Norethisterone acetateProduct ingredient for Norethisterone
- Name
- Norethisterone acetate
- Drug Entry
- Norethisterone
Norethisterone, also known as norethindrone, is a synthetic progestational hormone belonging to the 19-nortestosterone-derived class of progestins.8 It is further classified as a second-generation progestin, along with levonorgestrel and its derivatives, and is the active form of several other progestins including norethynodrel and lynestrenol.8 Norethisterone mimics the actions of endogenous progesterone, albeit with a greater potency,5 and is used on its own or in combination with estrogen derivatives in a variety of applications including contraception and hormone replacement therapy.14,15,16,19 First derived in 1951 in Mexico City, norethisterone was originally intended for use as a remedy for irregular menstruation and endometriosis, and was not marketed for use as an oral contraceptive until 1962.21
- Accession Number
- DBSALT000129
- Structure
Structure for Norethisterone acetate (DBSALT000129)
- Synonyms
- Norethindrone acetate
- UNII
- 9S44LIC7OJ
- CAS Number
- 51-98-9
- Weight
- Average: 340.4559
Monoisotopic: 340.203844762 - Chemical Formula
- C22H28O3
- InChI Key
- IMONTRJLAWHYGT-ZCPXKWAGSA-N
- InChI
- InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
- IUPAC Name
- (1R,3aS,3bR,9aR,9bS,11aS)-1-ethynyl-11a-methyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl acetate
- SMILES
- [H][C@@]12CC[C@@](OC(C)=O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
- External Links
- KEGG Drug
- D00953
- KEGG Compound
- C08152
- PubChem Compound
- 5832
- ChemSpider
- 5627
- ChEBI
- 7628
- ChEMBL
- CHEMBL1201146
- ZINC
- ZINC000001849528
- Wikipedia
- Norethisterone_acetate
- Predicted Properties
Property Value Source Water Solubility 0.00542 mg/mL ALOGPS logP 3.58 ALOGPS logP 3.66 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 18.25 Chemaxon pKa (Strongest Basic) -4.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 43.37 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 96.58 m3·mol-1 Chemaxon Polarizability 39.15 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon