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
Thumb
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
(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-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
PropertyValueSource
Water Solubility0.00542 mg/mLALOGPS
logP3.58ALOGPS
logP3.66ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)19.28ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.58 m3·mol-1ChemAxon
Polarizability39.14 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon