Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H30N5O10P.C4H4O4 |
| Molecular Weight | 635.5149 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C(O)=O.CC(C)OC(=O)OCOP(=O)(CO[C@H](C)CN1C=NC2=C1N=CN=C2N)OCOC(=O)OC(C)C
InChI
InChIKey=VCMJCVGFSROFHV-WZGZYPNHSA-N
InChI=1S/C19H30N5O10P.C4H4O4/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
| Molecular Formula | C19H30N5O10P |
| Molecular Weight | 519.4428 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20439609https://www.ncbi.nlm.nih.gov/pubmed/8452366Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9765248 | http://www.sciencedirect.com/science/article/pii/S2211383512001402
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609https://www.ncbi.nlm.nih.gov/pubmed/8452366
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9765248 | http://www.sciencedirect.com/science/article/pii/S2211383512001402
(R)-9-(2-Phosphonylmethoxypropyl)adenine (PMPA known as tenofovir) is an antiviral drug. Diphosphate of PMPA acts as a selective inhibitor of the HIV-1 reverse
transcriptase. Tenofovir disoproxil was approved for clinical use for the treatment of HIV infection (AIDS) and chronic HBV infection.
CNS Activity
Originator
Sources: http://adisinsight.springer.com/drugs/800020504https://www.ncbi.nlm.nih.gov/pubmed/8452366
Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S2211383512001402
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9765248 |
58.0 µM [Kd] | ||
Target ID: HIV-1, subtype A 92RW009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609 |
3.3 nM [EC50] | ||
Target ID: HIV-2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609 |
3.5 nM [EC50] | ||
Target ID: HBV replication Sources: https://www.ncbi.nlm.nih.gov/pubmed/17646420 |
0.49 µM [EC50] | ||
Target ID: CHEMBL1892 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18060794 |
0.3 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | VIREAD Approved UseTenofovir disoproxil fumarate is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV and HBV infections Launch Date2012 |
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| Primary | VIREAD Approved UseTenofovir disoproxil fumarate is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV and HBV infections Launch Date2012 |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
209.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
456.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
448.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
989.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
523.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.03 μg/mL |
25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
326 ng/mL |
245 mg 1 times / day multiple, oral dose: 245 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2079.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3006.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3408.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
6373.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4476.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.4 μg × h/mL |
25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
3324 ng × h/mL |
245 mg 1 times / day multiple, oral dose: 245 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
18.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
17.56 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
16.86 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
18.92 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
17.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23278367 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
18 h |
245 mg 1 times / day multiple, oral dose: 245 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
99.3% |
TENOFOVIR plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
||
99.3% |
245 mg 1 times / day multiple, oral dose: 245 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TENOFOVIR serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV. | 2010-07 |
|
| Selective inhibition of HIV-1 reverse transcriptase by an antiviral inhibitor, (R)-9-(2-Phosphonylmethoxypropyl)adenine. | 1998-10-16 |
|
| Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine. | 1993-02 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02710604
For hepatitis B - 5-100mg tablet
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609
CMX-157 was active against all major subtypes of HIV-1 and HIV-2 in fresh human peripheral blood mononuclear cells (PBMCs) and against all HIV-1 strains evaluated in monocyte-derived macrophages, with 50% effective concentrations (EC(50)s) ranging between 0.20 and 7.2 nM.
| Substance Class |
Chemical
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OTT9J7900I
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| Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
VIREAD (AUTHORIZED: HEPTATITS B, CHRONIC)
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NCI_THESAURUS |
C97452
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EU-Orphan Drug |
EU/3/14/1419
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EMA ASSESSMENT REPORTS |
EVIPLERA (AUTHORIZED: HIV INFECTIONS)
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FDA ORPHAN DRUG |
538416
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ATRIPLA (AUTHORIZED: HIV INFECTIONS)
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FDA ORPHAN DRUG |
559316
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EMA ASSESSMENT REPORTS |
TRUVADA (AUTHORIZED: HIV INFECTIONS)
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.1
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EMA ASSESSMENT REPORTS |
VIREAD (AUTHORIZED: HIV INFECTIONS)
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202138-50-9
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m10559
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PRIMARY | Merck Index | ||
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63717
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322248
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PRIMARY | RxNorm | ||
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DTXSID5050426
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TENOFOVIR DISOPROXIL FUMARATE
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PRIMARY | Description: White to almost-white, crystalline powder. Solubility: Slightly soluble in water, soluble in methanol, very slightly soluble in dichloromethane. Category: Antiretroviral (Nucleotide Reverse Transcriptase Inhibitor). Storage: Tenofovir disoproxil fumarate should be kept in a tightly closed container, protected from light and stored at a temperature between 2?8 ?C. Additional information: Tenofovir disoproxil fumarate may exhibit polymorphism. Definition: Tenofovir disoproxil fumarate contains not less than 98.5% and not more than 101.0% of tenofovir disoproxil fumarate(C19H30N5O10P,C4H4O4), calculated with reference to the anhydrous substance. Manufacture: The production method is validated to ensure that the substance, if tested, would comply with: ? a limit of not more than 5 ppm for the mutagenic impurity 9-propenyladenine (impurity K), which may be a synthesis related substance, using a suitable method; ? a limit of not more than 1.0% for the tenofovir disoproxil (S)-enantiomer (impurity G) using a suitable chiral chromatographic method. | ||
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SUB12607MIG
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100000092141
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KK-89
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
In the chromatogram obtained with solution (1) the area of any peak due to tenofovir monosoproxil (impurity A) is not greater than twice the area of the principal peak obtained with solution (2) (1.0%).
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IMPURITY -> PARENT |
The production method is validated to ensure that the substance, if tested, would comply with: ? a limit of not more than 1.0% for the tenofovir disoproxil (S)-enantiomer (impurity G) using a suitable chiral chromatographic method.
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