Tìm theo
Atazanavir
Các tên gọi khác (5 ) :
  • Atazanavirum
  • ATV
  • ATZ
  • Latazanavir
  • Zrivada
anti hiv agents, hiv protease inhibitors
Thuốc Gốc
Small Molecule
CAS: 198904-31-3
ATC: J05AE08
ĐG : A-S Medication Solutions LLC , http://orders.a-smeds.com
CTHH: C38H52N6O7
PTK: 704.8555
Atazanavir (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. [Wikipedia]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C38H52N6O7
Phân tử khối
704.8555
Monoisotopic mass
704.389748048
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
InChI Key
InChIKey=AXRYRYVKAWYZBR-GASGPIRDSA-N
IUPAC Name
methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanamido]-4-phenylbutyl]-N'-{[4-(pyridin-2-yl)phenyl]methyl}hydrazinecarbonyl}-2,2-dimethylpropyl]carbamate
Traditional IUPAC Name
methyl N-[(1S)-1-{N'-[(2S,3S)-2-hydroxy-3-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanamido]-4-phenylbutyl]-N'-{[4-(pyridin-2-yl)phenyl]methyl}hydrazinecarbonyl}-2,2-dimethylpropyl]carbamate
SMILES
COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C=C1)C1=CC=CC=N1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C(C)(C)C
Độ hòa tan
Free base slightly soluble (4-5 mg/mL)
logP
4.5
logS
-5.3
pKa (strongest acidic)
11.92
pKa (Strongest Basic)
4.42
PSA
171.22 Å2
Refractivity
191.8 m3·mol-1
Polarizability
76.83 Å3
Rotatable Bond Count
18
H Bond Acceptor Count
7
H Bond Donor Count
5
Physiological Charge
0
Number of Rings
3
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : Atazanavir (ATV) is an azapeptide HIV-1 protease inhibitor (PI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Atazanavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs. Atazanivir is pharmacologically related but structurally different from other protease inhibitors and other currently available antiretrovirals.
Cơ Chế Tác Dụng : Atazanavir (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. [Wikipedia] Atazanavir selectively inhibits the virus-specific processing of viral Gag and Gag-Pol polyproteins in HIV-1 infected cells by binding to the active site of HIV-1 protease, thus preventing the formation of mature virions. Atazanavir is not active against HIV-2.
Dược Động Học :
▧ Absorption :
Atazanavir is rapidly absorbed with a Tmax of approximately 2.5 hours. Administration of atazanavir with food enhances bioavailability and reduces pharmacokinetic variability. Oral bioavailability is 60-68%.
▧ Protein binding :
86% bound to human serum proteins (alpha-1-acid glycoprotein and albumin). Protein binding is independent of concentration.
▧ Metabolism :
Atazanavir is extensively metabolized in humans, primarily by the liver. The major biotransformation pathways of atazanavir in humans consisted of monooxygenation and dioxygenation. Other minor biotransformation pathways for atazanavir or its metabolites consisted of glucuronidation, N-dealkylation, hydrolysis, and oxygenation with dehydrogenation. In vitro studies using human liver microsomes suggested that atazanavir is metabolized by CYP3A.
▧ Half Life :
Elimination half-life in adults (healthy and HIV infected) is approximately 7 hours (following a 400 mg daily dose with a light meal). Elimination half-life in hepatically impaired is 12.1 hours (following a single 400 mg dose).
Chỉ Định : Used in combination with other antiretroviral agents for the treatment of HIV-1 infection, as well as postexposure prophylaxis of HIV infection in individuals who have had occupational or nonoccupational exposure to potentially infectious body fluids of a person known to be infected with HIV when that exposure represents a substantial risk for HIV transmission.
Tương Tác Thuốc :
  • Abacavir The serum concentration of Abacavir may be decreased by protease inhibitors such as Atazanavir. The antiviral response should be closely monitored.
  • Abiraterone Strong CYP3A4 inhibitors may increase levels of abiraterone. Monitor concomitant therapy closely.
