ContaminantDB: Fosamprenavir calcium

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:56:34 UTC

Update Date

2016-11-09 01:15:57 UTC

Accession Number

CHEM019243

Identification

Common Name

Fosamprenavir calcium

Class

Small Molecule

Description

Fosamprenavir (marketed by ViiV Healthcare as the calcium salt under the trade names Lexiva in the U.S. and Telzir in Europe) is a drug for the treatment of HIV infections. It is a pro-drug of the protease inhibitor and antiretroviral drug amprenavir. The FDA approved it October 20, 2003, while the EMA approved it on July 12, 2004. The human body metabolizes fosamprenavir in order to form amprenavir, which is the active ingredient. That metabolization increases the duration that amprenavir is available, making fosamprenavir a slow-release version of amprenavir and thus reducing the number of pills required versus standard amprenavir. A head-to-head study with lopinavir showed the two drugs to have comparable potency, but patients on fosamprenavir tended to have a higher serum cholesterol. Fosamprenavir's main advantage over lopinavir is that it is cheaper.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Lexiva	Kegg
Telzir	Kegg
(3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-(phenylmethyl)-2-(phosphonooxy)propyl)carbamic acid C-(tetrahydro-3-furanyl) ester	MeSH
VX175 CPD	MeSH
Fos-amprenavir	MeSH
Fosamprenavir	MeSH
GW908 CPD	MeSH
Calcium;[(2R,3S)-1-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-[[(3S)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphoric acid	Generator
Calcium;[(2R,3S)-1-[(4-aminophenyl)sulphonyl-(2-methylpropyl)amino]-3-[[(3S)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphate	Generator
Calcium;[(2R,3S)-1-[(4-aminophenyl)sulphonyl-(2-methylpropyl)amino]-3-[[(3S)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphoric acid	Generator
Fosamprenavir calcium	MeSH
Calcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidic acid	Generator
Calcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulphonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidate	Generator
Calcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulphonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidic acid	Generator

Chemical Formula

C₂₅H₃₄CaN₃O₉PS

Average Molecular Mass

623.670 g/mol

Monoisotopic Mass

623.138 g/mol

CAS Registry Number

226700-81-8

IUPAC Name

calcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidate

Traditional Name

calcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidate

SMILES

[Ca++].[H][C@](CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1)(OP(O)([O-])=O)[C@]([H])(CC1=CC=CC=C1)N=C([O-])O[C@@]1([H])CCOC1

InChI Identifier

InChI=1S/C25H36N3O9PS.Ca/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21;/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32);/q;+2/p-2/t21-,23-,24+;/m0./s1

InChI Key

PMDQGYMGQKTCSX-HQROKSDRSA-L

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Phenylbutylamine
Amphetamine or derivatives
Benzenesulfonyl group
Phosphoethanolamine
Aniline or substituted anilines
Organic phosphoric acid derivative
Phosphoric acid ester
Organosulfonic acid amide
Alkyl phosphate
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Carbamic acid ester
Tetrahydrofuran
Sulfonyl
Carbonic acid derivative
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Ether
Organic calcium salt
Organic nitrogen compound
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Organic salt
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary amine
Organic zwitterion
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.072 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.65	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
pKa (Strongest Basic)	2.43	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	186.87 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	155.17 m³·mol⁻¹	ChemAxon
Polarizability	56.69 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000009000-95a294b3c9beee05048d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000009000-95a294b3c9beee05048d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0000009000-95a294b3c9beee05048d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000009000-f67ad6df1b5fddfff332	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0000009000-f67ad6df1b5fddfff332	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0000009000-f67ad6df1b5fddfff332	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DBSALT001228

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Fosamprenavir

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

131535

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Fosamprenavir calcium (CHEM019243)

Structure for CHEM019243: Fosamprenavir calcium