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Norethindrone Basic information
Norethindrone Chemical Properties
  • Melting point:205-206 °C(lit.)
  • alpha D20 -31.7° (chloroform); D20 -25° (chloroform)
  • Boiling point:379.83°C (rough estimate)
  • Density 1.0766 (rough estimate)
  • refractive index 1.4800 (estimate)
  • storage temp. -20°C Freezer
  • solubility chloroform: ≥50 mg/mL, clear, colorless
  • pka13.09±0.40(Predicted)
  • form powder
  • color white to off-white
  • Water Solubility 7.043mg/L(25 ºC)
  • Merck 6697
  • BRN 1915671
  • CAS DataBase Reference68-22-4(CAS DataBase Reference)
  • NIST Chemistry ReferenceNorethindrone(68-22-4)
  • EPA Substance Registry SystemNorethisterone (68-22-4)
Safety Information
Norethindrone Usage And Synthesis
  • DescriptionNorethindrone is a progestin (a synthetic substance with properties similar to progesterone) that is best known as the first female oral contraceptive, or the “pill.”Norethindrone’s global impact on society and culture has made it one of the most important inventions in history.
  • Chemical PropertiesOff-White to Pale Yellow Solid
  • HistoryThe development of norethindrone as a female oral contraceptive took place indirectly over 30 years as a result of steroid research.This research accelerated in the 1930s when structures and medical applications of steroidal compounds were determined.Steroids are lipids, which include cholesterol, bile salts,and sex hormones,that are characterized by a structure of three fused six-carbon rings and a five-carbon ring.
    In 1957, both norethindrone and norethynodrel were approved by the Food and Drug Administration (FDA) for treating menstrual problems and infertility. In 1960, the FDA approved Searle's norethynodrel under the trade name Enovid. Norethindrone was approved as an oral contraceptive in 1962 under the trade name Ortho-Novum.
  • UsesProgestin contraceptives work by producing pregnant-like conditions in a female to preventovulation.During pregnancy, progesterone is released by the placenta during development ofthe fetus.This in turn suppresses development of egg follicles and ovulation. Progestins mimicthis condition and thus prevent or delay ovulation.Oral contraceptives currently use progestinand estrogen in combination to prevent ovulation and thicken cervical mucus.The latter makeit harder for sperm to enter the uterus and for an egg to implant on the uterine wall.
  • Usesprogestogen
  • UsesA synthetic progestin
  • UsesProgesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen
  • DefinitionChEBI: A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.
  • brand nameCamila (Barr); Errin (Barr); Micronor (OrthoMcNeil); Nor-QD (Watson); Norlutin (Parke-Davis).
  • General DescriptionNorethindrone, 17α-ethinyl-19-nortestosterone, and itsΔ5(10)-isomer, norethynodrel, might appear at first glance tobe subtle copies of each other. One would predict that theΔ5(10)-double bond would isomerize in the stomach’s acid tothe Δ4-position. However, the two drugs were actually developedsimultaneously and independently; hence, neither can beconsidered a copy of the other. Furthermore, norethindrone isabout 10 times more active than norethynodrel, indicating that isomerization is not as facile in vivo asone might predict. Although they are less active than progesteronewhen given subcutaneously, they have the importantadvantage of being orally active. The discovery of the potentprogestin activity of 17α-ethinyltestosterone (ethisterone) and19-norprogesterone preceded the development of these potentprogestins. Both are orally active, with the 17α-ethinyl groupblocking oxidation to the less active 17-one. The rich electrondensity of the ethinyl group and the absence of the 19-methylgroup greatly enhance progestin activity. Both compoundswere of great importance as progestin components of oralcontraceptives, although currently, use of norethynodrel isminimal. Norethindrone, USP, and norethindrone acetate,USP, are widely used for all the usual indications of the progestins,as well as being components of oral contraceptives.Because these compounds retain key features of the testosteronestructure, including the 17β-OH, it is not surprisingthat they possess some androgenic side effects.
  • Safety ProfileConfirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Mddly toxic by ingestion. Human systemic effects by ingestion: dermatitis and androgenic effects. Human teratogenic effects: developmental abnormalities of the musculoskeletal system and urogenital system; and behavioral effects in the newborn. Human reproductive effects: spermatogenesis; testes, epididymis, sperm duct changes; impotence; male breast development; other male effects; ovaries, fallopian tube changes; menstrual cycle effects; postpartum effects; changes in female fertility. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
  • CarcinogenicityNorethisterone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Norethindrone Preparation Products And Raw materials
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