19-Norethindrone acetate

Modify Date: 2024-01-02 16:39:18

19-Norethindrone acetate Structure
19-Norethindrone acetate structure
Common Name 19-Norethindrone acetate
CAS Number 51-98-9 Molecular Weight 340.456
Density 1.1±0.1 g/cm3 Boiling Point 454.7±45.0 °C at 760 mmHg
Molecular Formula C22H28O3 Melting Point N/A
MSDS Chinese USA Flash Point 197.1±28.8 °C
Symbol GHS08
GHS08
Signal Word Warning

 Use of 19-Norethindrone acetate


Norethindrone acetate is a female progestin approved by FDA for the treatment of endometriosis, uterine bleeding caused by abnormal hormone levels, and secondary amenorrhea.

 Names

Name norethisterone acetate
Synonym More Synonyms

 19-Norethindrone acetate Biological Activity

Description Norethindrone acetate is a female progestin approved by FDA for the treatment of endometriosis, uterine bleeding caused by abnormal hormone levels, and secondary amenorrhea.
Related Catalog
Target

Progesterone Receptor[1]

In Vivo Norethindrone acetate could be a cost-effective alternative with relatively mild side effects in the treatment of symptomatic endometriosis. Subjects treated with norethindrone acetate obtain dysmenorrhea and noncyclic pelvic pain relief[1]. Norethindrone acetate alone is a well-tolerated, effective option to manage pain and bleeding for all stages of endometriosis. Post-Norethindrone acetate bleeding scores are improved regardless of prior hormonal regimen, and post-Norethindrone acetate pain scores improved in all patients except for those previously prescribed GnRH-agonist plus add-back[2]. Norethindrone acetate shows low acute toxicity in experimental animals and is consistent with the lack of toxicity seen in humans. Administration of norethindrone acetate alone to rodents at several multiples of the human dose results in no treatment related mortality, hematological changes, behavioral changes, or organ pathology[3]. Norethindrone acetate administration leads to significant and proportional reductions of the concentrations of triglycerides, cholesterol and phospholipids of plasma lipoproteins of density <1.006 of rats fed a high carbohydrate diet. Norethindrone acetate (0.1 mM) also significantly inhibits the incorporation of both palmitate and glycerol into triglycerides of isolated hepatocytes from fed rats[4].
Animal Admin Rats: Female Sprague-Dawley rats (200-210 g), 6 of which serve as controls, are individually caged in an animal room illuminated from 9:00 a.m. to 9:00 p.m. Each of the 7 rats receiving norethindrone acetate is fed 35 μg/day for 2 weeks. Water and the rat chow which is high in carbohydrate are available ad libitum[4].
References

[1]. Muneyyirci-Delale O, et al. Effect of norethindrone acetate in the treatment of symptomatic endometriosis. Int J Fertil Womens Med. 1998 Jan-Feb;43(1):24-7.

[2]. Kaser DJ, et al. Use of norethindrone acetate alone for postoperative suppression of endometriosis symptoms. J Pediatr Adolesc Gynecol. 2012 Apr;25(2):105-8.

[3]. Maier WE, et al. Pharmacology and toxicology of ethinyl estradiol and norethindrone acetate in experimental animals. Regul Toxicol Pharmacol. 2001 Aug;34(1):53-61.

[4]. Cheng DC, et al. Norethindrone acetate inhibition of triglyceride synthesis and release by rat hepatocytes. Atherosclerosis. 1983 Jan;46(1):41-8.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 454.7±45.0 °C at 760 mmHg
Molecular Formula C22H28O3
Molecular Weight 340.456
Flash Point 197.1±28.8 °C
Exact Mass 340.203857
PSA 43.37000
LogP 3.99
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.556
Storage condition 2~8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RC8965000
CHEMICAL NAME :
19-Nor-17-alpha-pregn-4-en-20-yn-3-one, 17-acetoxy-
CAS REGISTRY NUMBER :
51-98-9
BEILSTEIN REFERENCE NO. :
2064104
LAST UPDATED :
199612
DATA ITEMS CITED :
37
MOLECULAR FORMULA :
C22-H28-O3
MOLECULAR WEIGHT :
340.50
WISWESSER LINE NOTATION :
L E5 B666 OV MUTJ E1 FOV1 F1UU1 -B&EF

