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Chemistry

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Also known as: 152-43-2, Estrovis, Estradiol-17-beta 3-cyclopentyl ether, Quinestrolo [dcit], Quinestrolum, Quinestrolum [inn-latin]
Molecular Formula
C25H32O2
Molecular Weight
364.5  g/mol
InChI Key
PWZUUYSISTUNDW-VAFBSOEGSA-N
FDA UNII
JR0N7XD5GZ

Quinestrol
The 3-cyclopentyl ether of ETHINYL ESTRADIOL. After gastrointestinal absorption, it is stored in ADIPOSE TISSUE, slowly released, and metabolized principally to the parent compound. It has been used in ESTROGEN REPLACEMENT THERAPY. (From AMA Drug Evaluations Annual, 1992, p1011)
1 2D Structure

Quinestrol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC 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
2.1.2 InChI
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/t21-,22-,23+,24+,25+/m1/s1
2.1.3 InChI Key
PWZUUYSISTUNDW-VAFBSOEGSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC5CCCC5
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC5CCCC5
2.2 Other Identifiers
2.2.1 UNII
JR0N7XD5GZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Estrovis

2. Ethinyl Estradiol 3 Cyclopentyl Ether

3. Ethinyl Estradiol 3-cyclopentyl Ether

2.3.2 Depositor-Supplied Synonyms

1. 152-43-2

2. Estrovis

3. Estradiol-17-beta 3-cyclopentyl Ether

4. Quinestrolo [dcit]

5. Quinestrolum

6. Quinestrolum [inn-latin]

7. Estrovister

8. Plestrovis

9. Eston

10. 17-alpha-ethinylestradiol 3-cyclopentyl Ether

11. 17alpha-ethynylestradiol 3-cyclopentyl Ether

12. Qui-lea

13. Eecpe

14. Estrovis 4000

15. W 3566

16. W-3566

17. (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

18. Jr0n7xd5gz

19. Mls000069756

20. Chebi:8716

21. Nsc-759637

22. Ncgc00166146-01

23. Quinestrolo

24. Smr000058815

25. Dsstox_cid_26553

26. Dsstox_rid_81714

27. Dsstox_gsid_46553

28. Quilea

29. 3-o-cyclopentyl-17alpha-ethinyl-estra-1,3,5(10)-triene-3,17beta-diol

30. 17alpha-ethylnyl-1,3,5[10]estratriene-3,17beta-diol 3-cyclopentyl Ether

31. Estrovis (tn)

32. Cas-152-43-2

33. Quinestrol (usan/inn)

34. Einecs 205-803-1

35. Unii-jr0n7xd5gz

36. Quinestriol

37. 3-cyclopentyloxy-17alpha-ethynylestra-1,3,5(10)-trien-17beta-ol

38. Quinestrol [usan:usp:inn:ban]

39. 3-(cyclopentyloxy)-19-nor-17alpha-pregna-1,3,5(10)-trien-20-yn-17-ol

40. Ee2cpe

41. Opera_id_502

42. Quinestrol [mi]

43. Quinestrol [inn]

44. Quinestrol [usan]

45. Quinestrol [vandf]

46. Quinestrol [mart.]

47. Quinestrol [who-dd]

48. Mls001077287

49. Schembl221134

50. Gtpl7097

51. Chembl1201165

52. Dtxsid6046553

53. Quinestrol [orange Book]

54. Hms2235a05

55. 3-(cyclopentyloxy)-17beta-ethynylestra-1,3,5(10)-trien-17-ol

56. Hy-b1012

57. Zinc3875993

58. Ethinylestradiol 3-cyclopentyl Ether

59. Tox21_112340

60. Lmst02010037

61. Mfcd00079189

62. S3671

63. Ethynyl Estradiol-3-cyclopentyl Ether

64. 19-nor-17-alpha-pregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-

65. Akos025310158

66. Tox21_112340_1

67. Ccg-268221

68. Cs-4525

69. Db04575

70. Nsc 759637

71. 19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-, (17alpha)-

72. Ncgc00166146-02

73. 17?-ethynylestradiol 3-cyclopentyl Ether

74. As-13038

75. Q0091

76. C07619

77. C72888

78. D00576

79. 152q432

80. A809306

81. Sr-01000759180

82. Q3927871

83. Sr-01000759180-3

84. W-108053

85. 17a-ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-cyclopentyl Ether

86. 3-(cyclopentyloxy)-19-norpregna-1,3,5(10)-trien-20-yn-17.alpha.-ol

87. Estra-1(10),2,4-trien-17-ol, 3-(cyclopentyloxy)-17-ethynyl-, (17)-

88. 19-norpregna-1,3,5(10)-trien-20-yn-17-ol, 3-(cyclopentyloxy)-, 17.alpha.

89. 3-(cyclopentyloxy)-19-nor-17.alpha.-pregna-1,3,5(10)-trien-20-yn-17-ol

90. (1s,10r,11s,14r,15s)-5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0?,?.0??,??]heptadeca-2,4,6-trien-14-ol

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 364.5 g/mol
