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convert into a sulfate
a salt or ester of sulphuric acid (同)sulphate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/02/13 15:57:37」(JST)

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Two Reyataz 200 mg capsules

Atazanavir (pronunciation: /ˌæ.tə.ˈzæ.nə.vɪər/, A-tə-ZA-nə-vir),^[1] marketed under the trade name Reyataz by Bristol Myers, (formerly known as BMS-232632) is an antiretroviral drug of the protease inhibitor (PI) class. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus (HIV).

Atazanavir is distinguished from other PIs in that it can be given once-daily (rather than requiring multiple doses per day) and has lesser effects on the patient's lipid profile (the amounts of cholesterol and other fatty substances in the blood). Like other protease inhibitors, it is used only in combination with other HIV medications.

The U.S. Food and Drug Administration (FDA) approved atazanavir on June 20, 2003. Atazanavir is the first PI approved for once-daily dosing, and also appears to be less likely to cause lipodystrophy and elevated cholesterol as side effects. It may also not be cross-resistant with other PIs. When boosted with ritonavir it is equivalent in potency to lopinavir for use in salvage therapy in patients with a degree of drug resistance, although boosting with ritonavir reduces the metabolic advantages of atazanavir.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[2]

Medical uses

Atazanavir is used in the treatment of HIV. The efficacy of atazanavir has been assessed in a number of well designed trials in ART-naive and ART-experienced adults.^[3]

Adverse effects

Bilirubin levels in the blood are normally asymptomatically raised with atazanavir. A single case of torsades de pointes attributable to atazanavir therapy has been described.^[4] Atazanavir has less effect on glucose levels than ritonavir.

Contraindications

In April 2009, the US FDA issued a warning: atazanavir should not be used with proton-pump inhibitors, such as omeprazole (Prilosec), esomeprazole (Nexium), or rabeprazole (Aciphex). According to the FDA, "A 76% reduction in atazanavir area under the concentration-time curve (AUC) and a 78% reduction in atazanavir trough plasma concentration (Cmin) were observed when Reyataz/ritonavir [another protease inhibitor, often prescribed with azatanavir] 300/100 mg was coadministered with omeprazole 40 mg."^[5] In other words, proton pump inhibitors reduce the absorption and effects of atazanavir due to their effect in decreasing stomach acidity.

Chemistry

Bold, Guido; Fässler, Alexander; Capraro, Hans-Georg; Cozens, Robert; Klimkait, Thomas; Lazdins, Janis; Mestan, JüRgen; Poncioni, Bernard et al. (1998). "New Aza-Dipeptide Analogues as Potent and Orally Absorbed HIV-1 Protease Inhibitors: Candidates for Clinical Development". Journal of Medicinal Chemistry 41 (18): 3387–401. doi:10.1021/jm970873c. PMID 9719591.

Society and culture

On October 20, 2006, the FDA approved a new formulation of atazanavir (300 mg capsules) to be taken as part of combination drug therapy.^[6] This formulation should reduce pill burden, as one 300 mg capsule may replace two 150 mg capsules.

References

^ "Atazanavir". MedlinePlus. National Institutes of Health. October 15, 2012. Retrieved August 3, 2013.
^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.
^ Croom KF, Dhillon S, Keam SJ.[1].Drugs 2009;69(8):1107-1140. doi:10.2165/00003495-200969080-00009.
^ Ly T, Ruiz M (March 2007). "Prolonged QT interval and torsades de pointes associated with atazanavir therapy Question: Have patients developed Liver stones as a side-effect of this medication?". Clin Infect Dis 44 (6): e67–8. doi:10.1086/511875. PMID 17304444.
^ "Atazanavir, with or without ritonavir should not be coadministered with proton pump inhibitors". Food and Drug Administration. March 27, 2009. Retrieved August 26, 2013.
^ "Bristol wins U.S. approval for single anti-HIV pill". Reuters. October 20, 2006. Retrieved October 25, 2006.

UpToDate Contents

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1. HIV抗レトロウイルス療法に関する臨床試験：プロテアーゼ阻害剤と非ヌクレオシド系逆転写酵素阻害剤の比較 clinical trials of hiv antiretroviral therapy protease inhibitors versus non nucleoside reverse transcriptase inhibitors
2. HIV抗レトロウイルス療法に関する臨床試験：ブーストしたプロテアーゼ阻害剤の単剤療法試験 clinical trials of hiv antiretroviral therapy boosted protease inhibitor monotherapy studies
3. HIV抗レトロウイルス療法に関する臨床試験：プロテアーゼ阻害剤 clinical trials of hiv antiretroviral therapy protease inhibitors
4. 未治療HIV感染患者のための抗レトロウイルス療法の選択 selecting antiretroviral regimens for the treatment naive hiv infected patient
5. 結晶誘発性急性腎障害（急性腎不全） crystal induced acute kidney injury acute renal failure

English Journal

Severe atazanavir-associated hyperbilirubinemia revealing Canton G6PD deficiency in an Asian HIV-infected patient.

