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MedKoo Cat#: 318600 | Name: Quinestrol
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Description:

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

Quinestrol is an antifertility agent and a compound used in estrogen replacement therapy. Quinestrol has the potential to reduce fecundity and post control rebuildup of B. bengalensis populations.

Chemical Structure

Quinestrol
Quinestrol
CAS#152-43-2

Theoretical Analysis

MedKoo Cat#: 318600

Name: Quinestrol

CAS#: 152-43-2

Chemical Formula: C25H32O2

Exact Mass: 364.2402

Molecular Weight: 364.52

Elemental Analysis: C, 82.37; H, 8.85; O, 8.78

Price and Availability

Size Price Availability Quantity
100mg USD 250.00 2 Weeks
200mg USD 450.00 2 Weeks
500mg USD 750.00 2 Weeks
1g USD 1,250.00 2 Weeks
2g USD 2,250.00 2 Weeks
5g USD 4,650.00 2 Weeks
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Related CAS #
No Data
Synonym
EECPE; Eston; Estrovis; Estrovis 4000; Estrovister; Ethynylestradiol-3-cyclopentyl ether; MeSH ID: D011800; Plestrovis; Qui-Lea; Quinestrol; W 3566;
IUPAC/Chemical Name
(8R,9S,13S,14S,17R)-3-cyclopentyloxy-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
InChi Key
PWZUUYSISTUNDW-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H32O2/c1-3-25(26)15-13-23-22-10-8-17-16-19(27-18-6-4-5-7-18)9-11-20(17)21(22)12-14-24(23,25)2/h1,9,11,16,18,21-23,26H,4-8,10,12-15H2,2H3
SMILES Code
CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC5CCCC5
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
>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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Quinestrol is absorbed via the lymphatic system, then stored in adipose tissue, and is gradually released from adipose tissue.
In vitro activity:
Quinestrol was selected for in vitro testing and demonstrated inhibited putrescine uptake in biochemical assay. Furthermore, all the confirmed hits proved to inhibit epimastigote proliferation. Quinestrol was able to inhibit, in the low micromolar range, the viability of trypomastigotes and the intracellular growth of amastigotes.These findings are being used to investigate the potential drug repurposing of quinestrol in treating Chagas disease. Reference: J Comput Aided Mol Des. 2023 Feb;37(2):75-90. https://pubmed.ncbi.nlm.nih.gov/36494599/
In vivo activity:
This study demonstrated that quinestrol has an inhibitory effect on a range of reproductive parameters in the plateau zokors, an Asiatic burrowing rodent. Further assessment is required to determine the effects on breeding and recruitment in enclosure or field experiments. Reference: Integr Zool. 2022 Nov;17(6):1002-1016. https://pubmed.ncbi.nlm.nih.gov/35271766/
Solvent mg/mL mM
Solubility
DMSO 30.0 82.30
Ethanol 20.0 54.87
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 364.52 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. Llanos MA, Alberca LN, Ruiz MD, Sbaraglini ML, Miranda C, Pino-Martinez A, Fraccaroli L, Carrillo C, Alba Soto CD, Gavernet L, Talevi A. A combined ligand and target-based virtual screening strategy to repurpose drugs as putrescine uptake inhibitors with trypanocidal activity. J Comput Aided Mol Des. 2023 Feb;37(2):75-90. doi: 10.1007/s10822-022-00491-0. Epub 2022 Dec 10. PMID: 36494599. 2. Hashimoto M, Inoue S, Muramatsu M, Masliah E. Estrogens stimulate tamoxifen-induced neuronal cell apoptosis in vitro: a possible nongenomic action. Biochem Biophys Res Commun. 