Molecular Formula C25H32O2
XLogP35.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass364.240230259 g/mol
Monoisotopic Mass364.240230259 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count27
Formal Charge0
Complexity613
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Used in hormone replacement therapy, treating symptoms of menopause such as hot flashes. Also used to treat breast and prostate cancer.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Quinestrol is the 3-cyclopentyl ether of ethinyl estradiol (the active metabolite). After gastrointestinal absorption, it is stored in adipose tissue where it is slowly released and metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol.


5.2 MeSH Pharmacological Classification

Estrogens

Compounds that interact with ESTROGEN RECEPTORS in target tissues to bring about the effects similar to those of ESTRADIOL. Estrogens stimulate the female reproductive organs, and the development of secondary female SEX CHARACTERISTICS. Estrogenic chemicals include natural, synthetic, steroidal, or non-steroidal compounds. (See all compounds classified as Estrogens.)


5.3 Absorption, Distribution and Excretion

Absorption

Absorbed following oral administration.


5.4 Metabolism/Metabolites

Metabolized principally to the parent compound, ethinyl estradiol. Ethinyl estradiol is metabolized in the liver. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.


5.5 Mechanism of Action

Estrogens diffuse into their target cells and interact with a protein receptor (the estrogen receptor). Estrogen interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).


API SUPPLIERS

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ABOUT THIS PAGE

Quinestrol Manufacturers

A Quinestrol manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Quinestrol, including repackagers and relabelers. The FDA regulates Quinestrol manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Quinestrol API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Quinestrol Suppliers

A Quinestrol supplier is an individual or a company that provides Quinestrol active pharmaceutical ingredient (API) or Quinestrol finished formulations upon request. The Quinestrol suppliers may include Quinestrol API manufacturers, exporters, distributors and traders.

click here to find a list of Quinestrol suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Quinestrol USDMF

A Quinestrol DMF (Drug Master File) is a document detailing the whole manufacturing process of Quinestrol active pharmaceutical ingredient (API) in detail. Different forms of Quinestrol DMFs exist exist since differing nations have different regulations, such as Quinestrol USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Quinestrol DMF submitted to regulatory agencies in the US is known as a USDMF. Quinestrol USDMF includes data on Quinestrol's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Quinestrol USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Quinestrol suppliers with USDMF on PharmaCompass.

Quinestrol GMP

Quinestrol Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Quinestrol GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Quinestrol GMP manufacturer or Quinestrol GMP API supplier for your needs.

Quinestrol CoA

A Quinestrol CoA (Certificate of Analysis) is a formal document that attests to Quinestrol's compliance with Quinestrol specifications and serves as a tool for batch-level quality control.

Quinestrol CoA mostly includes findings from lab analyses of a specific batch. For each Quinestrol CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Quinestrol may be tested according to a variety of international standards, such as European Pharmacopoeia (Quinestrol EP), Quinestrol JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Quinestrol USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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