Compound: norethynodrel
SMILES: O=C1CC2=C([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C#C)CC4)(C)CC3)CC2)CC1
InChIKey: ICTXHFFSOAJUMG-SLHNCBLASA-N
Synonyms: norethynodrel, 68-23-5, Noretynodrel, Norethinodrel, Enidrel, Lynestrol, 19-Norethynodrel, SC-4642, Noretinodrel, NSC-15432, Noretynodrelum, 19-Nor-ethinyl-5,10-testosterone, DTXSID3021069, 88181ACA0M, 17-alpha-Ethynyl-5(10)-estren-17-ol-3-one, 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-, (17alpha)-, 17-alpha-Ethynyl-estr-5(10)-en-3-on-17-beta-ol, DTXCID60563, 17-beta-Hydroxy-17-alpha-ethinyl-5(10)-estren-3-one, (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one, (17-alpha)-17-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one, 19-Nor-17alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-, 17-alpha-Ethinyl-17-beta-hydroxy-delta(sup 5(10))-estren-3-one, 17-alpha-Ethynyl-17-beta-hydroxy-3-oxo-delta(sup 5(10))-estrene, 17-alpha-Ethynyl-17-beta-hydroxy-delta(sup. 5(10))-estren-3-one, NSC15432, (17beta-ethynyl-17-hydroxyestr-5(10)-en-3-one, (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-3-one, RefChem:854723, 200-682-1, 17-Ethinyl-5(10)-estraeneolone, Norethinynodrel, Noretynodrel [INN], MLS000069824, Norethynodral, 17-Hydroxy-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one, Noretynodrel (INN), Norethynodrel (USAN), SMR000058915, Norethynodrel (>90%), NORETHYNODREL [USAN], (1R,3aS,3bR,9bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,6H,7H,8H,9H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one, (17beta)-17-ethynyl-17-hydroxyestr-5(10)-en-3-one, Noretinodrel [DCIT], Norethindrone EP Impurity D, Noretynodrelum [INN-Latin], CCRIS 486, 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-, (17.alpha.)-, HSDB 2951, 17alpha-Ethinyl-5,10-estrenolone, 17-alpha-Ethinyl-5,10-estrenolone, EINECS 200-682-1, NSC 15432, Norethynodrel [Progestins], Norethynodrel [USAN:USP], CB 8023, BRN 2389771, UNII-88181ACA0M, 17alpha-Ethynyl-5(10)-estren-17-ol-3-one, CAS-68-23-5, 17alpha-Ethinyl-5(10)estraen-17beta-ol-3-one, NCGC00016304-01, 17alpha-Ethynyl-estr-5(10)-en-3-on-17beta-ol, Prestwick_883, 17-alpha-Ethynyl-17-hydroxyestr-5(10)-en-3-one, 17alpha-Ethinyl-delta(sup)-5,10-19-nortestosterone, 17alpha-Ethynyl-17beta-hydroxyestr-5(10)-en-3-one, Estr-5(10)-en-3-one, 17alpha-ethynyl-17-hydroxy-, 17-alpha-Ethinyl-delta(super)-5,10-19-nortestosterone, 17-Hydroxy(17alpha)-19-norpregn-5(10)-en-20-yn-3-one, 17alpha-Ethynyl-19-nor-5(10)-androsten-17beta-ol-3-one, 17-alpha-Ethynyl-19-nor-5(10)-androsten-17-beta-ol-3-one, 17alpha-Ethinyl-17beta-hydroxy-delta(sup 5(10))-estren-3-one, 17alpha-Ethinyl-19-nor-delta-5(10)-androstene-17beta-ol-3one, 17alpha-Ethynyl-17beta-hydroxy-delta(sup 5(10))-estren-3-one, 17alpha-Ethynyl-17beta-hydroxy-3-oxo-delta(sup 5(10))-estrene, Opera_ID_1052, Prestwick0_000024, Prestwick1_000024, Prestwick2_000024, Prestwick3_000024, 17-.alpha.-Ethynyl-17-hydroxyestr-5(10)-en-3-one, 17.alpha.-Ethinyl-.DELTA.5(10)-19-nortestosterone, NORETHYNODREL [MI], 17-.alpha.-Ethinyl-.DELTA.5(10)-19-nortestosterone, 17.alpha.-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one, 5(10)-Estren-3-one, 17alpha-ethynyl-17beta-hydroxy-, 17.alpha.-Ethinyl-.delta.(sup)-5,10-19-nortestosterone, CHEMBL1387, NORETHYNODREL [HSDB], SCHEMBL37838, BSPBio_000087, Norethisterone EP Impurity D, NORETHYNODREL [VANDF], NORETYNODREL [MART.], 13-Methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16,17-tetradecahydro-15H-cyclopenta(a)-phenanthrene-3-one, 17-.alpha.