Piritramide

Piritramide
Clinical data


Trade names	Dipidolor
AHFS/Drugs.com	International Drug Names
Pregnancy category	No teratogenic effects in preclinical studies; but, as with other opioids it may cause reversible adverse effects in the newborn.
Routes of administration	Oral, IM, IV
ATC code	N02AC03 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Prescription only) US: Schedule I
Pharmacokinetic data
Protein binding	95%
Metabolism	Liver
Biological half-life	4-10 hours (acute dosing), 17.4 hours (chronic dosing)
Identifiers
IUPAC name 1-(3-Cyano-3,3-diphenyl-propyl)-4-(1-piperidyl)piperidine-4-carboxamide
CAS Number	302-41-0^N
PubChem CID	9331
ChemSpider	8967^Y
UNII	4RP92LYZ2F
KEGG	D07288^Y
ChEMBL	CHEMBL559288^Y
ECHA InfoCard	100.005.569
Chemical and physical data
Formula	C₂₇H₃₄N₄O
Molar mass	430.585 g/mol
3D model (Jmol)	Interactive image
SMILES N#CC(C1=CC=CC=C1)(CCN2CCC(N3CCCCC3)(CC2)C(N)=O)C4=CC=CC=C4
InChI 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)^Y Key:IHEHEFLXQFOQJO-UHFFFAOYSA-N^Y
^NY (what is this?)

Piritramide (R-3365, trade names Dipidolor, Piridolan, Pirium and others) is a synthetic opioid analgesic (narcotic painkiller) that is marketed in certain European countries including: Austria, Belgium, Czech Republic, Germany and the Netherlands. It comes in free form, is about 0.75x times as potent as morphine and is given parenterally (by injection) for the treatment of severe pain. Nausea, vomiting, respiratory depression and constipation are believed to be less frequent with piritramide than with morphine (which is the gold standard opioid against which other opioids are compared and contrasted) and it produces more rapid-onset analgesia (pain relief) when compared to morphine and pethidine, after intravenous administration the onset of analgesia is as little as 1–2 minutes, which may be related to its great lipophilicity. The analgesic and sedative effects of piritramide are believed to be potentiated with phenothiazines and its emetic (nausea/vomiting-inducing) effects are suppressed. The volume of distribution is 0.7-1 L/kg after a single dose, 4.7-6 L/kg after steady-state concentrations are achieved and up to 11.1 L/kg after prolonged dosing.

Piritramide was developed and patented in Belgium, at Janssen, in 1960. It is part of an eponymous two-member class of opioids in clinical use with the other being bezitramide (Burgodin). The closest chemical and structural relatives of piritramide in clinical use include the diphenoxylate family, fentanyl (both Janssen discoveries) and somewhat more distantly alphaprodine.

Not being in clinical use in the United States, it is a Schedule I Narcotic controlled substance with a DEA ACSCN of 9642 and manufacturing quota of zero.

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