Structure via PubChem · Public domain (PubChem)
prodine
Sign in to saveAlso known as (3RS,4RS)-1,3-dimethyl-4-phenyl-4-piperidinyl propionate
Prodine (trade names Prisilidine and Nisentil) is an opioid analgesic that is an analog of pethidine (meperidine). It was developed in Germany in the late 1940s.
In the Vinony graph
Within Vinony's link graph, prodine is referenced by 831 other articles, and connects out to optical rotation, (+)-catechin and butorphanol.
Vinony files it under 4-Phenylpiperidines, Chemical articles with multiple CAS registry numbers and Chemical pages without DrugBank identifier.
Its subject is documented across 7 Wikipedia language editions.
Chemical data
- Formula
- C16H23NO2
- Molecular weight
- 261.36 g/mol
- IUPAC name
- (1,3-dimethyl-4-phenylpiperidin-4-yl) propanoate
- SMILES
- CCC(=O)OC1(CCN(CC1C)C)C2=CC=CC=C2
- InChIKey
- UVAZQQHAVMNMHE-UHFFFAOYSA-N
- XLogP
- 2.8
- Polar surface area
- 29.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 261.172879
Show 4 more facts
- subject has role
- analgesic
- chemical formula
- C₁₆H₂₃NO₂
- canonical SMILES
- CCC(=O)OC1(CCN(CC1C)C)C2=CC=CC=C2
- Commons category
- Prodine
Sources (1)
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- Regulation
- See also
- References
Prodine (trade names Prisilidine and Nisentil) is an opioid analgesic that is an analog of pethidine (meperidine). It was developed in Germany in the late 1940s.
There are two isomers of the trans form of prodine, alphaprodine and betaprodine. Both exhibit optical isomerism and alphaprodine and betaprodine are racemates. Alphaprodine is closely related to desomorphine in steric configuration. The cis form also has active isomers but none are used in medicine. Betaprodine is around five times more potent than alphaprodine but is metabolized more rapidly, and only alphaprodine was developed for medicinal use. It has similar activity to pethidine, but with a more rapid onset and shorter duration of effects. Betaprodine produces more euphoria and side effects than alphaprodine at all dose levels, and it was found that 5 to 10 mg of betaprodine is equivalent to 25 to 40 mg of alphaprodine.
Excerpted from Wikipedia’s “prodine” article, available under the CC BY-SA 4.0 licence.