Nandrolone

Nandrolone
Clinical data
Pronunciation	/ˈnændrəloʊn/
Trade names	• Deca-Durabolin (as NDTooltip nandrolone decanoate); • Durabolin (as NPPTooltip nandrolone phenylpropionate); • Many others (see here)
Other names	• 19-Nortestosterone; • 10-Nortestosterone; • Estr-4-en-17β-ol-3-one; • Estrenolone; • Oestrenolone; • 19-Norandrost-4-en-17β-ol-3-one; • Norandrostenolone; • Nortestrionate; • Nortestonate; • Norandroone; • SG-4341
Pregnancy; category	AU: D;
Routes of; administration	• IM injection (esters); • SC injection (esters); • Eye drops (NSTooltip nandrolone sulfate)
Drug class	Androgen; Anabolic steroid; Progestogen
ATC code	A14AB01 (WHO) S01XA11 (WHO);
Legal status
Legal status	BR: Class C5 (Anabolic steroids); CA: Schedule IV; UK: Class C; US: Schedule III;
Pharmacokinetic data
Bioavailability	• Oral: <3% (pigs); • Intramuscular: high
Metabolism	Liver (reduction)
Metabolites	• 5α-Dihydronandrolone; • 19-Norandrosterone; • 19-Noretiocholanolone; • Conjugates
Elimination half-life	• Nandrolone: <4.3 hours; • NDTooltip Nandrolone decanoate (IMTooltip Intramuscular injection): 6–12 days; • NPPTooltip Nandrolone phenylpropionate: 2.7 days
Duration of action	• ND (IM): 2–3 weeks; • NPP (IM): 5–7 days
Excretion	Urine
Identifiers
	IUPAC name (8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one;
CAS Number	434-22-0 ;
PubChem CID	9904;
IUPHAR/BPS	6949;
DrugBank	DB13169;
ChemSpider	9520 ;
UNII	6PG9VR430D;
ChEBI	CHEBI:7466 ;
ChEMBL	ChEMBL757 ;
CompTox Dashboard (EPA)	DTXSID7023350 ;
ECHA InfoCard	100.006.457
Chemical and physical data
Formula	C18H26O2
Molar mass	274.404 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4\C=C2/[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4;
	InChI InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1 ; Key:NPAGDVCDWIYMMC-IZPLOLCNSA-N ;
	(verify)

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolone esters are used in the treatment of anemias, cachexia (muscle wasting syndrome), osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

Side effects of nandrolone esters include symptoms of masculinization like acne, increased hair growth, and voice changes. They are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). Nandrolone has strong anabolic effects and weak androgenic effects, which give them a mild side effect profile and make them especially suitable for use in women and children. There are metabolites of Nandrolone that act as long-lasting prodrugs in the body, such as 5α-Dihydronandrolone.

Nandrolone esters were first described and introduced for medical use in the late 1950s. They are among the most widely used anabolic steroid worldwide. In addition to their medical use, nandrolone esters are used to improve physique and performance, and are said to be the most widely used anabolic steroid for such purposes. The drugs are controlled substances in many countries and so non-medical use is generally illicit.

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