Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H27NO4 |
Molecular Weight | 357.4434 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12OC3=C4C(C[C@H]5N(CC6CCC6)CC[C@@]14[C@@]5(O)CC[C@@H]2O)=CC=C3O
InChI
InChIKey=NETZHAKZCGBWSS-CEDHKZHLSA-N
InChI=1S/C21H27NO4/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12/h4-5,12,15-16,19,23-25H,1-3,6-11H2/t15-,16+,19-,20-,21+/m0/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00844 | https://www.drugs.com/cdi/nalbuphine.html | http://reference.medscape.com/drug/nalbuphine-343329
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00844 | https://www.drugs.com/cdi/nalbuphine.html | http://reference.medscape.com/drug/nalbuphine-343329
Nalbuphine is a semi-synthetic opioid agonist-antagonist used commercially as an analgesic under a variety of trade names, including Nubain and Manfine. Nalbuphine is an agonist at kappa opioid receptors and an antagonist at mu opioid receptors. Nalbuphine analgesic potency is essentially equivalent to that of morphine on a milligram basis up to a dosage of approximately 30 mg. The opioid antagonist activity of Nalbuphine is one-fourth as potent as nalorphine and 10 times that of pentazocine. Nalbuphine is indicated for the management of pain severe enough to require an opioid analgesic and for which alternative treatments are inadequate. Nalbuphine can also be used as a supplement to balanced anesthesia, for preoperative and postoperative analgesia, and for obstetrical analgesia during labor and delivery. The onset of action of Nalbuphine occurs within 2 to 3 minutes after intravenous administration, and in less than 15 minutes following subcutaneous or intramuscular injection. The plasma half-life of nalbuphine is 5 hours, and in clinical studies, the duration of analgesic activity has been reported to range from 3 to 6 hours. Like pure µ-opioids, the mixed agonist-antagonist opioid class of drugs can cause side effects with initial administration of the drug but which lessen over time (“tolerance”). This is particularly true for the side effects of nausea, sedation and cognitive symptoms. These side effects can in many instances be ameliorated or avoided at the time of drug initiation by titrating the drug from a tolerable starting dose up to the desired therapeutic dose. An important difference between nalbuphine and the pure mu-opioid analgesic drugs is the “ceiling effect” on respiration. Respiratory depression is a potentially fatal side effect from the use of pure mu opioids. Nalbuphine has limited ability to depress respiratory function.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22204910 |
65.0 nM [EC50] | ||
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17407276 |
110.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | NUBAIN Approved UseIndications and Usage Nalbuphine hydrochloride is indicated for the relief of moderate to severe pain. Nalbuphine hydrochloride can also be used as a supplement to balanced anesthesia, for preoperative and postoperative analgesia, and for obstetrical analgesia during labor and delivery. Launch Date2.95574405E11 |
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Primary | NUBAIN Approved UseIndications and Usage Nalbuphine hydrochloride is indicated for the relief of moderate to severe pain. Nalbuphine hydrochloride can also be used as a supplement to balanced anesthesia, for preoperative and postoperative analgesia, and for obstetrical analgesia during labor and delivery. Launch Date2.95574405E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.3 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2758732 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
24.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9107559 |
0.3 mg/kg single, rectal dose: 0.3 mg/kg route of administration: Rectal experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
139.9 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2758732 |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
25.8 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2758732 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
58.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9107559 |
0.3 mg/kg single, rectal dose: 0.3 mg/kg route of administration: Rectal experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.28 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2758732 |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2758732 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9107559 |
0.3 mg/kg single, rectal dose: 0.3 mg/kg route of administration: Rectal experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2758732 |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALBUPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
40 mg single, intravenous Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: |
healthy, 37 years n = 1 Health Status: healthy Age Group: 37 years Sex: F Population Size: 1 Sources: |
Other AEs: Pulmonary edema... |
10 mg single, intramuscular Recommended Dose: 10 mg Route: intramuscular Route: single Dose: 10 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression... Other AEs: Respiratory depression (serious|grade 5) Sources: |
10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression... Other AEs: Respiratory depression (serious|grade 5) Sources: |
10 mg single, subcutaneous Recommended Dose: 10 mg Route: subcutaneous Route: single Dose: 10 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression... Other AEs: Respiratory depression (serious|grade 5) Sources: |
160 mg multiple, intramuscular (total) Studied dose Dose: 160 mg Route: intramuscular Route: multiple Dose: 160 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
160 mg multiple, intravenous (total) Studied dose Dose: 160 mg Route: intravenous Route: multiple Dose: 160 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
160 mg multiple, subcutaneous (total) Studied dose Dose: 160 mg Route: subcutaneous Route: multiple Dose: 160 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
15 mg single, oral |
unhealthy n = 39 |
Other AEs: Dizzy, Sleepy... Other AEs: Dizzy (1 patient) Sources: Sleepy (4 patients) Headache (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Pulmonary edema | 1 patient | 40 mg single, intravenous Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: |
healthy, 37 years n = 1 Health Status: healthy Age Group: 37 years Sex: F Population Size: 1 Sources: |
