Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H29N6O5P |
| Molecular Weight | 476.4659 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)OC(=O)[C@H](C)N[P@](=O)(CO[C@H](C)CN1C=NC2=C(N)N=CN=C12)OC3=CC=CC=C3
InChI
InChIKey=LDEKQSIMHVQZJK-CAQYMETFSA-N
InChI=1S/C21H29N6O5P/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33+/m1/s1
| Molecular Formula | C21H29N6O5P |
| Molecular Weight | 476.4659 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| 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
Created
by
admin
on
Edited
Mon Mar 31 21:35:23 GMT 2025
by
admin
on
Mon Mar 31 21:35:23 GMT 2025
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| Record UNII |
EL9943AG5J
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| Record Status |
Validated (UNII)
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Preferred Name | English | ||
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Official Name | English | ||
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Code | English | ||
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Common Name | English | ||
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Code | English | ||
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Systematic Name | English | ||
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Common Name | English |
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WHO-ATC |
J05AF13
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EMA ASSESSMENT REPORTS |
GENVOYA (AUTHORIZED: HIV INFECTIONS)
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WHO-ATC |
J05AR19
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EMA ASSESSMENT REPORTS |
DESCOVY (AUTHORIZED: HIV INFECTIONS )
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WHO-ATC |
J05AR22
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FDA ORPHAN DRUG |
569716
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WHO-ATC |
J05AR18
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NCI_THESAURUS |
C97452
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NCI_THESAURUS |
C281
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WHO-ATC |
J05AR20
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4944
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Tenofovir alafenamide
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9980
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379270-37-8
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CHEMBL2107825
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EL9943AG5J
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SUB121761
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90926
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100000144893
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DB09299
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1721603
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EL9943AG5J
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C148276
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ZZ-65
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m12126
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DTXSID50958941
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9574768
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| Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE |
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ENANTIOMER -> ENANTIOMER |
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METABOLIC ENZYME -> SUBSTRATE |
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
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TRANSPORTER -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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| Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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