Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H19NO3 |
Molecular Weight | 285.3377 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]15CCN(C)[C@]([H])(C4)[C@]5([H])C=C[C@@H]2O
InChI
InChIKey=BQJCRHHNABKAKU-KBQPJGBKSA-N
InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
Molecular Formula | C17H19NO3 |
Molecular Weight | 285.3377 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Morphine is one of the most important and widely used opioid for the treatment of chronic and acute pain: the very wide interindividual variability in the patients’ response to the drug may have genetic derivations. Sulphate salt of morphine sold under the many brand names, one of them, DURAMORPH, which is indicated for the management of pain severe enough to require use of an opioid analgesic by intravenous administration, and for which alternative treatments are not expected to be adequate. In addition for the epidural or intrathecal management of pain without attendant loss of motor, sensory, or sympathetic function. Morphine is a full opioid agonist and is relatively selective for the mu-opioid receptor, although it can bind to other opioid receptors at higher doses. The principal therapeutic action of morphine is analgesia. Like all full opioid agonists, there is no ceiling effect for analgesia with morphine. The precise mechanism of the analgesic action is unknown. However, specific CNS opioid receptors for endogenous compounds with opioid-like activity have been identified throughout the brain and spinal cord and are thought to play a role in the analgesic effects of this drug. Morphine has a high potential for addiction and abuse. Common side effects include drowsiness, vomiting, and constipation. Caution is advised when used during pregnancy or breast-feeding, as morphine will affect the baby.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16580639 |
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Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16530171 |
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Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10670411 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | DURAMORPH PF Approved UseDURAMORPH is indicated for: the management of pain severe enough to require use of an opioid analgesic by intravenous administration, and for which alternative treatments are not expected to be adequate.For the epidural or intrathecal management of pain without attendant loss of motor, sensory, or sympathetic function. Launch Date1984 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
63 nM |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MORPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
165 nM × h |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MORPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.1 h |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MORPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
65% |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
MORPHINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg single, oral Highest studied dose |
healthy, adult |
|
180 mg 1 times / day steady, oral Dose: 180 mg, 1 times / day Route: oral Route: steady Dose: 180 mg, 1 times / day Sources: |
unhealthy, adult n = 152 Health Status: unhealthy Condition: neuropathic pain Age Group: adult Sex: unknown Population Size: 152 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
yes [Km 10100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 12600 uM] | |||
Page: - |
yes [Km 14150 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 18000 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 18700 uM] | |||
Page: - |
yes [Km 25400 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 2600 uM] | |||
Page: - |
yes [Km 3.4 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 3200 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 37400 uM] | |||
Page: - |
yes [Km 380 uM] | |||
Page: - |
yes [Km 4800 uM] | |||
Page: - |
yes [Km 6400 uM] | |||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Reduction of dyskinesia and induction of akinesia induced by morphine in two parkinsonian patients with severe sciatica. | 1999 |
|
The involvement of noradrenergic transmission in the morphine-induced locomotor hyperactivity in mice withdrawn from repeated morphine treatment. | 1999 Apr |
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Prenatal morphine exposure differentially alters seizure susceptibility in developing female rats. | 1999 Aug 5 |
|
