Piritramide

Piritramide

Systematic (IUPAC) name
1-(3-cyano-3,3-diphenyl-propyl)-4-(1-piperidyl)piperidine-4-carboxamide
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.
Legal status	AU: S8 (Controlled) DE: Anlage III (Prescription only) US: Schedule I
Routes of administration	Oral, IM, IV
Pharmacokinetic data
Protein binding	95%
Metabolism	Liver
Biological half-life	4-10 hours (acute dosing), 17.4 hours (chronic dosing)
Identifiers
CAS Number	302-41-0 N
ATC code	N02AC03 (WHO)
PubChem	CID: 9331
ChemSpider	8967 Y
UNII	4RP92LYZ2F Y
KEGG	D07288 Y
ChEMBL	CHEMBL559288 Y
Chemical data
Formula	C27H34N4O
Molecular mass	430.585 g/mol
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?)  (verify)

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 against) 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.

History & Regulation

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. It presumably has abuse potential, and appears on the European black market on occasion and has a handful of street names including "Pierrette" and "P". LEXIS-NEXIS and other database searches do not show mentions of law enforcement contact with this drug in the United States. Piritramide is specifically exempted from the Canadian controlled-substances law, and its relative bezitramide is a Schedule II controlled substance in the US, although not used there as of 2014.

Synthesis

• DE 1238472 

See also

• Diphenoxylate
• Bezitramide
• Pipamperone