Prednylidene: Difference between revisions

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{{drugbox |
{{Drugbox
| IUPAC_name =  
| Verifiedfields = changed
| image = Prednylidene.svg
| verifiedrevid = 464213580
| IUPAC_name = (11β)-11,17,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
| image = Prednylidene.png
 
<!--Clinical data-->
| 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  / S8 -->
| legal_UK = <!-- GSL        / P      / POM / CD -->
| legal_US = <!-- OTC                  / Rx-only  -->
| legal_status = 
| routes_of_administration = 
 
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 599-33-7
| CAS_number = 599-33-7
| ATC_prefix = H02
| ATC_prefix = H02
| ATC_suffix = AB11
| ATC_suffix = AB11
| PubChem = 11740
| PubChem = 20055008
| DrugBank =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C=22 | H=28 | O5
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16735979
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = IF8PQP966U
 
<!--Chemical data-->
| C=22 | H=28 | O=5
| molecular_weight = 372.455
| molecular_weight = 372.455
| bioavailability =  
| smiles = OCC(=O)[C@@]2(O)C(=C)C[C@H]3[C@@H]4CC\C1=C\C(=O)\C=C/[C@]1(C)[C@H]4[C@@H](O)C[C@]23C
| protein_bound =  
| InChI = 1/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-20(13,2)19(15)17(25)10-21(16,3)22(12,27)18(26)11-23/h6-7,9,15-17,19,23,25,27H,1,4-5,8,10-11H2,2-3H3/t15-,16-,17-,19+,20-,21-,22-/m0/s1
| metabolism =  
| InChIKey = WSVOMANDJDYYEY-CWNVBEKCBU
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion =  
| StdInChI = 1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-20(13,2)19(15)17(25)10-21(16,3)22(12,27)18(26)11-23/h6-7,9,15-17,19,23,25,27H,1,4-5,8,10-11H2,2-3H3/t15-,16-,17-,19+,20-,21-,22-/m0/s1
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US =  <!-- A / B            / C / D / X -->
| StdInChIKey = WSVOMANDJDYYEY-CWNVBEKCSA-N
| pregnancy_category =
| synonyms = <small>(8''S'',9''S'',10''R'',11''S'',13''S'',14''S'',17''R'')-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-16-methylidene-6,7,8,9,11,12,14,15-octahydrocyclopenta[''a'']phenanthren-3-one</small>
| legal_AU =     <!-- Unscheduled / S2 / S3 / S4  / S8 -->
| legal_UK =     <!-- GSL        / P      / POM / CD -->
| legal_US =      <!-- OTC                  / Rx-only  -->
| legal_status =
| routes_of_administration =
}}
}}
'''Prednylidene''' is a [[glucocorticoid]] for systemic use.


{{Corticosteroids}}
'''Prednylidene''' is a [[glucocorticoid]]<ref name="pmid10423179">{{cite journal |author=Buttgereit F, Brand MD, Burmester GR |title=Equivalent doses and relative drug potencies for non-genomic glucocorticoid effects: a novel glucocorticoid hierarchy |journal=Biochem. Pharmacol. |volume=58 |issue=2 |pages=363–8 |date=July 1999 |pmid=10423179 |doi= 10.1016/S0006-2952(99)00090-8|url=http://linkinghub.elsevier.com/retrieve/pii/S0006-2952(99)00090-8}}</ref> for systemic use.
{{Corticosteroids for systemic use}}
 
Substitution at position 16 also leads to more potent corticosteroids. The additional steric bulk introduced by such substituents adjacent to the dihydroxyacetone side chain also protects that moiety against metabolic degradation.
 
==Synthesis==
[[Curvularia]]
[[File:Prednylidene synthesis.png|thumb|center|700px|Prednylidene synthesis:<ref>{{Cite doi|10.1016/S0040-4039(01)99336-0}}</ref>]]
 
==References==
{{Reflist|2}}
 
 
{{Glucocorticoids}}
{{Glucocorticoidics}}
 
[[Category:Glucocorticoids]]
[[Category:Glucocorticoids]]
{{treatment-stub}}
 
 
{{systemic-hormonal-drug-stub}}

Revision as of 19:49, 15 April 2015

Prednylidene
Clinical data
Synonyms(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-16-methylidene-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-one
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC22H28O5
Molar mass372.455
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Prednylidene is a glucocorticoid[1] for systemic use.

Substitution at position 16 also leads to more potent corticosteroids. The additional steric bulk introduced by such substituents adjacent to the dihydroxyacetone side chain also protects that moiety against metabolic degradation.

Synthesis

Curvularia

Prednylidene synthesis:[2]

References

  1. ↑ Buttgereit F, Brand MD, Burmester GR (July 1999). "Equivalent doses and relative drug potencies for non-genomic glucocorticoid effects: a novel glucocorticoid hierarchy". Biochem. Pharmacol. 58 (2): 363–8. doi:10.1016/S0006-2952(99)00090-8. PMID 10423179.
  2. ↑ Template:Cite doi


Template:Glucocorticoids


Template:Systemic-hormonal-drug-stub

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