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

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
Structure of TENOFOVIR DISOPROXIL FUMARATE

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

HIDE SMILES / InChI

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

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 17:58:14 GMT 2025
Edited
by admin
on Mon Mar 31 17:58:14 GMT 2025
Record UNII
OTT9J7900I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOFOVIR DISOPROXIL FUMARATE
EMA EPAR   HSDB   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN  
Official Name English
DELSTRIGO COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Preferred Name English
TENOFOVIR DISOPROXIL FUMARATE [JAN]
Common Name English
TENOFOVIR DISOPROXIL FUMARATE [HSDB]
Common Name English
GS-4331-05
Code English
TENOFOVIR DISOPROXIL FUMARATE [USAN]
Common Name English
9-((R)-2-((BIS(((ISOPROPOXYCARBONYL)OXY)-METHOXY)PHOSPHINYL)METHOXY)PROPYL)ADENINE FUMARATE (1:1)
Common Name English
TENOFOVIR DF
Common Name English
TENOFOVIR (AS DISOPROXIL FUMARATE)
Common Name English
TENOFOVIR DISOPROXIL FUMARATE [VANDF]
Common Name English
GSK548470
Code English
TENOFOVIR DISOPROXIL FUMARATE [WHO-IP]
Common Name English
Tenofovir disoproxil fumarate [WHO-DD]
Common Name English
TENOFOVIR DISOPROXIL FUMARATE [MI]
Common Name English
TENOFOVIRI DISOPROXILI FUMARAS [WHO-IP LATIN]
Common Name English
EVIPLERA COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Brand Name English
TENOFOVIR DISOPROXIL FUMARATE [EMA EPAR]
Common Name English
ATRIPLA COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Common Name English
TEMIXYS COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Common Name English
VIREAD
Brand Name English
TENOFOVIR DISOPROXIL FUMARATE [ORANGE BOOK]
Common Name English
GSK-548470
Code English
ODEFSEY COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Common Name English
TENOFOVIR DISOPROXIL FUMARATE [MART.]
Common Name English
STRIBILD COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Brand Name English
PMPA-PRODRUG
Code English
TENOFOVIR DISOPROXIL FUMARATE [USP-RS]
Common Name English
Bis(hydroxymethyl) [[(R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonate, bis(isopropyl carbonate) (ester), fumarate (1:1)
Common Name English
GS-4331-05-
Code English
PMPA PRODRUG
Code English
TENOFOVIR DISOPROXIL FUMARATE COMPONENT DELSTRIGO
Brand Name English
TRUVADA COMPONENT TENOFOVIR DISOPROXIL FUMARATE
Brand Name English
(R)-5-((2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-2,4,6,8-TETRAOXA-5-PHOSPHANONANEDIOIC ACID, BIS(1-METHYLETHYL) ESTER, 5-OXIDE, (E)-2-BUTENEDIOATE (1:1)
Common Name English
VIREA
Brand Name English
TDF
Common Name English
9-((R)-2-((BIS(((ISOPROPOXYCARBONYL)OXY)METHOXY)PHOSPHINYL)METHOXY)PROPYL)ADENINE FUMARATE (1:1)
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS VIREAD (AUTHORIZED: HEPTATITS B, CHRONIC)
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
NCI_THESAURUS C97452
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
EU-Orphan Drug EU/3/14/1419
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
EMA ASSESSMENT REPORTS EVIPLERA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
FDA ORPHAN DRUG 538416
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
EMA ASSESSMENT REPORTS ATRIPLA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
FDA ORPHAN DRUG 559316
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
EMA ASSESSMENT REPORTS TRUVADA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.4.2.1
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
EMA ASSESSMENT REPORTS VIREAD (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
Code System Code Type Description
CAS
202138-50-9
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
MERCK INDEX
m10559
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY Merck Index
CHEBI
63717
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
RXCUI
322248
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID5050426
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
TENOFOVIR DISOPROXIL FUMARATE
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
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.
DAILYMED
OTT9J7900I
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
NCI_THESAURUS
C47747
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
EVMPD
SUB12607MIG
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
SMS_ID
100000092141
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
PUBCHEM
6398764
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
CHEBI
63718
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
USAN
KK-89
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
DRUG BANK
DBSALT000172
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
RS_ITEM_NUM
1643656
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
FDA UNII
OTT9J7900I
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL1538
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
HSDB
7165
Created by admin on Mon Mar 31 17:58:14 GMT 2025 , Edited by admin on Mon Mar 31 17:58:14 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
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%).
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.
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
Amount Not Specified
IMPURITY -> PARENT
IMPURITY -> PARENT
Amount Not Specified
Related Record Type Details
ACTIVE MOIETY