Respiratory depression | serious|grade 5 | 10 mg single, intramuscular Recommended Dose: 10 mg Route: intramuscular Route: single Dose: 10 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Respiratory depression | serious|grade 5 | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Respiratory depression | serious|grade 5 | 10 mg single, subcutaneous Recommended Dose: 10 mg Route: subcutaneous Route: single Dose: 10 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Dizzy | 1 patient | 15 mg single, oral |
unhealthy n = 39 |
Headache | 1 patient | 15 mg single, oral |
unhealthy n = 39 |
Sleepy | 4 patients | 15 mg single, oral |
unhealthy n = 39 |
PubMed
Title | Date | PubMed |
---|---|---|
The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. | 1999 Nov |
|
Transdermal delivery of nalbuphine and nalbuphine pivalate from hydrogels by passive diffusion and iontophoresis. | 2001 |
|
Sex differences in opioid antinociception: kappa and 'mixed action' agonists. | 2001 Aug 1 |
|
Nalbuphine versus propofol for treatment of intrathecal morphine-induced pruritus after cesarean delivery. | 2001 Jul |
|
Pharmacological control of opioid-induced pruritus: a quantitative systematic review of randomized trials. | 2001 Jun |
|
Intravesical morphine analgesia is not effective after bladder surgery in children: results of a randomied double-blind study. | 2002 Aug |
|
Investigation of 4,5-epoxymorphinan degradation during analysis by HPLC. | 2002 Aug 22 |
|
Minidose lidocaine-fentanyl spinal anesthesia in ambulatory surgery: prophylactic nalbuphine versus nalbuphine plus droperidol. | 2002 Dec |
|
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials. | 2002 Feb |
|
Effects of gonadal steroid hormone treatments on opioid antinociception in ovariectomized rhesus monkeys. | 2002 Jan |
|
Differences in systemic opioid use do not explain increased fever incidence in parturients receiving epidural analgesia. | 2002 Jul |
|
Dexamethasone 8 mg in combination with ondansetron 4 mg appears to be the optimal dose for the prevention of nausea and vomiting after laparoscopic cholecystectomy. | 2002 Nov |
|
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors. | 2002 Nov 18 |
|
Comparison of the discriminative and neuroendocrine effects of centrally penetrating kappa-opioid agonists in rhesus monkeys. | 2002 Oct |
|
Sex-related differences in mechanical nociception and antinociception produced by mu- and kappa-opioid receptor agonists in rats. | 2002 Oct 4 |
|
Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence. | 2003 Aug |
|
An optimal dose study of intrathecal morphine in gynecological patients. | 2003 Jun |
|
Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor. | 2003 May |
|
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans. | 2003 Nov 6 |
|
Bilateral interpleural versus lumbar epidural bupivacaine-morphine analgesia for upper abdominal surgery. | 2003 Oct |
|
Modulation of the discriminative stimulus effects of mu opioid agonists in rats: II. Effects of dopamine D2/3 agonists. | 2004 Feb |
|
Modulation of the discriminative stimulus effects of mu opioid agonists in rats: I. Effects of dopamine D2/3 antagonists. | 2004 Feb |
|
Undocumented drug utilization and drug waste increase costs of pediatric anesthesia care. | 2004 Feb |
|
Effects of opioids in morphine-treated pigeons trained to discriminate among morphine, the low-efficacy agonist nalbuphine, and saline. | 2004 Jul |
|
Antinociceptive effect of a novel long-acting nalbuphine preparation. | 2004 May |
|
Reducing cardiovascular responses to laryngoscopy and tracheal intubation: a comparison of equipotent doses of tramadol, nalbuphine and pethidine, with placebo. | 2004 Oct |
|
The preoperative administration of ketoprofen improves analgesia after laparoscopic cholecystectomy in comparison with propacetamol or postoperative ketoprofen. | 2005 Mar |
|
In vitro and in vivo evaluation of the metabolism and pharmacokinetics of sebacoyl dinalbuphine. | 2005 Mar |
|
Effects of the mixed mu/kappa opioid nalbuphine on cocaine-induced changes in subjective and cardiovascular responses in men. | 2005 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: http://reference.medscape.com/drug/nalbuphine-343329
Non-opioid-tolerant patients: 10-20 mg/70kg IV/IM/SC q3-6hr PRN; individual dose not to exceed 20 mg
Opioid-dependent patients: Administer ¼ dose, and observe for withdrawal signs
Not to exceed 160 mg/day
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8620555
Bac 1.2F5 P2 membranes were incubated with [N-methyl-3H]morphine in the presence and absence of Nalbuphine (0.1 nM–10 mkM). Mixtures were filtered and washed, and binding was determined by measuring the radioactivity retained on the filter discs.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175685
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WHO-ATC |
N02AF02
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WHO-VATC |
QN02AF02
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NDF-RT |
N0000175692
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NCI_THESAURUS |
C67413
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NCI_THESAURUS |
C1506
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NDF-RT |
N0000175686
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LIVERTOX |
662
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Code System | Code | Type | Description | ||
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NALBUPHINE
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CHEMBL895
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7454
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C61854
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Nalbuphine
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2623
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D009266
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L2T84IQI2K
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1663
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7238
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PRIMARY | RxNorm | ||
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L2T84IQI2K
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m7711
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DTXSID8023345
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20594-83-6
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243-901-6
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100000084460
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5311304
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SUB09137MIG
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DB00844
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1874
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)