Delavirdine

Title: Delavirdine
CAS Registry Number: 136817-59-9
CAS Name: 1-[3-[(1-Methylethyl)amino]-2-pyridinyl]-4-[[5-[(methylsulfonyl)amino]-1H-indol-2-yl]carbonyl]piperazine
Additional Names: 1-(5-methanesulfonamido-1H-indol-2-ylcarbonyl)-4-[3-(1-methylethylamino)pyridinyl]piperazine; 1-[3-(isopropylamino)-2-pyridyl]-4-[(5-methanesulfonamidoindol-2-yl)carbonyl]piperazine
Manufacturers' Codes: U-90152
Molecular Formula: C22H28N6O3S
Molecular Weight: 456.56
Percent Composition: C 57.88%, H 6.18%, N 18.41%, O 10.51%, S 7.02%
Literature References: Bisheteroarylpiperazine non-nucleoside reverse transcriptase inhibitor of HIV-1. Prepn: D. L. Romero et al., WO 9109849; J. R. Palmer et al., US 5563142 (1991, 1996 both to Upjohn). Structure-activity studies: D. L. Romero et al., J. Med. Chem. 36, 1505 (1993). In vitro activity vs HIV-1: T. J. Dueweke et al., Antimicrob. Agents Chemother. 37, 1127 (1993); P. J. Pagano, K.-T. Chong, J. Infect. Dis. 171, 61 (1995). Enzyme kinetic studies: I. W. Althaus et al., Biochem. Pharmacol. 47, 2017 (1994). NMR characterization of crystalline forms: P. Gao, Pharm. Res. 15, 1425 (1998). HPLC determn in plasma: C.-L. Cheng et al., J. Chromatogr. B 769, 297 (2002). Review of discovery and development: W. J. Adams et al., in Pharm. Biotechnol., R. T. Borchardt et al., Eds. (Plenum Press, New York, 1998) pp 285-312; of clinical use in HIV infection: L. J. Scott, C. M. Perry, Drugs 60, 1411-1444 (2000).
Properties: Crystals from ethyl acetate + hexane, mp 226-228°. Aqueous soly at 23° (mg/ml): 2942 (pH 1.0); 295 (pH 2.0); 0.81 (pH 7.4). pKa1 4.56. pKa2 8.9. Log P (n-octanol/water): 2.84.
Melting point: mp 226-228°
pKa: pKa1 4.56; pKa2 8.9
Log P: Log P (n-octanol/water): 2.84
Derivative Type: Methanesulfonate
CAS Registry Number: 147221-93-0
Additional Names: Delavirdine mesylate
Manufacturers' Codes: U-90152S
Trademarks: Rescriptor (Pharmacia & Upjohn)
Molecular Formula: C22H28N6O3S.CH3SO3H
Molecular Weight: 552.67
Percent Composition: C 49.98%, H 5.84%, N 15.21%, O 17.37%, S 11.60%
Therap-Cat: Antiviral.
Keywords: Antiviral; Reverse Transcriptase Inhibitor.
Delmadinone Acetate Delmopinol Delphinidin Delphinine Delsoline

Delavirdine
Delavirdine.svg
Delavirdine ball-and-stick.png
Systematic (IUPAC) name
N-[2-({4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl}carbonyl)-1H-indol-5-yl]methanesulfonamide
Clinical data
Trade names Rescriptor
AHFS/Drugs.com monograph
MedlinePlus a600034
Pregnancy cat. B3 (AU) C (US)
Legal status -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 85%
Protein binding 98%
Metabolism Hepatic (CYP3A4- and CYP2D6-mediated)
Half-life 5.8 hours
Excretion Renal (51%) and fecal (44%)
Identifiers
CAS number 136817-59-9 YesY
ATC code J05AG02
PubChem CID 5625
DrugBank DB00705
ChemSpider 5423 YesY
UNII DOL5F9JD3E YesY
KEGG D07782 YesY
ChEBI CHEBI:119573 YesY
ChEMBL CHEMBL593 YesY
NIAID ChemDB 005059
Chemical data
Formula C22H28N6O3S 
Mol. mass 456.562 g/mol
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Delavirdine (DLV) (brand name Rescriptor) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) marketed by ViiV Healthcare. It is used as part of highly active antiretroviral therapy (HAART) for the treatment of human immunodeficiency virus (HIV) type 1. It is presented as the mesylate. The recommended dosage is 400 mg, three times a day.

Although delavirdine was approved by the U.S. Food and Drug Administration in 1997, its efficacy is lower than other NNRTIs, especially efavirenz, and it also has an inconvenient schedule. These factors have led the U.S. DHHS not to recommend its use as part of initial therapy.[1] The risk of cross-resistance across the NNRTI class, as well as its complex set of drug interactions, make the place of delavirdine in second-line and salvage therapy unclear, and it is currently rarely used.