Ruboxistaurin

Title: Ruboxistaurin
CAS Registry Number: 169939-94-0
CAS Name: (9S)-9-[(Dimethylamino)methyl]-6,7,10,11-tetrahydro-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione
Additional Names: (S)-3,4-[(N,N¢-1,1¢-((2¢¢-ethoxy)-3¢¢¢(O)-4¢¢¢-(N,N-dimethylamino)butane)-bis-(3,3¢-indolyl))]-1(H)-pyrrole-2,3-dione
Manufacturers' Codes: LY-333531
Molecular Formula: C28H28N4O3
Molecular Weight: 468.55
Percent Composition: C 71.77%, H 6.02%, N 11.96%, O 10.24%
Literature References: Protein kinase Cb (PKCb) inhibitor; macrocyclic bisindolylmaleimide. Prepn: W. F. Heath, Jr. et al., EP 657458; eidem, US 5552396 (1995, 1996 both to Eli Lilly); M. R. Jirousek et al., J. Med. Chem. 39, 2664 (1996); M. M. Faul et al., J. Org. Chem. 63, 1961 (1998). Characterization of salt forms: G. L. Engel et al., Int. J. Pharm. 198, 239 (2000). Enantioselective synthesis: B. M. Trost, W. Tang, Org. Lett. 3, 3409 (2001). Antiangiogenic activity: R. P. Danis et al., Invest. Ophthalmol. Visual Sci. 39, 171 (1998). Clinical trial in diabetic retinopathy: PKC-DRS Study Group, Diabetes 54, 2188 (2005); in diabetic neuropathy: A. I. Vinik et al., Clin. Ther. 27, 1164 (2005); in diabetic nephropathy: K. R. Tuttle et al., Diabetes Care 28, 2686 (2005). Review of pharmacology and therapeutic potential: S. V. Joy et al., Ann. Pharmacother. 39, 1693-1699 (2005); A. Vinik, Expert Opin. Invest. Drugs 14, 1547-1559 (2005).
Properties: uv max (ethanol): 493, 382, 282, 232, 204 nm (e 3944, 3796, 9946, 38382, 43887). Soly in water: <1 mg/ml.
Absorption maximum: uv max (ethanol): 493, 382, 282, 232, 204 nm (e 3944, 3796, 9946, 38382, 43887)
Derivative Type: Hydrochloride
CAS Registry Number: 169939-93-9
Molecular Formula: C28H28N4O3.HCl
Molecular Weight: 505.01
Percent Composition: C 66.59%, H 5.79%, N 11.09%, O 9.50%, Cl 7.02%
Properties: Orange cake. [a]D25 -28.7° (c = 1.0 in ethanol). Soly in water: 0.1 mg/ml.
Optical Rotation: [a]D25 -28.7° (c = 1.0 in ethanol)
Derivative Type: Methanesulfonate monohydrate
CAS Registry Number: 202260-21-7; 192050-59-2 (anhydrous)
Additional Names: Ruboxistaurin mesylate monohydrate
Trademarks: Arxxant (Lilly)
Molecular Formula: C28H28N4O3.CH4O3S.H2O
Molecular Weight: 582.67
Percent Composition: C 59.78%, H 5.88%, N 9.62%, O 19.22%, S 5.50%
Properties: Thin red or red-orange plates from acetone/water. Dec 270°. Soly in water: 0.5 mg/ml.
Therap-Cat: In treatment of diabetic microvascular complications.
Rubus Rufigallol Rufinamide Rufloxacin Rugulovasines

Ruboxistaurin
Ruboxistaurin.svg
Systematic (IUPAC) name
(9S)-9-[(dimethylamino)methyl]-6,7,10,11-tetrahydro-9H,18H-5,21:12,17-di(metheno)dibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20-dione
Clinical data
Legal status  ?
Identifiers
CAS number 169939-94-0 N
ATC code None
PubChem CID 153999
ChemSpider 135727 YesY
UNII 721809WQCP YesY
ChEMBL CHEMBL91829 YesY
Chemical data
Formula C28H28N4O3 
Mol. mass 468.546 g/mol
 N (what is this?)  (verify)

Ruboxistaurin (proposed brand name Arxxant) is an investigational drug for diabetic peripheral retinopathy. It is being investigated by Eli Lilly and Company.

On February 2006, Lilly submitted a New Drug Application for ruboxistaurin, and on August 18, 2006, Lilly received an "approvable" letter from the United States Food and Drug Administration for ruboxistaurin,[1] with a request for an additional clinical trial, which would take 5 years to complete.[2]