(14R)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase ID: 179
• Molecular Formular: C22H28O2
• Molecular Mass: 324.45652
• Monoisotopic Mass: 324.20893014
• SMILES: O[C@@]1(C2(C(C3C(C4C(=CC(=O)CC4)CC3)C(=C)C2)CC1)CC)C#C
• Canonical SMILES: C#C[C@]1(O)CCC2C1(CC)CC(=C)C1C2CCC2=CC(=O)CCC12
• InChI: InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17?,18?,19?,20?,21?,22-/m0/s1
• InChIKey: GCKFUYQCUCGESZ-KIIRVTSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (14R)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• IUPAC Traditional name: etonogestrel
• Brand Name: Implanon
• Synonyms: etonogestrel; Etonogestrel

Database IDs

• CAS Number: 54048-10-1
• PubChem SID: 160963642
• PubChem CID: 40976

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.993504
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6011698
• LogD (pH = 7.4): 3.6011698
• Log P: 3.6011698
• Molar Refractivity: 96.3516 cm^3
• Polarizability: 37.451656 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.19
• LOG S: -4.64
• Solubility (Water): 7.37e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.4

DETAILS

DrugBank - DB00294

• Drug Groups: approved; investigational
• Description: Etonogestrel is a molecule used in hormonal contraceptives, most notably the subdermal implant Implanon. [Wikipedia]
• Indication: For use as a female contraceptive (depot).
• Pharmacology: Etonogestrel is used as a female contraceptive. Etonogestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Etonogestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
• Toxicity: Symptoms of overdose include nausea, vomiting, vaginal bleeding, and other menstrual irregularities.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 25 hours
• Elimination: Excretion of ENG and its metabolites, either as free steroid or as conjugates, is mainly in urine and to a lesser extent in feces.
• Distribution: * 201 L
• External Links: Wikipedia; PDRhealth; Drugs.com