This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Tenofovir
Accession Number
DB14126
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • (R)-PMPA
  • Anhydrous tenofovir
  • Tenofovir (anh.)
  • Tenofovir (anhydrous)
  • Tenofovir anhydrous
External IDs
GS 1275 / GS-1275
Product Ingredients
IngredientUNIICASInChI Key
Tenofovir hydrate99YXE507IL206184-49-8PINIEAOMWQJGBW-FYZOBXCZSA-N
Categories
UNII
W4HFE001U5
CAS number
147127-20-6
Weight
Average: 287.2123
Monoisotopic: 287.078340473
Chemical Formula
C9H14N5O4P
InChI Key
SGOIRFVFHAKUTI-ZCFIWIBFSA-N
InChI
InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1
IUPAC Name
({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid
SMILES
C[C@H](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirTenofovir may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibThe serum concentration of Tenofovir can be increased when it is combined with Abemaciclib.
AcarboseTenofovir may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Tenofovir.
AceclofenacAceclofenac may increase the nephrotoxic activities of Tenofovir.
AcemetacinAcemetacin may increase the nephrotoxic activities of Tenofovir.
AcetaminophenTenofovir may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Tenofovir which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may increase the nephrotoxic activities of Tenofovir.
AclidiniumTenofovir may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014445
ChemSpider
408154
ChEBI
63625
ChEMBL
CHEMBL483
PharmGKB
PA10204
HET
TFO
Wikipedia
Tenofovir_disoproxil
PDB Entries
1t03

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingOtherHIV Prevention / Medication Adherence1
1TerminatedTreatmentViral Hepatitis B1
1, 2CompletedTreatmentHepatitis B Chronic Infection1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)1
2Enrolling by InvitationTreatmentHepatitis B Chronic Infection1
2RecruitingTreatmentViral Hepatitis B / Virus Hepatitis1
3Not Yet RecruitingTreatmentHepatitis B Chronic Infection1
4RecruitingPreventionHIV, Prevention1
Not AvailableRecruitingNot AvailableAcquired Immune Deficiency Syndrome (AIDS)1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Inflammation Vagina / Menopause1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.87 mg/mLALOGPS
logP-1.5ALOGPS
logP-3.4ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)3.74ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area136.38 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.54 m3·mol-1ChemAxon
Polarizability25.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0290000000-3e1938b3d02b375e35df
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001r-1930000000-d365f36771addeb5b51c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-2900000000-c8f91e6bb9d4588f055d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-2900000000-099f967e8f8229f1fb82
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-3900000000-521761795a56429a8f51
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-06si-5900000000-b88fc7e5619f18889624
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0090000000-e85e6b9ea88e6c214687
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0190000000-405fbe60309faffed10c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004r-0950000000-d7cec4ba580879c76061
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0910000000-f2abf612e945d8c69371
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-056r-1900000000-c48435c099065334ef3e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0570-1900000000-7b90db7cba32420df6d1

Taxonomy

Description
This compound belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
6-aminopurines
Alternative Parents
Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Organic phosphonic acids / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds
show 2 more
Substituents
6-aminopurine / Aminopyrimidine / N-substituted imidazole / Pyrimidine / Imidolactam / Azole / Imidazole / Organophosphonic acid / Organophosphonic acid derivative / Heteroaromatic compound
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phosphonic acids (CHEBI:63625)

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Murakami E, Wang T, Park Y, Hao J, Lepist EI, Babusis D, Ray AS: Implications of efficient hepatic delivery by tenofovir alafenamide (GS-7340) for hepatitis B virus therapy. Antimicrob Agents Chemother. 2015;59(6):3563-9. doi: 10.1128/AAC.00128-15. Epub 2015 Apr 13. [PubMed:25870059]
  2. Droste JA, Verweij-van Wissen CP, Kearney BP, Buffels R, Vanhorssen PJ, Hekster YA, Burger DM: Pharmacokinetic study of tenofovir disoproxil fumarate combined with rifampin in healthy volunteers. Antimicrob Agents Chemother. 2005 Feb;49(2):680-4. doi: 10.1128/AAC.49.2.680-684.2005. [PubMed:15673751]
  3. Begley R, Das M, Zhong L, Ling J, Kearney BP, Custodio JM: Pharmacokinetics of Tenofovir Alafenamide When Coadministered With Other HIV Antiretrovirals. J Acquir Immune Defic Syndr. 2018 Aug 1;78(4):465-472. doi: 10.1097/QAI.0000000000001699. [PubMed:29649076]
  4. Custodio JM, Fordyce M, Garner W, Vimal M, Ling KH, Kearney BP, Ramanathan S: Pharmacokinetics and Safety of Tenofovir Alafenamide in HIV-Uninfected Subjects with Severe Renal Impairment. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5135-40. doi: 10.1128/AAC.00005-16. Print 2016 Sep. [PubMed:27216057]
  5. Moss DM, Domanico P, Watkins M, Park S, Randolph R, Wring S, Rajoli RKR, Hobson J, Rannard S, Siccardi M, Owen A: Simulating Intestinal Transporter and Enzyme Activity in a Physiologically Based Pharmacokinetic Model for Tenofovir Disoproxil Fumarate. Antimicrob Agents Chemother. 2017 Jun 27;61(7). pii: AAC.00105-17. doi: 10.1128/AAC.00105-17. Print 2017 Jul. [PubMed:28416547]
  6. Soriano V, Labarga P, Fernandez-Montero JV, Mendoza C, Benitez-Gutierrez L, Pena JM, Barreiro P: Drug interactions in HIV-infected patients treated for hepatitis C. Expert Opin Drug Metab Toxicol. 2017 Aug;13(8):807-816. doi: 10.1080/17425255.2017.1351942. Epub 2017 Jul 13. [PubMed:28689442]

Drug created on June 24, 2018 10:23 / Updated on December 07, 2018 15:42