Dimemorfan

Dimemorfan
Systematic (IUPAC) name
(4bS,8aS,9S)-3,11-Dimethyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 36309-01-0 YesY
ATC code R05DA11 (WHO)
PubChem CID 3037918
ChemSpider 16735785 YesY
UNII 623OAC38YU YesY
KEGG D07848 YesY
ChEMBL CHEMBL2106325
Chemical data
Formula C18H25N
Molar mass 255.398 g/mol
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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, 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 σ1 receptor (Ki = 4421 nM).[6]

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. Cite uses deprecated parameter |coauthors= (help)
  3. 1 2 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.
  6. 1 2 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.
  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.


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