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MedKoo Cat#: 598744 | Name: Levormeloxifene

Description:

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

Levormeloxifene is a selective estrogen receptor modulator. It inhibits vaginal tropoelastin and transforming growth factor beta 1 production.

Chemical Structure

Levormeloxifene
CAS#78994-23-7

Theoretical Analysis

MedKoo Cat#: 598744

Name: Levormeloxifene

CAS#: 78994-23-7

Chemical Formula: C30H35NO3

Exact Mass: 457.2617

Molecular Weight: 457.61

Elemental Analysis: C, 78.74; H, 7.71; N, 3.06; O, 10.49

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
199583-01-2 (fumarate) 78994-23-7 (free)
Synonym
Levormeloxifene;
IUPAC/Chemical Name
1-(2-(4-((3R,4R)-7-methoxy-2,2-dimethyl-3-phenylchroman-4-yl)phenoxy)ethyl)pyrrolidine
InChi Key
XZEUAXYWNKYKPL-WDYNHAJCSA-N
InChi Code
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
SMILES Code
CC1(C)[C@@H](C2=CC=CC=C2)[C@H](C3=CC=C(OCCN4CCCC4)C=C3)C5=CC=C(OC)C=C5O1
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levormeloxifene is a selective estrogen receptor modulator.
In vitro activity:
SMC proliferation was significantly increased by levormeloxifene [relative cell number, mean ± SE, levormeloxifene 0.1 µM 130 ± 13% of control (P=NS), 1 µM 151 ± 19% of control (P<0.05)]. Tropoelastin production was significantly decreased by levormeloxifene [mean ± SE, levormeloxifene 0.1 µM 75 ± 4% of control (P=NS), 1 µM 64 ± 2% of control (P<0.05)]. Reference: J Smooth Muscle Res. 2011;47(1):11-9. https://pubmed.ncbi.nlm.nih.gov/21757851/
In vivo activity:
Ovariectomy resulted in an increase in these markers; the increase was prevented by estradiol or levormeloxifene. Estradiol or levormeloxifene inhibited loss of lumbar spine bone mineral density (BMD) following ovariectomy compared with untreated monkeys (ovx -5.0%; sham -0.4%; est +0.2%; L1 -3.6%, L2 -2.0%, L3 -2.5%). Reference: Bone. 2001 Jul;29(1):7-15. https://pubmed.ncbi.nlm.nih.gov/11472885/

Preparing Stock Solutions

The following data is based on the product molecular weight 457.61 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.

