasia MK, Gayen JR. Enhanced oral bioavailability of levormeloxifene and raloxifene by nanoemulsion: simultaneous bioanalysis using liquid chromatography-tandem mass spectrometry. Nanomedicine (Lond). 2024;19(12):1051-1068. doi: 10.2217/nnm-2024-0023. Epub 2024 Apr 19. PMID: 38639565; PMCID: PMC11225398. 15: Condi FLF, Fuchs LFP, Carvalho KC, Baracat EC. Treatment with Raloxifene Induces the Expression of Kisspeptin, Insulin, and Androgen Receptors in Bones of Castrated Adult Female Rats. Rev Bras Ortop (Sao Paulo). 2024 Apr 10;59(2):e228-e234. doi: 10.1055/s-0044-1779319. PMID: 38606141; PMCID: PMC11006519. 16: Surowiec RK, Reul ON, Chowdhury NN, Rai RK, Segvich D, Tomaschke AA, Damrath J, Jacobson AM, Allen MR, Wallace JM. Combining raloxifene and mechanical loading improves bone composition and mechanical properties in a murine model of chronic kidney disease (CKD). Bone. 2024 Jun;183:117089. doi: 10.1016/j.bone.2024.117089. Epub 2024 Apr 3. PMID: 38575047; PMCID: PMC11210703. 17: Liu Q, Ma L, Chen F, Zhang S, Huang Z, Zheng X, Chen Z, Ye J, Hou N, Yi W, Zhou Z. Raloxifene-driven benzothiophene derivatives: Discovery, structural refinement, and biological evaluation as potent PPARγ modulators based on drug repurposing. Eur J Med Chem. 2024 Apr 5;269:116325. doi: 10.1016/j.ejmech.2024.116325. Epub 2024 Mar 15. PMID: 38527378. 18: Debs SR, Conn I, Navaneethan B, Penklis AG, Meyer U, Killcross S, Weickert CS, Purves-Tyson TD. Maternal immune activation and estrogen receptor modulation induce sex-specific dopamine-related behavioural and molecular alterations in adult rat offspring. Brain Behav Immun. 2024 May;118:236-251. doi: 10.1016/j.bbi.2024.02.034. Epub 2024 Feb 29. PMID: 38431238. 19: Zaraei SO, Dohle W, Anbar HS, El-Gamal R, Leblond B, Foster PA, Al-Tel TH, Potter BVL, El-Gamal MI. Synthesis, biological evaluation, and stability studies of raloxifene mono- and bis-sulfamates as dual-targeting agents. Bioorg Med Chem. 2024 Mar 1;101:117645. doi: 10.1016/j.bmc.2024.117645. Epub 2024 Feb 16. PMID: 38401456. 20: Aldawsari HM, Ahmed OAA, Alhakamy NA, Neamatallah T, Fahmy UA, Badr-Eldin SM. RETRACTED: Aldawsari et al. Lipidic Nano-Sized Emulsomes Potentiates the Cytotoxic and Apoptotic Effects of Raloxifene Hydrochloride in MCF-7 Human Breast Cancer Cells: Factorial Analysis and In Vitro Anti-Tumor Activity Assessment. Pharmaceutics 2021, 13, 783. Pharmaceutics. 2024 Jan 30;16(2):195. doi: 10.3390/pharmaceutics16020195. PMID: 38399356; PMCID: PMC10892574.