Norethisterone enanthate

Names

[ Name ]:
Norethisterone enanthate

[Synonym ]:
[(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] heptanoate
17α-Ethynyl-19-nortestosterone 17-heptanoate
MFCD01741291
17-α-Ethynyl-17-β-heptanoyloxy-4-estren-3-one
17α-Ethynyl-19-nortestosterone enanthate
Heptanoic acid, (17β)-17-ethynyl-3-oxoestr-4-en-17-yl ester
Noristerat
Norethisterone enanthate
17α-Ethynyl-17β-heptanoyloxy-4-estren-3-one
EINECS 223-326-7
NEE
Norethisterone oenanthate
19-Nor-17α-pregn-4-en-20-yn-3-one, 17-hydroxy-, heptanoate (8CI)
(17α)-17-((1-Oxoheptyl)oxy)-19-norpregn-4-en-20-yn-3-one
Norlutin enanthate
(17α)-3-Oxo-19-norpregn-4-en-20-yn-17-yl heptanoate
Norigest
19-Nor-17α-pregn-4-en-20-yn-3-one, 17-hydroxy-, heptanoate
17-β-Heptanoyloxy-17-α-ethynyl-4-oestren-3-one
Norethindrone enanthate

Biological Activity

[Description]:

Norethisterone enanthate is a long-acting parenteral progestogen. Norethisterone enanthate is orally active[1][2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Progesterone Receptor

Research Areas >> Endocrinology

[In Vitro]

Norethisterone enanthate can be used as an intramuscular contraceptive agent[1].

[In Vivo]

Norethisterone enanthate (20-60 mg; p.o.;5 days) inhibits fertility in female rats[3]. Animal Model: Female adult albino rats (Wistar/NIN) weighing around 160-180 g[1] Dosage: 20, 30, 40, 50, 60 mg Administration: P.o.; 5 days Result: A significant reduction in fertility was seen with doses 30 to 60 mg in rats.

[References]

[1]. Kesserü-Koós E, Larrañaga-Legufa A, Hurtado-Koo H, Scharff HJ. Fertility control with norethindrone enanthate, a long-acting parenteral progestogen. Acta Eur Fertil. 1973;4(4):203‐221.

[2]. Ravinder P, Shatrugna V, Nair KM, Sivakumar B. Pharmacokinetics of orally administered norethisterone enanthate in rabbit, monkey, and women. Contraception. 1997;55(6):373‐379.

[3]. Ravinder P, Nair KM, Sivakumar B. Biological efficacy and plasma norethisterone levels of orally administered norethisterone enanthate in rat and hamster. Indian J Physiol Pharmacol. 1998;42(4):485‐490.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
515.3±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₇H₃₈O₃

[ Molecular Weight ]:
410.589

[ Flash Point ]:
219.0±30.2 °C

[ Exact Mass ]:
410.282104

[ PSA ]:
43.37000

[ LogP ]:
6.64

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.540

[ Storage condition ]:
2~8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RC8973000

CHEMICAL NAME :: 19-Nor-17-alpha-pregnen-20-ynone, 17-beta-heptanoyloxy-

CAS REGISTRY NUMBER :: 3836-23-5

BEILSTEIN REFERENCE NO. :: 3176529

LAST UPDATED :: 199612

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C27-H38-O3

MOLECULAR WEIGHT :: 410.65

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - increased intraocular pressure

REFERENCE :: ADVPB4 Advances in Planned Parenthood. (Excerpta Medica, Inc., POB 3085, Princeton, NJ 08540) V.1-16, 1967-81. Volume(issue)/page/year: 8,103,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Metabolism (Intermediary) - other proteins

REFERENCE :: SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 12(4),13,1992 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7000 mg/kg/70W

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Endocrine - tumors Skin and Appendages - tumors

REFERENCE :: 36PYAS "Pharmacology of Steroid Contraceptive Drugs," Garattini, S. and H.W. Berendes, eds., New York, Raven Press, 1977 Volume(issue)/page/year: -,163,1977 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 4 mg/kg

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

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 5,21,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 4 mg/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: AZOGBS Australian & New Zealand Journal of Obstetrics & Gynaecology. (254 Albert St., E. Melbourne, Vic., Australia) V.1- 1961- Volume(issue)/page/year: 11,233,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 4 mg/kg

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

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 13,415,1968

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 24 mg/kg

SEX/DURATION :: female 6 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 25,333,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 12 mg/kg

SEX/DURATION :: female 3 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders

REFERENCE :: IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 69,93,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 150 mg/kg

SEX/DURATION :: female 14-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system

REFERENCE :: ENDOAO Endocrinology (Baltimore). (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21203) V.1- 1917- Volume(issue)/page/year: 71,448,1962

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 48 mg/kg

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

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 24,61,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 100 mg/kg

SEX/DURATION :: female 10 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: IJPPAZ Indian Journal of Physiology and Pharmacology. (All India Institute of Medical Sciences, Dept. of Physiology, Ansari Nagar, New Delhi 110 029, India) V.1- 1957- Volume(issue)/page/year: 25,151,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

DOSE :: 3483 ug/kg

SEX/DURATION :: male 6 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

REFERENCE :: ANDRDQ Andrologia. (Grosse Verlag GmbH, Kurfuerstenstr. 112-113, D-1000 Berlin 30, Fed. Rep. Ger.) V.6- 1974- Volume(issue)/page/year: 15,333,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 4 mg/kg

SEX/DURATION :: female 5 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

REFERENCE :: CCPTAY Contraception. (Geron-X, Inc., POB 1108, Los Altos, CA 94022) V.1- 1970- Volume(issue)/page/year: 12,529,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 475 mg/kg

SEX/DURATION :: female 4-23 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - stillbirth

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 89,701,1964

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

DOSE :: 5038 ug/kg

SEX/DURATION :: female 56 day(s) pre-mating female 1-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility

REFERENCE :: IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 19,416,1981

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds

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