Delavirdine

Các tên gọi khác (9 ) :

(N-[2-[4-[3-(1-Methylethylamino)pyridin-2-yl]piperazin-1-yl]carbonyl-1H-indol-5-yl] methanesulfonamide)
1-(3-((1-Methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulfonyl)amino)-1H-indol-2-yl)carbonyl)piperazine
2-(4-(5-Methanesulfonamido-1H-indol-2-ylcarbonyl)-1-piperazinyl)-N-(1-methylethyl)-3-pyridinamine
Delavirdin
Delavirdina
Delavirdine
Delavirdinum
N-(2-(1-(3-(Isopropylamino)pyridin-2-yl)piperazine-4-carbonyl)-1H-indol-5-yl)methanesulfonamide
N-{2-[4-(3-isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1H-indol-5-yl}-methanesulfonamide

reverse transcriptase inhibitors

Thuốc Gốc

Small Molecule

CAS: 136817-59-9

ATC: J05AG02

ĐG : Agouron Pharmaceuticals Inc.

CTHH: C₂₂H₂₈N₆O₃S

PTK: 456.561

A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. [PubChem]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₂₂H₂₈N₆O₃S

Phân tử khối

456.561

Monoisotopic mass

456.194359482

InChI

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

InChI Key

InChIKey=WHBIGIKBNXZKFE-UHFFFAOYSA-N

IUPAC Name

N-{2-[(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazin-1-yl)carbonyl]-1H-indol-5-yl}methanesulfonamide

Traditional IUPAC Name

delavirdine

SMILES

CC(C)NC1=C(N=CC=C1)N1CCN(CC1)C(=O)C1=CC2=C(N1)C=CC(NS(C)(=O)=O)=C2

Độ tan chảy

226-228 °C

Độ hòa tan

8.60e-02 g/l

logP

2.8

logS

-3.7

pKa (strongest acidic)

9.39

pKa (Strongest Basic)

6.82

PSA

110.43 Å²

Refractivity

126.64 m³·mol^-1

Polarizability

50.01 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : Delavirdine is a non-nucleoside reverse transcriptase inhibitor (nNRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Delavirdine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzyme's catalytic site. The activity of Delavirdine does not compete with template or nucleoside triphosphates. HIV-2 RT and eukaryotic DNA polymerases (such as human DNA polymerases alpha, beta, or sigma) are not inhibited by Delavirdine.

Cơ Chế Tác Dụng : A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. [PubChem] Delavirdine binds directly to viral reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by disrupting the enzyme's catalytic site.

Dược Động Học :

▧ Absorption :
Rapidly absorbed
▧ Protein binding :
98%
▧ Metabolism :
Hepatic
▧ Route of Elimination :
Delavirdine is extensively converted to several inactive metabolites by cytochrome P450 3A (CYP3A). Delavirdine was excreted in the milk of lactating rats at a concentration three to five times that of rat plasma.
▧ Half Life :
5.8 hours

Độc Tính : Major toxicity of delavirdine is rash and should be advised to promptly notify their physician should rash occur. The majority of rashes associated with delavirdine occur within 1 to 3 weeks after initiating treatment with delavirdine. The rash normally resolves in 3 to 14 days and may be treated symptomatically while therapy with delavirdine is continued. Any patient experiencing severe rash or rash accompanied by symptoms such as fever, blistering, oral lesions, conjunctivitis, swelling, muscle or joint aches should discontinue medication and consult a physician.

Chỉ Định : For the treatment of HIV-1 infection in combination with appropriate antiretroviral agents when therapy is warranted

Tương Tác Thuốc :

