Hypoxanthine

Identification

Generic Name
Hypoxanthine
DrugBank Accession Number
DB04076
Background

Hypoxanthine is a purine and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 136.1115
Monoisotopic: 136.03851077
Chemical Formula
C5H4N4O
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Adenylosuccinate Lyase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
Xanthinuria Type IDisease
Mitochondrial DNA Depletion SyndromeDisease
Myoadenylate Deaminase DeficiencyDisease
Purine MetabolismMetabolic
Purine Nucleoside Phosphorylase DeficiencyDisease
Lesch-Nyhan Syndrome (LNS)Disease
Gout or Kelley-Seegmiller SyndromeDisease
Mercaptopurine Action PathwayDrug action
Adenine Phosphoribosyltransferase Deficiency (APRT)Disease
Adenosine Deaminase DeficiencyDisease
AICA-RibosiduriaDisease
Molybdenum Cofactor DeficiencyDisease
Azathioprine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria Type IIDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Hypoxanthine.
AbametapirThe serum concentration of Hypoxanthine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Hypoxanthine can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Hypoxanthine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Hypoxanthine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. 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
Hypoxanthines
Alternative Parents
6-oxopurines / Pyrimidones / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
6-oxopurine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Hypoxanthine / Imidazole / Organic nitrogen compound / Organic oxide
show 7 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxopurine, nucleobase analogue, purine nucleobase (CHEBI:17368) / Purine alkaloids (C00262) / a purine-related compound, a purine base (HYPOXANTHINE)
Affected organisms
Not Available

Chemical Identifiers

UNII
2TN51YD919
CAS number
68-94-0
InChI Key
FDGQSTZJBFJUBT-UHFFFAOYSA-N
InChI
InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
IUPAC Name
6,7-dihydro-3H-purin-6-one
SMILES
O=C1N=CNC2=C1NC=N2

References

Synthesis Reference

Alvin J. Glasky, Heinrich Bollinger, Hans Rudolf Muller, "Methods of synthesis for 9-substituted hypoxanthine derivatives." U.S. Patent US06849735, issued February 01, 2005.

