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

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	C19H30N5O10P
Molecular Weight	519.4428
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	C4H4O4
Molecular Weight	116.0722
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
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

Showing 1 to 5 of 51 entries

Previous1 2 3 4 5…11Next

PubMed

Show entries

Title	Date	PubMed
Development of hexadecyloxypropyl tenofovir (CMX157) for treatment of infection caused by wild-type and nucleoside/nucleotide-resistant HIV.	2010 Jul	20439609

Showing 1 to 1 of 1 entries

Previous1Next

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	OTT9J7900I
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

TENOFOVIR DISOPROXIL FUMARATE

Official Name

English

TENOFOVIR DISOPROXIL FUMARATE [JAN]

Common Name

English

TENOFOVIR DISOPROXIL FUMARATE COMPONENT OF ODEFSEY

Common Name

English

TENOFOVIR DISOPROXIL FUMARATE [HSDB]

Common Name

English

TENOFOVIR DISOPROXIL FUMARATE COMPONENT OF TEMIXYS

Common Name

English

Showing 1 to 5 of 42 entries

Previous1 2 3 4 5…9Next

Show entries

Classification Tree

Code System

Code

HEPTATIS, CHRONIC

EMA ASSESSMENT REPORTS

VIREAD (AUTHORIZED: HEPTATITS B, CHRONIC)

Reverse Transcriptase Inhibitor

NCI_THESAURUS

C97452

Positive

EU-Orphan Drug

EU/3/14/1419

SEXUALLY TRANSMITTED DISEASES, VIRAL

EMA ASSESSMENT REPORTS

EVIPLERA (AUTHORIZED: HIV INFECTIONS)

Designated/Withdrawn

FDA ORPHAN DRUG

538416

Showing 1 to 5 of 10 entries

Previous1 2Next

Show entries

Code System

Code

Type

Description

CAS

202138-50-9

PRIMARY

MERCK INDEX

m10559

PRIMARY

Merck Index

CHEBI

63717

PRIMARY

RXCUI

322248

PRIMARY

RxNorm

EPA CompTox

DTXSID5050426

PRIMARY

Showing 1 to 5 of 18 entries

Previous1 2 3 4Next

Show entries

Related Record

Type

Details


					F4YU4LON7I

TENOFOVIR DISOPROXIL

PARENT -> SALT/SOLVATE

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

Show entries

Related Record

Type

Details


					D36VL0A00C

TENOFOVIR DISOPROXIL DIMER

IMPURITY -> PARENT

Comments:

Amount Not Specified

Amount:


					QB3AC2AM3R

ETHYL 1-METHYLETHYL (5RS)-5-(((1R)-2-(6-AMINO-9H-PURIN-9-YL)-1-METHYLETHOXY)METHYL)-5-OXO-2,4,6,8-TETRAOXA-5-.LAMBDA.5-PHOSPHANONANEDIOATE

IMPURITY -> PARENT

Comments:

Amount Not Specified

Amount:


					Z6QS39K36S

TENOFOVIR MONO POC DIMER

IMPURITY -> PARENT

Amount:


					ZKS5H56W6A

TENOFOVIR ISOPROXIL MONOESTER

IMPURITY -> PARENT

Comments:

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%).

Amount:

RELATIONSHIP_AMOUNT 1 WEIGHT PERCENT (average)


					TLO785XZL3

TENOFOVIR DISOPROXIL (S)-ENANTIOMER

IMPURITY -> PARENT

Comments:

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.

Amount:

RELATIONSHIP_AMOUNT 1 WEIGHT PERCENT (average)

Showing 1 to 5 of 17 entries

Previous1 2 3 4Next

Show entries

Related Record

Type

Details


					W4HFE001U5

TENOFOVIR ANHYDROUS

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

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