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{{Drugbox {{Drugbox
| verifiedrevid = 407229371
| IUPAC_name = (5R)-5-(3,4-dichlorophenyl)bicyclohexane | IUPAC_name = (5R)-5-(3,4-dichlorophenyl)bicyclohexane
| image = DOV-102,677 structure.png | image = DOV-102,677 structure.png

Revision as of 17:35, 14 January 2011

Pharmaceutical compound
DOV-102,677
Identifiers
IUPAC name
  • (5R)-5-(3,4-dichlorophenyl)bicyclohexane
CompTox Dashboard (EPA)
  (verify)

DOV 102,677 is a psychoactive drug being developed by Merck as an antidepressant and is currently in clinical trials. It is a so-called triple (re)uptake inhibitor (TUI), or serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).

Instead of being developed for depression, DOV-102,677 is being developed for the treatment of alcoholism.

IC50 values for the SERT, NET and DAT are 129 nM, 103 nM, and 133 nM.

Com Uptake Binding
5-HT NE DA SERT NET DAT
216303 14 20 78 190 380 190
21947 12 23 96 100 260 210
102677 130 100 130 740 1000 220

"DOV 102,677 (20 mg/kg IP) increased extracellular levels of DA and 5-HT in the prefrontal cortex to 320 and 280% above baseline 100 min after administration. DA levels were stably increased for the duration (240 min) of the study, but serotonin levels declined to baseline by 200 min after administration. NE levels increased linearly to a maximum of 348% at 240 min post-dosing."

Chemistry

DOV scientists and their collaborators have developed an efficient, asymmetric synthesis of 102,677. This economical and robust new route uses phenylacetonitrile and (R)-epichlorohydrin as starting materials to synthesize 102,677 in 3 steps:

  1. Phenylacetonitrile is reacted with (R)-epichlorohydrin in the presence of base to give the cyclopropyl compounds.
  2. The nitrile group is then hydrogenated into the amino alcohol compounds.
  3. Cyclization is achieved with SOCl2 under acidic conditions.
  4. The product is neutralized with base.

References

  1. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 16636898, please use {{cite journal}} with |pmid=16636898 instead.
  2. Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 17908267, please use {{cite journal}} with |pmid=17908267 instead.
  3. Skolnick P, Basile A, Chen Z (2006) WO 2006096810 


Antidepressants (N06A)
Specific reuptake inhibitors and/or receptor modulators
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
Tricyclic and tetracyclic antidepressants
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Monoamine oxidase inhibitors
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Adjunctive therapies
Miscellaneous
Anxiolytics (N05B)
5-HT1ARTooltip 5-HT1A receptor agonists
GABAARTooltip GABAA receptor PAMsTooltip positive allosteric modulators
Hypnotics
Gabapentinoids
(α2δ VDCC blockers)
Antidepressants
Antipsychotics
Sympatholytics
(Antiadrenergics)
Others
Stimulants
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
ATC code: N06B
Stimulants
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
ATC code: N06B
Adrenergic receptor modulators
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
Dopamine receptor modulators
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
Serotonin receptor modulators
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7


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