CHEBI:90923 - tenofovir alafenamide fumarate

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ChEBI Name tenofovir alafenamide fumarate
ChEBI ID CHEBI:90923
Definition A fumarate salt prepared from tenofovir alafenamide by reaction of one molecule of fumaric acid for every two molecules of tenofovir alafenamide. A prodrug for tenofovir, it is used in combination therapy for the treatment of HIV-1 infection.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C46H62N12O14P2
Net Charge 0
Average Mass 1069.006
Monoisotopic Mass 1068.39837
InChI InChI=1S/2C21H29N6O5P.C4H4O4/c2*1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27;5-3(6)1-2-4(7)8/h2*5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24);1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*15-,16+,33+;/m11./s1
InChIKey SVUJNSGGPUCLQZ-FQQAACOVSA-N
SMILES C(/C=C/C(O)=O)(O)=O.N1=CN=C2C(=C1N)N=CN2C[C@H](OC[P@](N[C@H](C(OC(C)C)=O)C)(=O)OC3=CC=CC=C3)C.N1=CN=C2C(=C1N)N=CN2C[C@H](OC[P@](N[C@H](C(OC(C)C)=O)C)(=O)OC3=CC=CC=C3)C
Roles Classification
Biological Role(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tenofovir alafenamide fumarate (CHEBI:90923) has part tenofovir alafenamide(1+) (CHEBI:90927)
tenofovir alafenamide fumarate (CHEBI:90923) has role antiviral drug (CHEBI:36044)
tenofovir alafenamide fumarate (CHEBI:90923) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
tenofovir alafenamide fumarate (CHEBI:90923) has role prodrug (CHEBI:50266)
tenofovir alafenamide fumarate (CHEBI:90923) is a fumarate salt (CHEBI:50921)
Incoming Descovy (CHEBI:133007) has part tenofovir alafenamide fumarate (CHEBI:90923)
Genvoya (CHEBI:90922) has part tenofovir alafenamide fumarate (CHEBI:90923)
Odefsey (CHEBI:133010) has part tenofovir alafenamide fumarate (CHEBI:90923)
IUPAC Names
bis{9-[(2R,5S,7E)-2,7,10-trimethyl-5,8-dioxo-5-phenoxy-3,9-dioxa-6-aza-5λ5-phosphaundecan-1-yl]-9H-purin-6-aminium} (2E)-but-2-enedioate
bis{propan-2-yl N-[(S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl]-L-alaninate} (2E)-but-2-enedioate
Synonyms Sources
GS-7340-03 ChemIDplus
TAF ChemIDplus
tenofovir alafenamide hemifumarate ChEBI
Brand Name Source
Vemlidy ChEBI
Manual Xrefs Databases
D10605 KEGG DRUG
DB09299 DrugBank
Tenofovir_alafenamide Wikipedia
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Registry Numbers Types Sources
1392275-56-7 CAS Registry Number KEGG DRUG
1392275-56-7 CAS Registry Number ChemIDplus
23336042 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
24289800 PubMed citation Europe PMC
25102336 PubMed citation Europe PMC
25134808 PubMed citation Europe PMC
25745115 PubMed citation Europe PMC
25965310 PubMed citation Europe PMC
26503655 PubMed citation Europe PMC
26640223 PubMed citation Europe PMC
26658300 PubMed citation Europe PMC
Last Modified
22 February 2017