-Ethynyl-17-.beta.-hydroxy-5(10)-estren-3-one, 17-.beta.-Hydroxy-17-.alpha.-ethinyl-5(10)-estren-3-one, BIDD:ER0192, NORETYNODREL [WHO-DD], SPBio_002008, (17-.alpha.)-17-Hydroxy-19-norpregn-5(10)-en-20-yn-3-one, 17-.alpha.-Ethynyl-17-.beta.-hydroxy-.DELTA.5(10)-estren-3-one, 17.alpha.-Ethinyl-17.beta.-hydroxy-.DELTA.5(10)-estren-3-one, 17.alpha.-Ethynyl-17.beta.-hydroxy-.DELTA.5(10)-estren-3-one, 17.alpha.-Ethynyl-17.beta.-hydroxy-3-oxo-.DELTA.5(10)-estrene, BPBio1_000097, orb1710744, CHEBI:34895, 17-Ethynyl-17-hydroxyestr-.DELTA.5(10)-en-3-one, (17.alpha.,17.beta.)-, HMS1568E09, HMS2095E09, HMS2232J10, HMS3712E09, NORETHYNODREL [ORANGE BOOK], 19-Nor-17-alpha-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-, HY-B1341, NORETHYNODREL [USP IMPURITY], Tox21_110359, BDBM50410507, EBC-26516, ENOVID COMPONENT NORETHYNODREL, AKOS026749810, CCG-220024, DB09371, FN26448, NCGC00179666-01, CS-0013090, NS00006110, D05207, G89723, NORETHISTERONE IMPURITY D [EP IMPURITY], WLN: L E5 B666OV MUTJ E1 F1UU1 QQ, EN300-7481217, F600857, SR-01000721945, Q5659069, SR-01000721945-2, BRD-K80334323-001-03-5, Estr-5(10)-en-3-one,17.alpha.-ethynyl-17-hydroxy-, (17?)-17-hydroxy-19-norpregn-5(10)-en-20- yn-3-one, 17-Hydroxy-17alpha-19-norpregn-5(10)-en-20-yn-3-one, 17-Hydroxy-19-nor- 17?-pregn-5(10)-en-20-yn-3-one, 17-hydroxy-19-nor-17alpha-pregn-5(10)en-20-yn-3-one, (8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, 13-Methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16 ,17-tetradecahydro-15H-cyclopenta[a]phenanthren-3-one, 13-METHYL-17-ETHYNYL-17-HYDROXY-1,2,3,4,6,7,8,9,11,12,13,14,16,17-TETRADECAHYDRO-15H-CYCLOPENTA(A)PHENANTHREN-3-ONE
Theoretical properties:
molecular_formula: C20H26O2
molecular_weight: 298.4 g/mol
exact_mass: 298.193280068 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from aqueous methanol
color: Crystals from aqueous methanol
odor: Odorless
melting_point: 170 °C
solubility: Very slightly soluble in water; freely soluble in chloroform; soluble in acetone; sparingly soluble in ethanol.
Descriptions:
pubchem: Norethynodrel can cause cancer according to The World Health Organization's International Agency for Research on Cancer (IARC).
chembl: NORETHYNODREL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Noretynodrel, or norethynodrel, sold under the brand name Enovid among others, is a progestin medication which was previously used in birth control pills and in the treatment of gynecological disorders but is now no longer marketed. It was available both alone and in combination with an estrogen. The medication is taken by mouth.
Noretynodrel is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It is a relatively weak progestogen. The medication has weak estrogenic activity, no or only very weak androgenic activity, and no other important hormonal activity. It is a prodrug of various active metabolites in the body, such as norethisterone among others.
Noretynodrel was introduced for medical use in 1957. It was specifically approved at this time in combination with mestranol for the treatment of gynecological and menstrual disorders. Subsequently, in 1960, this formulation was approved for use as a birth control pill. It was the first birth control pill to be introduced, and was followed by birth control pills containing norethisterone and other progestins shortly thereafter. Due to its nature as a relatively weak progestogen, noretynodrel is no longer used in medicine. As such, it is no longer marketed.