Recalculate based on batch purity %
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. Takacs P, Yavagal S, Zhang Y, Candiotti K, Medina CA. Levormeloxifene inhibits vaginal tropoelastin and transforming growth factor beta 1 production. J Smooth Muscle Res. 2011;47(1):11-9. doi: 10.1540/jsmr.47.11. PMID: 21757851. 2. Hotchkiss CE, Stavisky R, Nowak J, Brommage R, Lees CJ, Kaplan J. Levormeloxifene prevents increased bone turnover and vertebral bone loss following ovariectomy in cynomolgus monkeys. Bone. 2001 Jul;29(1):7-15. doi: 10.1016/s8756-3282(01)00465-3. PMID: 11472885. 3. Holm P, Shalmi M, Korsgaard N, Guldhammer B, Skouby SO, Stender S. A partial estrogen receptor agonist with strong antiatherogenic properties without noticeable effect on reproductive tissue in cholesterol-fed female and male rabbits. Arterioscler Thromb Vasc Biol. 1997 Oct;17(10):2264-72. doi: 10.1161/01.atv.17.10.2264. PMID: 9351399.
In vitro protocol:
1. Takacs P, Yavagal S, Zhang Y, Candiotti K, Medina CA. Levormeloxifene inhibits vaginal tropoelastin and transforming growth factor beta 1 production. J Smooth Muscle Res. 2011;47(1):11-9. doi: 10.1540/jsmr.47.11. PMID: 21757851.
In vivo protocol:
1. Hotchkiss CE, Stavisky R, Nowak J, Brommage R, Lees CJ, Kaplan J. Levormeloxifene prevents increased bone turnover and vertebral bone loss following ovariectomy in cynomolgus monkeys. Bone. 2001 Jul;29(1):7-15. doi: 10.1016/s8756-3282(01)00465-3. PMID: 11472885. 2. Holm P, Shalmi M, Korsgaard N, Guldhammer B, Skouby SO, Stender S. A partial estrogen receptor agonist with strong antiatherogenic properties without noticeable effect on reproductive tissue in cholesterol-fed female and male rabbits. Arterioscler Thromb Vasc Biol. 1997 Oct;17(10):2264-72. doi: 10.1161/01.atv.17.10.2264. PMID: 9351399.
1: Surin WR, Bhalla H, Kuriakose GC, Singh MM. Assessment of raloxifene, estradiol-17β, dl-ormeloxifene and levormeloxifene on thrombin activity. J Basic Clin Physiol Pharmacol. 2014 Jan 27:1-8. doi: 10.1515/jbcpp-2013-0056. [Epub ahead of print] PubMed PMID: 24468615. 2: Takacs P, Yavagal S, Zhang Y, Candiotti K, Medina CA. Levormeloxifene inhibits vaginal tropoelastin and transforming growth factor beta 1 production. J Smooth Muscle Res. 2011;47(1):11-9. PubMed PMID: 21757851. 3: Ravn P, Nielsen TF, Christiansen C. What can be learned from the levormeloxifene experience? Acta Obstet Gynecol Scand. 2006;85(2):135-42. Review. PubMed PMID: 16532904. 4: Ning N, Lin G, Lue TF, Lin CS. Effects of estrogen, raloxifene, and levormeloxifene on the expression of Rho-kinase signaling molecules in urethral smooth muscle cells. Urology. 2010 Dec;76(6):1517.e6-11. doi: 10.1016/j.urology.2010.07.470. Epub 2010 Oct 23. PubMed PMID: 20970835; PubMed Central PMCID: PMC3537261. 5: Wood CE, Stavisky RC, Nowak J, Kaplan JR. Stimulatory adrenocortical effects of a selective estrogen receptor modulator in ovariectomized female macaques. Toxicol Pathol. 2012;40(1):55-61. doi: 10.1177/0192623311425509. Epub 2011 Oct 21. PubMed PMID: 22021168. 6: Banie L, Lin G, Ning H, Wang G, Lue TF, Lin CS. Effects of estrogen, raloxifene and levormeloxifene on alpha1A-adrenergic receptor expression. J Urol. 2008 Nov;180(5):2241-6. doi: 10.1016/j.juro.2008.07.020. Epub 2008 Sep 19. PubMed PMID: 18804812. 7: Hotchkiss CE, Stavisky R, Nowak J, Brommage R, Lees CJ, Kaplan J. Levormeloxifene prevents increased bone turnover and vertebral bone loss following ovariectomy in cynomolgus monkeys. Bone. 2001 Jul;29(1):7-15. PubMed PMID: 11472885. 8: Goldstein SR, Nanavati N. Adverse events that are associated with the selective estrogen receptor modulator levormeloxifene in an aborted phase III osteoporosis treatment study. Am J Obstet Gynecol. 2002 Sep;187(3):521-7. PubMed PMID: 12237621. 9: Mountfield RJ, Kiehr B, John BA. Metabolism, disposition, excretion, and pharmacokinetics of levormeloxifene, a selective estrogen receptor modulator, in the rat. Drug Metab Dispos. 2000 May;28(5):503-13. PubMed PMID: 10772628. 10: Alexandersen P, Riis BJ, Stakkestad JA, Delmas PD, Christiansen C. Efficacy of levormeloxifene in the prevention of postmenopausal bone loss and on the lipid profile compared to low dose hormone replacement therapy. J Clin Endocrinol Metab. 2001 Feb;86(2):755-60. PubMed PMID: 11158042. 11: Warming L, Christoffersen C, Riis BJ, Stakkestad JA, Delmas PD, Christiansen C. Adverse effects of a SERM (Levormeloxifene). Safety parameters and bone mineral density 12 months after treatment withdrawal. Maturitas. 2003 Mar 28;44(3):189-99. PubMed PMID: 12648882. 12: Mountfield RJ, Panduro AM, Wassmann O, Thompson M, John B, van der Merbel N. Metabolism of levormeloxifene, a selective oestrogen receptor modulator, in the Sprague-Dawley rat, Cynomolgus monkey and postmenopausal woman. Xenobiotica. 2000 Feb;30(2):201-17. PubMed PMID: 10718126. 13: Kiehr B, Skrumsager BK, Müller M, Pedersen PC. Pharmacokinetics of levormeloxifene in young versus elderly postmenopausal women. Clin Ther. 2001 Jan;23(1):62-71. PubMed PMID: 11219480. 14: Ewies AA, Elshafie M, Li J, Stanley A, Thompson J, Styles J, White I, Al-Azzawi F. Changes in transcription profile and cytoskeleton morphology in pelvic ligament fibroblasts in response to stretch: the effects of estradiol and levormeloxifene. Mol Hum Reprod. 2008 Feb;14(2):127-35. doi: 10.1093/molehr/gam090. Epub 2008 Jan 9. PubMed PMID: 18184756. 15: Skrumsager BK, Kiehr B, Pedersen PC, Gerrits M, Watson N, Bjarnason K. Levormeloxifene: safety, pharmacodynamics and pharmacokinetics in healthy postmenopausal women following single and multiple doses of a new selective oestrogen receptor modulator. Br J Clin Pharmacol. 2002 Mar;53(3):284-95. PubMed PMID: 11874392; PubMed Central PMCID: PMC1874307. 16: Østerberg O, Kiehr B, Erichsen L, Poulsen HE, Ingwersen SH. Pharmacokinetics and allometric scaling of levormeloxifene, a selective oestrogen receptor modulator. Biopharm Drug Dispos. 2003 Apr;24(3):121-9. PubMed PMID: 12673670. 17: Holm P, Shalmi M, Korsgaard N, Guldhammer B, Skouby SO, Stender S. A partial estrogen receptor agonist with strong antiatherogenic properties without noticeable effect on reproductive tissue in cholesterol-fed female and male rabbits. Arterioscler Thromb Vasc Biol. 1997 Oct;17(10):2264-72. PubMed PMID: 9351399. 18: Kiehr B, Christensen MS. Assay for levormeloxifene, a selective estrogen receptor modulator, in human and monkey plasma employing high-performance liquid chromatography and solid-phase extraction. J Chromatogr B Biomed Sci Appl. 1999 Jun 11;729(1-2):315-22. PubMed PMID: 10410957. 19: Bloch-Thomsen A, Silvestri S, Christiansen C, Bjarnason NH. Associated response in bone mineral density and atherogenic lipid profile during treatment with two different selective estrogen receptor modulators: levormeloxifene and raloxifene. Climacteric. 2003 Jun;6(2):159-67. PubMed PMID: 12841887. 20: Goodrich JA, Clarkson TB, Cline JM, Jenkins AJ, Del Signore MJ. Value of the micropig model of menopause in the assessment of benefits and risks of postmenopausal therapies for cardiovascular and reproductive tissues. Fertil Steril. 2003 Mar;79 Suppl 1:779-88. PubMed PMID: 12620491.