Naminidil

Naminidil
Clinical data
Other namesBMS-234303; BMS234303
Routes of
administration		Topical[1]
Drug classATP-sensitive potassium channel opener; Vasodilator
ATC code
  • None
Identifiers
  • 1-cyano-3-(4-cyanophenyl)-2-[(2R)-3,3-dimethylbutan-2-yl]guanidine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H19N5
Molar mass269.352 g·mol−1
3D model (JSmol)
  • C[C@H](C(C)(C)C)N=C(NC#N)NC1=CC=C(C=C1)C#N
  • InChI=1S/C15H19N5/c1-11(15(2,3)4)19-14(18-10-17)20-13-7-5-12(9-16)6-8-13/h5-8,11H,1-4H3,(H2,18,19,20)/t11-/m1/s1
  • Key:PGYDRGZVXVVZQC-LLVKDONJSA-N

Naminidil (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name; developmental code name BMS-234303) is an ATP-sensitive potassium channel opener with vasodilator activity which was under development as a topical medication for the treatment of androgenic alopecia (pattern hair loss) but was never marketed.[2][3][1] The drug was under development by Bristol-Myers Squibb and reached phase 2 clinical trials by 2001.[2] One of the phase 2 trials compared naminidil, minoxidil, and placebo for alopecia.[1] However, no results of the study appear to have been made available.[1] Development of naminidil was discontinued by 2008.[2] In terms of chemical structure, naminidil is a guanidine derivative and is structurally distinct from minoxidil.[2][4]

Synthesis

Although patented versions of the synthesis exist (c.f. Lednicer book), the earliest recorded synthesis is for the racemic compound and dates back to 1992.[5]

See also

References

  1. 1 2 3 4 Poulos GA, Mirmirani P (February 2005). "Investigational medications in the treatment of alopecia". Expert Opinion on Investigational Drugs. 14 (2): 177–184. doi:10.1517/13543784.14.2.177. PMID 15757393.
  2. 1 2 3 4 "Naminidil". AdisInsight. 17 January 2008. Retrieved 23 July 2025.
  3. ↑ "Delving into the Latest Updates on Naminidil with Synapse". Synapse. 20 July 2025. Retrieved 23 July 2025.
  4. ↑ "Naminidil". PubChem. U.S. National Library of Medicine. Retrieved 24 July 2025.
  5. ↑ Atwal, K. S., Moreland, S., McCullough, J. R., O’Reilly, B. C., Ahmed, S. Z., Normandin, D. E. (January 1992). "Aryl cyanoguanidine potassium channel openers". Bioorganic & Medicinal Chemistry Letters. 2 (1): 83–86. doi:10.1016/S0960-894X(00)80661-7. ISSN 0960-894X. Retrieved 1 June 2026.
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