1997 Nov 17;240(2):464-70. doi: 10.1006/bbrc.1997.7681. PMID: 9388502. 3. Sidhu A, Singla N. Antifertility effects of quinestrol in male lesser bandicoot rat, Bandicota bengalensis, and potential in managing rodent population under field conditions. Integr Zool. 2023 May 25. doi: 10.1111/1749-4877.12733. Epub ahead of print. PMID: 37231968. Shg 4. Kang Y, Tan Y, Wang C, Yao B, An K, Liu M, Su J. Antifertility effects of levonorgestrel, quinestrol, and their mixture (EP-1) on plateau zokor in the Qinghai-Tibetan Plateau. Integr Zool. 2022 Nov;17(6):1002-1016. doi: 10.1111/1749-4877.12642. Epub 2022 Mar 31. PMID: 35271766.
In vitro protocol:
1. Llanos MA, Alberca LN, Ruiz MD, Sbaraglini ML, Miranda C, Pino-Martinez A, Fraccaroli L, Carrillo C, Alba Soto CD, Gavernet L, Talevi A. A combined ligand and target-based virtual screening strategy to repurpose drugs as putrescine uptake inhibitors with trypanocidal activity. J Comput Aided Mol Des. 2023 Feb;37(2):75-90. doi: 10.1007/s10822-022-00491-0. Epub 2022 Dec 10. PMID: 36494599. 2. Hashimoto M, Inoue S, Muramatsu M, Masliah E. Estrogens stimulate tamoxifen-induced neuronal cell apoptosis in vitro: a possible nongenomic action. Biochem Biophys Res Commun. 1997 Nov 17;240(2):464-70. doi: 10.1006/bbrc.1997.7681. PMID: 9388502.
In vivo protocol:
1. Sidhu A, Singla N. Antifertility effects of quinestrol in male lesser bandicoot rat, Bandicota bengalensis, and potential in managing rodent population under field conditions. Integr Zool. 2023 May 25. doi: 10.1111/1749-4877.12733. Epub ahead of print. PMID: 37231968. Shg 2. Kang Y, Tan Y, Wang C, Yao B, An K, Liu M, Su J. Antifertility effects of levonorgestrel, quinestrol, and their mixture (EP-1) on plateau zokor in the Qinghai-Tibetan Plateau. Integr Zool. 2022 Nov;17(6):1002-1016. doi: 10.1111/1749-4877.12642. Epub 2022 Mar 31. PMID: 35271766.
1: Li J, Chen F, Chen Y, Wang Z. Mitochondrial- and Fas-L-mediated pathways involved in quinestrol induced spermatogenic apoptosis in adult rat testes. Toxicol Mech Methods. 2014 Dec;24(9):609-15. doi: 10.3109/15376516.2014.970680. Epub 2014 Oct 10. Review. PubMed PMID: 25258304. 2: Li J, Chen F, Li C, Chen Y. Quinestrol induces spermatogenic apoptosis in vivo via increasing pro-apoptotic proteins in adult male mice. Tissue Cell. 2014 Oct;46(5):318-25. doi: 10.1016/j.tice.2014.05.012. Epub 2014 Jun 27. PubMed PMID: 25038589. 3: Geng Q, Li P, Zhang W, Deng Y, Duan Y, Cao Y. The bioaccumulation and biotransformation of synthetic estrogen quinestrol in crucian carp. Aquat Toxicol. 2014 Oct;155:84-90. doi: 10.1016/j.aquatox.2014.06.011. Epub 2014 Jun 24. PubMed PMID: 24997302. 4: Li J, Wang H, Zhang J, Zhou B, Si L, Wei L, Li X. Abnormal secretion of reproductive hormones and antioxidant status involved in quinestrol-induced reproductive toxicity in adult male rat. Tissue Cell. 2014 Feb;46(1):27-32. doi: 10.1016/j.tice.2013.09.002. Epub 2013 Oct 1. PubMed PMID: 24183492. 5: Zhang Q, Wang C, Liu W, Qu J, Liu M, Zhang Y, Zhao M. Degradation of the potential rodent contraceptive quinestrol and elimination of its estrogenic activity in soil and water. Environ Sci Pollut Res Int. 2014 Jan;21(1):652-9. doi: 10.1007/s11356-013-1941-1. Epub 2013 Jul 2. PubMed PMID: 23818077. 6: Fu H, Zhang J, Shi D, Wu X. Effects of levonorgestrel-quinestrol (EP-1) treatment on Mongolian gerbil wild populations: a case study. Integr Zool. 2013 Sep;8(3):277-84. doi: 10.1111/1749-4877.12018. PubMed PMID: 24020466. 