デラビルジン
WordNet
- a non-nucleoside reverse transcriptase inhibitor (trade name Rescriptor) used to treat AIDS and HIV (同)Rescriptor
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/10/08 13:54:32」(JST)
[Wiki en表示]
Delavirdine
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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 |
DB00705 |
ChemSpider |
5423 Y |
UNII |
DOL5F9JD3E Y |
KEGG |
D07782 Y |
ChEBI |
CHEBI:119573 Y |
ChEMBL |
CHEMBL593 Y |
NIAID ChemDB |
005059 |
Chemical data |
Formula |
C22H28N6O3S |
Mol. mass |
456.562 g/mol |
SMILES
- O=S(=O)(Nc1cc2cc(nc2cc1)C(=O)N4CCN(c3ncccc3NC(C)C)CC4)C
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InChI
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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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Y (what is this?) (verify)
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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.
Contents
- 1 Interactions
- 2 Adverse effects
- 3 External links
- 4 References
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Interactions
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]
Adverse effects
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.
External links
- Delavirdine bound to proteins in the PDB
References
- ^ 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)
- ^ RESCRIPTOR brand of delavirdine mesylate tablets. Product information.
Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)
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Entry/fusion inhibitors
(Discovery & development) |
- gp41 (Enfuvirtide)
- CCR5 (Maraviroc
- Vicriviroc†, Cenicriviroc†, PRO 140†)
- CD4 (Ibalizumab†)
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Reverse-transcriptase
inhibitors (RTIs) |
Nucleoside &
Nucleotide (NRTI)
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- Nucleoside analogues/NARTIs: Abacavir (ABC)°#
- Emtricitabine (FTC)°#
- Lamivudine (3TC)°#
- Didanosine (ddI)#
- Zidovudine (AZT)#
- Apricitabine†
- Stampidine†
- Elvucitabine†
- Racivir†
- Amdoxovir†
- Stavudine (d4T)#
- Zalcitabine (ddC)◊
- Festinavir†
- Nucleotide analogues/NtRTIs: Tenofovir°#
- GS 7340
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Non-Nucleoside (NNRTI)
(Discovery & development)
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- (1st generation) Efavirenz°#
- Nevirapine#
- Loviride◊
- Delavirdine◊
(2nd generation) diarylpyrimidines (Etravirine
- Rilpivirine)
- Lersivirine†
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Integrase inhibitors |
- Raltegravir°
- Elvitegravir†
- Dolutegravir†
- Globoidnan A (experimental)
- MK-2048†
- BI 224436†
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Maturation inhibitors |
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Protease Inhibitors (PI)
(Discovery and development) |
1st generation
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- Fosamprenavir°
- Lopinavir°#
- Nelfinavir#
- Ritonavir#
- Saquinavir#
- Amprenavir◊
- Indinavir◊#
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2nd generation
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- Atazanavir°
- Darunavir°
- Tipranavir
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Combined formulations |
- Lamivudine/zidovudine
- Emtricitabine/tenofovir/efavirenz
- Abacavir/lamivudine/zidovudine
- Tenofovir/emtricitabine
- Lopinavir/ritonavir
- Abacavir/lamivudine
- Emtricitabine/rilpivirine/tenofovir
- Elvitegravir/cobicistat/emtricitabine/tenofovir
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Experimental agents |
Uncoating inhibitors
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Transcription inhibitors
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Translation inhibitors
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Other
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- Abzyme
- Calanolide A
- Ceragenin
- Cyanovirin-N
- Diarylpyrimidines
- Epigallocatechin gallate (EGCG)
- Foscarnet
- Griffithsin
- Hydroxycarbamide
- Miltefosine
- Portmanteau inhibitors
- Seliciclib†
- Synergistic enhancers
- Tre recombinase
- Zinc finger protein transcription factor
- KP-1461†
- Cobicistat†
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Failed agents
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- Dexelvucitabine
- Capravirine
- Emivirine
- Lodenosine
- Atevirdine
- Brecanavir
- Aplaviroc
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
°DHHS preferred first-line agent. ◊Formerly or rarely used agent.
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cutn/syst (hppv/hiva, infl/zost/zoon)/epon
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drug(dnaa, rnaa, rtva, vacc)
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UpToDate Contents
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English Journal
- Structural optimization of pyridine-type DAPY derivatives to exploit the tolerant regions of the NNRTI binding pocket.
- Chen W1, Zhan P1, Daelemans D2, Yang J1, Huang B1, De Clercq E2, Pannecouque C3, Liu X4.
- European journal of medicinal chemistry.Eur J Med Chem.2016 Oct 4;121:352-63. doi: 10.1016/j.ejmech.2016.05.054. Epub 2016 May 25.
- Based on the crystallographic studies of diarylpyrimidines (DAPYs), we embarked on incorporating the hydrophilic piperidyl or morpholinyl group into the known DAPY derivatives bearing the pyridine moiety as a core structure, with the double aim to exploit additional interactions with the HIV-1 NNRTI
- PMID 27267005
- Antileishmanial activity of antiretroviral drugs combined with miltefosine.
- Costa S1,2, Machado M3,4, Cavadas C2,5, do Céu Sousa M6,7.
- Parasitology research.Parasitol Res.2016 Oct;115(10):3881-7. doi: 10.1007/s00436-016-5153-8. Epub 2016 Jun 1.
- Co-infection of Leishmaniasis, a neglected tropical disease, with human immunodeficiency virus (HIV) has hindered treatment efficacy. In this study, we aim to evaluate the antileishmanial activity of two protease inhibitors (darunavir and atazanavir) and four reverse transcriptase inhibitors (tenofo
- PMID 27249967
- An accelerated background subtraction algorithm for processing high-resolution MS data and its application to metabolite identification.
- Shekar V1, Shah A1, Shadid M1, Wu JT1, Bolleddula J1, Chowdhury S1.
- Bioanalysis.Bioanalysis.2016 Aug;8(16):1693-707. doi: 10.4155/bio-2016-0101. Epub 2016 Jul 27.
- BACKGROUND: Metabolite identification without radiolabeled compound is often challenging because of interference of matrix-related components.RESULTS: A novel and an effective background subtraction algorithm (A-BgS) has been developed to process high-resolution mass spectral data that can selective
- PMID 27460980
Japanese Journal
- Pharmacokinetic interaction between amprenavir and delavirdine : evidence of induced clearance by amprenavir
- Synthesis and Anti-HIV-1 Activity of New Delavirdine Analogues Carrying Arylpyrrole Moieties
- Randomized study of saquinavir with ritonavir or nelfinavir together with delavirdine, adefovir, or both in human immunodeficiency virus-infected adults with virologic failure on indinavir : AIDS Clinical Trials Group Study 359
Related Links
- Drug information on Delavirdine for patients and consumers. ... What is delavirdine? Delavirdine is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV infection in ...
- Delavirdine may cause side effects. Tell your doctor if any of these symptoms are severe or do not go away: excessive tiredness headache nausea diarrhea rash Some side effects can be serious. If you experience any of ...
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