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SKF-81,297

Synthetic drug, a stimulant From Wikipedia, the free encyclopedia

SKF-81,297 is a dopamine D1-like receptor agonist and stimulant-like drug of the 3-benzazepine family which was under development for the treatment of Parkinson's disease but was never marketed.[1][2][3] It is a cyclized phenethylamine and catecholamine and is a modified derivative of the monoamine neurotransmitter dopamine.[4] The drug is taken orally.[1]

Other namesSKF81297; SKF-81297; SK&F-81297; SK&F-81,297; SK&F81297
ATC code
  • None
Quick facts Clinical data, Other names ...
SKF-81,297
Clinical data
Other namesSKF81297; SKF-81297; SK&F-81297; SK&F-81,297; SK&F81297
Routes of
administration
Oral[1]
Drug classDopamine receptor agonist; Dopamine D1-like receptor agonist; Stimulant; Antiparkinsonian agent
ATC code
  • None
Identifiers
  • 9-chloro-5-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H16ClNO2
Molar mass289.76 g·mol−1
3D model (JSmol)
  • C1CNCC(C2=CC(=C(C(=C21)Cl)O)O)C3=CC=CC=C3
  • InChI=1S/C16H16ClNO2/c17-15-11-6-7-18-9-13(10-4-2-1-3-5-10)12(11)8-14(19)16(15)20/h1-5,8,13,18-20H,6-7,9H2
  • Key:GHWJEDJMOVUXEC-UHFFFAOYSA-N
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The drug acts as a selective dopamine D1 and D5 receptor full agonist.[3] In addition, it acts as a partial agonist at dopamine D1–D2 receptor heteromers.[5] It produces a characteristic stimulant-like pattern of effects including anorexia, hyperactivity, and self-administration in animals.[3] This profile is shared with several related drugs such as 6-Br-APB and SKF-82,958,[6] but not with certain other dopamine D1 receptor full agonists such as A-77,636, reflecting functional selectivity of dopamine D1 receptor activation.[7][8][9] The drug also produces pro-motivational effects in animals.[10]

Although it produces stimulant-like effects in animals, SKF-81,297 did not substitute for dextroamphetamine in rodent drug discrimination tests in multiple studies.[11][12] This is in notable contrast to dopamine D2 receptor agonists like quinpirole and RU-24213, which fully substitute for dextroamphetamine in such tests.[13] However, in another study, higher doses of SKF-81,297 were able to partially substitute for dextroamphetamine.[13]

SKF-81,297 readily crosses the blood–brain barrier in rodents and shows substantially greater penetration than the related dopamine D1-like receptor agonist SKF-38,393.[12] Its predicted log P is 2.7.[14]

SKF-81,297 was first described in the scientific literature by 1988.[15] It was developed by GlaxoSmithKline.[1][2] The drug reached the preclinical research stage of development for Parkinson's disease prior to the discontinuation of its development.[1][2] One of the patented uses for SKF-81,297 is as an augmentation agent when combined with an appropriate choice of an antidepressant.[16]

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