(1S,10R,11S,14R,15S)-5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol

• ChemBase ID: 4143
• Molecular Formular: C25H32O2
• Molecular Mass: 364.52038
• Monoisotopic Mass: 364.24023026
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(OC3CCCC3)cc2)CC1)C)C#C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OC1CCCC1
• 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
• InChIKey: PWZUUYSISTUNDW-VAFBSOEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol; (1S,10R,11S,14R,15S)-5-(cyclopentyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-ol
• IUPAC Traditional name: quinestrol
• Brand Name: Estrovis; Plestrovis; Qui-lea; Estrovister; Estrovis 4000; Eston
• Synonyms: Quinestrolo [dcit]; Quinestrolum [inn-latin]; Estradiol-17-beta 3-cyclopentyl ether; 17-alpha-Ethinylestradiol 3-cyclopentyl ether; 17alpha-Ethynylestradiol 3-cyclopentyl ether; Quinestrol; 17α-Ethynyl-1,3,5(10)-estratriene-3,17β-diol 3-cyclopentyl ether; Quinestrol; 17α-Ethynylestradiol 3-cyclopentyl ether

Database IDs

• CAS Number: 152-43-2
• EC Number: 205-803-1
• MDL Number: MFCD00079189
• PubChem SID: 24894659; 46508939; 160967575
• PubChem CID: 9046

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.59492
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.397949
• LogD (pH = 7.4): 5.397949
• Log P: 5.397949
• Molar Refractivity: 108.27 cm^3
• Polarizability: 42.456947 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.19
• LOG S: -5.37
• Solubility (Water): 1.57e-03 g/l

PROPERTIES

Safety Information

• RTECS: RC8948000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-61-20/21/22
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H332-H350-H360
• GHS Precautionary statements: P201-P280-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Empirical Formula (Hill Notation): C25H32O2

DETAILS

DrugBank - DB04575

• Drug Groups: approved
• Description: The 3-cyclopentyl ether of ethinyl estradiol.
• Indication: Used in hormone replacement therapy, treating symptoms of menopause such as hot flashes. Also used to treat breast and prostate cancer.
• 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.
• Toxicity: Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: Absorbed following oral administration.
• External Links: Wikipedia