Altrenogest

Altrenogest

Names
IUPAC name (8S,13S,14S,17R)-17-hydroxy-13-methyl-17-prop-2-enyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Other names Allyltrenbolone; Regumate; RU 2267
Identifiers
CAS Number	850-52-2
ChEMBL	ChEMBL1315492
ChemSpider	8216634
Jmol interactive 3D	Image Image
KEGG	D02840
PubChem	10041070
UNII	2U0X0JA2NB
InChI InChI=1S/C21H26O2/c1-3-10-21(23)12-9-19-18-6-4-14-13-15(22)5-7-16(14)17(18)8-11-20(19,21)2/h3,8,11,13,18-19,23H,1,4-7,9-10,12H2,2H3/t18-,19+,20+,21+/m1/s1 Key: VWAUPFMBXBWEQY-ANULTFPQSA-N InChI=1/C21H26O2/c1-3-10-21(23)12-9-19-18-6-4-14-13-15(22)5-7-16(14)17(18)8-11-20(19,21)2/h3,8,11,13,18-19,23H,1,4-7,9-10,12H2,2H3/t18-,19+,20+,21+/m1/s1 Key: VWAUPFMBXBWEQY-ANULTFPQBN
SMILES C[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(CC=C)O O=C4\C=C3/C(=C2/C=C\[C@]1([C@@H](CC[C@@]1(O)C\C=C)[C@@H]2CC3)C)CC4
Properties
Chemical formula	C21H26O2
Molar mass	310.42994
Pharmacology
ATCvet code	QG03DX90
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Altrenogest (INN, USAN, BAN) (brand name Regumate), also known as allyltrenbolone, is a steroidal progestin that is widely used in veterinary medicine to suppress estrus in animals.^[1][2][3]

Syntheses

Bertin, D.; Pierdet, A.DE 1618810 ; FR 1503984 ; GB 1128787 ; NL 6702462 

This compound can be prepared by two different ways:

1. The Grignard reaction of 3-oximino-17-oxoestre-4,9,11-triene (I) with allylmagnesium bromide in ether - benzene gives 3-oximino-17alpha-allyl-17-hydroxyestra-4,9,11-triene (2), which pyruvic acid - acetic acid .
2. The dehydration of 17alpha-allyl-11beta,17beta-dihydroxyestra-4,9-dien-3-one (IV) eith refluxing aqueous 60% formic acid.

See also

• Trenbolone

References

1. 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.
2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 33–. ISBN 978-3-88763-075-1.
3. Jim E. Riviere; Mark G. Papich (13 May 2013). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. pp. 727–. ISBN 978-1-118-68590-7.