Dapiprazole

Dapiprazole (brand name Rev-Eyes) is an alpha-1 blocker. It is used to reverse mydriasis after eye examination.[1]

Not to be confused with aripiprazole or brexpiprazole.
Dapiprazole
Clinical data
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa601043
Pregnancy
category
  • B
Routes of
administration		Topical (eye drops)
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityNegligible when administered topically
Identifiers
IUPAC name
  • 3-{2-[4-(2-methylphenyl)piperazin-1-yl]ethyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,5-a]pyridine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H27N5
Molar mass325.460 g·mol−1
3D model (JSmol)
SMILES
  • n1nc(n2c1CCCC2)CCN4CCN(c3ccccc3C)CC4
InChI
  • InChI=1S/C19H27N5/c1-16-6-2-3-7-17(16)23-14-12-22(13-15-23)11-9-19-21-20-18-8-4-5-10-24(18)19/h2-3,6-7H,4-5,8-15H2,1H3 Y
  • Key:RFWZESUMWJKKRN-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis

Dapiprazole uses a sidechain building strategy that was also used for Lorpiprazole

Thieme Patent:[2]

Conjugate addition of acrylonitrile to ortho-tolylpiperazine affords 3-[4-(2-methylphenyl)piperazin-1-yl]propanenitrile [65876-30-4] (1) in 99% yield. Hydrolysis of the nitrile group to an acid and subsequent esterification with ethanol gives ethyl 3-[4-(2-methylphenyl)piperazin-1-yl]propanoate, CID:417142 (2) .

Ex 2: Upon treatment with hydrazine, ester FGI to the hydrazide (3) CID:12785764 occurs. This is then reacted with the iminoether of 2-piperidone, i.e. o-methylvalerolactim [5693-62-9] (3). An unisolated intermediate such as (5), formed by an addition–elimination (curly arrows not displayed) is likely to account for the reaction mechanism sequence. The second step involves an attack on the carbonyl group by the now quite basic ring amidine nitrogen.

References
  1. Doughty MJ, Lyle WM (May 1992). "A review of the clinical pharmacokinetics of pilocarpine, moxisylyte (thymoxamine), and dapiprazole in the reversal of diagnostic pupillary dilation". Optometry and Vision Science. 69 (5): 358–68. doi:10.1097/00006324-199205000-00005. PMID 1350669. S2CID 22781280.
  2. DE2915318 idem Bruno Silvestrini, Leandro Baiocchi, U.S. Patent 4,252,721 & U.S. Patent 4,325,952 (1981 & 1982 both to Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A.).


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