Delavirdine

Delavirdine

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 Y
ATC code	J05AG02
PubChem	CID 5625
DrugBank	APRD00149
ChemSpider	5423 Y
UNII	DOL5F9JD3E Y
KEGG	D07782 Y
ChEBI	CHEBI:119573 Y
ChEMBL	CHEMBL593 Y
Chemical data
Formula	C22H28N6O3S
Mol. mass	456.562 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C22H28N6O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20/h4-8,13-15,24-26H,9-12H2,1-3H3 Y Key:WHBIGIKBNXZKFE-UHFFFAOYSA-N Y
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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.

Like ritonavir, delavirdine is an inhibitor of cytochrome P450 isozyme CYP3A4, and interacts with many medications. It should not be administered with a wide range of drugs, including amprenavir, fosamprenavir, simvastatin, lovastatin, rifampin, rifabutin, rifapentine, St John's wort, astemizole, midazolam, triazolam, ergot medications, and several medications for acid reflux.^[1]

The most common adverse event is moderate to severe rash, which occurs in up to 20% of patients.^[2] Other common adverse events include fatigue, headache and nausea. Liver toxicity has also been reported.

References

1. ^ ^{a b} DHHS panel. Guidelines for the use of antiretroviral agents in HIV-1-infected adults and adolescents (May 4, 2006). (Available for download from AIDSInfo)
2. ^ RESCRIPTOR brand of delavirdine mesylate tablets. Product information.