U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30N5O10P
Molecular Weight 519.4428
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR DISOPROXIL

SMILES

CC(C)OC(=O)OCOP(=O)(CO[C@H](C)CN1C=NC2=C1N=CN=C2N)OCOC(=O)OC(C)C

InChI

InChIKey=JFVZFKDSXNQEJW-CQSZACIVSA-N
InChI=1S/C19H30N5O10P/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/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22)/t14-/m1/s1

HIDE SMILES / InChI

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

Description
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.

Originator

Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S2211383512001402

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
58.0 µM [Kd]
3.3 nM [EC50]
3.5 nM [EC50]
0.49 µM [EC50]
0.3 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIREAD

Approved Use

Tenofovir 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 Date

2012
Primary
VIREAD

Approved Use

Tenofovir 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 Date

2012
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
209.6 ng/mL
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2079.1 ng × h/mL
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
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
18.54 h
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
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
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

For hepatitis B - 5-100mg tablet
Route of Administration: Oral
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 Mon Mar 31 18:07:34 GMT 2025
Edited
by admin
on Mon Mar 31 18:07:34 GMT 2025
Record UNII
F4YU4LON7I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR BIS(ISOPROPYLOXYCARBONYLOXYMETHYL) ESTER
MI  
Preferred Name English
TENOFOVIR DISOPROXIL
EMA EPAR   WHO-DD  
Common Name English
GS-4331
Code English
TENOFOVIR BIS(ISOPROPYLOXYCARBONYLOXYMETHYL) ESTER [MI]
Common Name English
TENOFOVIR DISOPROXIL [EMA EPAR]
Common Name English
STRIBILD COMPONENT TENOFOVIR DISOPROXIL
Brand Name English
BIS-POC-PMPA
Common Name English
(R)-BIS(POC)PMPA
Common Name English
Tenofovir disoproxil [WHO-DD]
Common Name English
2,4,6,8-TETRAOXA-5-PHOSPHANONANEDIOIC ACID, 5-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, 1,9-BIS(1-METHYLETHYL) ESTER, 5-OXIDE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QJ05AR09
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
EMA ASSESSMENT REPORTS STRIBILD (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-ATC J05AR24
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-ATC J05AR09
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-ATC J05AR12
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-ATC J05AF07
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-VATC QJ05AR11
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-ATC J05AR11
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-VATC QJ05AR06
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-ATC J05AR06
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-ATC J05AR08
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-VATC QJ05AR03
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-ATC J05AR03
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-VATC QJ05AF07
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
WHO-VATC QJ05AR08
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
Code System Code Type Description
DRUG BANK
DB00300
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
DRUG CENTRAL
2593
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
MESH
C418563
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
EVMPD
SUB20643
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
SMS_ID
100000088017
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
WIKIPEDIA
Tenofovir disoproxil
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
PUBCHEM
5481350
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID5052757
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
CAS
201341-05-1
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
MERCK INDEX
m10559
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY Merck Index
FDA UNII
F4YU4LON7I
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
RXCUI
300195
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY RxNorm
CHEBI
63717
Created by admin on Mon Mar 31 18:07:34 GMT 2025 , Edited by admin on Mon Mar 31 18:07:34 GMT 2025
PRIMARY
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