Details of the Drug

General Information of Drug (ID: DMTQF4A)

Drug Name

Tenofovir alafenamide

Synonyms

Tenofovir Alafenamide (GS-7340); Tenofovir Alafenamide [USAN:INN]; UNII-EL9943AG5J; UNII-J4414G3BUK; Vemlidy; Tenofovir; UNII-W4HFE001U5; W4HFE001U5; (R)-(((1-(6-AMINO-9H-PURIN-9-YL)PROPAN-2-YL)OXY)METHYL)PHOSPHONIC ACID; (R)-(1-(6-amino-9H-purin-9-yl)propan-2-yloxy)methylphosphonic acid; (R)-9-(2-Phosphonomethoxypropyl)adenine; (R)-9-[2-(Phosphonomethoxy)propyl]adenine; (R)-PMPA; ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid; 147127-20-6; 9-[(R)-2-(phosphonomethoxy)propyl]adenine; Apropovir; CHEBI:63625; D,L-Tenofovir; GS-1278; PMPA; PMPA gel; (S)-Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate; 379270-37-8; AK109983; EL9943AG5J; GS 7340; GS-7339; GS-7340; GS7340; J4414G3BUK; L-Alanine, N-((S)-(((1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-, 1-methylethyl ester; TENOFOVIR ALAFENAMIDE

Indication

Disease Entry	ICD 11	Status	REF
HIV infectious disease	N.A.	Approved	[1]
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Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

476.5

Logarithm of the Partition Coefficient (xlogp)

1.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C21H29N6O5P
IUPAC Name: propan-2-yl (2S)-2-[[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-phenoxyphosphoryl]amino]propanoate
Canonical SMILES: CC(C)OC(=O)C(C)NP(=O)(COC(C)CN1C=NC2=C(N=CN=C21)N)OC3=CC=CC=C3
InChI: LDEKQSIMHVQZJK-CAQYMETFSA-N
InChIKey: 1S/C21H29N6O5P/c1-14(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/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33+/m1/s1

Cross-matching ID

PubChem CID: 9574768
ChEBI ID: CHEBI:90926
CAS Number: 379270-37-8
DrugBank ID: DB09299
INTEDE ID: DR1552

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[2]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[2]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[3]
Cathepsin A (CTSA)	DE14JZK	PPGB_HUMAN	Substrate	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Pharmacokinetics of Tenofovir Alafenamide When Coadministered With Other HIV Antiretrovirals. J Acquir Immune Defic Syndr. 2018 Aug 1;78(4):465-472.
3	FDA label of Bictegravir, emtricitabine, and tenofovir alafenamide. The 2020 official website of the U.S. Food and Drug Administration.
4	Bictegravir/Emtricitabine/Tenofovir Alafenamide: a review in HIV-1 infection. Drugs. 2018 Nov;78(17):1817-1828.