  • Acenocoumarol The protease inhibitor, atazanavir, may increase the anticoagulant effect of acenocoumarol.
  • Aluminium This gastric pH modifier decreases the levels/effects of atazanavir
  • Amiodarone Increased risk of cardiotoxicity and arrhythmias.
  • Amitriptyline Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, amitriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amitriptyline if atazanavir if initiated, discontinued or dose changed.
  • Amoxapine Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, amoxapine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amoxapine if atazanavir if initiated, discontinued or dose changed.
  • Anisindione The protease inhibitor, atazanavir, may increase the anticoagulant effect of anisindione.
  • Atorvastatin Atazanavir may increase the serum concentration of atorvastatin by decreasing its metabolism. Concomitant therapy is contraindicated.
  • Bepridil Atazanavir may increase the effect and toxicity of bepridil.
  • Bismuth Subsalicylate This gastric pH modifier decreases the levels/effects of atazanavir
  • Bromazepam Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if atazanavir is initiated, discontinued or dose changed. Dosage adjustments may be required.
  • Buprenorphine Atazanavir may increase the serum concentration of Buprenorphine. Buprenorphine may decrease the serum concentration of Atazanavir. Avoid use of buprenorphine in patients receiving atazanavir without ritonavir boosting due to possible decreases in atazanavir exposure. In patients receiving buprenorphine with atazanavir/ritonavir, monitor for increased buprenorphine effects and consider dose reductions if patients experience adverse effects.
  • Cabazitaxel Concomitant therapy with a strong CYP3A4 inhibitor may increase concentrations of cabazitaxel. Avoid concomitant therapy.
  • Calcium This gastric pH modifier decreases the levels/effects of atazanavir
  • Cimetidine This gastric pH modifier decreases the levels/effects of atazanavir
  • Cisapride Increased risk of cardiotoxicity and arrhythmias
  • Clarithromycin Atazanavir may increase serum level of clarithromycin.
  • Clomipramine Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, clomipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of clomipramine if atazanavir is initiated, discontinued or dose changed.
  • Cyclosporine Atazanavir may increase the therapeutic and adverse effects of cyclosporine.
  • Dantrolene Atazanavir may increase the serum concentration of dantrolene by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of dantrolene if atazanavir is initiated, discontinued or dose changed.
  • Desipramine Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, desipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of desipramine if atazanavir is initiated, discontinued or dose changed.
  • Dicoumarol The protease inhibitor, atazanavir, may increase the anticoagulant effect of dicumarol.
  • Dihydroergotamine Atazanavir may increase the therapeutic and adverse effects of dihydroergotamine.
  • Dihydroquinidine barbiturate Increased risk of cardiotoxicity and arrhythmias
  • Dihydroxyaluminium This gastric pH modifier decreases the levels/effects of atazanavir
  • Diltiazem Atazanavir may increase the therapeutic and adverse effects of diltiazem resulting in increased risk of AV block. Consider alternate therapy, a 50% dose reduction of diltiazem and monitor for changes in the therapeutic and adverse effects of diltiazem if atazanavir is initiated, discontinued or dose changed.
  • Doxepin Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if atazanavir if initiated, discontinued or dose changed.
  • Efavirenz Efavirenz decreases the levels/effects of atazanavir
  • Eltrombopag Decreases metabolism, will increase effect/level of eltrombopag. UDP-glucuronosyltransferase inhibition.
  • Ergotamine Atazanavir may increase the effect and toxicity of ergotamine.
  • Erlotinib This CYP3A4 inhibitor increases levels/toxicity of erlotinib
  • Esomeprazole This gastric pH modifier decreases the levels/effects of atazanavir
  • Etravirine Atazanavir, when administered concomitantly with etravirine, may experience a decrease in serum concentrations. Etravirine, when administered concomitantly with Atazanavir, may expereince an increase in serum concentrations. Recommended to avoid use of this combination.
  • Famotidine This gastric pH modifier decreases the levels/effects of atazanavir
  • Imipramine Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if atazanavir if initiated, discontinued or dose changed.
  • Indinavir Increased risk of hyperbilirubinemia with this association
  • Irinotecan Increases levels/effect of irinotecan
  • Lansoprazole This gastric pH modifier decreases the levels/effects of atazanavir
  • Lidocaine Increased risk of cardiotoxicity and arrhythmias
  • Lovastatin Atazanavir may increase the effect and toxicity of lovastatin. Concomitant therapy is contraindicated.
  • Lurasidone Concomitant therapy with a strong CYP3A4 inhibitor will increase level or effect of lurasidone. Coadministration with lurasidone is contraindicated.
  • Magnesium This gastric pH modifier decreases the levels/effects of atazanavir
  • Magnesium oxide This gastric pH modifier decreases the levels/effects of atazanavir
  • Magnesium Sulfate This gastric pH modifier decreases the levels/effects of atazanavir
  • Methylergometrine Increases the effect and toxicity of ergot derivative
  • Midazolam Atazanavir may increase the effect and toxicity of the benzodiazepine, midazolam.
  • Nevirapine Nevirapine, a strong CYP3A4 inducer, may decrease the serum concentration of atazanavir by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of atazanavir if nevirapine is initiated, discontinued or dose changed.
  • Nizatidine This gastric pH modifier decreases the levels/effects of atazanavir
  • Nortriptyline Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if atazanavir if initiated, discontinued or dose changed.
  • Omeprazole This gastric pH modifier decreases the levels/effects of atazanavir
  • Pantoprazole This gastric pH modifier decreases the levels/effects of atazanavir
  • Pimozide The protease inhibitor, atazanavir, may increase the effect and toxicity of pimozide.
  • Pitavastatin Increases serum concentration of pitavastatin and the potential for adverse drug reactions. Avoid concomitant drug therapy.
  • Protriptyline Atazanavir may increase the effect and toxicity of the tricyclic antidepressant, protriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of protriptyline if atazanavir if initiated, discontinued or dose changed.
  • Quinidine Increased risk of cardiotoxicity and arrhythmias.
  • Quinidine barbiturate Increased risk of cardiotoxicity and arrhythmias
  • Rabeprazole Rabeprazole may decrease the serum levels and therapeutic effects of atazanavir.
  • Ramelteon Atazanavir increases levels/toxicity of ramelteon
  • Ranitidine Ranitidine may decrease the levels/effects of atazanavir.
  • Ranolazine Atazanavir, a strong CYP3A4 inhibitor, may increase the serum level of ranolazine. Concomitant therapy is contraindicated.
  • Rifabutin Atazanavir may increase levels/toxicity of rifabutin.
  • Rifampicin Rifampin reduces levels and efficacy of atazanavir
  • Ritonavir Association with dose adjustment
  • Sildenafil Increases the effect and toxicity of sildenafil
  • Simvastatin Increased risk of myopathy/rhabdomyolysis
  • Sirolimus Increases the effect and toxicity of immunosuppressant
  • Sodium bicarbonate This gastric pH modifier decreases the levels/effect of atazanavir
  • St. John's Wort St. John's Wort decreases the levels/effects of atazanavir
  • Sunitinib Possible increase in sunitinib levels
  • Tacrolimus The protease inhibitor, Atazanavir, may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Atazanavir therapy is initiated, discontinued or altered.
  • Tadalafil Atazanavir may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Tamoxifen Atazanavir may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
  • Tamsulosin Atazanvir, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Atazanavir is initiated, discontinued, or dose changed.
  • Telithromycin Co-administration may result in altered plasma concentrations of Atazanavir and/or Telithromycin. Consider alternate therapy or monitor the therapeutic/adverse effects of both agents.
  • Temsirolimus Atazanavir may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
  • Teniposide The strong CYP3A4 inhibitor, Atazanavir, may decrease the metabolism and clearance of Teniposide, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Teniposide if Atazanavir is initiated, discontinued or dose changed.
