Etonogestrel

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Names

[ Name ]:
Etonogestrel

[Synonym ]:
EINECS 258-936-2
3-Ketodesogestrel,3-Oxodesogestrel,Org-3236,Implanon
Etonoestrel
3-Keto-desogestrel 3-Oxo-desogestrel
(17a)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one
3-Oxodesogestrel
3-Keto-Org 2969
18,19-Dinor-17α-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-
3-keto-desogestrel
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
13-Ethyl-17-hydroxy-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-3-one
3-Ketodesogestrel
Etonogestrel
Nexplanon
Desogestrel Related Compound C (25 mg) (3-Keto-desogestrel)
(8S,9S,10R,13S,14S,17R)-17-Ethinyl-13-ethyl-17-hydroxy-11-methyliden-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-on
UNII-304GTH6RNH
MFCD00867863
Implanon
[3H]-3-keto-Desogestrel
org3236
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (non-preferred name)
17-Ethinyl-17b-hydroxy-18-methyl-11-methylene-4-estren-3-one
(8S,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-11-methylene-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
473.1±45.0 °C at 760 mmHg

[ Melting Point ]:
182-184ºC

[ Molecular Formula ]:
C₂₂H₂₈O₂

[ Molecular Weight ]:
324.457

[ Flash Point ]:
201.1±21.3 °C

[ Exact Mass ]:
324.208923

[ PSA ]:
37.30000

[ LogP ]:
4.22

[ Vapour Pressure ]:
0.0±2.7 mmHg at 25°C

[ Index of Refraction ]:
1.575

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JF8290000

CHEMICAL NAME :: 18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-, (17-alpha)-

CAS REGISTRY NUMBER :: 54048-10-1

LAST UPDATED :: 198910

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C22-H28-O2

MOLECULAR WEIGHT :: 324.50

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10500 ng/kg

SEX/DURATION :: female 21 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 17,19,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 50 ug/kg

SEX/DURATION :: female 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 35,459,1985

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H351-H360

[ Precautionary Statements ]:
P201-P280-P308 + P313

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
60-40

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
JF8290000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
Desogestrel
13-ethyl-gona-4-ene-11α,17β-diol
13-ethyl-11-methylenegon-4-en-17-one
3,3-ethylenedithio-18a-homo-estr-4-ene-11α,17β-diol
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

DownStream

Articles

Effect of progestins on immunity: medroxyprogesterone but not norethisterone or levonorgestrel suppresses the function of T cells and pDCs.

Contraception 90(2) , 123-9, (2014)

The potential effect of hormonal contraception on HIV-1 acquisition and transmission represents an important public health issue. Several observational studies have suggested an association between th...

Newer non-oral hormonal contraception.

BMJ 346 , f341, (2013)

The combined etonogestrel/ethinyl estradiol contraceptive vaginal ring.

Expert Opin. Pharmacother. 8(11) , 1769-77, (2007)

Many factors influence the effectiveness of contraceptive methods. Oral contraceptives are the second most popular contraceptive method after female sterilization in the US. A total of 25% of women do...

18-Demethyl Etonogestrel
Etonogestrel and ethinyl estradiol
5-chloro-N-{1-[(3,5-dimethoxyphenyl)methyl]piperidin-4-yl}-N-methylpyrimidin-2-amine
2-({1-[(3,4-Difluorophenyl)methyl]pyrrolidin-3-yl}methoxy)-5-fluoropyridine
1-(4-{[1-(3-Methyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl]oxy}but-2-yn-1-yl)-4-(pyridin-2-yl)piperazine
2-Methyl-4-[4-({4-[4-(pyridin-2-yl)piperazin-1-yl]but-2-yn-1-yl}oxy)piperidin-1-yl]pyrimidine
3-Fluoro-4-[(3-{[(6-methoxypyridin-2-yl)oxy]methyl}piperidin-1-yl)methyl]benzonitrile
N,N-dimethyl-6-(4-{thieno[3,2-d]pyrimidin-4-yl}piperazin-1-yl)pyridazin-3-amine
5-Chloro-2-[4-({4-[4-(pyridin-2-yl)piperazin-1-yl]but-2-yn-1-yl}oxy)piperidin-1-yl]pyrimidine
2-{4-[6-methyl-2-(morpholin-4-yl)pyrimidin-4-yl]piperazin-1-yl}-5H,7H,8H-pyrano[4,3-b]pyridine-3-carbonitrile
3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-[4-(6-methylpyridazin-3-yl)piperazin-1-yl]pyridazine
2,4-Dimethyl-6-[4-({4-[4-(pyridin-2-yl)piperazin-1-yl]but-2-yn-1-yl}oxy)piperidin-1-yl]pyrimidine

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