Norethisterone

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Norethisterone
Norethisterone.svg
Norethindrone ball-and-stick.png
Systematic (IUPAC) name
(17β)-17-ethynyl-17-hydroxyestr-4-en-3-one;
(8R,9S,10R,13S,14S,17S)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa604034
Legal status
?
Pharmacokinetic data
Bioavailability64%
Protein binding>95%
Half-life7 hours
Identifiers
CAS number68-22-4 YesY
ATC codeG03AC01 G03DC02
PubChemCID 6230
DrugBankDB00717
ChemSpider5994 YesY
UNIIT18F433X4S YesY
KEGGD00182 YesY
ChEBICHEBI:7627 YesY
ChEMBLCHEMBL1162 YesY
Chemical data
FormulaC20H26O2 
Mol. mass298.419 g/mol
 YesY (what is this?)  (verify)
 
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Norethisterone
Norethisterone.svg
Norethindrone ball-and-stick.png
Systematic (IUPAC) name
(17β)-17-ethynyl-17-hydroxyestr-4-en-3-one;
(8R,9S,10R,13S,14S,17S)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa604034
Legal status
?
Pharmacokinetic data
Bioavailability64%
Protein binding>95%
Half-life7 hours
Identifiers
CAS number68-22-4 YesY
ATC codeG03AC01 G03DC02
PubChemCID 6230
DrugBankDB00717
ChemSpider5994 YesY
UNIIT18F433X4S YesY
KEGGD00182 YesY
ChEBICHEBI:7627 YesY
ChEMBLCHEMBL1162 YesY
Chemical data
FormulaC20H26O2 
Mol. mass298.419 g/mol
 YesY (what is this?)  (verify)

Norethisterone (or norethindrone) (or 19-nor-17α-ethynyltestosterone) is a molecule used in some combined oral contraceptive pills, progestogen only pills and is also available as a stand-alone drug. It is a progestogen and can be used to treat premenstrual syndrome, painful periods, abnormal heavy bleeding, irregular periods, menopausal syndrome (in combination with oestrogen), or to postpone a period. It is also commonly used to help prevent uterine hemorrhage in complicated non-surgical or pre-surgical gynecologic cases. Norethindrone was the first orally highly active progestin to be synthesized. It was synthesized for the first time by chemists Luis Miramontes, Carl Djerassi, and George Rosenkranz at Syntex in Mexico City in 1951.[1] It was the progestin used in one of the first three oral contraceptives. Its related ester, norethisterone acetate, is used for the same indications.

Synthesis[edit]

References[edit]

  1. ^ a b Djerassi, C.; Miramontes, L.; Rosenkranz, G.; Sondheimer, F. (1954). "Steroids. LIV.1Synthesis of 19-Nov-17α-ethynyltestosterone and 19-Nor-17α-methyltestosterone2". Journal of the American Chemical Society 76 (16): 4092. doi:10.1021/ja01645a010.  edit
  2. ^ Ringold, H. J.; Rosenkranz, G.; Sondheimer, F. (1956). "Steroids. LXXX.11-Methyl-19-nortestosterone and 1-Methyl-17α-ethinyl-19-nortestosterone". Journal of the American Chemical Society 78 (11): 2477. doi:10.1021/ja01592a037.  edit
  3. ^ Ueberwasser, H.; Heusler, K.; Kalvoda, J.; Meystre, C.; Wieland, P.; Anner, G.; Wettstein, A. (1963). "19-Norsteroide II. Ein einfaches Herstellungsverfahren f�r 19-Norandrostan-Derivate. �ber Steroide, 193. Mitteilung". Helvetica Chimica Acta 46: 344. doi:10.1002/hlca.19630460135.  edit
  4. ^ Onken, D; Heublein, D (1970). "Ethinylated steroids". Die Pharmazie 25 (1): 3–9. PMID 4914401.  edit