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

MedKoo CAT#: 318600

CAS#: 152-43-2

Description: Quinestrol is a compound used in estrogen replacement therapy.


Chemical Structure

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Quinestrol
CAS# 152-43-2

Theoretical Analysis

MedKoo Cat#: 318600
Name: Quinestrol
CAS#: 152-43-2
Chemical Formula: C25H32O2
Exact Mass: 364.24
Molecular Weight: 364.520
Elemental Analysis: C, 82.37; H, 8.85; O, 8.78

Price and Availability

Size Price Availability Quantity
5g USD -1
10g USD -1
100mg USD 250
200mg USD 450
500mg USD 650
1g USD 950
2g USD 1450
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Synonym: Quinestrol; Estrovis; Quinestrolum; Estrovister; Plestrovis; Eston; Ethinyl; Estradiol 3 Cyclopentyl Ether; Ethinyl Estradiol 3-Cyclopentyl Ether; Parke Davis Brand of Quinestrol ;Quinestrol;

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:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 82.30
Ethanol 20.0 54.87

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.

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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.