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
Molecular Formula | C21H27NO4 |
Molecular Weight | 357.4434 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 Date1979 |
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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 Date1979 |
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 |
---|---|---|
Survey of pain management therapy provided for children with sickle cell disease. | 1992 Apr |
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Nalbuphine is better than naloxone for treatment of side effects after epidural morphine. | 1992 Nov |
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Tolerance to the analgesic effect of buprenorphine, butorphanol, nalbuphine, and cyclorphan, and cross-tolerance to morphine. | 2001 |
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The analgesic effect of nalbuphine and its long-acting prodrug, nalbuphine pivalate, in rats. | 2002 Dec |
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[Nalbuphine (Nubain) dependence: 2 cases]. | 2002 Sep-Oct |
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Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats. | 2003 Apr |
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Summary version of the Standards, Options and Recommendations for the use of analgesia for the treatment of nociceptive pain in adults with cancer (update 2002). | 2003 Aug |
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A review of emergency equipment carried and procedures performed by UK front line paramedics. | 2003 Aug |
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Sensitivity to the effects of opioids in rats with free access to exercise wheels: mu-opioid tolerance and physical dependence. | 2003 Aug |
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Pharmacogenetic analysis of sex differences in opioid antinociception in rats. | 2003 Dec |
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Opioid interactions in rhesus monkeys: effects of delta + mu and delta + kappa agonists on schedule-controlled responding and thermal nociception. | 2003 Dec |
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Differential effects of agonists on adenylyl cyclase superactivation mediated by the kappa opioid receptors: adenylyl cyclase superactivation is independent of agonist-induced phosphorylation, desensitization, internalization, and down-regulation. | 2003 Dec |
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Transdermal delivery of nalbuphine and its prodrugs by electroporation. | 2003 Jan |
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The sedative and behavioral effects of nalbuphine in dogs. | 2003 Jul |
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Absence of nalbuphine anti-analgesia in the rat. | 2003 Jul 24 |
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An optimal dose study of intrathecal morphine in gynecological patients. | 2003 Jun |
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Nalbuphine versus ondansetron for prevention of intrathecal morphine-induced pruritus after cesarean delivery. | 2003 Jun |
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Response of neuropathic trigeminal pain to the combination of low-dose nalbuphine plus naloxone in humans. | 2003 Jun 5 |
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Effect of nalbuphine on the motility of the sphincter of Oddi in patients with suspected sphincter of Oddi dysfunction. | 2003 Mar |
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Sexual dimorphism in very low dose nalbuphine postoperative analgesia. | 2003 Mar 13 |
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Interactions between opioids and cocaine on locomotor activity in rats: influence of an opioid's relative efficacy at the mu receptor. | 2003 May |
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Biodegradable polymeric microspheres for nalbuphine prodrug controlled delivery: in vitro characterization and in vivo pharmacokinetic studies. | 2003 May 12 |
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Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans. | 2003 Nov 6 |
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Bilateral interpleural versus lumbar epidural bupivacaine-morphine analgesia for upper abdominal surgery. | 2003 Oct |
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A comparison of morphine and nalbuphine for intraoperative and postoperative analgesia. | 2003 Sep |
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The antinociceptive effect of a long-acting nalbuphine preparation in rabbits. | 2003 Sep |
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The antinociceptive effect of nalbuphine and its long-acting esters in rats. | 2003 Sep |
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Three-port vs standard four-port laparoscopic cholecystectomy. | 2003 Sep |
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Relative efficacy of buprenorphine, nalbuphine and morphine in opioid-treated rhesus monkeys discriminating naltrexone. | 2003 Sep |
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Sub-Tenon infiltration or classical analgesic drugs to relieve postoperative pain. | 2004 Apr |
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[Medical termination of pregnancy at 9-14 weeks gestation. Prospective study of 105 cases in Saint-Laurent-du-Maroni (French Guyana)]. | 2004 Apr |
|
[National survey of emergency management of acute pain in prehospital setting]. | 2004 Dec |
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Modulation of the discriminative stimulus effects of mu opioid agonists in rats: II. Effects of dopamine D2/3 agonists. | 2004 Feb |
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Modulation of the discriminative stimulus effects of mu opioid agonists in rats: I. Effects of dopamine D2/3 antagonists. | 2004 Feb |
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Undocumented drug utilization and drug waste increase costs of pediatric anesthesia care. | 2004 Feb |
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Effects of opioids in morphine-treated pigeons trained to discriminate among morphine, the low-efficacy agonist nalbuphine, and saline. | 2004 Jul |
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Nalbuphine and slow release morphine. | 2004 Jun 12 |
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Experimental pain models reveal no sex differences in pentazocine analgesia in humans. | 2004 May |
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Less IS less: a randomised controlled trial comparing cautious and rapid nalbuphine dosing regimens. | 2004 May |
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Antinociceptive effect of a novel long-acting nalbuphine preparation. | 2004 May |
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Reducing cardiovascular responses to laryngoscopy and tracheal intubation: a comparison of equipotent doses of tramadol, nalbuphine and pethidine, with placebo. | 2004 Oct |
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In vitro evaluation of the potential role of sulfite radical in morphine-associated histamine release. | 2004 Oct 6 |
|
In rats, acute morphine dependence results in antagonist-induced response suppression of intracranial self-stimulation. | 2004 Sep |
|
[Analgesic alternatives for the control of postoperatory pain in radical mastectomy]. | 2004 Sep-Oct |
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Using mixed agonist-antagonists. | 2005 Feb |
|
Dextromethorphan differentially affects opioid antinociception in rats. | 2005 Feb |
|
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 |
|
Self-Administration of cocaine-opioid combinations by rhesus monkeys: evaluation of the role of mu receptor efficacy using labor supply analysis. | 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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:35:40 GMT 2023
by
admin
on
Sat Dec 16 16:35:40 GMT 2023
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Record UNII |
L2T84IQI2K
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Record Status |
Validated (UNII)
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Record Version |
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Systematic Name | English |
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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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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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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