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QuickView for Meperidine (compound)

Summary
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PubChem

PubChem Compound 4058

PubChem Compound 4058

Name:	Meperidine
PubChem Compound ID:	4058
Description:	A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.
Molecular formula:	C₁₅H₂₁NO₂
Molecular weight:	247.333 g/mol
Synonyms:	S 140; Antidurol; Demerol; 1-Methyl-4-phenylisonipecotic acid ethyl ester hydrochloride; Chlorbycyclen; Dolenal; Dolosal; Meperidine hydrochloride; Centralgin; 1-Methyl-4-phenylisonipecotic acid, ethyl ester. show more » S 140; Antidurol; Demerol; 1-Methyl-4-phenylisonipecotic acid ethyl ester hydrochloride; Chlorbycyclen; Dolenal; Dolosal; Meperidine hydrochloride; Centralgin; 1-Methyl-4-phenylisonipecotic acid, ethyl ester; Dolaren; Isonipecaine hydrochloride; Ethyl-1-methyl-4-phenylisonipecotate hydrochloride; 1-Methyl-4-phenylpiperidine-4-carboxylic acid ethyl ester; Dolcontral; N-Methyl-4-phenyl-4-carbethoxypiperidine; Lydol; NSC400479; 4-Piperidinecarboxylic acid, 1-methyl-4-phenyl-, ethyl ester, hydrochloride; 50-13-5; HSDB 3116; DEA No. 9230; Doloneurine; NINDS_000983; Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate, hydrochloride; Alodan; Isonipecotic acid, 1-methyl-4-phenyl-, ethyl ester, hydrochloride; Petantin; Pethanol; 1-Methyl-4-phenyl-piperidin-4-carbon-saeure-aethylester [German]; Petidin; EINECS 200-329-1; Pethidinum [INN-Latin]; Dolantal; Isonipecotic acid, 1-methyl-4-phenyl-, ethyl ester; Dolestine; YIsonipecotic acid, 1-methyl-4-phenyl-, ethyl ester (8CI); Dolantin hydrochloride; Mepadin; Antiduol; Dolantin; KBio1_000983; Petydyna [Polish]; 1-Methyl-4-phenyl-4-piperidinecarboxylic acid ethyl ester; WY 554; Isonipecaine; Methyl phenylpiperidine carbonic acid ethyl ester; 1-Methyl-4-phenyl-4-carboethoxypiperidine hydrochloride; Chlorbicyclene; Operidine; Demerol hydrochloride; Piridosal; Pethidine; Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate; 4-Piperidinecarboxylic acid, 1-methyl-4-phenyl-, ethyl ester; DivK1c_000983; Meperidine; Dispadol; Ethyl 1-methyl-4-phenylisonipecotate; Dolenol; Petidina [INN-Spanish]; Pipersal; Ethyl 1-methyl-4-phenylpiperidyl-4-carboxylate hydrochloride; Pethidine hydrochloride; Pethidin; Algil; Pethidine chloride; Synelaudine; 4-Carbethoxy-1-methyl-4-phenylpiperidine; Pethidineter; Lidol; N-Methyl-4-phenyl-4-carbethoxypiperidine hydrochloride; Phetidine; Meperidol; Nemerol; Alodan (gerot); Dolin; Dolvanolendolatethyl 1-methyl-4-phenylpiperidine-4-carboxylate hydrochloride; Petantin hydrochloride; Dolargan; 57-42-1; 1-Methyl-4-carbethoxy-4-phenylpiperidine hydrochloride; Dolantol; C07128 show less «

DrugBank

Identification

Name:	Meperidine
Name (isomeric):	DB00454
Drug Type:	small molecule
Description:	A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.
Brand:	Dolantin, Piridosal, Nemerol, Demerol, Piperosal, Pethidine, Petydyna, Dispadol, Pethidin, Methyl phenylpiperidine carbonic acid ethyl ester, Lydol, Pipersal, Pethanol, Meperidine Hcl, Phetidine, Dolcontral, Centralgin, Operidine, Petantin, Lidol, Isonipecaine, Demarol, Pethidineter, Meperidol, Dolsin, Dolosal
Category:	Adjuvants, Anesthesia, Narcotics, Adjuvants, Analgesics, Opiate Agonists, Analgesics, Opioid
CAS number:	57-42-1