US06849735
General References
Not Available
Human Metabolome Database
HMDB0000157
KEGG Compound
C00262
PubChem Compound
790
PubChem Substance
46507200
ChemSpider
768
BindingDB
50200102
ChEBI
17368
ChEMBL
CHEMBL1427
ZINC
ZINC000018153302
PDBe Ligand
HPA
Wikipedia
Hypoxanthine
PDB Entries
1a9q / 1a9r / 1a9t / 1bdh / 1bdi / 1jfs / 1jft / 1jh9 / 1pnr / 1qp0
show 41 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedOtherParkinson's Disease (PD)1
2CompletedTreatmentParkinson's Disease (PD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)150 dec °CPhysProp
water solubility700 mg/L (at 23 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.11HANSCH,C ET AL. (1995)
logS-2.29ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility2.2 mg/mLALOGPS
logP-0.74ALOGPS
logP-0.36Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.41Chemaxon
pKa (Strongest Basic)2.28Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area70.14 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity35.61 m3·mol-1Chemaxon
Polarizability11.78 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9758
Caco-2 permeable-0.7161
P-glycoprotein substrateNon-substrate0.6693
P-glycoprotein inhibitor INon-inhibitor0.9462
P-glycoprotein inhibitor IINon-inhibitor0.9626
Renal organic cation transporterNon-inhibitor0.8869
CYP450 2C9 substrateNon-substrate0.8095
CYP450 2D6 substrateNon-substrate0.7824
CYP450 3A4 substrateNon-substrate0.6692
CYP450 1A2 substrateInhibitor0.6493
CYP450 2C9 inhibitorNon-inhibitor0.913
CYP450 2D6 inhibitorNon-inhibitor0.9212
CYP450 2C19 inhibitorNon-inhibitor0.8549
CYP450 3A4 inhibitorNon-inhibitor0.9202
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8962
Ames testNon AMES toxic0.6541
CarcinogenicityNon-carcinogens0.9686
BiodegradationNot ready biodegradable0.8452
Rat acute toxicity2.1622 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9781
hERG inhibition (predictor II)Non-inhibitor0.9305
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0159-3970000000-0d844fae4a1ffe158823
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-014i-1790000000-ae93bf8bf07b30b65e1a
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-9340000000-1184c503fb61344c4853
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-014i-3590000000-a419976950afe7934cbc
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a5i-8900000000-e20eb5d939a2c406a6e2
GC-MS Spectrum - EI-BGC-MSsplash10-000i-9800000000-9c266d6963658e9d2cf1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-3970000000-0d844fae4a1ffe158823
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1790000000-ae93bf8bf07b30b65e1a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9340000000-1184c503fb61344c4853
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-3590000000-a419976950afe7934cbc
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-2890000000-3be4d08be45781881bc1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1590000000-bb6f003bfa7bd04628a1
Mass Spectrum (Electron Ionization)MSsplash10-000i-8900000000-ebf57ea530a2d4e31ffa
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-0900000000-2b36c20acd9973b317f5
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0api-9800000000-fb4e3cccb7d27d119feb
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0aor-9200000000-33c2f9eedf9a878530be
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-000i-9800000000-9c266d6963658e9d2cf1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0910000000-4da64abddc3ac8ab573a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-1900000000-859f61101b12be0b2978
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-1900000000-f5d899e7988568d5bcab
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-e19e6d04568d3560eb4a
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0910000000-8def0d2ec82152826763
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-2900000000-a8361951a2f702a217c7
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-3f653a7c81b328e46cb5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0080290000-be98ce43421dbf9007fa
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000i-0930030000-56ea204dcb077bc174c2
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-9000000000-4c2d1980f9e5e4b720a5
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-000i-0900000000-26b3c93bc9dea5a88032
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-1900000000-c367cd4c23aea0f74ecb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-000l-8900000000-91e35cdcc11d357119f0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0006-9100000000-4fb8f4ee2d35aa874617
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-014l-9000000000-7934b3037f39d69fc40a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-014i-9000000000-ad93e267446292bf247b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-014i-9000000000-4b8f9e13ed7adf0888c2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-014i-9000000000-f295755f591e27bb9f07
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-014i-9000000000-aee48a44f42a4b767844
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014i-9000000000-f5ebd92e86cf00f28cf1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9000000000-9a1ad1aa2d8fb621b608
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-1900000000-c367cd4c23aea0f74ecb
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000l-8900000000-f8c3fcf312f201115f52
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9100000000-1088187ef16c41e5fd58
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014l-9000000000-7934b3037f39d69fc40a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-9000000000-ad93e267446292bf247b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-9000000000-fba535f8767b852493f1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-26b3c93bc9dea5a88032
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000l-5900000000-835823cc21e116df8128
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-4b8f9e13ed7adf0888c2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-f295755f591e27bb9f07
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-aee48a44f42a4b767844
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-f5ebd92e86cf00f28cf1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9000000000-9a1ad1aa2d8fb621b608
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-2900000000-dc5e86acd04180efda0a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-2900000000-a8361951a2f702a217c7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-3f653a7c81b328e46cb5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0900000000-eff9983d19a7717c7d0d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-244706a8700c5b44660d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-d0a504875c449aaf6ffe
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-3900000000-fab0a17aa0e784d5c82a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aor-5900000000-ce345ab08c63e19beee2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xu-9500000000-8152dcf1e706d2c23f1d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9000000000-7f0e80ec0148815ece65
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-244706a8700c5b44660d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-3900000000-880690f56d392b31f14e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-091d50cdaaafbc0e67b1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xu-9400000000-f4ea0d34819de51a79f8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aor-6900000000-de88cc8d702d4a8505b6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9000000000-9336e786eca483e09b7a
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-121.381752
predicted
DarkChem Lite v0.1.0
[M-H]-121.328552
predicted
DarkChem Lite v0.1.0
[M-H]-121.471852
predicted
DarkChem Lite v0.1.0
[M-H]-122.39554
predicted
DeepCCS 1.0 (2019)
[M-H]-121.381752
predicted
DarkChem Lite v0.1.0
[M-H]-121.328552
predicted
DarkChem Lite v0.1.0
[M-H]-121.471852
predicted
DarkChem Lite v0.1.0
[M-H]-122.39554
predicted
DeepCCS 1.0 (2019)
[M+H]+122.382552
predicted
DarkChem Lite v0.1.0
[M+H]+122.442352
predicted
DarkChem Lite v0.1.0
[M+H]+122.364452
predicted
DarkChem Lite v0.1.0
[M+H]+124.537766
predicted
DeepCCS 1.0 (2019)
[M+H]+122.382552
predicted
DarkChem Lite v0.1.0
[M+H]+122.442352
predicted
DarkChem Lite v0.1.0
[M+H]+122.364452
predicted
DarkChem Lite v0.1.0
[M+H]+124.537766
predicted
DeepCCS 1.0 (2019)
[M+Na]+121.893052
predicted
DarkChem Lite v0.1.0
[M+Na]+121.948852
predicted
DarkChem Lite v0.1.0
[M+Na]+133.26193
predicted
DeepCCS 1.0 (2019)
[M+Na]+121.893052
predicted
DarkChem Lite v0.1.0
[M+Na]+121.948852
predicted
DarkChem Lite v0.1.0
[M+Na]+133.26193
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Purine-nucleoside phosphorylase activity
Specific Function
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine ...
Gene Name
PNP
Uniprot ID
P00491
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
32117.69 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Smith AG, Davies R, Dalton TP, Miller ML, Judah D, Riley J, Gant T, Nebert DW: Intrinsic hepatic phenotype associated with the Cyp1a2 gene as shown by cDNA expression microarray analysis of the knockout mouse. EHP Toxicogenomics. 2003 Jan;111(1T):45-51. [Article]
  2. Carrillo JA, Christensen M, Ramos SI, Alm C, Dahl ML, Benitez J, Bertilsson L: Evaluation of caffeine as an in vivo probe for CYP1A2 using measurements in plasma, saliva, and urine. Ther Drug Monit. 2000 Aug;22(4):409-17. [Article]
  3. Yin OQ, Lam SS, Lo CM, Chow MS: Rapid determination of five probe drugs and their metabolites in human plasma and urine by liquid chromatography/tandem mass spectrometry: application to cytochrome P450 phenotyping studies. Rapid Commun Mass Spectrom. 2004;18(23):2921-33. doi: 10.1002/rcm.1704. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52