Prodine (trade names Prisilidine and Nisentil) is an
opioid
Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioi ...
analgesic
An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...
that is an
analog
Analog or analogue may refer to:
Computing and electronics
* Analog signal, in which information is encoded in a continuous variable
** Analog device, an apparatus that operates on analog signals
*** Analog electronics, circuits which use analo ...
of
pethidine
Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Ei ...
(meperidine). It was developed in Germany in the late 1940s.
There are two
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
...
s of the trans form of prodine, alphaprodine and betaprodine. Both exhibit optical isomerism and alphaprodine and betaprodine are
racemate
In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...
s.
Alphaprodine is closely related to
desomorphine
Desomorphine is a semi-synthetic opioid commercialized by Roche, with powerful, fast-acting effects, such as sedation and analgesia. It was first discovered and patented by a German team working for Knoll in 1920 but was not generally recogni ...
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
Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and dan ...
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.[
Testing in rats showed alphaprodine to be 97% the strength of ]morphine
Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies ('' Papaver somniferum''). It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. Ther ...
via the subcutaneous Subcutaneous may refer to:
* Subcutaneous injection
* Subcutaneous tissue
The subcutaneous tissue (), also called the hypodermis, hypoderm (), subcutis, superficial fascia, is the lowermost layer of the integumentary system in vertebrates. The ...
route and 140% the strength of oral methadone
Methadone, sold under the brand names Dolophine and Methadose among others, is a synthetic opioid agonist used for chronic pain and also for opioid dependence. It is used to treat chronic pain, and it is also used to treat addiction to hero ...
.[ Betaprodine was 550% stronger than morphine SC, the laevorotatory cis isomer was 350% stronger, and the dextrorotatory cis isomer was 790% stronger.][ Betaprodine taken orally was 420% stronger than oral methadone, the cis form was 390% stronger for the laevorotatory and 505% stronger for the dextrorotatory isomers.][
Alphaprodine was sold under several brand names, mainly Nisentil and Prisilidine. It was most commonly used for pain relief during ]childbirth
Childbirth, also known as labour and delivery, is the ending of pregnancy where one or more babies exits the internal environment of the mother via vaginal delivery or caesarean section. In 2019, there were about 140.11 million births glo ...
and dentistry
Dentistry, also known as dental medicine and oral medicine, is the branch of medicine focused on the teeth, gums, and mouth. It consists of the study, diagnosis, prevention, management, and treatment of diseases, disorders, and conditions ...
, as well as for some minor surgical procedures. Alphaprodine has a duration of action of 1 to 2 hours, and 40 to 60 mg is equivalent to 10 mg of subcutaneous morphine.
Prodine has broadly similar effects to other opioids, producing analgesia
Pain management is an aspect of medicine and health care involving relief of pain (pain relief, analgesia, pain control) in various dimensions, from acute and simple to chronic and challenging. Most physicians and other health professionals ...
, sedation
Sedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure. Examples of drugs which can be used for sedation include isoflurane, diethyl ethe ...
and euphoria. Side effects can include excessive itching
Itch (also known as pruritus) is a sensation that causes the desire or reflex to scratch. Itch has resisted many attempts to be classified as any one type of sensory experience. Itch has many similarities to pain, and while both are unpleasant ...
, nausea
Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...
, vomiting
Vomiting (also known as emesis and throwing up) is the involuntary, forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose.
Vomiting can be the result of ailments like food poisoning, gastroenteri ...
and potentially serious respiratory depression
Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide ( hypercapn ...
which can lead to life-threatening respiratory arrest
Respiratory arrest is a sickness caused by apnea (cessation of breathing) or respiratory dysfunction severe enough it will not sustain the body (such as agonal breathing). Prolonged apnea refers to a patient who has stopped breathing for a long pe ...
. Respiratory depression can be a problem with alphaprodine even at normal therapeutic doses. Unlike pethidine, prodine does not produce toxic metabolites and is therefore more suitable for high-dose therapy.
Regulation
Alphaprodine has a DEA ACSCN of 9010 and 2013 manufacturing quota of 3 grams; betaprodine has an ACSCN of 9611 and a 2 grams quota.
See also
* Trimeperidine
Trimeperidine (Promedol) is an opioid analgesic that is an analogue of prodine. It was developed in the early 1950s in the USSR during research into the related drug pethidine.
Trimeperidine has four structural isomers, of which two are act ...
References
{{Opioidergics
Mu-opioid receptor agonists
Opioids
4-Phenylpiperidines
Propionate esters