2-PMPA

Details

Stereochemistry	RACEMIC
Molecular Formula	C6H11O7P
Molecular Weight	226.1211
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)CCC(CP(O)(O)=O)C(O)=O

InChI

InChIKey=ISEYJGQFXSTPMQ-UHFFFAOYSA-N

InChI=1S/C6H11O7P/c7-5(8)2-1-4(6(9)10)3-14(11,12)13/h4H,1-3H2,(H,7,8)(H,9,10)(H2,11,12,13)

HIDE SMILES / InChI

Molecular Formula	C6H11O7P
Molecular Weight	226.1211
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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

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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
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	XH88WJG9LJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-PMPA

Common Name

English

2-(Phosphonomethyl)pentanedioic acid

Systematic Name

English

Pentanedioic acid, 2-(phosphonomethyl)-

Systematic Name

English

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Code System

Code

Type

Description

PUBCHEM

10130754

PRIMARY

EPA CompTox

DTXSID90436036

PRIMARY

CAS

173039-10-6

PRIMARY

FDA UNII

XH88WJG9LJ

PRIMARY

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Related Record

Type

Details


					DE99E6YD6A

Tris-POC-2-PMPA

PRODRUG -> METABOLITE ACTIVE

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