Amadinone acetate

Amadinone acetate
Clinical data
Synonyms	RS-2208; 19-Norchlormadinone acetate; 6-Chloro-17α-acetoxy-19-norpregna-4,6-diene-3,20-dione
Drug class	Progestogen; Progestogen ester
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-acetyl-6-chloro-13-methyl-3-oxo-1,2,8,9,10,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate;
CAS Number	22304-34-3 ;
PubChem CID	9977739 ;
ChemSpider	8153331 ;
UNII	3E13526FYB ;
KEGG	D02881 ;
ChEMBL	CHEMBL2104011 ;
Chemical and physical data
Formula	C22H27ClO4
Molar mass	390.900 g/mol
3D model (JSmol)	Interactive image ;
	SMILES CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)CC[C@H]34)Cl)C)OC(=O)C;
	InChI InChI=1S/C22H27ClO4/c1-12(24)22(27-13(2)25)9-7-19-17-11-20(23)18-10-14(26)4-5-15(18)16(17)6-8-21(19,22)3/h10-11,15-17,19H,4-9H2,1-3H3/t15-,16-,17-,19+,21+,22+/m1/s1; Key:PSJMYDLEWUWIAN-KYPKCDLESA-N;

Last updated March 08, 2019

Amadinone acetate (USAN) (developmental code name RS-2208), also known as 19-norchlormadinone acetate, is a steroidal progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups that was never marketed.^[1]^[2] It is the acetate ester of amadinone, which, similarly, was never marketed.^[1]^[2]

United States Adopted Names are unique nonproprietary names assigned to pharmaceuticals marketed in the United States. Each name is assigned by the USAN Council, which is co-sponsored by the American Medical Association (AMA), the United States Pharmacopeial Convention (USP), and the American Pharmacists Association (APhA).

A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes which alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene.

A progestin (P) is a type of medication which is used most commonly in hormonal birth control and menopausal hormone therapy. They can also be used in the treatment of gynecological conditions, to support fertility and pregnancy, to lower sex hormone levels for various purposes, and for other indications. Progestins are used alone or in combination with estrogens. They are available in a wide variety of formulations and for use by many different routes of administration.

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Flumedroxone is a steroidal progestogen of the 17α-hydroxyprogesterone group that was never marketed. The C17α acetate ester of flumedroxone, flumedroxone acetate, has been marketed as an antimigraine drug.

Cloxotestosterone (INN), also known as 17β-chloral hemiacetal testosterone, is a synthetic anabolic–androgenic steroid (AAS) and an androgen ether – specifically, the 17β-trichloro hemiacetal ether of testosterone – which was never marketed. The O-acetate ester of cloxotestosterone, cloxotestosterone acetate, in contrast to cloxotestosterone, has been marketed.

Hydromadinone acetate, also known as chloroacetoxyprogesterone (CAP), as well as 6α-chloro-17α-acetoxyprogesterone or 6α-chloro-17α-acetoxypregn-4-ene-3,20-dione, is a steroidal progestin of the 17α-hydroxyprogesterone group that was never marketed. It is the C17α acetate ester of hydromadinone, which, similarly, was never marketed.

Cloxestradiol acetate, also known as 17-(2,2,2-trichloroethoxy)estradiol O,O-diacetate, is a synthetic, steroidal estrogen derived from estradiol. It is the O,O-diacetate ester of cloxestradiol, which, in contrast to cloxestradiol acetate, was never marketed.

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Clogestone acetate (USAN), also known as chlormadinol acetate or as 3β,17α-diacetoxy-6-chloropregna-4,6-diene-20-one, is a steroidal progestin which was investigated as a progestin-only contraceptive and postcoital contraceptive but was never marketed. It is the diacetate ester of clogestone, which, similarly was never marketed. Clogestone acetate produces chlormadinone acetate as an active metabolite.

Clomegestone (INN), or clomagestone, also known as 6-chloro-17α-hydroxy-16α-methylpregna-4,6-diene-3,20-dione, is a steroidal progestin of the 17α-hydroxyprogesterone group that was never marketed. An acetate ester, clomegestone acetate, also exists, and similarly was never marketed.

Norethisterone acetate oxime, or norethindrone acetate oxime, is a steroidal progestin of the 19-nortestosterone group which was developed as a postcoital contraceptive but was never marketed. It is the C3 oxime and C17β-acetate ester of norethisterone.

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6,6-Difluoronorethisterone chemical compound

6,6-Difluoronorethisterone, also known as 6,6-difluoro-17α-ethynyl-19-nortestosterone or as 6,6-difluoro-17α-ethynylestr-4-en-17β-ol-3-one, is a steroidal progestin of the 19-nortestosterone group that was described in 1971 but was never marketed. It is a fluorinated derivative of norethisterone. The C17β acetate ester, 6,6-difluoronorethisterone acetate, has also been synthesized and described.

6,6-Difluoronorethisterone acetate, also known as 6,6-difluoro-17α-ethynyl-19-nortestosterone 17β-acetate or as 6,6-difluoro-17α-ethynylestr-4-en-17β-ol-3-one 17β-acetate, is a steroidal progestin of the 19-nortestosterone group which was never marketed. In comparison to other steroids, is the C17β acetate ester of 6,6-difluoronorethisterone and the 6,6-difluoro analog of norethisterone acetate.

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Androstenediol 3β-acetate, or 5-androstenediol 3β-acetate, also known as androst-5-ene-3β,17β-diol 3β-acetate, is a synthetic anabolic-androgenic steroid and an androgen ester – specifically, the C3β acetate ester of 5-androstenediol (androst-5-ene-3β,17β-diol) – which was never marketed.

References

1 2 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 35–. ISBN 978-1-4757-2085-3.
1 2 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 206–. ISBN 978-0-8155-1856-3.

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[Elks2014-1] 1 2 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 35–. ISBN 978-1-4757-2085-3.

[Publishing2013-2] 1 2 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 206–. ISBN 978-0-8155-1856-3.

Amadinone acetate

See also

Related Research Articles

References