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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H14N5O4P.H2O
Molecular Weight 305.2276
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TENOFOVIR

SMILES

O.C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O

InChI

InChIKey=PINIEAOMWQJGBW-FYZOBXCZSA-N
InChI=1S/C9H14N5O4P.H2O/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14;/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17);1H2/t6-;/m1./s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H14N5O4P
Molecular Weight 287.2123
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 18:06:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:06:14 GMT 2025
Record UNII
99YXE507IL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR
MART.   USAN   USP-RS   VANDF  
USAN  
Official Name English
GS-1278
Preferred Name English
PMPA
Code English
[[(R)-2-(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic acid, monohydrate
Common Name English
TENOFOVIR [USAN]
Common Name English
TENOFOVIR [VANDF]
Common Name English
(R)-((2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)PHOSPHONIC ACID MONOHYDRATE
Systematic Name English
9-((R)-2-PHOSPHONOMETHOXY-PROPYL)ADENINE MONOHYDRATE
Systematic Name English
PHOSPHONIC ACID, P-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-, HYDRATE (1:1)
Systematic Name English
TENOFOVIR MONOHYDRATE
Common Name English
PMP-A
Code English
TENOFOVIR [MART.]
Common Name English
TENOFOVIR HYDRATE
Common Name English
TENOFOVIR [USP-RS]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AR11
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (FTC/TEN)
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
WHO-ATC J05AR18
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
NDF-RT N0000175656
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
NCI_THESAURUS C97452
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
FDA ORPHAN DRUG 276209
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (EFV/FTC/TEN)
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
NDF-RT N0000175462
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
LIVERTOX NBK548917
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
WHO-ATC J05AR03
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
NCI_THESAURUS C1556
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
WHO-ATC J05AR17
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
Code System Code Type Description
DRUG CENTRAL
2592
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
EVMPD
SUB25433
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
NCI_THESAURUS
C29490
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
LACTMED
Tenofovir
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
FDA UNII
99YXE507IL
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL1538
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL483
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
SMS_ID
100000089445
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
WIKIPEDIA
TENOFOVIR
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
CHEBI
134504
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
CHEBI
63716
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
DAILYMED
99YXE507IL
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
MESH
C096918
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
DRUG BANK
DB14126
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
MESH
C046573
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
RS_ITEM_NUM
1643601
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
USAN
KK-88
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
RXCUI
117466
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY RxNorm
CAS
206184-49-8
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
PUBCHEM
21146529
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
CHEBI
63625
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
EVMPD
SUB04721MIG
Created by admin on Mon Mar 31 18:06:14 GMT 2025 , Edited by admin on Mon Mar 31 18:06:14 GMT 2025
PRIMARY
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ANHYDROUS->SOLVATE
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ACTIVE MOIETY