TENOFOVIR DISOPROXIL FUMARATE

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

Structure Search

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

Description
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Human immunodeficiency virus type 1 reverse transcriptase 70 Target ID: CHEMBL247 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9765248	Inhibitor 8504	58.0 µM [Kd]
HIV-1, subtype A 92RW009 22 Target ID: HIV-1, subtype A 92RW009 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Inhibitor 8504	3.3 nM [EC50]
HIV-2 22 Target ID: HIV-2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Inhibitor 8504	3.5 nM [EC50]
HBV replication 22 Target ID: HBV replication Sources: https://www.ncbi.nlm.nih.gov/pubmed/17646420	Inhibitor 8504	0.49 µM [EC50]
Glutamate carboxypeptidase II 26 Target ID: CHEMBL1892 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18060794	Inhibitor 8504	0.3 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
HIV-1 infection 156 Sources: https://aidsinfo.nih.gov/drugs/290/tenofovir-disoproxil-fumarate/0/patient	Primary	Approved 8583	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
HBV infections 22 Sources: https://aidsinfo.nih.gov/drugs/290/tenofovir-disoproxil-fumarate/0/patient	Primary	Approved 8583	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
Hepatitis B 59 Sources: https://clinicaltrials.gov/ct2/show/NCT02710604	Primary	Phase II 1147	Unknown Approved Use Unknown
HIV-1 infection 156 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20439609	Primary	Basic research	Unknown Approved Use Unknown

C_max

Value	Dose	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208464s000lbl.pdf	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 OTHER https://www.medicines.org.uk/emc/product/8138/smpc#PRODUCTINFO	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	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208464s000lbl.pdf	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 OTHER https://www.medicines.org.uk/emc/product/8138/smpc#PRODUCTINFO	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

T_1/2

Value	Dose	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 OTHER https://www.medicines.org.uk/emc/product/8138/smpc#PRODUCTINFO	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
99.3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021356s042,022577s002lbl.pdf			TENOFOVIR plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
99.3% OTHER https://www.medicines.org.uk/emc/product/8138/smpc#PRODUCTINFO	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

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0205	http://www.3bsc.com/index/pro_info.php?id=19561
AA Blocks	AA001EJQ	http://www.aablocks.com/goods/Goods/detail?id=AA001EJQ
Aaron Chemicals	AR001FBI	http://www.aaronchem.com/147127-20-6
abcr GmbH	AB437841	http://www.abcr.com/shop/en/AB437841
AbMole Bioscience	M5051	http://www.abmole.com/products/tenofovir.html
Acorn PharmaTech	ACN-029240	http://www.acornpharmatech.com/
Active Biopharma	ABP000917	http://www.activebiopharma.com/147127-20-6
Adooq BioScience	A10908	https://www.adooq.com/tenofovir-viread.html
AEchem Scientific Corp., USA	AE1-016163	http://www.aechemsc.com/info_products/AE1-016163.php
AHH Chemical co.,ltd	API-1191	http://www.ahhchemical.com/product/API-1191.html
AK Scientific, Inc. (AKSCI)	J90012	http://www.aksci.com/item_detail.php?cat=J90012
Alsachim	1763	http://www.alsachim.com/product-C2530-glo.bal-view.html
Angene	AGN-PC-0PZUPY	http://www.angenechemical.com/productshow/AGN-PC-0PZUPY.html
ApexBio Technology	A5275	http://www.apexbt.com/tenofovir.html
AstaTech, Inc.	34244	http://www.astatechinc.com/CPSResult.php?CRNO=35657
Aurum Pharmatech LLC	S-2389	http://www.Aurumpharmatech.com/Product/ProductDetails/S_2389
AvaChem Scientific	2678	http://www.avachem.com/productSearch.asp?2678
Axon MedChem	3157	https://www.axonmedchem.com/product/3157
BioCrick	BCC2500	http://www.biocrick.com/Tenofovir-BCC2500.html
BioSynth	Q-201787	https://www.biosynth.com/en/products/life-science/enzyme-substrates-reagents/products/Q-201787.html
BLD Pharm	BD01204701	http://www.bldpharm.com/products/107021-12-5.html
BLD Pharm	BD18435	http://www.bldpharm.com/products/147127-20-6.html
Boerchem	BC208449	http://www.boerchem.com/?product_35256.html
Capot Chemical	9452	http://www.capotchem.com/en/9452.htm
Capot Chemical	PubChem9452	http://www.capotchem.com/en/9452.htm
Chem Scene	CS-1609	http://www.chemscene.com/147127-20-6.html
Chemenu	CM110444	http://www.chemenu.com/products/CM110444
ChemMol	1032196	http://www.chemmol.com/chemmol/1032196.html
ChemMol	30108887	http://www.chemmol.com/chemmol/30108887.html
ChemMol	44003255	http://www.chemmol.com/chemmol/44003255.html
ChemMol	97900713	http://www.chemmol.com/chemmol/97900713.html
ChemReagents	80014913	http://www.chemreagents.com/Product/Product.asp?ProductID=80014913
Chemspace	CSSB00016987604	https://chem-space.com/CSSB00016987604
Chiralblock Biosciences	CB10985	http://www.chiralblock.com/products/147127-20-6.html
CSNpharm	CSN12559	https://www.csnpharm.com/products/tenofovir.html
eNovation Chemicals	D275770	https://www.enovationchem.com/ProductDetails.asp?ProductID=D275770
eNovation Chemicals	D320167	http://www.enovationchem.com/productDetails.asp?productID=D320167
iChemical	EBD47973	http://www.ichemical.com/products/147127-20-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Matrix Scientific	74030	https://www.matrixscientific.com/074030.html
MedChem Express	HY-13910	https://www.medchemexpress.com/tenofovir.html
Oakwood	77792	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=62966&ExtHyperLink=1
OChem	5252	http://www.ocheminc.com/index.php?act=psearch&pid=127T206
Selleck Chemicals	S1401	http://www.selleckchem.com/products/Tenofovir.html
Sigma-Aldrich	SML1795_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/sml1795?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S544915	http://www.smolecule.com/products/s544915
Smolecule	S752291	https://www.smolecule.com/products/s752291
TCI (Tokyo Chemical Industry)	T3006	http://www.tcichemicals.com/eshop/en/us/commodity/T3006/index.html
THE BioTek	bt-284194	https://www.thebiotek.com/product/inhibitors/bt-284194
THE BioTek	bt-293647	https://www.thebiotek.com/product/others/bt-293647
Tocris	3666	https://www.tocris.com/products/tenofovir_3666
Yuhao Chemical	A0500092	http://www.chemyuhao.com/147127-20-6.html

PubMed

Title	Date	PubMed
Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV.	2010-07	20439609
Selective inhibition of HIV-1 reverse transcriptase by an antiviral inhibitor, (R)-9-(2-Phosphonylmethoxypropyl)adenine.	1998-10-16	9765248
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	8452366

Patents

Sample Use Guides

In Vivo Use Guide

For hepatitis B - 5-100mg tablet

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

TENOFOVIR DISOPROXIL FUMARATE

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)