7: Wang DW, Ouyang CB, Liu Q, Yuan HL, Liu XH. Inclusion of quinestrol and 2,6-di-O-methyl-β-cyclodextrin: Preparation, characterization, and inclusion mode. Carbohydr Polym. 2013 Apr 2;93(2):753-60. doi: 10.1016/j.carbpol.2012.12.007. Epub 2012 Dec 12. PubMed PMID: 23499120. 8: Liu Q, Qin J, Chen Q, Wang D, Shi D. Fertility control of Rattus nitidus using quinestrol: effects on reproductive organs and social behavior. Integr Zool. 2013 Apr;8 Suppl 1:9-17. doi: 10.1111/j.1749-4877.2012.00296.x. Epub 2012 Oct 31. PubMed PMID: 23621467. 9: Lv X, Guo Y, Shi D. Effects of quinestrol and levonorgestrel on prolactin serum concentration in lactating Mongolian gerbils (Meriones unguiculatus) and reproductive parameters of their offspring. Reprod Biol. 2012 Nov;12(3):285-92. doi: 10.1016/j.repbio.2012.09.005. Epub 2012 Oct 17. PubMed PMID: 23153699. 10: Tang T, Qian K, Shi T, Wang F, Li P, Li J, Cao Y. Photodegradation of quinestrol in waters and the transformation products by UV irradiation. Chemosphere. 2012 Nov;89(11):1419-25. doi: 10.1016/j.chemosphere.2012.06.011. Epub 2012 Jul 5. PubMed PMID: 22771000. 11: Shen W, Shi D, Wang D, Guo Y. Inhibitive effects of quinestrol on male testes in Mongolian gerbils (Meriones unguiculatus). Res Vet Sci. 2012 Oct;93(2):907-13. doi: 10.1016/j.rvsc.2011.10.010. Epub 2011 Dec 5. PubMed PMID: 22153020. 12: Lv X, Guo Y, Shi D. Effects of quinestrol on reproductive hormone expression, secretion, and receptor levels in female Mongolian gerbils (Meriones unguiculatus). Theriogenology. 2012 Apr 1;77(6):1223-31. doi: 10.1016/j.theriogenology.2011.10.030. Epub 2012 Jan 26. PubMed PMID: 22284225. 13: Liu M, Qu J, Yang M, Wang Z, Wang Y, Zhang Y, Zhang Z. Effects of quinestrol and levonorgestrel on populations of plateau pikas, Ochotona curzoniae, in the Qinghai-Tibetan Plateau. Pest Manag Sci. 2012 Apr;68(4):592-601. doi: 10.1002/ps.2302. Epub 2012 Jan 9. PubMed PMID: 22232019. 14: Liu M, Wan X, Yin Y, Li YX, Sun F, Zhang Z, Wang YL. Subfertile effects of quinestrol and levonorgestrel in male rats. Reprod Fertil Dev. 2012;24(2):297-308. doi: 10.1071/RD10221. PubMed PMID: 22281075. 15: Lv X, Shi D. Combined effects of levonorgestrel and quinestrol on reproductive hormone levels and receptor expression in females of the Mongolian gerbil (Meriones unguiculatus). Zoolog Sci. 2012 Jan;29(1):37-42. doi: 10.2108/zsj.29.37. PubMed PMID: 22233494. 16: Wang D, Li N, Liu M, Huang B, Liu Q, Liu X. Behavioral evaluation of quinestrol as a sterilant in male Brandt's voles. Physiol Behav. 2011 Oct 24;104(5):1024-30. doi: 10.1016/j.physbeh.2011.06.024. Epub 2011 Jul 7. PubMed PMID: 21763706. 17: Lv XH, Shi DZ. Effects of quinestrol as a contraceptive in mongolian gerbils (Meriones unguiculatus). Exp Anim. 2011;60(5):489-96. PubMed PMID: 22041286. 18: Shen W, Shi D, Wand D, Guo Y, Hai S, Yue Z. Quinestrol treatment induced testicular damage via oxidative stress in male Mongolian gerbils (Meriones unguiculatus). Exp Anim. 2011;60(5):445-53. PubMed PMID: 22041281. 19: Tang T, Li P, Luo L, Shi D, Li J, Cao Y. Development and validation of a HPLC method for determination of levonorgestrel and quinestrol in rat plasma. Biomed Chromatogr. 2010 Jul;24(7):706-10. doi: 10.1002/bmc.1350. PubMed PMID: 19882745. 20: Löw O, Grimm S. Morphometric investigations on endocrine glands. VIII. Karyometry in epithelial cells of thyroid glands during inhibition of lactation by quinestrol. Exp Toxicol Pathol. 1992 Jun;44(3):141-3. PubMed PMID: 1504578.

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