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Diclofensine

Diclofensine
Systematic (IUPAC) name
4-(3,4-dichlorophenyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Clinical data
Legal status
  • Legal
Identifiers
CAS Registry Number  YesY
ATC code None
PubChem CID:
ChemSpider  N
UNII  YesY
ChEMBL  N
Chemical data
Formula C17H17Cl2NO
Molecular mass 322.229 g/mol
 N   

Diclofensine (Ro 8-4650) was developed by Hoffman-La Roche in the 1970s[1] in the search for a new antidepressant. It was found that the (S) isomer was responsible for activity.[2] Is a stimulant drug which acts as a triple monoamine reuptake inhibitor,[3][4] primarily inhibiting the reuptake of dopamine[5] and norepinephrine,[6] with affinities (Ki) of 16.8nM, 15.7nM, and 51nM for DA, NE, and 5-HT transporters, respectively.[7] It was found to be an effective antidepressant in human trials,[8][9][10] with relatively few side effects,[11] but was ultimately dropped from clinical development, possibly due to concerns about its abuse potential.[12][13]

Diclofensine is chemically a tetrahydroisoquinoline (THIQ) derivative, as is nomifensine.

See also

References

  1. ^ US 3947456 - Substituted 4-phenyl isoquinolines
  2. ^ 'Chirality and Biological Activity of Drugs' page 138
  3. ^ Keller HH, Schaffner R, Carruba MO, Burkard WP, Pieri M, Bonetti EP, Scherschlicht R, Da Prada M, Haefely WE. Diclofensine (Ro 8-4650)--a potent inhibitor of monoamine uptake: biochemical and behavioural effects in comparison with nomifensine. Advances in Biochemical Psychopharmacology. 1982;31:249-63. PMID 6979165
  4. ^ Omer LM. Pilot trials with diclofensine, a new psychoactive drug in depressed patients. International Journal of Clinical Pharmacology, Therapy and Toxicology. 1982 Jul;20(7):320-6. PMID 7107085
  5. ^ Di Renzo G, Amoroso S, Taglialatela M, Canzoniero LM, Maida P, Lombardi G, Annunziato L. Pure uptake blockers of dopamine can reduce prolactin secretion: studies with diclofensine. Life Sciences. 1988;42(21):2161-9. PMID 2968488
  6. ^ Gasić S, Korn A, Eichler HG. Effect of diclofensine, a novel antidepressant, on peripheral adrenergic function. Clinical Pharmacology and Therapeutics. 1986 May;39(5):582-5. PMID 3698467
  7. ^ Andersen PH. The dopamine inhibitor GBR 12909: selectivity and molecular mechanism of action. Eur J Pharmacol. 1989 Aug 3;166(3):493-504. PubMed PMID 2530094
  8. ^ Cherpillod C, Omer LM. A controlled trial with diclofensine, a new psychoactive drug, in the treatment of depression. Journal of International Medical Research. 1981;9(5):324-9. PMID 7028532
  9. ^ Omer OL, Díaz-Olivera M, Ismail S. Therapeutic efficacy and tolerance of diclofensine in psychoreactive depression - a double-blind comparison with placebo. Methods and Findings in Experimental and Clinical Pharmacology. 1984 Mar;6(3):147-51. PMID 6379345
  10. ^ Funke HJ, Holtmann W, Ismail S, Jansen W, Leonhardt KF, Muth H, Omer LM, O'Connolly M, Ramm H. Double-blind comparison of diclofensine with nomifensine in outpatients with dysphoric mood. Pharmacopsychiatry. 1986 May;19(3):120-3. PMID 3725890
  11. ^ Culig J, Ehsanullah RS, Hallett C, Iliopoulou A, Matheson I, Turner P. A clinical pharmacological comparison of diclofensine (Ro 8-4650) with nomifensine and amitriptyline in normal human volunteers. British Journal of Clinical Pharmacology. 1983 May;15(5):537-43. PMID 6860528
  12. ^ Lamb RJ, Griffiths RR. Self-administration in baboons and the discriminative stimulus effects in rats of bupropion, nomifensine, diclofensine and imipramine. Psychopharmacology (Berlin). 1990;102(2):183-90. PMID 2125734
  13. ^ Nakachi N, Kiuchi Y, Inagaki M, Inazu M, Yamazaki Y, Oguchi K. Effects of various dopamine uptake inhibitors on striatal extracellular dopamine levels and behaviours in rats. European Journal of Pharmacology. 1995 Aug 4;281(2):195-203. PMID 7589207
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