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54048-10-1 molecular structure
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(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 and InChIs

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

Cite this record

CBID:179 http://www.chembase.cn/molecule-179.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
54048-10-1
PubChem SID
160963642
PubChem CID
40976

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 40976 external link
DrugBank DB00294 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 17.993504  H Acceptors
H Donor LogD (pH = 5.5) 3.6011698 
LogD (pH = 7.4) 3.6011698  Log P 3.6011698 
Molar Refractivity 96.3516 cm3 Polarizability 37.451656 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.19  LOG S -4.64 
Solubility (Water) 7.37e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
3.4 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00294 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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