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Tenofovir Disoproxil

HCID 5481350
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
201341-05-1
Standard-SMILES
CC(C)OC(=O)OCOP(=O)(CO[C@H](C)Cn1cnc2c(N)ncnc21)OCOC(=O)OC(C)C
InChIKey
JFVZFKDSXNQEJW-CQSZACIVSA-N
Summenformel
C19H30N5O10P
Durchschnittliche Molmasse
519,4 g/mol
Monoisotopische Masse
519,17302879

Überblick

Tenofovir disoproxil is an organic phosphonate that is the disoproxil ester of tenofovir. A prodrug for tenofovir, an HIV-1 reverse transcriptase inhibitor, tenofovir disoproxil is used as the fumaric acid salt in combination therapy for the treatment of HIV infection. It has a role as an antiviral drug, a prodrug and a HIV-1 reverse transcriptase inhibitor. It is functionally related to a tenofovir (anhydrous).

Namen und Bezeichner

Bevorzugter Name
Tenofovir Disoproxil
IUPAC
[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate
Englischer Name
Tenofovir disoproxil
Summenformel
C19H30N5O10P
Molmasse
519.44

Namen und Synonyme

Tenofovir disoproxil201341-05-1Bis(POC)PMPA(r)-bis(poc)pmpabis-POC-PMPAtenofovir bis(isopropyloxycarbonyloxymethyl) esterF4YU4LON7I9-((R)-2-((Bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine2,4,6,8-Tetraoxa-5-phosphanonanedioic acid, 5-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]-, 1,9-bis(1-methylethyl) ester, 5-oxideGS-4331DTXSID5052757CHEBI:63717
Weitere Namen anzeigen
Tenofovir disoproxil aspartateTenofovir AxetilenofovirdisoproxilTenofov ir Disoprox5-[[(1r)-2-(6-Amino-9h-Purin-9-Yl)-1-Methylethoxy]Methyl]-2,4,6,8-Tetraoxa-5-Phosphanononanedioic Acid Bis(1-Methylethyl) Ester 5-Oxide2,4,6,8-Tetraoxa-5-phosphanonanedioicacid, 5-[[(1R)-2-(6-aMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-,1,9-bis(1-Methylethyl) ester, 5-oxideSRYCS-589GS 4331Aids080741
STRIBILD COMPONENT TENOFOVIR DISOPROXIL2,4,6,8-TETRAOXA-5-PHOSPHANONANEDIOIC ACID, 5-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, 1,9-BIS(1-METHYLETHYL) ESTER, 5-OXIDEbis({[(propan-2-yloxy)carbonyl]oxy}methyl) ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonate9-[(r)-2-[[bis[[(isopropoxycarbonyl)oxy]methoxy]phosphinyl]methoxy]propyl]adeninebis((((propan-2-yloxy)carbonyl)oxy)methyl) ((((2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonateRefChem:187852DTXCID2031249606-442-6

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,6
Polarare Oberfläche (TPSA)
185 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
14
Frei drehbare Bindungen
17
Schwere Atome
35
Formalladung
0
Komplexität
698

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Human Drugs · 3 Einträge

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Melting Point113-115
Dissociation Constants3.75

Physikochemische Eigenschaften

Siedepunkt
642.7 · 642.7±65.0 °C(Predicted)
Dichte
1.45 · 1.45±0.1 g/cm3(Predicted)
storage temp.
2 · Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit
38 mg/mL · DMSO: ≥ 38 mg/mL (73.16 mM)
Aggregatzustand
Solid
pka
4.2 · 4.20±0.10(Predicted)
Farbe
White to off-white

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H319

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

J05AF13

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding_In vitro_ binding of tenofovir to human plasma or serum proteins is <0.7 and <7.2%, respectively, over the tenofovir concentration range 0.01 to 25 μg/mL.
Pharmacodynamics · 1 Eintrag

This drug prevents viral DNA chain elongation through inhibition of enzymes necessary for host cell infection viral replication in HIV-1 and Hepatitis B infections,. **In vitro effects** The antiviral activity of tenofovir against in laboratory and clinical isolates of HIV-1 was studied in lymphoblastoid cell lines, primary monocyte/macrophage cells, in addition to peripheral blood lymphocytes. The EC50 (50% effective concentration) values of tenofovir against HIV-1 virus ranged between 0.04 μM to 8.5 μM. **Combination of tenofovir disoproxil with other drugs** In drug combination studies of tenofovir with nucleoside reverse transcriptase inhibitors (abacavir, didanosine, lamivudine, stavudine, zalcitabine, zidovudine), non-nucleoside reverse transcriptase inhibitors (delavirdine, efavirenz, nevirapine), and protease inhibitors (amprenavir, indinavir, nelfinavir, ritonavir, saquinavir), additive and synergistic effects were seen. Tenofovir demonstrated antiviral activities in cell cultures against HIV-1.

Mechanism of Action · 1 Eintrag

Tenofovir belongs to a class of antiretroviral drugs known as nucleotide analog reverse transcriptase inhibitors (NtRTIs), which block reverse transcriptase, an enzyme necessary for viral production in HIV-infected individuals. This enables the management of HIV viral load through decreased viral replication. Tenofovir disoproxil fumarate is the fumarate salt of the prodrug _tenofovir disoproxil_. Tenofovir disoproxil is absorbed and converted to its active form, _tenofovir_, a nucleoside monophosphate (nucleotide) analog. Tenofovir is then converted to the active metabolite, _tenofovir diphosphate_, a chain terminator, by constitutively expressed enzymes in the cell. Tenofovir diphosphate inhibits HIV-1 reverse transcriptase and the Hepatitis B polymerase by direct binding competition with the natural deoxyribonucleotide substrate (deoxyadenosine 5’-triphosphate) and, after integration into DNA, causes viral DNA chain termination,. **A note on resistance** HIV-1 isolates with decreased susceptibility to tenofovir have been identified in cell culture studies. These viruses expressed a _K65R_ substitution in reverse transcriptase and showed a 2– 4 fold decrease in susceptibility to treatment with tenofovir.

