노르에티스테론

노르에티스테론 · 노레티스테론 · NORETHISTERONE · NET · ENT · Norethindrone (Norethisterone) · 19-NORETHINDRONE · Elk

식별자 및 물리적 특성

CAS No.	68-22-4
분자식	C20H26O2
평균 분자량	298.4 g/mol
단동위원소 질량	298.19328007 g/mol
SMILES	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
InChIKey	VIKNJXKGJWUCNN-XGXHKTLJSA-N
PubChem CID	6230
ChEMBL	CHEMBL1162
ChEBI	CHEBI:7627
EC No.	200-681-6
DTXSID	DTXSID9023380
현지명	노르에티스테론

화학 및 물리적 성질

XLogP	3
극성 표면적	37.3
수소 결합 공여자 수	1
수소 결합 수용자 수	2
회전 가능 결합 수	1
무거운 원자 수	22
형식 전하	0
복잡도	594
물질 분류	Pharmaceutical and(or) hormone
의약품	Pharmaceuticals -> Listed in ZINC15
지질	Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
LogP(분배 계수)	log Kow = 2.973.2
냄새	ODORLESS
맛	Slightly bitter taste
Color/Form	White crystalline powderCrystals from ethyl acetate
용해도	PRACTICALLY INSOL IN WATERSOL IN CHLOROFORM, ETHER, DIOXANESOL @ 25 °C: 1 IN 12.5 PARTS 95% ETHANOL, 1 IN 4 PARTS ACETONE /ACETATE/Solubility in double-distilled water, 0.98 mg/L /Norethindrone acetate/SLIGHTLY SOL IN VEGETABLE OILSOL @ 25 °C: 1 IN 150 PARTS 95% ETHANOL, 1 IN 5 PARTS PYRIDINE, 1 IN 80 PARTS ACETONE, 1 IN 30 PARTS CHLOROFORMSparingly soluble in alcoholsoluble in chloroform and dioxaneslightly soluble in ether.In double-distilled water, 1.44 mg/LIn water, 7.04 mg/L water at 25 °C클로로포름: 50mg/mL, 투명, 무색
Human Drugs	Breast FeedingLactationMilk, HumanContraceptive Agents, FemaleContraceptives, Oral, SyntheticFDA approved drugs -> Active ingredientPharmaceuticalsOral hormonal contraceptives
Endocrine Disruptors	Potential endocrine disrupting compound
Decomposition	When heated to decomposition, it emits acrid smoke and fumes.
녹는점	202-208C204 °CCrystals from methylene chloride and hexanemax absorption: 240 nm (e = 18,690)MP: 161-162 °C /Norethindrone acetate/203.5 °C397.4 °F205-206 °C (lit.)
끓는 점	379.83°C (rough estimate)
밀도	1.0766 (rough estimate)
굴절률	1.4800 (estimate)
저장 조건	2-8°C
물리적 상태	가루
pKa(산도 계수)	13.09±0.40(Predicted)
색상	흰색에서 황백색까지
생물학적 소스	rabbit
용해도	7.043mg/L(25 ºC)
Merck	6697
BRN	1915671
Specific Activity	122-165nmol/min·mg
헨리 상수	1.7×104 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class	1
주요 응용	의약품(소분자)
InChI	1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
InChIKey	VIKNJXKGJWUCNN-XGXHKTLJSA-N
SMILES	O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@H]4CCC(=O)C=C4CC3)CC2)CC1)C)C#C
NIST	Norethindrone(68-22-4)
EPA	Norethisterone (68-22-4)

화학적 성질

Off-White to Pale Yellow Solid

안전 및 규제

GHS 분류	DangerH312 (28.4%): Harmful in contact with skin [Warning Acute toxicity, dermal]P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 67 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보	Hazard Traits - CarcinogenicityDevelopmental ToxicityStatus: Active Update: 27-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/21038Norethindrone: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보	IMAP assessments - 19-Norpregn-4-en-20-yn-3-one, 17-hydroxy-, (17.alpha.)-: Human health tier I assessment
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including norethindrone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including norethindrone acetate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Norethindrone acetate/
Special Reports	National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Norethisterone (68-22-4) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s139nore.pdf]
Hazard Classes and Categories	Acute Tox. 4 (28.4%)
보관 조건	Norethindrone acetate tablets should be stored in well-closed containers at room temperature (approximately 25 °C).
처리 방법	SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

용도

개요

Norethindrone is a progestin (a synthetic substance with properties similar to progesterone) that is best known as the first female oral contraceptive, or the “pill.”Norethindrone’s global impact on society and culture has made it one of the most important inventions in history.

역사

The development of norethindrone as a female oral contraceptive took place indirectly over 30 years as a result of steroid research.This research accelerated in the 1930s when structures and medical applications of steroidal compounds were determined.Steroids are lipids, which include cholesterol, bile salts,and sex hormones,that are characterized by a structure of three fused six-carbon rings and a five-carbon ring. In 1957, both norethindrone and norethynodrel were approved by the Food and Drug Administration (FDA) for treating menstrual problems and infertility. In 1960, the FDA approved Searle's norethynodrel under the trade name Enovid. Norethindrone was approved as an oral contraceptive in 1962 under the trade name Ortho-Novum.

용도

Progesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen