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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:51:54 UTC
Update Date2022-03-07 02:57:14 UTC
HMDB IDHMDB0041990
Secondary Accession Numbers
  • HMDB41990
Metabolite Identification
Common NamePiritramide
DescriptionPiritramide (R-3365, trade names Dipidolor, Piridolan, Pirium and others) is a synthetic opioid analgesic with a potency 0.65 to 0.75 times that of morphine. A common starting dose is 15 mg IV, equivalent to 10 mg of morphine hydrochloride. Piritramide is commonly used for the treatment of postoperative pain. Piritramide was discovered at Janssen Pharmaceutica in 1960 and is currently manufactured and distributed within continental Europe and some other places by Janssen-Cilag. Piritramide is a strong opioid and therefore is regulated much the same as morphine in all known jurisdictions. It was never introduced in the United States and is therefore a Schedule I/Narcotic controlled substance. It is listed under international treaties and other laws such as the German Betabungsmittelgesetz, the Austrian Suchtgiftmittelgesetz, the Opium Laws of various other European countries, Canadian controlled substances act, UK Misuse of Drugs Act of 1971, and equivalents elsewhere. Strangely enough, bezitramide, which is not currently marketed in the United States is a Schedule II/Narcotic controlled substance. Piritramide is also known as pirinitramide. Its closest chemical relatives amongst well-known drugs are diphenoxylate (Lomotil) and bezitramide (Burgodin). Piritramide is available in tablets and ampoules of sterile solution for injection by all routes, and is used in Patient Controlled Analgesia units. In addition to PCA, piritramide is most often used in post-operative situations and emergency departments; some of its properties would seem to lend it well to chronic pain control as well. It is one of the longer-lasting opioids and has a plasma half-life of 3 to 12 hours. Piritramide tends to cause less respiratory depression than morphine and can take a while to have full effect especially if taken by mouth.
Structure
Data?1563863720
Synonyms
ValueSource
DipidolorKegg
PirinitramideHMDB
DipydolorHMDB
Janssen brand OF pirinitramideHMDB
PiritramidHMDB
Chemical FormulaC27H34N4O
Average Molecular Weight430.5851
Monoisotopic Molecular Weight430.27326173
IUPAC Name1-(3-cyano-3,3-diphenylpropyl)-4-(piperidin-1-yl)piperidine-4-carboximidic acid
Traditional Namepiritramid
CAS Registry Number302-41-0
SMILES
OC(=N)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)N1CCCCC1
InChI Identifier
InChI=1S/C27H34N4O/c28-22-26(23-10-4-1-5-11-23,24-12-6-2-7-13-24)14-19-30-20-15-27(16-21-30,25(29)32)31-17-8-3-9-18-31/h1-2,4-7,10-13H,3,8-9,14-21H2,(H2,29,32)
InChI KeyIHEHEFLXQFOQJO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylacetonitriles. These are cyclic aromatic compounds containing a diphenylacetonitrile moiety, which consists of a diphenylmethane linked to and acetonitrile to form 2,2-diphenylacetonitrile.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylacetonitriles
Direct ParentDiphenylacetonitriles
Alternative Parents
Substituents
  • Diphenylacetonitrile
  • Diphenylmethane
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Piperidinecarboxamide
  • 4-aminopiperidine
  • Aralkylamine
  • Piperidine
  • Amino acid or derivatives
  • Carboxamide group
  • Primary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Nitrile
  • Carbonitrile
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point149.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.91Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP3.58ALOGPS
logP1.45ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.71ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.35 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity150.74 m³·mol⁻¹ChemAxon
Polarizability49.27 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.30731661259
DarkChem[M-H]-196.56131661259
DeepCCS[M+H]+205.71830932474
DeepCCS[M-H]-203.3630932474
DeepCCS[M-2H]-237.12930932474
DeepCCS[M+Na]+212.35730932474
AllCCS[M+H]+204.932859911
AllCCS[M+H-H2O]+202.732859911
AllCCS[M+NH4]+206.832859911
AllCCS[M+Na]+207.432859911
AllCCS[M-H]-201.432859911
AllCCS[M+Na-2H]-202.332859911
AllCCS[M+HCOO]-203.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PiritramideOC(=N)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)N1CCCCC12928.2Standard polar33892256
PiritramideOC(=N)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)N1CCCCC13406.3Standard non polar33892256
PiritramideOC(=N)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC1)N1CCCCC13428.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Piritramide,1TMS,isomer #1C[Si](C)(C)OC(=N)C1(N2CCCCC2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC13360.1Semi standard non polar33892256
Piritramide,1TMS,isomer #2C[Si](C)(C)N=C(O)C1(N2CCCCC2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC13408.1Semi standard non polar33892256
Piritramide,2TMS,isomer #1C[Si](C)(C)N=C(O[Si](C)(C)C)C1(N2CCCCC2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC13387.2Semi standard non polar33892256
Piritramide,2TMS,isomer #1C[Si](C)(C)N=C(O[Si](C)(C)C)C1(N2CCCCC2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC13218.5Standard non polar33892256
Piritramide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=N)C1(N2CCCCC2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC13595.1Semi standard non polar33892256
Piritramide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(O)C1(N2CCCCC2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC13665.1Semi standard non polar33892256
Piritramide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)C1(N2CCCCC2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC13837.9Semi standard non polar33892256
Piritramide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(O[Si](C)(C)C(C)(C)C)C1(N2CCCCC2)CCN(CCC(C#N)(C2=CC=CC=C2)C2=CC=CC=C2)CC13644.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Piritramide GC-MS (Non-derivatized) - 70eV, Positivesplash10-008i-4967000000-98351d91fa44f62e846d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piritramide GC-MS (1 TMS) - 70eV, Positivesplash10-000i-1229100000-92e9b29f615b196ec03c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piritramide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 10V, Negative-QTOFsplash10-004i-0001900000-10fa748e1d24c9cc73482017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 20V, Negative-QTOFsplash10-01t9-2554900000-4b8b465687eec62bf59c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 40V, Negative-QTOFsplash10-016u-2910000000-5437b6b34eb661836bf82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 10V, Negative-QTOFsplash10-004i-0000900000-8a3e205880265040e5582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 20V, Negative-QTOFsplash10-004i-1006900000-a773f591f1b76bda84b02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 40V, Negative-QTOFsplash10-014l-2692100000-d2863817839d70606d7d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 10V, Positive-QTOFsplash10-01q9-0013900000-6c90517c14dc6045ba992017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 20V, Positive-QTOFsplash10-00ri-0219100000-558ea112c519bb7157bc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 40V, Positive-QTOFsplash10-00xr-2963000000-aa8c9a18c6dd4520c39e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 10V, Positive-QTOFsplash10-001i-0002900000-9d7a0fb697bb237c7da72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 20V, Positive-QTOFsplash10-00kb-0229000000-35840be2b88cda999fd32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piritramide 40V, Positive-QTOFsplash10-060u-0925100000-3b5332db3dad544feba22021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12492
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8967
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiritramide
METLIN IDNot Available
PubChem Compound9331
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available