Alprazolam The antiviral agent, delavirdine, may increase the effect and toxicity of the benzodiazepine, alprazolam.
Aluminium The antiacid decreases the effect of delavirdine
Amprenavir Decreased levels of delavirdine with increased levels of amprenavir
Astemizole Increased risk of cardiotoxicity and arrhythmias
Atorvastatin Delavirdine, a strong CYP3A4 inhibitor, may increase the serum concentration of atorvastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of atorvastatin if delavirdine is initiated, discontinued or dose changed.
Bromazepam Delavirdine, 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 delavirdine is initiated, discontinued or dose changed. Dosage adjustments may be required.
Calcium The antiacid decreases the effect of delavirdine
Carbamazepine The anticonvulsant, carbamazepine, decreases the effect of delavirdine.
Carisoprodol Strong CYP2C19 inhibitors such as delavirdine may decrease the metabolism of CYP2C19 substrates such as carisoprodol. Consider an alternative for one of the interacting drugs in order to avoid toxicity of the substrate. Some combinations are specifically contraindicated by manufacturers. Suggested dosage adjustments are also offered by some manufacturers. Please review applicable package inserts. Monitor for increased effects of the CYP substrate if a CYP inhibitor is initiated/dose increased, and decreased effects if a CYP inhibitor is discontinued/dose decreased.
Cisapride Delavirdine, a strong CYP3A4 inhibitor, may increase the metabolism of cisapride. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of cisapride if delavirdine is initiated, discontinued or dose changed.
Dantrolene Delavirdine 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 delavirdine is initiated, discontinued or dose changed.
Dihydroergotamine Delavirdine, a strong CYP3A4 inhibitor, may increase the serum concentration of dihydroergotamine by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of dihydroergotamine if delavirdine is initiated, discontinued or dose changed.
Ergonovine The antiretroviral agent may increase the ergot derivative toxicity
Ergotamine The antiretroviral agent may increase the ergot derivative toxicity
Etravirine Etravirine, when used concomitantly with Delaviridine, may experience an increase in serum concentration. Combination of two NNRTIs has not been demonstrated to be of benefit to HIV therapy. It is recommended to avoid this combination.
Fosamprenavir Decreased levels of delavirdine with increased levels of amprenavir
Fosphenytoin The anticonvulsant, fosphenytoin, decreases the effect of delavirdine.
Indinavir Delavirdine may increase the effect of indinavir.
Lovastatin Delavirdine, a strong CYP3A4 inhibitor, may increase the serum concentration of lovastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of lovastatin if delavirdine is initiated, discontinued or dose changed.
Lurasidone Concomitant therapy with a strong CYP3A4 inhibitor will increase level or effect of lurasidone. Coadministration with lurasidone is contraindicated.
Magnesium Magnesium antacids may decrease the absorption of delavirdine.
Magnesium oxide The antiacid decreases the effect of delavirdine
Methylergometrine The antiretroviral agent may increase the ergot derivative toxicity
Methylphenobarbital The anticonvulsant, methylphenobarbital, decreases the effect of delavirdine.
Methysergide The antiretroviral agent may increase the ergot derivative toxicity
Midazolam The antiviral agent, delavirdine, may increase the effect and toxicity of the benzodiazepine, midazolam.
Phenobarbital The anticonvulsant, phenobarbital, decreases the effect of delavirdine.
Phenytoin The anticonvulsant, phenytoin, decreases the effect of delavirdine.
Quinupristin This combination presents an increased risk of toxicity
Rifabutin Rifabutin decreases the effect of delavirdine
Rifampicin Rifampin decreases the effect of delavirdine
Rilpivirine Concentration of rilpivirine increases by affecting CYP3A4 metabolism. Concomitant use is contraindicated. Rilpivirine should not be used with other NNRTI's.
Ritonavir Increases the effect of ritonavir
Saquinavir Increases the effect of saquinavir and hepatic toxicity
Simvastatin Delavirdine, a strong CYP3A4 inhibitor, may increase the serum concentration of simvastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of simvastatin if delavirdine is initiated, discontinued or dose changed.
St. John's Wort St. John's Wort decreases the antiretroviral effect
Tacrolimus The strong CYP3A4 inhibitor, Delavirdine, may decrease the metabolism and clearance of Tacrolimus, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Tacrolimus if Delavirdine is initiated, discontinued or dose changed.
Tadalafil Delavirdine may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
Tamoxifen Delavirdine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
Tamsulosin Delavirdine, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Delavirdine is initiated, discontinued, or dose changed.
Telithromycin Delavirdine may increase the plasma concentration of Telithromycin. Consider alternate therapy or monitor therapeutic/adverse effects.
