TENOFOVIR EXALIDEX

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H52N5O5P
Molecular Weight	569.7167
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCCCCCCCCCCCCCCCOCCCOP(O)(=O)CO[C@H](C)CN1C=NC2=C1N=CN=C2N

InChI

InChIKey=SCTJKHUUZLXJIP-RUZDIDTESA-N

InChI=1S/C28H52N5O5P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-36-19-17-20-38-39(34,35)24-37-25(2)21-33-23-32-26-27(29)30-22-31-28(26)33/h22-23,25H,3-21,24H2,1-2H3,(H,34,35)(H2,29,30,31)/t25-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C28H52N5O5P
Molecular Weight	569.7167
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

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 70	Inhibitor 8,504	58.0 µM [Kd]
HIV-1, subtype A 92RW009 22	Inhibitor 8,504	3.3 nM [EC50]
HIV-2 22	Inhibitor 8,504	3.5 nM [EC50]
HBV replication 22	Inhibitor 8,504	0.49 µM [EC50]
Glutamate carboxypeptidase II 26	Inhibitor 8,504	0.3 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
HIV-1 infection 156	Primary	Approved 8,583	VIREAD
HBV infections 22	Primary	Approved 8,583	VIREAD
Hepatitis B 59	Primary	Phase II 1,147	Unknown
HIV-1 infection 156	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

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

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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	K7J545MEMA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

tenofovir exalidex [INN]

Preferred Name

English

TENOFOVIR EXALIDEX

Official Name

English

CMX157

Code

English

HDP-TENOFOVIR

Common Name

English

3-(HEXADECYLOXY)PROPYL HYDROGEN ((((2R)-1-(6-AMINO-9H-PURIN-9-YL)PROPAN-2-YL)OXY)METHYL)PHOSPHONATE

Systematic Name

English

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Classification Tree

Code System

Code

Reverse Transcriptase Inhibitor

NCI_THESAURUS

C97452

Anti-Infective Agent

NCI_THESAURUS

C281

Designated

FDA ORPHAN DRUG

583917

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Code System

Code

Type

Description

INN

10396

PRIMARY

FDA UNII

K7J545MEMA

PRIMARY

PUBCHEM

23628250

PRIMARY

DRUG BANK

DB14925

PRIMARY

NCI_THESAURUS

C152560

PRIMARY

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METABOLITE ACTIVE -> PRODRUG

Amount:

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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