  • Tenofovir Concomitant therapy may result in decreased serum levels of Atazanavir and increased levels of Tenofovir. Concomitant therapy should only be used with the inclusion of Ritonavir.
  • Tiagabine The strong CYP3A4 inhibitor, Atazanavir, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Atazanavir is initiated, discontinued or dose changed.
  • Tipranavir Tipranavir, co-administered with Ritonavir, may decrease the plasma concentration of Atazanavir. Consider alternate therapy.
  • Tolterodine Atazanavir may decrease the metabolism and clearance of Tolterodine. Adjust the Tolterodine dose and monitor for efficacy and toxicity.
  • Tramadol Atazanavir may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
  • Trazodone The protease inhibitor, Atazanavir, may increase the efficacy/toxicity of Trazodone by inhibiting Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Atazanavir is initiated, discontinued or dose changed.
  • Tretinoin The strong CYP2C8 inhibitor, Atazanavir, may decrease the metabolism and clearance of oral Tretinoin. Consider alternate therapy or monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Atazanavir is initiated, discontinued to dose changed.
  • Triazolam Atazanavir may increase the effect and toxicity of the benzodiazepine, triazolam.
  • Trimipramine The strong CYP3A4 inhibitor, Atazanavir, may decrease the metabolism and clearance of Trimipramine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Atazanavir is initiated, discontinued or dose changed.
  • Vardenafil Atazanavir, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Vemurafenib Strong CYP3A4 inhibitors may increase levels of vemurafenib. Monitor concomitant therapy closely.
  • Venlafaxine Atazanavir, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Atazanavir is initiated, discontinued, or dose changed.
  • Verapamil Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Atazanavir is initiated, discontinued or dose changed.
  • Vilazodone CYP3A4 Inhibitors (Strong) may increase the serum concentration of Vilazodone. imit maximum adult vilazodone dose to 20 mg/day in patients receiving strong CYP3A4 inhibitors.
  • Vinblastine Atazanavir, a strong CYP3A4 inhibitor, may decrease the metabolism of Vinblastine. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Atazanavir is initiated, discontinued or dose changed.
  • Vincristine Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Vincristine by decreasing its metabolism. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Atazanavir is initiated, discontinued or dose changed.
  • Vinorelbine Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Vinorelbine by decreasing its metabolism. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Atazanavir is initiated, discontinued or dose changed.
  • Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of atazanavir by decreasing its metabolism. The serum concentration of voriconazole may be increased by atazanavir. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
  • Warfarin The protease inhibitor, atazanavir, may increase the anticoagulant effect of warfarin.
  • Zolpidem Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if atazanavir is initiated, discontinued or dose changed.
  • Zonisamide Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zonisamide by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zonisamide if atazanavir is initiated, discontinued or dose changed.
  • Zopiclone Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of zopiclone by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if atazanavir is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Capsule - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Reyataz 100 mg capsule
    Giá bán buôn : USD >18.12
    Đơn vị tính : capsule
  • Biệt dược thương mại : Reyataz 150 mg capsule
    Giá bán buôn : USD >18.49
    Đơn vị tính : capsule
  • Biệt dược thương mại : Reyataz 200 mg capsule
    Giá bán buôn : USD >18.49
    Đơn vị tính : capsule
  • Biệt dược thương mại : Reyataz 300 mg capsule
    Giá bán buôn : USD >36.63
    Đơn vị tính : capsule
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Latazanavir
  • Công ty :
    Sản phẩm biệt dược : Reyataz
  • Công ty :
    Sản phẩm biệt dược : Zrivada
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01072
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=148192
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508504
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D01276
ChemSpider
http://www.chemspider.com/Chemical-Structure.130642.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=13934
PharmGKB
http://www.pharmgkb.org/drug/PA10251
Wikipedia
http://en.wikipedia.org/wiki/Atazanavir
RxList
http://www.rxlist.com/cgi/generic/reyataz.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/rey1671.shtml
Drugs.com
http://www.drugs.com/cdi/atazanavir.html
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