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Norethisterone acetate

Norethisterone acetate structure

CAS No:
51-98-9
Formula:
C22H28O3
Chemical Name:
Norethisterone acetate
Synonyms:
19-Norpregn-4-en-20-yn-3-one,17-(acetyloxy)-,(17α)-;19-Nor-17α-pregn-4-en-20-yn-3-one,17-hydroxy-,acetate;(17α)-17-(Acetyloxy)-19-norpregn-4-en-20-yn-3-one;17-Acetoxy-19-nor-17α-pregn-4-en-20-yn-3-one;17α-Ethinyl-19-nortestosterone acetate;17β-Hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one acetate;Norethindrone acetate;Norethisteron acetate;Norethisterone acetate;Norethynyltestosterone acetate;Norethysterone acetate;Norlutate;Norlutin acetate;17α-Ethynyl-19-nortestosterone acetate;17α-Ethinyl-19-nortestosterone 17β-acetate;17α-Ethinyl-4-estrene-17β-ol-acetate-3-one;17β-Acetoxy-19-nor-17α-pregn-4-en-20-yn-3-one;19-Norethynyltestosterone acetate;Norethindrone 17-acetate;19-Norethisterone acetate;17β-Acetoxy-17α-ethinyl-4-estren-3-one;Norlutin A;Orlutate;Primolut-Nor;SH 420;Norethisterone 17-acetate;Milli-Anovlar;Progylut;Gynophase;Gynovlane;Miniphase;Aygestin;Milligynon;NSC 22844;Estalis
Categories:
Organic Chemistry > Carboxylic Acids and Derivatives

Description

Norethindrone acetate is a female progestin approved by FDA for the treatment of endometriosis, uterine bleeding caused by abnormal hormone levels, and secondary amenorrhea.

Norethisterone acetate is a 3-oxo Delta(4)-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester. It has a role as a synthetic oral contraceptive and a progestin. It is a 3-oxo-Delta(4) steroid, a terminal acetylenic compound and an acetate ester. It derives from a norethisterone.|Norethindrone Acetate is the orally bioavailable acetate salt of norethindrone, a synthetic progestin with some anabolic, estrogenic, and androgenic activities. As do all progestins, norethindrone binds to and activates nuclear progesterone receptors (PRs) in target tissues such as the pituitary and reproductive system; ligand-receptor complexes are translocated to the nucleus where they bind to progesterone response elements (PREs) located on target genes, followed by various transcriptional events and histone acetylation. Physiological effects include the inhibition of luteinizing hormone (LH) release, an increase in the endometrial luteal-phase, and alterations in endocervical mucus secretion.|Acetate ester of norethindrone that is used as a long-term contraceptive (CONTRACEPTIVE AGENTS).

Norethisterone acetate Basic Attributes

Molecular Weight：

340.46

Exact Mass：

340.46

EC Number：

200-132-0

UNII：

9S44LIC7OJ

NSC Number：

22844

DSSTox ID：

DTXSID4023381

NCI Thesaurus Code：

C702

ATC Code：

H01CC54

HScode：

2915299090

Characteristics

PSA：

43.37000

XLogP3：

3.99

Density：

1.1±0.1 g/cm3

Melting Point：

161.5 °C

Boiling Point：

454.7±45.0 °C at 760 mmHg

Flash Point：

197.1±28.8 °C

Refractive Index：

1.556

Water Solubility：

3.162mg/L(10 ºC)

Toxicity：

dlt-mus-orl 1120 mg/kg/4W MUREAV 26,535,74

Collision Cross Section：

186.3 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

40-48

safety instructions：

36/37

RTECS Number：

RC8965000

Marks：

Precautionary statement(s)：

P281

Hazard Statements：

H351

GHS Classification：

|Danger|H302 (15.93%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P263, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P391, P405, and P501|Aggregated GHS information provided by 113 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Treatment of endometriosis|Treatment of leiomyoma of uterus|Ryeqo is indicated for treatment of moderate to severe symptoms of uterine fibroids in adult women of reproductive age.

MeSH：

Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Female.)|Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)

MeSH Entry Terms：

Aygestin

Norethisterone acetate Use and Manufacturing

Uses

Oral contraceptive (in combination with estrogen)

Use Classification：

Human Drugs -> EU pediatric investigation plans|Human drugs -> Ryeqo -> EMA Drug Category|Pituitary and hypothalamic hormones and analogues -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:340.5
XLogP3:3.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:340.20384475
Monoisotopic Mass:340.20384475
Topological Polar Surface Area:43.4
Heavy Atom Count:25
Complexity:695
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Norethindrone acetate
Manufacturer	Kunming Sinoway NATURAL Pharmaceuticals Co., Ltd.

Norethindrone acetate
Manufacturer	Zhejiang Xianju Pharmaceutical Co., Ltd.

Estradiol compound patch
Ingredients	This product is a compound preparation. Each tablet contains 10 mg of estradiol and 30 mg of norethindrone acetate.
Indication	Liver microsome inducers such as barbiturates, phenytoin, carbamazepine, meprobamate (Meprobamate), and indomethacin may reduce the activity of estrogen and progesterone.
Specifications	Estradiol 10mg + norethindrone acetate 30mg (5.0cm×4.1cm)
Manufacturer	Zhejiang Yatai Pharmaceutical Co., Ltd.

Registered Holders

NAARI PTE LTD

United States
Active
STEROID SPA

United States
Active
Bayer Ag

Finland
Active

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