Javelle E, Oliver M, Savini H, Aubry C, Badens C, Simon F.SourceDepartment of Infectious Diseases and Tropical Medicine, Department of Biochemistry, Laveran Military Teaching Hospital, 4 Boulevard Laveran, Marseille Cedex, France.
AIDS (London, England).AIDS.2012 Jan 14;26(2):249-51.
PMID 22179231

Incidence of HIV-1 Drug Resistance Among Antiretroviral Treatment-Naive Individuals Starting Modern Therapy Combinations.

von Wyl V, Yerly S, Böni J, Shah C, Cellerai C, Klimkait T, Battegay M, Bernasconi E, Cavassini M, Furrer H, Hirschel B, Vernazza PL, Ledergerber B, Günthard HF; the Swiss HIV Cohort Study.SourceDivision of Infectious Diseases and Hospital Epidemiology, University Hospital Zurich, University of Zurich, Switzerland.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.Clin Infect Dis.2012 Jan;54(1):131-140. Epub 2011 Nov 4.
Background. Estimates of drug resistance incidence to modern first-line combination antiretroviral therapies against human immunodeficiency virus (HIV) type 1 are complicated by limited availability of genotypic drug resistance tests (GRTs) and uncertain timing of resistance emergence. Methods.
PMID 22057700

A Randomized, Pilot Trial to Evaluate Glomerular Filtration Rate by Creatinine or Cystatin C in Naive HIV-Infected Patients After Tenofovir/Emtricitabine in Combination With Atazanavir/Ritonavir or Efavirenz.

Albini L, Cesana BM, Motta D, Focà E, Gotti D, Calabresi A, Izzo I, Bellagamba R, Fezza R, Narciso P, Sighinolfi L, Maggi P, Quiros-Roldan E, Manili L, Guaraldi G, Lapadula G, Torti C.Source*Department of Materno Infantile e Tecnologie Biomediche, Institute of Infectious and Tropical Diseases, University of Brescia, Brescia, Italy †Department of Scienze Biomediche e Biotecnologie, Institute of Statistics in Medicine, University of Brescia, Brescia, Italy ‡National Institute of Infectious Diseases, I.N.M.I. Lazzaro Spallanzani, Rome, Italy §Azienda Ospedialiero-Universitaria of Ferrara, department of Infectious Diseases, Sant'Anna Hospital, Ferrara, Italy ||Operative Unit of Infectious Disease, Policlinico di Bari and Ospedale Gionvanni XXIII, Bari, Italy ¶Department of Nephrology, Spedali Civili di Brescia, Brescia, Italy #Department of Medicine e Specialitá Mediche, Institute of Infectious Diseases, University of Modena and Reggio Emilia, Modena, Italy **Institute of Infectious Diseases, San Gerardo Hospital, Monza, Italy.
Journal of acquired immune deficiency syndromes (1999).J Acquir Immune Defic Syndr.2012 Jan 1;59(1):18-30.
BACKGROUND: Glomerular filtration rate (GFR) estimated by Chronic Kidney Disease Epidemiology Collaboration (CKD-EPI) equation based on creatinine or cystatine C may be more accurate methods especially in patients without chronic kidney disease. There is lack of data on GFR estimated by these method
PMID 21992924

Japanese Journal

Pharmaceutical Approach to HIV Protease Inhibitor Atazanavir for Bioavailability Enhancement Based on Solid Dispersion System(Biopharmacy)

FUKUSHIMA Keizo,TERASAKA Shuichi,HARAYA Kenta,KODERA Satoshi,SEKI Yuichiro,WADA Ayako,ITO Yukako,SHIBATA Nobuhito,SUGIOKA Nobuyuki,TAKADA Kanji
Biological & pharmaceutical bulletin 30(4), 733-738, 2007-04-01
… Atazanavir (ATV) is a low oral bioavailability (BA) compound and, clinically, is generally coadministrated with ritonavir (RTV), which boosts the oral BA of ATV by inhibiting cytochrome P450 (CYP) 3A, and P-glyco-protein (Pgp) via the same metabolic pathway. … In this study we demonstrated the pharmaceutical approach to BA improvement of ATV without RTV in rats, based on the solid dispersion system using sodium lauryl sulfate (SLS) as a carrier and Gelucire^[○!R] 50/13 as an absorption enhancer. …
NAID 110006271215

Related Pictures

★リンクテーブル★

リンク元	「アタザナビル」
関連記事	「sulfate」「sulfated」「sulfa」

「アタザナビル」

Atazanavir
Systematic (IUPAC) name
	methyl N-[(1S)-1-{[(2S,3S)-3-hydroxy-4-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a603019
Pregnancy; category	AU: B2; US: B;
Legal status	UK: POM; US: ℞-only;
Routes	Oral
Pharmacokinetic data
Bioavailability	60-68%
Protein binding	86%
Metabolism	Hepatic (CYP3A4-mediated)
Half-life	6.5 hours
Excretion	Fecal and renal
Identifiers
CAS number	198904-31-3
ATC code	J05AE08
PubChem	CID 148192
DrugBank	DB01072
ChemSpider	130642
UNII	QZU4H47A3S
KEGG	D01276
ChEBI	CHEBI:37924
ChEMBL	CHEMBL1163
NIAID ChemDB	057755
Chemical data
Formula	C38H52N6O7
Molecular mass	704.856 g/mol
	SMILES O=C(OC)N[C@H](C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)Cc3ccc(c2ncccc2)cc3)C(C)(C)C;
	InChI InChI=1S/C38H52N6O7/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47)/t29-,30-,31+,32+/m0/s1 ; Key:AXRYRYVKAWYZBR-GASGPIRDSA-N ;
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