(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,12-dien-5-one

• ChemBase ID: 4461
• 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)[C@@H]2C(=CC(=O)CC2)CC3)C=C1)CC)C#C
• Canonical SMILES: C#C[C@]1(O)C=C[C@@H]2[C@]1(CC)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
• InChIKey: SIGSPDASOTUPFS-XUDSTZEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,12-dien-5-one; (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,12-dien-5-one
• IUPAC Traditional name: gestodene
• Synonyms: Gestoden; Gestodeno [inn-spanish]; Gestodenum [inn-latin]; Gestodene; SH B 331; (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one

Database IDs

• CAS Number: 60282-87-3
• PubChem SID: 99443276; 160967893
• PubChem CID: 3033968

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.083544
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4557824
• LogD (pH = 7.4): 3.4557824
• Log P: 3.4557824
• Molar Refractivity: 92.9881 cm^3
• Polarizability: 35.607704 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.15
• LOG S: -4.73
• Solubility (Water): 5.81e-03 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform
• Apperance: White Solid
• Melting Point: 190-192°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Pharmacology Properties

• Target: P450

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB06730

• Drug Groups: approved
• Description: Gestodene is a progestogen hormonal contraceptive. Products containing gestoden include Meliane, which contains 20 mcg of ethinylestradiol and 75 mcg of gestodene; and Gynera, which contains 30 mcg of ethinylestradiol and 75 mcg of gestodene.
• Absorption: in vitro 99% using 3H=R5020 / in vivo similar to progesterone
• Half Life: 16 to 18 hrs.
• External Links: Wikipedia

Selleck Chemicals - S1376

Research Area: Endocrinology
Biological Activity:
Estrogens and progestins are female hormones. They are produced by the body and are necessary for the normal sexual development of the female and for the regulation of the menstrual cycle during the childbearing years. Gestodene is a progestogen hormonal contraceptive. [1]

Toronto Research Chemicals - G368250

Orally active gestogen with progesterone-like profile of activity. Used in combination with estrogen as oral contraceptive.

REFERENCES

• http://en.wikipedia.org/wiki/Gestodene
• Duesterberg, B., et al.: Contraception, 24, 673 (1981)
• Duesterberg, B., et al.: Seroids, 43, 43 (1981)
• Losert, W., et al.: Arzneim.-Forsch., 35, 459 (1981)