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Bolmantalate

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Bolmantalate
Clinical data

Other names	LY-38851; Lilly 38851; Nandrolone adamantoate; Nandrolone adamantane-1-carboxylate; 19-Nortestosterone 17β-adamantoate
Routes of administration	Intramuscular injection
Drug class	Androgen; Anabolic steroid; Androgen ester; Progestogen
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] adamantane-1-carboxylate
CAS Number	1491-81-2^Y
PubChem CID	11954312
ChemSpider	10128607
UNII	7IKT9C4TYI
KEGG	D03147
ChEMBL	ChEMBL2104237
CompTox Dashboard (EPA)	DTXSID60164172
Chemical and physical data
Formula	C₂₉H₄₀O₃
Molar mass	436.636 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)C45CC6CC(C4)CC(C6)C5)CCC7=CC(=O)CC[C@H]37
InChI InChI=1S/C29H40O3/c1-28-9-8-23-22-5-3-21(30)13-20(22)2-4-24(23)25(28)6-7-26(28)32-27(31)29-14-17-10-18(15-29)12-19(11-17)16-29/h13,17-19,22-26H,2-12,14-16H2,1H3/t17?,18?,19?,22-,23+,24+,25-,26-,28-,29?/m0/s1 Key:NCXAMLZZPQRJGY-PVAKYVEVSA-N

Bolmantalate (developmental code name LY-38851orLilly 38851), also known as 19-nortestosterone 17β-adamantoate (ornandrolone adamantoate), is an androgen and anabolic steroid and a nandrolone ester which was synthesized and developed by Eli Lilly in 1865 but was never marketed.^[1]^[2]

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Relative affinities (%) of nandrolone and related steroids
Compound	PRTooltip Progesterone receptor	ARTooltip Androgen receptor	ERTooltip Estrogen receptor	GRTooltip Glucocorticoid receptor	MRTooltip Mineralocorticoid receptor	SHBGTooltip Sex hormone-binding globulin	CBGTooltip Corticosteroid-binding globulin
Nandrolone	20	154–155	<0.1	0.5	1.6	1–16	0.1
Testosterone	1.0–1.2	100	<0.1	0.17	0.9	19–82	3–8
Estradiol	2.6	7.9	100	0.6	0.13	8.7–12	<0.1
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, estradiol for the ERTooltip estrogen receptor, dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, dihydrotestosterone for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip corticosteroid-binding globulin. Sources: See template.

References

[edit]

^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 168–. ISBN 978-1-4757-2085-3.

^ Rapala RT, Kraay RJ, Gerzon K (September 1965). "The adamantyl group in medicinal agents. II. Anabolic steroid 17-beta-adamantoates". J. Med. Chem. 8 (5): 580–3. doi:10.1021/jm00329a007. PMID 5867938.