Pharmacology

Indication:	Used to control moderate to severe pain.
Pharmacology:	Meperidine is a synthetic opiate agonist belonging to the phenylpiperidine class. Meperidine may produce less smooth muscle spasm, constipation, and depression of the cough reflex than equivalent doses of morphine. The onset of action is lightly more rapid than with morphine, and the duration of action is slightly shorter. The chemical structure of... show more » Meperidine is a synthetic opiate agonist belonging to the phenylpiperidine class. Meperidine may produce less smooth muscle spasm, constipation, and depression of the cough reflex than equivalent doses of morphine. The onset of action is lightly more rapid than with morphine, and the duration of action is slightly shorter. The chemical structure of meperidine is similar to local anesthetics. Meperidine is recommended for relief of moderate to severe acute pain and has the unique ability to interrupt postoperative shivering and shaking chills induced by amphotericin B. Meperidine has also been used for intravenous regional anesthesia, peripheral nerve blocks and intraarticular, epidural and spinal analgesia. Meperidine is considered a second-line agent for the treatment of acute pain. show less «
Mechanism of Action:	Meperidine is primarily a kappa-opiate receptor agonist and also has local anesthetic effects. Meperidine has more affinity for the kappa-receptor than morphine. Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding... show more » Meperidine is primarily a kappa-opiate receptor agonist and also has local anesthetic effects. Meperidine has more affinity for the kappa-receptor than morphine. Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability. show less «
Absorption:	The oral bioavailability of meperidine in patients with normal hepatic function is 50-60% due to extensive first-pass metabolism. Bioavailability increases to 80-90% in patients with hepatic impairment (e.g. liver cirrhosis). Meperidine is less than half as effective when administered orally compared to parenteral administration. One study reported that 80-85% of the drug administered intramuscularly was absorbed within 6 hours of intragluteal injection in health adults; however, inter-individual variation and patient-specific variable appear to cause considerable variations in absorption upon IM injection.
Protein binding:	60-80% bound to plasma proteins, primarily albumin and α₁-acid glycoprotein. The presence of cirrhosis or active viral hepatitis does not appear to affect the extent of protein binding.
Biotransformation:	Meperidine is metabolized in the liver by hydrolysis to meperidinic acid followed by partial conjugation with glucuronic acid. Meperidine also undergoes N-demethylation to normeperidine, which then undergoes hydrolysis and partial conjugation. Normeperidine is about half as potent as meperidine, but it has twice the CNS stimulation effects.
Route of elimination:	Excreted in the urine. The proportion of drug that is excreted unchanged or as metabolites is dependent on pH. When urine pH is uncontrolled, 5-30% of the meperidine dose is excreted as normeperidine and approximately 5% is excreted unchanged. Meperidine and normeperidine are found in acidic urine, while the free and conjugated forms of meperidinic and normperidinic acids are found in alkaline urine.
Half Life:	Initial distribution phase (t_{1/2 α}) = 2-11 minutes; terminal elimination phase (t_{1/2 β}) = 3-5 hours. In patients with hepatic dysfunction (e.g. liver cirrhosis or active viral hepatitis) the t_{1/2 β} is prolonged to 7-11 hours.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals. Avoid alcohol.

Drug interaction:

Ritonavir	Ritonavir increases the levels of analgesic
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Isoniazid	Possible episodes of hypotension
Chlorpromazine	Increased sedation and hypotension
Trimipramine	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.

Targets

Kappa-type opioid receptor

Glutamate [NMDA] receptor subunit zeta-1

Glutamate [NMDA] receptor subunit epsilon-2

Glutamate [NMDA] receptor subunit epsilon-1

Glutamate [NMDA] receptor subunit epsilon-3

Glutamate [NMDA] receptor subunit epsilon-4

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2C19

Cytochrome P450 2B6

Cytochrome P450 2D6

Carriers

Alpha-1-acid glycoprotein 1