同: Reyataz, ATV

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/10 12:33:02」(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. 抗レトロウイルス療法の潜在的副作用に関するHIV感染患者を対象とした
カウンセリング counseling hiv infected patients regarding potential side effects of antiretroviral therapy
2. 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
3. ヌクレオシド系逆転写酵素阻害剤の薬理学 pharmacology of nucleoside reverse transcriptase inhibitors
4. 結晶誘発性急性腎障害（急性腎不全） crystal induced acute kidney injury acute renal failure
5. 未治療HIV感染患者のための選択的抗レトロウイルス療法 selecting antiretroviral regimens for the treatment naive hiv infected patient

English Journal

Pharmacodynamics of long-acting folic acid-receptor targeted ritonavir-boosted atazanavir nanoformulations.

Puligujja P1, Balkundi SS2, Kendrick LM1, Baldridge HM1, Hilaire JR1, Bade AN1, Dash PK1, Zhang G1, Poluektova LY1, Gorantla S1, Liu XM3, Ying T4, Feng Y5, Wang Y5, Dimitrov DS5, McMillan JM1, Gendelman HE6.
Biomaterials.Biomaterials.2015 Feb;41:141-50. doi: 10.1016/j.biomaterials.2014.11.012. Epub 2014 Dec 9.
Long-acting nanoformulated antiretroviral therapy (nanoART) that targets monocyte-macrophages could improve the drug's half-life and protein-binding capacities while facilitating cell and tissue depots. To this end, ART nanoparticles that target the folic acid (FA) receptor and permit cell-based dru
PMID 25522973

Pharmacokinetic and pharmacodynamic drug interactions between antiretrovirals and oral contraceptives.

Tittle V1, Bull L, Boffito M, Nwokolo N.
Clinical pharmacokinetics.Clin Pharmacokinet.2015 Jan;54(1):23-34. doi: 10.1007/s40262-014-0204-8.
More than 50 % of women living with HIV in low- and middle-income countries are of reproductive age, but there are limitations to the administration of oral contraception for HIV-infected women receiving antiretroviral therapy due to drug-drug interactions caused by metabolism via the cytochrome P4
PMID 25331712

Increased exposure of norethindrone in HIV+ women treated with ritonavir-boosted atazanavir therapy.

DuBois BN1, Atrio J2, Stanczyk FZ3, Cherala G4.
Contraception.Contraception.2015 Jan;91(1):71-5. doi: 10.1016/j.contraception.2014.08.009. Epub 2014 Aug 30.
OBJECTIVE: Pharmacokinetics of norethindrone in combination oral contraceptive regimen are well described among HIV+ women treated with ritonavir-boosted protease inhibitor therapies; however, such characterization is lacking in women using progestin-only contraception. Our objective is to character
PMID 25245190

Japanese Journal

Abacavir/Lamivudine versus Tenofovir/Emtricitabine with Atazanavir/Ritonavir for Treatment-naive Japanese Patients with HIV-1 Infection: A Randomized Multicenter Trial

Nishijima Takeshi,Takano Misao,Ishisaka Michiyo,Komatsu Hirokazu,Gatanaga Hiroyuki,Kikuchi Yoshimi,Endo Tomoyuki,Horiba Masahide,Kaneda Satoru,Uchiumi Hideki,Koibuchi Tomohiko,Naito Toshio,Yoshida Masaki,Tachikawa Natsuo,Ueda Mikio,Yokomaku Yoshiyuki,Fujii Teruhisa,Higasa Satoshi,Takada Kiyonori,Yamamoto Masahiro,Matsushita Shuzo,Tateyama Masao,Tanabe Yoshinari,Mitsuya Hiroaki,Oka Shinichi
Internal Medicine 52(7), 735-744, 2013
… Objective To compare the efficacy and safety of fixed-dose abacavir/lamivudine (ABC/3TC) and tenofovir/emtricitabine (TDF/FTC) with ritonavir-boosted atazanavir (ATV/r) in treatment-naïve Japanese patients with HIV-1 infection. …
NAID 130003365967

Effects of hepatitis C virus infection on the pharmacokinetics of ritonavir-boosted atazanavir in HIV-1-infected patients

DI BIAGIO Antonio,ROSSO Raffaella,LOREGIAN Arianna,PAGNI Silvana,SORMANI Maria Pia,CENDERELLO Giovanni,PALU Giorgio,VISCOLI Claudio
Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 18(4), 587-590, 2012-08-01
NAID 10030948347

Diffuse Tubulointerstitial Nephritis Accompanied by Renal Crystal Formation in an HIV-infected Patient Undergoing Highly Active Antiretroviral Therapy

Kanzaki Go,Tsuboi Nobuo,Miyazaki Yoichi,Yokoo Takashi,Utsunomiya Yasunori,Hosoya Tatsuo
Internal Medicine 51(12), 1543-1548, 2012
… Tenofovir and Atazanavir were thought to be the causative drugs for the renal injury. …
NAID 130002062163

Related Pictures

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★リンクテーブル★

リンク元	「アタザナビル」「ATV」
拡張検索	「atazanavir sulfate」

「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 cat.	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
Mol. 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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