TENOFOVIR

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

SMILES

O.C[C@H](CN1C=NC2=C(N)N=CN=C12)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	C9H14N5O4P
Molecular Weight	287.2123
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

(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 67	Inhibitor 8,297	58.0 µM [Kd]
HIV-1, subtype A 92RW009 20	Inhibitor 8,297	3.3 nM [EC50]
HIV-2 20	Inhibitor 8,297	3.5 nM [EC50]
HBV replication 20	Inhibitor 8,297	0.49 µM [EC50]
Glutamate carboxypeptidase II 4	Inhibitor 8,297	0.3 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
HIV-1 infection 151	Primary	Approved 8,429	VIREAD
HBV infections 20	Primary	Approved 8,429	VIREAD
Hepatitis B 57	Primary	Phase II 1,132	Unknown
HIV-1 infection 151	Primary	Basic research	Unknown

C_max

Value	Dose	Analyte	Population
209.6 ng/mL	150 mg single, oral	TENOFOVIR plasma	Homo sapiens
456.7 ng/mL	300 mg single, oral	TENOFOVIR plasma	Homo sapiens
448.5 ng/mL	300 mg single, oral	TENOFOVIR plasma	Homo sapiens
989.8 ng/mL	600 mg single, oral	TENOFOVIR plasma	Homo sapiens
523.4 ng/mL	300 mg 1 times / day multiple, oral	TENOFOVIR plasma	Homo sapiens
0.03 μg/mL	25 mg 1 times / day multiple, oral	TENOFOVIR plasma	Homo sapiens
326 ng/mL	245 mg 1 times / day multiple, oral	TENOFOVIR serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
2079.1 ng × h/mL	150 mg single, oral	TENOFOVIR plasma	Homo sapiens
3006.1 ng × h/mL	300 mg single, oral	TENOFOVIR plasma	Homo sapiens
3408.2 ng × h/mL	300 mg single, oral	TENOFOVIR plasma	Homo sapiens
6373.9 ng × h/mL	600 mg single, oral	TENOFOVIR plasma	Homo sapiens
4476.7 ng × h/mL	300 mg 1 times / day multiple, oral	TENOFOVIR plasma	Homo sapiens
0.4 μg × h/mL	25 mg 1 times / day multiple, oral	TENOFOVIR plasma	Homo sapiens
3324 ng × h/mL	245 mg 1 times / day multiple, oral	TENOFOVIR serum	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
18.54 h	150 mg single, oral	TENOFOVIR plasma	Homo sapiens
17.56 h	300 mg single, oral	TENOFOVIR plasma	Homo sapiens
16.86 h	300 mg single, oral	TENOFOVIR plasma	Homo sapiens
18.92 h	600 mg single, oral	TENOFOVIR plasma	Homo sapiens
17.12 h	300 mg 1 times / day multiple, oral	TENOFOVIR plasma	Homo sapiens
18 h	245 mg 1 times / day multiple, oral	TENOFOVIR serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
99.3%			TENOFOVIR plasma	Homo sapiens
99.3%	245 mg 1 times / day multiple, oral		TENOFOVIR serum	Homo sapiens

Sourcing

Sourcing

Show entries

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

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PubMed

Title	Date	PubMed
No data available in table

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.

Substance Class	Chemical
Record UNII	99YXE507IL
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

TENOFOVIR

Official 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

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Classification Tree

Code System

Code

Antivirals for treatment of HIV infections, combinations

WHO-ATC

J05AR11

Antiretrovirals

WHO-ESSENTIAL MEDICINES LIST

6.4.2.3 (FTC/TEN)

Antivirals for treatment of HIV infections, combinations

WHO-ATC

J05AR18

Established Pharmacologic Class

NDF-RT

N0000175656

Reverse Transcriptase Inhibitor

NCI_THESAURUS

C97452

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Code System

Code

Type

Description

DRUG CENTRAL

2592

PRIMARY

EVMPD

SUB25433

PRIMARY

NCI_THESAURUS

C29490

PRIMARY

LACTMED

Tenofovir

PRIMARY

FDA UNII

99YXE507IL

PRIMARY

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Related Record

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Details


					W4HFE001U5

TENOFOVIR ANHYDROUS

PARENT -> SALT/SOLVATE


					W4HFE001U5

TENOFOVIR ANHYDROUS

ANHYDROUS->SOLVATE

Amount:

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					W4HFE001U5

TENOFOVIR ANHYDROUS

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound