Dimemorfan

Dimemorfan (INN) (or dimemorphan) (brand names Astomin, Dastosirr, Tusben), or dimemorfan phosphate (JAN), also known as 3,17-dimethylmorphinan, is an antitussive (cough suppressant) of the morphinan family that is widely used in Japan and is also marketed in Spain and Italy.[1][2][3][4] It was developed by Yamanouchi Pharmaceutical (now Astellas Pharma) and introduced in Japan in 1975.[3] It was later introduced in Spain in 1981 and Japan in 1985.[5]

Dimemorfan
Clinical data
Trade namesAstomin, Datosin, Gentus
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • (4bS,8aS,9S)-3,11-Dimethyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.048.134
Chemical and physical data
FormulaC18H25N
Molar mass255.405 g·mol−1
3D model (JSmol)
SMILES
  • CC1=CC2=C(C[C@@H]3N(CC[C@@]42CCCC[C@H]34)C)C=C1
InChI
  • 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 Y
  • Key:KBEZZLAAKIIPFK-NJAFHUGGSA-N Y
 NY (what is this?)  (verify)

Side effects

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

Pharmacology

Dimemorfan is an analogue of dextromethorphan (DXM) and its active metabolite dextrorphan (DXO), and similarly to them, acts as a potent agonist of the σ1 receptor (Ki = 151 nM).[6][7] However, unlike DXM and DXO, it does not act significantly as an NMDA receptor antagonist (Ki = 16,978 nM), and for this reason, lacks dissociative effects, thereby having reduced side effects and abuse potential in comparison.[8][9] Similarly to DXM and DXO, dimemorfan has only relatively low affinity for the σ2 receptor (Ki = 4,421 nM).[7]

See also

References
  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. Ida H (1997). "The nonnarcotic antitussive drug dimemorfan: a review". Clinical Therapeutics. 19 (2): 215–31. 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. Schlesser 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. Botana 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): 516–9. 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): 908–18. doi:10.1038/sj.bjp.0705998. PMC 1576070. PMID 15723099.
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