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Dimemorfan

From Wikipedia, the free encyclopedia
Cough suppressant
Pharmaceutical compound
Dimemorfan
Clinical data
Trade namesAstomin, Datosin, Gentus
Other names
  • Dimemorfan phosphate
  • Dimemorphan
  • 3,17-Dimethylmorphinan
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (4bS,8aS,9S)-3,11-Dimethyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.048.134Edit this at Wikidata
Chemical and physical data
FormulaC18H25N
Molar mass255.405 g·mol−1
3D model (JSmol)
  • CC1=CC2=C(C[C@@H]3N(CC[C@@]42CCCC[C@H]34)C)C=C1
  • InChI=1S/C18H25N/c1-13-6-7-14-12-17-15-5-3-4-8-18(15,16(14)11-13)9-10-19(17)2/h6-7,11,15,17H,3-5,8-10,12H2,1-2H3/t15-,17+,18+/m1/s1 checkY
  • Key:KBEZZLAAKIIPFK-NJAFHUGGSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dimemorfan (INN;JANdimemorfan phosphate; also known asdimemorphan and3,17-dimethylmorphinan; brand namesAstomin,Dastosirr, andTusben) is anantitussive (cough suppressant) of themorphinan family that is widely used inJapan and is also marketed inSpain andItaly.[1][2][3][4] It was developed byYamanouchi Pharmaceutical (nowAstellas Pharma) and introduced in Japan in 1975.[3] It was later introduced in Spain in 1981 and Japan in 1985.[5]

Side effects

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Adverse effects include nausea, somnolence, dry mouth, and decreased appetite.[5]

Pharmacology

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Dimemorfan is ananalogue ofdextromethorphan (DXM) and itsactive metabolitedextrorphan (DXO), and similarly to them, acts as a potentagonist of theσ1 receptor (Ki = 151 nM).[6][7] However, unlike DXM and DXO, it does not act significantly as anNMDA receptor antagonist (Ki = 16,978 nM), and for this reason, lacksdissociative effects, thereby having reducedside effects andabuse potential in comparison.[8][9] Similarly to DXM and DXO, dimemorfan has only relatively lowaffinity for theσ2 receptor (Ki = 4,421 nM).[7]

See also

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References

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  1. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 427–.ISBN 978-1-4757-2085-3.
  2. ^Bruera E, Higginson I, von Gunten CF, Morita T (15 January 2015).Textbook of Palliative Medicine and Supportive Care, Second Edition. CRC Press. pp. 677–.ISBN 978-1-4441-3526-8.
  3. ^abIda H (1997). "The nonnarcotic antitussive drug dimemorfan: a review".Clinical Therapeutics.19 (2):215–231.doi:10.1016/S0149-2918(97)80111-7.PMID 9152562.
  4. ^Armstrong LL, Goldman MP (1 January 2005).Lexi-Comp's Drug Information Handbook International: With Canadian and International Drug Monographs. Lexi-Comp.ISBN 978-1-59195-110-0.
  5. ^abSchlesser JL (1991).Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 66.ISBN 0-8103-7177-4.
  6. ^Maurice T, Su TP (November 2009)."The pharmacology of sigma-1 receptors".Pharmacology & Therapeutics.124 (2):195–206.doi:10.1016/j.pharmthera.2009.07.001.PMC 2785038.PMID 19619582.
  7. ^abBotana LM, Loza M (20 April 2012).Therapeutic Targets: Modulation, Inhibition, and Activation. John Wiley & Sons. pp. 234–.ISBN 978-1-118-18552-0.
  8. ^Chou YC, Liao JF, Chang WY, Lin MF, Chen CF (March 1999). "Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan".Brain Research.821 (2):516–519.doi:10.1016/S0006-8993(99)01125-7.PMID 10064839.S2CID 22762264.
  9. ^Shin EJ, Nah SY, Kim WK, Ko KH, Jhoo WK, Lim YK, et al. (April 2005)."The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan".British Journal of Pharmacology.144 (7):908–918.doi:10.1038/sj.bjp.0705998.PMC 1576070.PMID 15723099.
Expectorants
Mucolytics
Cough suppressants
Opium alkaloids,
opioids,
and derivatives
Other
σ1
σ2
Unsorted
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