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] 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).[5][6] 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.[7][8] Similarly to DXM and DXO, dimemorfan has only relatively low affinity for the σ2 receptor (Ki = 4,421 nM).[6]

Dimemorfan
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.048.134
Chemical and physical data
FormulaC18H25N
Molar mass255.398 g/mol g·mol−1
3D model (JSmol)
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See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 427–. ISBN 978-1-4757-2085-3.
  2. Eduardo Bruera; Irene Higginson; Charles F. von Gunten; Tatsuya Morita (15 January 2015). Textbook of Palliative Medicine and Supportive Care, Second Edition. CRC Press. pp. 677–. ISBN 978-1-4441-3526-8.
  3. Ida, Hisashi (1997). "The nonnarcotic antitussive drug dimemorfan: a review". Clinical Therapeutics. 19 (2): 215–231. doi:10.1016/S0149-2918(97)80111-7. ISSN 0149-2918.
  4. Lora L. Armstrong; Morton P. Goldman (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. Maurice, Tangui; Su, Tsung-Ping (2009). "The pharmacology of sigma-1 receptors". Pharmacology & Therapeutics. 124 (2): 195–206. doi:10.1016/j.pharmthera.2009.07.001. ISSN 0163-7258. PMC 2785038.
  6. Luis M. Botana; Mabel Loza (20 April 2012). Therapeutic Targets: Modulation, Inhibition, and Activation. John Wiley & Sons. pp. 234–. ISBN 978-1-118-18552-0.
  7. Chou, Yueh-Ching; Liao, Jyh-Fei; Chang, Wan-Ya; Lin, Ming-Fang; Chen, Chieh-Fu (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. ISSN 0006-8993. PMID 10064839.
  8. Shin, Eun-Joo; Nah, Seung-Yeol; Kim, Won-Ki; Ko, Kwang Ho; Jhoo, Wang-Kee; Lim, Yong-Kwang; Cha, Joo Young; Chen, Chieh-Fu; Kim, Hyoung-Chun (2005). "The dextromethorphan analog dimemorfan attenuates kainate-induced seizuresvia σ1receptor activation: comparison with the effects of dextromethorphan". British Journal of Pharmacology. 144 (7): 908–918. doi:10.1038/sj.bjp.0705998. ISSN 0007-1188. PMC 1576070. PMID 15723099.


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