(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-ol

• ChemBase ID: 1185
• Molecular Formular: C21H26O2
• Molecular Mass: 310.42994
• Monoisotopic Mass: 310.19328007
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@H](CC2)c2c(CC3)cc(OC)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)OC
• InChI: InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1
• InChIKey: IMSSROKUHAOUJS-MJCUULBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-ol; (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol; (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-14-ol; (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-14-ol
• IUPAC Traditional name: mestranol
• Synonyms: NSC 84032; 17α-Ethynyl-1,3,5(10)-estratriene-3,17β-diol 3-methyl ether; 17α-Ethynylestradiol 3-methyl ether; 3-Methoxy-17α-ethynylestradiol; Mestranol; (17α)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17-ol; 17α-Ethynyl-3-methoxy-17β-hydroxy-1,3,5(10)-estratriene; Devocin; EE 3ME; Menophase; Ovastol; Mestranol; (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol; (8''S'',9''S'',13''S'',14''S'',17''S'')-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthren-17-ol; 17α-乙炔基-1,3,5(10)-雌三烯-3,17β-二醇 3-甲醚; 17α-乙炔雌二醇 3-甲醚; 3-甲氧基-17α-乙炔雌二醇; 美雌醇

Database IDs

• CAS Number: 72-33-3
• EC Number: 200-777-8
• MDL Number: MFCD00003689
• Beilstein Number: 2625905
• PubChem SID: 160964647; 24888219; 24869992; 46507679
• PubChem CID: 6291
• CHEBI ID: 6784
• CHEMBL: 1201151
• Chemspider ID: 6054
• DrugBank ID: DB01357
• KEGG ID: D00575
• Unique Ingredient Identifier: B2V233XGE7
• Wikipedia Title: Mestranol
• Medline Plus: a601050

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.59492
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.043247
• LogD (pH = 7.4): 4.043247
• Log P: 4.043247
• Molar Refractivity: 91.8568 cm^3
• Polarizability: 35.813522 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.89
• LOG S: -4.92
• Solubility (Water): 3.77e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 139-141°C; 153-155 °C(lit.)
• Optical Rotation: [α]15/D +3°, c = 2 in dioxane

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: RC8960000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40-68
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H351
• GHS Precautionary statements: P281-P305 + P351 + P338
• 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

• Purity: 99%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C21H26O2

DETAILS

DrugBank - DB01357

• Drug Groups: approved
• Description: The 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives. [PubChem]
• Indication: Mestranol was used as one of the first oral contraceptives.
• External Links: Wikipedia

Selleck Chemicals - S2125

Research Area: Endocrinology
Biological Activity:
Mestranol is the 3-methyl ether of ethinylestradiol. It was the estrogen used in many of the first oral contraceptives. It is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70% (50 µg of mestranol is pharmacokinetically bioequivalent to 35 µg of ethinylestradiol). [1]

Sigma Aldrich - E5001

Application
Pharmacological estrogen molecule1,2,3

Sigma Aldrich - 855871

Packaging
500 mg in glass bottle
Application
Pharmacological estrogen molecule1,2,3

Sigma Aldrich - 31709

Application
Pharmacological estrogen molecule1,2,3
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 46264

Application
Pharmacological estrogen molecule1,2,3
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M258755

Orally active estrogenic steroid. It was the estrogen used in many of the first oral contraceptives.

REFERENCES

• http://en.wikipedia.org/wiki/Mestranol
• Goldzieher, J.W., et al.: Contraception, 21,17 (1980)
• El-Obeid, H.A., et al.: Anal. Profiles Drug Subs., 11, 375 (1980)
• Spellacy, W.N., et al.: Metabolism, 31, 106 (1980)