SC-17599

SC-17599 is a steroid derivative drug discovered in 1968 which acts as a selective μ-opioid receptor agonist, with little or no affinity for the δ-opioid or κ-opioid receptors. It is an active analgesic in vivo, more potent than codeine or pethidine but slightly less potent than morphine, [1] and produces similar effects to morphine in animals but with less sedation[2][3]

SC-17599
Clinical data
Other namesSC-17599; 17α-Acetoxy-6-dimethylaminomethyl-21-fluoro-3-ethoxypregna-3,5-dien-20-one; [(8R,9S,10R,13S,14S,17R)-6-(dimethylaminomethyl)-3-ethoxy-17-(2-fluoroacetyl)-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
Legal status
Legal status
  • In general: legal
Identifiers
IUPAC name
  • 6-[(dimethylamino)methyl]-3-ethoxy-21-fluoro-20-oxopregna-3,5-dien-17-yl acetate
PubChem CID
ChemSpider
Chemical and physical data
FormulaC28H42FNO4
Molar mass475.645 g·mol−1
3D model (JSmol)
SMILES
  • FCC(=O)[C@@]1(OC(=O)C)CC[C@H]2[C@H]4[C@H](CC[C@]12C)[C@@]3(C(\C=C(\OCC)CC3)=C(\CN(C)C)C4)C
InChI
  • InChI=1S/C28H42FNO4/c1-7-33-20-8-11-26(3)22-9-12-27(4)23(10-13-28(27,25(32)16-29)34-18(2)31)21(22)14-19(17-30(5)6)24(26)15-20/h15,21-23H,7-14,16-17H2,1-6H3/t21-,22+,23+,26-,27+,28+/m1/s1 N
  • Key:ZPVGJKVIJYUOCI-ORZTVLAMSA-N N
 NY (what is this?)  (verify)

See also

References
  1. Craig CR (1968). "Analgetic Activity and Other Pharmacological Properties of a Steroid; 17α-acetoxy-6-dimethylaminomethyl-21-fluoro-3-ethoxypregna-3,5-dien-20-one Hydrochloride (SC17599)". Journal of Pharmacology and Experimental Therapeutics. 164 (2): 371–379. PMID 5699098.
  2. McFadyen IJ, Houshyar H, Liu-Chen LY, Woods JH, Traynor JR (October 2000). "The steroid 17alpha-acetoxy-6-dimethylaminomethyl-21-fluoro-3-ethoxy-pregna-3, 5-dien-20-one (SC17599) is a selective mu-opioid agonist: implications for the mu-opioid pharmacophore". Molecular Pharmacology. 58 (4): 669–76. doi:10.1124/mol.58.4.669. PMID 10999935.
  3. Houshyar H, Mc Fadyen IJ, Woods JH, Traynor JR (April 2000). "Antinociceptive and other behavioral effects of the steroid SC17599 are mediated by the mu-opioid receptor". European Journal of Pharmacology. 395 (2): 121–8. doi:10.1016/s0014-2999(00)00176-x. PMID 10794817.
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