Indinavir

Indinavir
Indinavir
Systematic (IUPAC) name
(2S)-1-[(2S,4R)-4-benzyl-2-hydroxy-4-{[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamoyl}butyl]-N-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide
Clinical data
Trade names Crixivan
AHFS/Drugs.com monograph
MedlinePlus a696028
Licence data US FDA:link
Pregnancy cat. C(US)
Legal status  ?
Routes Oral
Pharmacokinetic data
Protein binding 60%
Metabolism Hepatic via CYP3A4
Half-life 1.8 (± 0.4) hours
Identifiers
CAS number 150378-17-9 YesY
ATC code J05AE02
PubChem CID 5362440
DrugBank APRD00069
ChemSpider 4515036 YesY
UNII 9MG78X43ZT YesY
KEGG C07051 N
ChEBI CHEBI:44032 N
ChEMBL CHEMBL540914 N
Chemical data
Formula C36H47N5O4 
Mol. mass 613.79 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Indinavir (IDV; trade name Crixivan, manufactured by Merck) is a protease inhibitor used as a component of highly active antiretroviral therapy (HAART) to treat HIV infection and AIDS.

Contents

History

The Food and Drug Administration (FDA) approved indinavir March 13, 1996, making it the eighth approved antiretroviral. Indinavir was much more powerful than any prior antiretroviral drug; using it with dual NRTIs set the standard for treatment of HIV/AIDS and raised the bar on design and introduction of subsequent antiretroviral drugs. Protease inhibitors changed the very nature of the AIDS epidemic from one of a terminal illness to a somewhat manageable one.

Increasingly, it is being replaced by newer drugs that are more convenient to take and less likely to promote resistant virus, such as lopinavir or atazanavir.

Administration

Unfortunately, indinavir wears off quickly after dosing and therefore requires dosing very precisely every eight hours in order to thwart HIV from forming drug resistant mutations including resistances to other protease inhibitors. It has restrictions on what sorts of food may be eaten concurrently.

Side effects

Side effects include:

Endothelial cells produce nitric oxide (NO) which causes blood vessels to dilate, lowers blood pressure, allows oxygen to reach and nutrients to reach tissues, and allows carbon dioxide and metabolic waste to be removed. Nitric oxide is highly reactive and quickly reacts with molecular oxygen (O2) to form nitrogen dioxide (NO2).

2NO + O2 → 2NO2

A further reaction between nitrogen dioxide (NO2) and water (H2O) can produce nitrate (NO3). The nitrate is then removed from the body in the urine. The kidney is filled with small blood vessels. In the absence of nitric oxide, these blood vessels may become constricted, and the kidney may become ischemic, leading to kidney disease.

Indinavir inhibits urinary nitrous oxide production and may inhibit nitric oxide production. Treatment with this drug is frequently associated with renal abnormalities, sterile leukocyturia, and reduced creatinine clearance.[1]

Indinavir impairs endothelial function in healthy HIV-negative men and may accelerate atherosclerotic disease.[2]

References

  1. ^ M. Eira, M. Araujo and A.C. Seguro. Urinary NO3 excretion and renal failure in indinavir-treated patients. Brazilian Journal of Medical and Biological Research (2006) 39: 1065-1070.
  2. ^ Shankar SS, Dubé MP, Gorski JC, Klaunig JE, Steinberg HO. Indinavir impairs endothelial function in healthy HIV-negative men. Am Heart J. 2005 Nov;150(5):933.

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Look at other dictionaries:

  • Indinavir — Nombre (IUPAC) sistemático 1 [2 hidroxi 4 [(2 hidroxi 2,3 dihidro 1H inden 1 il) carbamoil] 5 fenil pentil] 4 (piridina 3 ilmetil) N tert butil piperazi …   Wikipedia Español

  • indinavir — Inhibidor de una proteína antirretroviral. Indicaciones: se prescribe en el tratamiento de la infección por el virus de la inmunodeficiencia humana. Contraindicaciones: el fármaco no debe administrarse a pacientes con riesgo de cálculos renales.… …   Diccionario médico

  • Indinavir — Strukturformel Allgemeines Freiname Indinavir Summenformel …   Deutsch Wikipedia

  • indinavir — noun a protease inhibitor (trade name Crixivan) used for treating HIV • Syn: ↑Crixivan • Hypernyms: ↑protease inhibitor, ↑PI * * * inˈdinəvir noun ( s) Etymology: indina (perhaps a …   Useful english dictionary

  • indinavir — noun Etymology: indina (perhaps alteration of indanyl monovalent radical of the cyclic hydrocarbon indan) + vir (as in saquinavir) Date: 1995 a protease inhibitor C36H47N5O4 used in the form of its sulfate in combination with antiretroviral drugs …   New Collegiate Dictionary

  • indinavir — in·din·a·vir (ĭn dĭnʹə vîr) n. A protease inhibiting drug usually used in combination with other drugs to suppress the replication of HIV.   [Alteration of indene + navir, protease inhibitor suffix (from saquinavir).] * * * …   Universalium

  • indinavir — noun An anti retroviral drug of the protease inhibitor class that is used in to treat HIV infected patients …   Wiktionary

  • indinavir — in·din·a·vir (.)in din ə .vir n an antiviral protease inhibitor that is used in the form of its sulfate C36H47N5O4·H2SO4 in combination therapy with antiretroviral drugs (as AZT and lamivudine) to treat HIV infection see crixivan * * * n. see… …   Medical dictionary

  • indinavir — in·din·a·vir …   English syllables

  • indinavir — n.; see protease inhibitor …   The new mediacal dictionary

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