Temsirolimus Delavirdine may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
Teniposide The strong CYP3A4 inhibitor, Delavirdine, 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 Delavirdine is initiated, discontinued or dose changed.
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Tiagabine The strong CYP3A4 inhibitor, Delavirdine, 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 Delavirdine is initiated, discontinued or dose changed.
Tipranavir Concomitant use may result in increased Tipranavir and decreased Delavirdine concentrations. Monitor for altered therapeutic and adverse effects of both agents if either agent is initiated, discontinued or dose changed.
Tolbutamide Delavirdine, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Delavirdine is initiated, discontinued or dose changed.
Tolterodine Delavirdine may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Torasemide Delavirdine, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Delavirdine is initiated, discontinued or dose changed.
Tramadol Delavirdine may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Delavirdine may decrease the effect of Tramadol by decreasing active metabolite production.
Trazodone The CYP3A4 inhibitor, Delavirdine, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Consider alternate therapy or monitor for changes in Trazodone efficacy/toxicity if Delavirdine is initiated, discontinued or dose changed.
Triazolam The antiviral agent, delavirdine, may increase the effect and toxicity of the benzodiazepine, triazolam.
Trimethoprim The strong CYP2C9 inhibitor, Delavirdine, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Delavirdine is initiated, discontinued or dose changed.
Trimipramine The strong CYP3A4/CYP2D6 inhibitor, Delavirdine, may decrease the metabolism and clearance of Trimipramine, a CYP3A4/CYP2D6 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Delavirdine is initiated, discontinued or dose changed.
Vardenafil Delavirdine, 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.
Venlafaxine Delaviridine, a CYP2D6 and CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 and CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Delavirdine is initiated, discontinued, or dose changed.
Verapamil Delavirdine, 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 Delavirdine is initiated, discontinued or dose changed.
Vinblastine Delavirdine, 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 Delavirdine is initiated, discontinued or dose changed.
Vincristine Delavirdine, 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 Delavirdine is initiated, discontinued or dose changed.
Vinorelbine Delavirdine, 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 Delavirdine is initiated, discontinued or dose changed.
Voriconazole Delavirdine, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if delavirdine is initiated, discontinued or dose changed.
Warfarin Delavirdine, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if delavirdine is initiated, discontinued or dose changed.
Zafirlukast Delavirdine, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if delavirdine is initiated, discontinued or dose changed.
Zolpidem Delavirdine, 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 delavirdine is initiated, discontinued or dose changed.
Zonisamide Delavirdine, 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 delavirdine is initiated, discontinued or dose changed.
Zopiclone Delavirdine, 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 delavirdine is initiated, discontinued or dose changed.
Zuclopenthixol Delavirdine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if delavirdine is initiated, discontinued or dose changed.

Liều Lượng & Cách Dùng : Tablet - Oral

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Rescriptor 200 mg tablet

Giá bán buôn : USD >1.92

Đơn vị tính : tablet

Nhà Sản Xuất

Công ty : ViiV Healthcare

Sản phẩm biệt dược : Rescriptor

Đóng gói

Công ty : Agouron Pharmaceuticals Inc.
Công ty : A-S Medication Solutions LLC

Website : http://orders.a-smeds.com
Công ty : Kaiser Foundation Hospital
Công ty : Pfizer Inc.

Website : http://www.pfizer.com
Công ty : Pharmacia Inc.

Website : http://www.pharmaciaupjohn.com
Công ty : Physicians Total Care Inc.

Website : http://www.physicianstotalcare.com
Công ty : ViiV Healthcare ULC

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00705

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5625

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508878

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C06941

ChemSpider

http://www.chemspider.com/Chemical-Structure.5423.html

BindingDB

http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=1944

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/63010-020-36

PharmGKB

http://www.pharmgkb.org/drug/PA449223

Wikipedia

http://en.wikipedia.org/wiki/Delavirdine

Drugs.com

http://www.drugs.com/cdi/delavirdine.html

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