Norgestimate

Names

[ Name ]:
Norgestimate

[Synonym ]:
(3E,8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-3-(hydroxyimino)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
(+)-13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one Oxime Acetate (Ester)
d-17beta-acetoxy-13beta-ethyl-17alpha-ethinyl-gon-4en-3-one oxime
dexnorgestrelacetime
Norgestimat
Norgestimate
NORGESTIMATE,USP STANDARD
levonorgestrel acetate 3-oxime
(3E,8R,9S,10R,13S,14S,17R)-17-Ethinyl-13-ethyl-3-(hydroxyimino)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ylacetat
acétate de (3E,8R,9S,10R,13S,14S,17R)-13-éthyl-17-éthynyl-3-(hydroxyimino)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-1H-cyclopenta[a]phénanthrén-17-yle

Biological Activity

[Description]:

Norgestimate, a synthetic progesterone analog, is an orally active progestin with highly selective progestational activity and minimal androgenicity. Norgestimate is used for an oral contraceptive[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Progesterone Receptor

Research Areas >> Endocrinology

[In Vitro]

Norgestimate is converted to at least two active metabolites: levonorgestrel 3-oxime (deacetylated norgestimate; norelgestromin) and levonorgestrel[1].

[References]

[1]. Stanczyk FZ, et al. All progestins are not created equal. Steroids. 2003 Nov;68(10-13):879-90.

[2]. Phillips A, et al. Preclinical evaluation of norgestimate, a progestin with minimal androgenic activity. Am J Obstet Gynecol. 1992 Oct;167(4 Pt 2):1191-6.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
497.9±45.0 °C at 760 mmHg

[ Melting Point ]:
216ºC

[ Molecular Formula ]:
C₂₃H₃₁NO₃

[ Molecular Weight ]:
369.497

[ Flash Point ]:
254.9±28.7 °C

[ Exact Mass ]:
369.230408

[ PSA ]:
58.89000

[ LogP ]:
5.00

[ Vapour Pressure ]:
0.0±2.9 mmHg at 25°C

[ Index of Refraction ]:
1.611

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JF7976000

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

CAS REGISTRY NUMBER :: 35189-28-7

LAST UPDATED :: 198910

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C23-H31-N-O3

MOLECULAR WEIGHT :: 369.55

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 mg/kg

SEX/DURATION :: female 2 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: 16,541,1977

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H361fd

[ Precautionary Statements ]:
P281-P305 + P351 + P338

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
63-22-36/38-62

[ Safety Phrases ]:
26-36/37

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
JF7976000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Types of combined oral contraceptives used by US women.

Contraception 86(6) , 659-65, (2012)

We sought to estimate the prevalence of types of combined oral contraceptives (COCs) used among US women.We analyzed interview-collected data from 12,279 women aged 15-44 years participating in the Na...

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Progestins in preventive hormone therapy. Including pharmacology of the new progestins, desogestrel, norgestimate, and gestodene: are there advantages?

Obstet. Gynecol. Clin. North Am. 21(2) , 299-319, (1994)

Clofarabine was the latest new drug to be approved, in 2004, for relapsed or refractory acute lymphoblastic leukaemia (ALL). To investigate its value in the frontline treatment of ALL we applied clofa...