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
303 ug/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2190 ug/kg
SEX/DURATION :
female 52 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2 mg/kg
SEX/DURATION :
female 20 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1150 ug/kg
SEX/DURATION :
female 23 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
45 ug/kg
SEX/DURATION :
lactating female 15 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Maternal Effects - postpartum
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
366 ug/kg
SEX/DURATION :
female 21 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
15 mg/kg
SEX/DURATION :
female 13-30 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - other neonatal measures or effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 mg/kg
SEX/DURATION :
female 1-3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
408 mg/kg
SEX/DURATION :
female 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1200 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
2800 ug/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
50 mg/kg
SEX/DURATION :
female 15-24 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
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 Reproductive - Effects on Newborn - live birth index (measured after birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
55 mg/kg
SEX/DURATION :
female 15-25 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Specific Developmental Abnormalities - homeostasis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
60 mg/kg
SEX/DURATION :
female 17-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
70 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
DOSE :
7500 ug/kg
SEX/DURATION :
female 1-3 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
25800 ug/kg
SEX/DURATION :
female 17 week(s) pre-mating
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 - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
2 ug/kg
SEX/DURATION :
female 1 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)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
80 mg/kg
SEX/DURATION :
female 16-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
20 mg/kg
SEX/DURATION :
female 1-4 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4 mg/kg
SEX/DURATION :
female 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3 mg/kg
SEX/DURATION :
female 3 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
125 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
7500 ug/kg
SEX/DURATION :
female 17 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Sister chromatid exchange
TYPE OF TEST :
Dominant lethal test

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
11200 mg/kg/4W
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 26,535,1974 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,294,1987 TOXICOLOGY REVIEW CMROCX Current Medical Research and Opinion. (Clayton-Wray Pub. Ltd., 1a High St., Alton, Hants., UK) V.1- 1972- Volume(issue)/page/year: 4,309,1976

 Safety Information

Symbol GHS08
GHS08
Signal Word Warning
Hazard Statements H351
Precautionary Statements P281
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xn:Harmful
Risk Phrases R40;R48
Safety Phrases S36/37
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS RC8965000
HS Code 2915299090

 Synthetic Route

~96%

19-Norethindrone acetate Structure

19-Norethindron...

CAS#:51-98-9

Literature: Leung; Karunanithy; Becket; Yeo Steroids, 1985 , vol. 46, # 1 p. 639 - 647

~87%

19-Norethindrone acetate Structure

19-Norethindron...

CAS#:51-98-9

Literature: Zhou, Dong; Carlson, Kathryn E.; Katzenellenbogen, John A.; Welch, Michael J. Journal of Medicinal Chemistry, 2006 , vol. 49, # 15 p. 4737 - 4744

~%

19-Norethindrone acetate Structure

19-Norethindron...

CAS#:51-98-9

Literature: Iriarte et al. Journal of the American Chemical Society, 1959 , vol. 81, p. 436

~%

19-Norethindrone acetate Structure

19-Norethindron...

CAS#:51-98-9

Literature: Iriarte et al. Journal of the American Chemical Society, 1959 , vol. 81, p. 436

 Customs

HS Code 2915299090
Summary 2915299090 salts of acetic acid。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:50.0%

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 Synonyms

17α-Ethinyl-19-nortestosterone acetate
NORLUTATE
17α-Ethynyl-19-nortestosterone acetate
Estr-4-en-3-one, 17-(acetyloxy)-17-ethynyl-, (17β)-
19-Norethindrone acetate
17β-Acetoxy-19-nor-17α-pregn-4-en-20-yn-3-one
(17α)-3-Oxo-19-norpregn-4-en-20-yn-17-yl acetate
19-Nor-17α-pregn-4-en-20-yn-3-one, 17-hydroxy-, acetate
17-α-Ethynyl-19-nortestosterone acetate
17α-Ethinyl-19-nortestosterone-17β-acetate
Milligynon
MFCD04039850
19-Norpregn-4-en-20-yn-3-one, 17-(acetyloxy)-, (17α)-
17α-Ethynyl-17β-acetoxy-19-norandrost-4-en-3-one
[(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] acetate
17-Acetoxy-19-nor-17α-pregn-4-en-20-yn-3-one
Norethindrone acetate
19-Norpregn-4-en-20-yn-3-one, 17- (acetyloxy)-, (17α)-
Norethisterone acetate
Primolut-Nor
17-Hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one acetate
EINECS 200-132-0
Norlutin A
17-α-Ethinyl-19-nortestosterone-17-β-acetate
Norlutin acetate
17α-Ethynyl-17-hydroxyestr-4-en-3-one acetate
Norethindrone 17-acetate
17β-Hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one acetate
19-nor-17α-Pregn-4-en-20-yn-3-one, 17-acetoxy-
19-Nor-17α-ethynyltestosterone Acetate
Estr-4-en-3-one, 17α-ethynyl-17-hydroxy-, acetate
19-Nor-17α-pregn-4-en-20-yn-3-one, 17-hydroxy-, acetate (8CI)
Aygestin
(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
Norethisteron acetate
Norlutin-A