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Datenbank-Bezeichner

CAS
201341-05-1
PubChem CID
5481350
DTXSID
DTXSID5052757
ChEMBL
CHEMBL1538
ChEBI
CHEBI:63717
UNII
F4YU4LON7I
EC Number
606-442-6
Nikkaji
J898.676B
InChIKey
JFVZFKDSXNQEJW-CQSZACIVSA-N
SMILES
C(OC(C)C)(=O)OCOP(=O)(CO[C@H](C)CN1C2C(N=C1)=C(N)N=CN=2)OCOC(OC(C)C)=O
CAS Datenbank
201341 · 201341-05-1
Biological Half-LifeWhen a single oral dose is given, the terminal elimination half-life is approximately 17 hours.
Metabolism/Metabolites · 1 Eintrag

Tenofovir disoproxil fumarate is the fumarate salt of the prodrug _tenofovir disoproxil_. Tenofovir disoproxil is absorbed and converted to its active form, _tenofovir_, a nucleoside monophosphate (nucleotide) analog. Tenofovir is then converted to the active metabolite, _tenofovir diphosphate_, a chain terminator, by constitutively expressed enzymes in the cell. Two phosphorylation steps are required to convert tenofovir disoproxil to the active drug form. The cytochrome P450 enzyme system is not involved with the metabolism of tenofovir disoproxil or tenofovir.

MeSH Pharmacological Classification · 3 Einträge

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template.

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS.

Absorption, Distribution and Excretion · 4 Einträge

After oral administration of tenofovir disoproxil to patients with HIV infection, tenofovir disoproxil is quickly absorbed and metabolized to tenofovir. Administration of tenofovir disoproxil 300 mg tablets after a high-fat meal increases the oral bioavailability of this drug, as demonstrated by an increase in tenofovir AUC0-∞ of about 40% as well as an increase in Cmax of about 14%. On the contrary, the administration of tenofovir disoproxil with a light meal did not exert a relevant effect on the pharmacokinetics of tenofovir when compared to administration under fasting conditions. The presence of ingested food slows the time to tenofovir Cmax by approximately 1 hour. Cmax and AUC of tenofovir are 0.33 ± 0.12 μg/mL and 3.32 ± 1.37 μg•hr/mL after several doses of tenofovir disoproxil 300 mg once daily in the fed state when meal content is not controlled.

Following IV administration of tenofovir, approximately 70–80% of the dose is recovered in the urine as unchanged tenofovir within 72 hours of dosing. Tenofovir is eliminated by a combination of glomerular filtration and active tubular secretion. There may be competition for elimination with other compounds that are also eliminated by the kidneys.

The volume of distribution at steady-state is 1.3 ± 0.6 L/kg and 1.2 ± 0.4 L/kg, following intravenous administration of tenofovir 1.0 mg/kg and 3.0 mg/kg. After oral administration of tenofovir disoproxil, tenofovir is distributed to the majority tissues with the highest concentrations measured in the kidney, liver and the intestinal contents (based on data from preclinical studies).

The clearance of tenofovir is highly dependent on renal function and may vary greatly. Total clearance has been estimated to be approximately 230 ml/h/kg (approximately 300 ml/min). On average, renal clearance has been estimated to be approximately 160 ml/h/kg (approximately 210 ml/min), which is in excess of the glomerular filtration rate. This shows that active tubular secretion is an essential part of the elimination of tenofovir. The FDA label provides specific guidelines for dosing according to renal function. It is important to consult product labeling before administering tenofovir to individuals with renal dysfunction, as the clearance of this drug may vary greatly among these patients.

Verwendung und Herstellung

UsesUse (kg) in Switzerland (2009): >500
Anwendungen · 2 Einträge

BeschreibungTenofovir disoproxil is a prodrug in a manner similar to that of adefovir dipivoxil. In both cases, the phosphate esters are removed through the action of plasma esterase, leading in this case to tenofovir, which differs from adefovir by the presence of the indicated methyl group. Tenofovir disoproxil exhibits good bioavailability (25%), which is improved in the presence of food (35%). The drug is approved for the treatment of HIV infections in adult patients. Tenofovir diphosphate is an HIV RT inhibitor. The active form of tenofovir is the tenofovir diphosphate, which competes with dATP for incorporation into viral DNA, and when incorporated, tenofovir diphosphate results in premature termination of DNA growth and inhibition of DNA polymerase. Tenofovir disoproxil is indicated for treatment-experienced patients with HIV-1. The drug also appears to be effective in treatment-naive patients, but initial approval is for treatment-experienced patients. The drug is administered as one tablet taken once daily. It is recommended that the drug be combined with other RT inhibitors or HIV PIs, which results in additive or synergistic activity.

VerwendenTenofovir Disoproxil is a therapeutic option for nucleos(t)ide analog (NA)-experienced chronic hepatitis B (CHB) patients infected with hepatitis B virus (HBV). Also, it is an intermediate used in the synthesis of Tenofovir Disoproxil Dimer (T018515), which is a Tenofovir Disoproxil impurity.

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: An organic phosphonate that is the disoproxil ester of tenofovir. A prodrug for tenofovir, an HIV-1 reverse transcriptase inhibitor, tenofovir disoproxil is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.