SC-17599: Difference between revisions

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{{Short description|Chemical compound}}
{{drugbox |
{{Drugbox
| IUPAC_name = 6-[(dimethylamino)methyl]-3-ethoxy-21-fluoro-20-oxopregna-3,5-dien-17-yl acetate
| Verifiedfields = changed
| image = SC-17599.svg
| Watchedfields = changed
| width = 200
| verifiedrevid = 403511063
| CAS_number =
| IUPAC_name = 6-[(dimethylamino)methyl]-3-ethoxy-21-fluoro-20-oxopregna-3,5-dien-17-yl acetate
| synonyms = SC-17599, 17α-Acetoxy-6-dimethylaminomethyl-21-fluoro-3-ethoxy-pregna-3,5-dien-20-one, [(8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-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
| image = SC-17599.svg
| ATC_prefix =
| width = 250
| ATC_suffix =
| PubChem = 10436424
| DrugBank =
| C = 28 | H = 42 | F = 1 | N = 1 | O = 4
| molecular_weight = 475.634 g/mol
| smiles = CC14CCC(OCC)=CC1=C(CN(C)C)CC3C4CCC2(C)C3CCC2(OC(C)=O)C(=O)CF
| melting_point =
| melting_high =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category=
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA =
| legal_UK =
| legal_US =
| legal_status = Legal
| routes_of_administration =
}}


<!--Clinical data-->
'''SC-17599''' is a [[steroid]] derivative drug discovered in 1968 which acts as a selective [[mu opioid receptor|μ-opioid]] [[Receptor (biochemistry)|receptor]] [[agonist]], with little or no affinity for the [[delta opioid receptor|δ-opioid]] or [[kappa opioid receptor|κ-opioid]] receptors. It is an active [[analgesic]] ''in vivo'', more potent than [[codeine]] or [[pethidine]] but slightly less potent than [[morphine]],<ref>Craig CR. 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'' 1968; 164(2):371-379.</ref> and produces similar effects to morphine in animals but with less [[sedation]].<ref>McFadyen IJ, Houshyar H, Liu-Chen LY, Woods JH, Traynor JR. 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''. 2000 Oct;58(4):669-76. PMID 10999935</ref><ref>Houshyar H, Mc Fadyen IJ, Woods JH, Traynor JR. Antinociceptive and other behavioral effects of the steroid SC17599 are mediated by the mu-opioid receptor. ''European Journal of Pharmacology''. 2000 Apr 28;395(2):121-8. PMID 10794817</ref>
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA =
| legal_UK =
| legal_US =
| legal_status = Legal
| routes_of_administration =


<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


<!--Identifiers-->
| CAS_number =
{{pharm-stub}}
| ATC_prefix =
| ATC_suffix =
| PubChem = 10436424
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8611848


<!--Chemical data-->
| C=28 | H=42 | F=1 | N=1 | O=4
| 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
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ZPVGJKVIJYUOCI-ORZTVLAMSA-N
| synonyms = SC-17599; 17α-Acetoxy-6-dimethylaminomethyl-21-fluoro-3-ethoxypregna-3,5-dien-20-one; [(8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-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
| melting_point =
| melting_high =
}}

'''SC-17599''' is a [[steroid]] derivative drug discovered in 1968 which acts as a selective [[mu opioid receptor|μ-opioid]] [[Receptor (biochemistry)|receptor]] [[agonist]], with little or no affinity for the [[delta opioid receptor|δ-opioid]] or [[kappa opioid receptor|κ-opioid]] receptors. It is an active [[analgesic]] ''in vivo'', more potent than [[codeine]] or [[pethidine]] but slightly less potent than [[morphine]], <ref>{{cite journal | vauthors = Craig CR | title = 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 = Journal of Pharmacology and Experimental Therapeutics | date = 1968 | volume = 164 | issue = 2 | pages = 371–379 | pmid = 5699098 }}</ref> and produces similar effects to morphine in animals but with less [[sedation]]<ref>{{cite journal | vauthors = McFadyen IJ, Houshyar H, Liu-Chen LY, Woods JH, Traynor JR | title = 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 | journal = Molecular Pharmacology | volume = 58 | issue = 4 | pages = 669–76 | date = October 2000 | pmid = 10999935 | doi = 10.1124/mol.58.4.669 }}</ref><ref>{{cite journal | vauthors = Houshyar H, Mc Fadyen IJ, Woods JH, Traynor JR | title = Antinociceptive and other behavioral effects of the steroid SC17599 are mediated by the mu-opioid receptor | journal = European Journal of Pharmacology | volume = 395 | issue = 2 | pages = 121–8 | date = April 2000 | pmid = 10794817 | doi = 10.1016/s0014-2999(00)00176-x }}</ref>

== See also ==
* [[Cyproterone acetate]]


== References ==
== References ==
{{Reflist|2}}
<references />


{{Opioid receptor modulators}}
{{opioids}}


[[Category:Opioids]]
[[Category:Opioids]]
[[Category:Steroids]]
[[Category:Pregnanes]]
[[Category:Ketones]]
[[Category:Ketones]]
[[Category:Organofluorides]]
[[Category:Organofluorides]]
[[Category:Acetate esters]]
[[Category:Acetate esters]]
[[Category:Mu-opioid agonists]]
[[Category:Mu-opioid receptor agonists]]
[[Category:Ethoxy compounds]]
[[Category:Dimethylamino compounds]]


{{analgesic-stub}}