Basic information
- Standard SMILES
C#C[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C- InChIKey
IMONTRJLAWHYGT-ZCPXKWAGSA-N- Molecular formula
- C22H28O3
- Average molar mass
- 340.5 g/mol
- Monoisotopic mass
- 340.20384476
Overview
Norethisterone Acetate (Norethindrone Acetate) can cause developmental toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Norethisterone Acetate
- IUPAC
- [(8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
- English name
- 19-Norethindrone acetate
- Molecular formula
- C22H28O3
- Molecular weight
- 340.46
Names & synonyms
Norethindrone acetateNorethisterone acetate51-98-919-Norethindrone acetateNorlutin acetateENTANorethisteron acetate19-Norethisterone acetateNorethindrone 17-acetate19-Norethynyltestosterone acetate(17-alpha)-Norethindrone acetateNorethynyltestosterone
Show more names
Aygestinsh42017-EntSH 420SH-420COrlutateprogylut
17alpha-Ethynyl-19-nortestosterone acetateDTXSID4023381Norethisterone 17-acetate17-alpha-Ethinyl-19-nortestosterone acetate17-alpha-Ethynyl-19-nortestosterone acetate9S44LIC7OJNorethindrone acetate [USP]NSC-22844
Database identifiers
- CAS
51-98-9- PubChem CID
- 5832
- DTXSID
DTXSID4023381- ChEMBL
CHEMBL1201146- ChEBI
CHEBI:7628- UNII
- 9S44LIC7OJ
- EC Number
- 200-132-0
- Nikkaji
- J1.910K
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 695
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section186.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 161 · 161-162°
- Boiling point
- 416.25 °C · 416.25°C (rough estimate)
- Density
- 1.1236 · 1.1236 (rough estimate)
- refractive index
- -34 ° · -34 ° (C=1, Dioxane)
- storage temp.
- 2 · 2-8°C
- solubility
- Practically insoluble in water, freely soluble in methylene chloride, soluble in alcohol.
- form
- Solid
- color
- 2 CO/hexane · Crystals from Me2CO/hexane
- Water Solubility
- 3.162 mg/L · 3.162mg/L(10 ºC)
- Merck
- 14 · 14,6697
- Major Application
- pharmaceutical small molecule
- InChI
- InChI=1/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-/s3
- InChIKey
- IMONTRJLAWHYGT-ZCPXKWAGSA-N
- SMILES
- C[C@]12CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]3([H])[C@]1([H])CC[C@]2(C#C)OC(=O)C |&1:1,4,6,16,18,22,r|
- CAS DataBase Reference
- 51 · 51-98-9(CAS DataBase Reference)
- FDA UNII
- 9 S44LIC7OJ · 9S44LIC7OJ
- Proposition 65 List
- Norethisterone Acetate (Norethindrone Acetate)
- NCI Drug Dictionary
- Aygestin
- NIST Chemistry Reference
- Norethindrone acetate(51-98-9)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 351 · H351
- Precautionary statements
- 201 · P201-P202-P280-P308+P313-P405-P501
- Hazard Codes
- Xn
- Risk Statements
- 40 · 40-48
- Safety Statements
- 36 · 36/37
- WGK Germany
- 3 · 3
- RTECS
- 8965000 · RC8965000
- HS Code
- 29372390 · 29372390
- Storage Class
- 6.1 D · 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Carc. 2Lact.Repr. 1A
- Toxicity
- 1120 mg/kg/4W · dlt-mus-orl 1120 mg/kg/4W MUREAV 26,535,74
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (16.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P263, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 115 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationHazard Traits - Developmental Toxicity
Other Safety InformationIMAP assessments - 19-Norpregn-4-en-20-yn-3-one, 17-(acetyloxy)-, (17.alpha.)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (16.5%)
Toxicology
Treatment
The treatment of choice for S. aureus infection is penicillin, but in most countries, penicillin-resistance is extremely common and first-line therapy is most commonly a penicillinase-resistant penicillin (for example, oxacillin or flucloxacillin). Combination therapy with gentamicin may be used to treat serious infections like endocarditis, but its use is controversial because of the high risk of damage to the kidneys. The duration of treatment depends on the site of infection and on severity. (L1773)
Health EffectsEnterotoxins are cytotoxic. (L1780)
Exposure RoutesIngestion (L1816) ; inhalation (L1816) ; dermal (L1816)
Toxicity Summary
The action of enterotoxins leads to increased chloride ion permeability of the apical membrane of intestinal mucosal cells. These membrane pores are activated by either increased cAMP or by increased calcium ion concentration intracellularly. The pore formation has a direct effect on the osmolarity of the luminal contents of the intestines. Increased chloride permeability leads to leakage into the lumen followed by sodium and water movement. This leads to a secretory diarrhea within a few hours of ingesting enterotoxin. (L1780)
Signs and SymptomsEnterotoxins cause diarrhea. (L1780)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Norethindrone acetate
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- rtecs
- RC8965000
- hs_code
- 29372390
- Toxicity
- dlt-mus-orl 1120 mg/kg/4W MUREAV 26,535,74
- risk_code
- 40-48
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 36/37
- Storage Class
- 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects
- Hazard statements
- H351
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Carc. 2Lact.Repr. 1A
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.
FDA Pharmacological Classification
NORETHINDRONE ACETATE
Progesterone Congeners [CS]; Progestin [EPC]
MeSH Pharmacological Classification
Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading.
Contraceptive agents that act on the ENDOCRINE SYSTEM.
Uses & manufacturing
UsesEnterotoxin type A is one of many enterotoxins produced by Staphylococcus aureus. (L1780)
Use ClassificationPharmaceuticals
Applications
UsesProgesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen.
UsesOral contraceptive (in combination with estrogen)
General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Upstream & downstream products
Upstream raw materials
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Additional notes
DefinitionChEBI: A 3-oxo Delta4-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester.
Related reactions
4 records
Linked notes
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