Raltegravir (CED0003162)

Record Information
Version1.0
Creation Date2016-05-22 06:36:35 UTC
Update Date2026-08-20 05:27:05 UTC
Accession NumberCHEM019895
Identification
Common NameRaltegravir
ClassSmall Molecule
Description
Raltegravir is an organic compound with the formula C20H21FN6O5 and an average molecular weight of 444.42 g/mol. Raltegravir belongs to the pyrimidines and pyrimidine derivatives, a subclass of diazines within the organic compounds. It is categorized as an organoheterocyclic compound. The compound is found in or released from three recorded sources: food, food processing & cookware (preparation of malt), electrical & electronic equipment (video games), and healthcare, pharmaceuticals & veterinary products (antivirals). The recorded route of exposure is oral. Raltegravir acts on two recorded protein targets, functioning as an inhibitor/modulator of the Gag-Pol polyprotein and targeting the Gag-Pol polyprotein (gag-pol).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MK 0518ChEBI
MK-0518ChEBI
MK0518ChEBI
RaltegravirumChEBI
IsentressMeSH, HMDB
Potassium, raltegravirMeSH, HMDB
Raltegravir potassiumMeSH, HMDB
N-[(4-Fluorophenyl)methyl]-5-hydroxy-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazol-2-yl)formamido]propan-2-yl}-6-oxo-1,6-dihydropyrimidine-4-carboximidateGenerator, HMDB
Chemical FormulaC20H21FN6O5
Average Molecular Mass444.416 g/mol
Monoisotopic Mass444.156 g/mol
CAS Registry Number518048-05-0
IUPAC NameN-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-2-{2-[(5-methyl-1,3,4-oxadiazol-2-yl)formamido]propan-2-yl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide
Traditional Nameraltegravir
SMILESCN1C(=O)C(O)=C(N=C1C(C)(C)NC(=O)C1=NN=C(C)O1)C(=O)NCC1=CC=C(F)C=C1
InChI IdentifierInChI=1S/C20H21FN6O5/c1-10-25-26-17(32-10)16(30)24-20(2,3)19-23-13(14(28)18(31)27(19)4)15(29)22-9-11-5-7-12(21)8-6-11/h5-8,28H,9H2,1-4H3,(H,22,29)(H,24,30)
InChI KeyCZFFBEXEKNGXKS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidinecarboxylic acids and derivatives. Pyrimidinecarboxylic acids and derivatives are compounds containing a pyrimidine ring which bears a carboxylic acid group (or a derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidinecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Pyrimidine-6-carboxylic acid or derivatives
  • 2-heteroaryl carboxamide
  • Fluorobenzene
  • Hydroxypyrimidine
  • Halobenzene
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Hydropyrimidine
  • Benzenoid
  • 1,3,4-oxadiazole
  • Azole
  • Heteroaromatic compound
  • Oxadiazole
  • Vinylogous acid
  • Lactam
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP-0.39ChemAxon
pKa (Strongest Acidic)5.62ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area150.02 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.59 m³·mol⁻¹ChemAxon
Polarizability42.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4l-5901100000-402e9e529e248f508e9fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0011900000-1f750fd89ed368c2519aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ot-0417900000-7f0f52f17ac409473482Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0011900000-1f750fd89ed368c2519aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0101-0901400000-9b8042c6c461dd4fad72Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-f00a70c9dfa901d921acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-5900000000-465f856a37914d77e3fbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-6006900000-c7ca4f296a13a927013cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ac3-2449300000-ac0de1977dc124fe404dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00c3-7694000000-1866c94f65b8fe9ccb57Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002f-6009000000-d1f29a25fb262468cda8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9121000000-3bd27eb556983ed36c17Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6u-9100000000-e5ee0f1c1ddd84c6fe41Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-1009000000-30c3a690fbd89dd9372bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9002000000-7b142c09660037254c26Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-25e5315d765107a9843aNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3758.0Log mg/kg[2100:6700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
351AntiviralsHealthcare, pharmaceuticals & veterinary productsNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
Pathways
3 pathways
Raltegravir Action Pathway
Raltegravir Action Pathway
Raltegravir Drug Metabolism
Raltegravir Drug Metabolism
Raltegravir Drug Metabolism Action Pathway
Raltegravir Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureGag-Pol polyproteinQ7ZJM1Human immunodeficiency virus 1Predicted (SEA)2.02408
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)4.35956
C-C chemokine receptor type 1 structureClick to view 3D structureC-C chemokine receptor type 1P32246HumansPredicted (SEA)4.12601
Click to view 3D structureIntegraseT1QYY3Human immunodeficiency virus 1Predicted (SEA)3.34752
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1878.81
DNA polymerase alpha catalytic subunit structureClick to view 3D structureDNA polymerase alpha catalytic subunitP09884HumansPredicted (SEA)2.95827
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)2240.97
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)2602.66
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)1621.52
DNA polymerase beta structureClick to view 3D structureDNA polymerase betaP06746HumansPredicted (SEA)6.92858
Click to view 3D structureRNA-directed RNA polymeraseO39930Hepatitis C VirusPredicted (SEA)28.1036
Click to view 3D structureNicotinamide phosphoribosyltransferaseQ80Z29Rattus norvegicusPredicted (SEA)36.4334
Click to view 3D structureTripartite terminase subunit 3P16732Human betaherpesvirus 5Predicted (SEA)11.0546
3',5'-cyclic-AMP phosphodiesterase 4B structureClick to view 3D structure3',5'-cyclic-AMP phosphodiesterase 4BQ07343HumansPredicted (SEA)200.851
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)3862.96
Neutrophil collagenase structureClick to view 3D structureNeutrophil collagenaseP22894HumansPredicted (SEA)708.584
Collagenase 3 structureClick to view 3D structureCollagenase 3P45452HumansPredicted (SEA)938.317
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)2958.27
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)1349.67
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)1346.71
Click to view 3D structureDual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11AQ9HCR9HumansPredicted (SEA)186.137
Macrophage metalloelastase structureClick to view 3D structureMacrophage metalloelastaseP39900HumansPredicted (SEA)903.518
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)1220.05
Click to view 3D structureInward rectifier potassium channel 2P35561Mus musculusPredicted (SEA)165.819
Stromelysin-1 structureClick to view 3D structureStromelysin-1P08254HumansPredicted (SEA)1073.23
Concentrations
Not Available
External Links
DrugBank IDDB06817
HMDB IDHMDB0257100
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRaltegravir
Chemspider ID16445111
ChEBI ID82960
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17133211
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17428043
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17569171
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18095922
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18174972
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20118915
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21030679
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24097843
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24145879
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24277175
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24397848
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24872134
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24962031
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=25114168
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25162818
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25162819
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=31525573
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=32448902
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=32661003
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=32675580
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=32728708
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=32925360
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=33099638
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=33136758
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=33163587
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=33369217
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=33493297
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=33527213
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=33667407
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=33670655
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=33779719
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=33831906
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=33993302
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=PMC6809206