Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C15H23NO |
| Molecular Weight | 233.3492 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1(CCCCN(C)C1)C2=CC(O)=CC=C2
InChI
InChIKey=JLICHNCFTLFZJN-UHFFFAOYSA-N
InChI=1S/C15H23NO/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13/h6-8,11,17H,3-5,9-10,12H2,1-2H3
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.shijiebiaopin.net/upload/product/201222217302623.PDF | https://www.drugs.com/uk/meptid-tablets-200mg-leaflet.html
Curator's Comment: description was created based on several sources, including:
http://www.shijiebiaopin.net/upload/product/201222217302623.PDF | https://www.drugs.com/uk/meptid-tablets-200mg-leaflet.html
Meptazinol is a unique opioid analgesic. Binding studies suggest a relative selectivity for mu-1 opioid receptor sites. Meptid is indicated for the treatment of moderate to severe pain, including post-operative pain, obstetric pain and the pain of renal colic. The most commonly reported adverse reactions after treatment with meptazinol are nausea, vomiting, dizziness, diarrhoea and increased sweating, constipation, abdominal pain, rash, vertigo, headache, drowsiness, somnolence and dyspepsia.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P81908 Gene ID: NA Gene Symbol: BCHE Target Organism: Equus caballus (Horse) |
3.6 µM [IC50] | ||
Target ID: CHEMBL3198 |
0.4 µM [IC50] | ||
| 8.0 nM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Meptid Approved UseThe drug is indicated for the treatment of moderate to severe pain, including post-operative pain, obstetric pain and the pain of renal colic. |
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| Primary | Meptid Approved UseThe drug is indicated for the treatment of moderate to severe pain, including post-operative pain, obstetric pain and the pain of renal colic. |
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| Primary | Meptid Approved UseThe drug is indicated for the treatment of moderate to severe pain, including post-operative pain, obstetric pain and the pain of renal colic. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
41.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6499901/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
55.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6499901/ |
200 mg 4 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
55.6 ng/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
53.5 ng/mL |
200 mg multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
22.91 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
55.11 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
118.07 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
202 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6499901/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
243 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6499901/ |
200 mg 4 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
156 ng × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
143 ng × h/mL |
200 mg multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
322.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6617729/ |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
316.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6617729/ |
25 mg single, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
216.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6617729/ |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
89.56 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
164.75 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
418.28 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6499901/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4.97 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6499901/ |
200 mg 4 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.94 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2.13 h |
200 mg multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2.93 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6617729/ |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6617729/ |
25 mg single, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2.06 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6617729/ |
25 mg single, intravenous dose: 25 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2.44 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19819764/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEPTAZINOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
66.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6499901/ |
200 mg dose: 200 mg route of administration: experiment type: co-administered: |
MEPTAZINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
400 mg single, oral Highest studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
10 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Respiratory arrest... AEs leading to discontinuation/dose reduction: Respiratory arrest Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Respiratory arrest | Disc. AE | 10 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Patient-controlled intravenous analgesia with remifentanil as an alternative to epidural analgesia during labor: case series and discussion of medicolegal aspects]. | 2010-08 |
|
| In situ and in vivo study of nasal absorption of paeonol in rats. | 2010 |
|
| Liquid chromatography/positive ion electrospray tandem mass spectrometry method for the quantification of hydrochloride meptazinol in human plasma: application to a pharmacokinetic study. | 2009-11-15 |
|
| The crystal structure of a complex of acetylcholinesterase with a bis-(-)-nor-meptazinol derivative reveals disruption of the catalytic triad. | 2009-04-23 |
|
| 1-Methyl-3-(3-oxocyclo-hex-1-en-yl)azepan-2-one. | 2008-09-13 |
|
| Bis-(-)-nor-meptazinols as novel nanomolar cholinesterase inhibitors with high inhibitory potency on amyloid-beta aggregation. | 2008-04-10 |
|
| (3S,4S)-3-Ethyl-4-hydr-oxy-3-(3-methoxy-phen-yl)-1-methyl-azepan-1-ium d-tartrate dihydrate. | 2008-04-02 |
|
| Prescribing intramuscular opioids for labour analgesia in consultant-led maternity units: a survey of UK practice. | 2008-01 |
|
| WITHDRAWN: Types of intra-muscular opioids for maternal pain relief in labour. | 2007-07-18 |
|
| Reflex activity caused by laryngoscopy and intubation is obtunded differently by meptazinol, nalbuphine and fentanyl. | 2007-01 |
|
| Conformational re-analysis of (+)-meptazinol: an opioid with mixed analgesic pharmacophores. | 2006-09 |
|
| Investigation of the binding mode of (-)-meptazinol and bis-meptazinol derivatives on acetylcholinesterase using a molecular docking method. | 2006-03 |
|
| Design, synthesis, and bioavailability evaluation of coumarin-based prodrug of meptazinol. | 2005-11-15 |
|
| Pharmacokinetic behavior in plasma, cerebrospinal fluid and cerebral cortex after intranasal administration of hydrochloride meptazinol. | 2005-09-30 |
|
| Enhancement of systemic and CNS delivery of meptazinol hydrochloride by intranasal administration to rats. | 2005-08 |
|
| Synthesis and relative bioavailability of meptazinol benzoyl esters as prodrugs. | 2005-05-16 |
|
| Structural comparisons of meptazinol with opioid analgesics. | 2005-03 |
|
| A novel method to calculate the extent and amount of drug transported into CSF after intranasal administration. | 2005-01-31 |
|
| Antinociceptive effects of meptazinol and its isomers on carrageenan-induced thermal hyperalgesia in rats. | 2004-06-25 |
|
| Inhibitory effect of intrathecal meptazinol on carrageenan-induced thermal hyperalgesia in rats. | 2004-02-06 |
|
| Lack of sensitization during place conditioning in rats is consistent with the low abuse potential of tramadol. | 2002-08-23 |
|
| Comparison of the cardiovascular effects of meptazinol and naloxone following haemorrhagic shock in rats and cats. | 1985-09 |
|
| Intramuscular on demand analgesia: double blind controlled trial of pethidine, buprenorphine, morphine, and meptazinol. | 1983-02-26 |
Patents
Sample Use Guides
Oral: One tablet (200 mg), with a glass of water, every four hours.
Intramuscular: 75-100mg. The injection may be repeated 2-4 hourly as required. For obstetric pain a dose of 100-150mg should be used according to weight. This dose should approximate 2mg/kg.
Intravenous: 50-100mg by slow intravenous injection. The injection may be repeated 2-4 hourly as required. If vomiting occurs, a suitable antiemetic should be given.
Route of Administration:
Other
| Name | Type | Language | ||
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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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WHO-VATC |
QN02AX05
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WHO-ATC |
N02AX05
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LIVERTOX |
602
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NCI_THESAURUS |
C67413
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54340-58-8
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MEPTAZINOL
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1706
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SUB08761MIG
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DTXSID6048543
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DB13478
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m7200
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100000081482
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D008621
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CHEMBL314437
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3605
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C87360
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259-109-9
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6761
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18Y7S5JKZD
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41049
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