Preliminary UK experience of dexmedetomidine, a novel agent for postoperative sedation in the intensive care unit. | 1999 Dec |
|
Seizure and electroencephalographic changes in the newborn period induced by opiates and corrected by naloxone infusion. | 1999 Mar |
|
The effects of dopamine D2 and D3 antagonists on spontaneous motor activity and morphine-induced hyperactivity in male mice. | 1999 Mar |
|
Sex differences in morphine-induced ventilatory depression reside within the peripheral chemoreflex loop. | 1999 May |
|
Sleep impairments in rats implanted with morphine pellets. | 1999 Nov |
|
Patient-controlled analgesia with morphine plus lysine acetyl salicylate. | 1999 Oct |
|
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice. | 1999 Sep |
|
Potentiation of narcosis after intravenous lidocaine in a patient given spinal opioids. | 1999 Sep |
|
Morphine induced allodynia in a child with brain tumour. | 1999 Sep 4 |
|
A comparison of continuous epidural infusion and intermittent intravenous bolus doses of morphine in children undergoing selective dorsal rhizotomy. | 1999 Sep-Oct |
|
Morphine inhibits human microglial cell production of, and migration towards, RANTES. | 2000 |
|
Intrathecal morphine suppresses NK cell activity following abdominal surgery. | 2000 Apr |
|
Prior experience of morphine application alters the c-fos response to MDMA ('ecstasy') and cocaine in the rat striatum. | 2000 Apr 14 |
|
The effect of spinal ibuprofen on opioid withdrawal in the rat. | 2000 Aug |
|
Preemptive intravenous morphine-6-glucuronide is ineffective for postoperative pain relief. | 2000 Feb |
|
Reversal of morphine-induced apnea in the anesthetized rat by drugs that activate 5-hydroxytryptamine(1A) receptors. | 2000 Feb |
|
Influence of morphine treatment in pregnant rats on the mineralocorticoid activity of the adrenals in their neonates. | 2000 Feb 18 |
|
Prenatal morphine exposure enhances seizure susceptibility but suppresses long-term potentiation in the limbic system of adult male rats. | 2000 Jun 30 |
|
Effects of the NMDA receptor channel blockers memantine and MRZ 2/579 on morphine withdrawal-facilitated aggression in mice. | 2000 May |
|
Lack of specific effects of selective D(1) and D(2) dopamine antagonists vs. risperidone on morphine-induced hyperactivity. | 2000 May |
|
Morphine-induced macrophage apoptosis: the role of transforming growth factor-beta. | 2000 May |
|
Insidious intoxication after morphine treatment in renal failure: delayed onset of morphine-6-glucuronide action. | 2000 May |
|
Systemic naloxone enhances cerebral blood flow in anesthetized morphine-dependent rats. | 2000 Nov 24 |
|
Enhanced spinal nociceptin receptor expression develops morphine tolerance and dependence. | 2000 Oct 15 |
|
Inhaled morphine to relieve dyspnea in advanced cystic fibrosis lung disease. | 2000 Sep |
|
Advantages of intrathecal nalbuphine, compared with intrathecal morphine, after cesarean delivery: an evaluation of postoperative analgesia and adverse effects. | 2000 Sep |
|
mGlu5 receptors and nociceptive function II. mGlu5 receptors functionally expressed on peripheral sensory neurones mediate inflammatory hyperalgesia. | 2001 |
|
Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection. | 2001 Feb |
|
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling. | 2001 Feb 2 |
|
Comparison of three methods to find the vapor activity of a hydration step. | 2001 Jan |
|
Circuitry underlying antiopioid actions of cholecystokinin within the rostral ventromedial medulla. | 2001 Jan |
|
Ketorolac reduces postoperative narcotic requirements. | 2001 Jan |
|
Morphine nerve paste. | 2001 Jan |
|
Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols. | 2001 Jan |
|
A prospective survey of patients after cessation of patient-controlled analgesia. | 2001 Jan |
|
Clonidine combined with a long acting local anesthetic does not prolong postoperative analgesia after brachial plexus block but does induce hemodynamic changes. | 2001 Jan |
|
Bupivacaine wound instillation via an electronic patient-controlled analgesia device and a double-catheter system does not decrease postoperative pain or opioid requirements after major abdominal surgery. | 2001 Jan |
|
A randomized, double-blinded comparison of intrathecal morphine, sufentanil and their combination versus IV morphine patient-controlled analgesia for postthoracotomy pain. | 2001 Jan |
|
Agmatine enhances the NADPH oxidase activity of neuronal NO synthase and leads to oxidative inactivation of the enzyme. | 2001 Jan |
|
Parental perceptions of comfort during mechanical ventilation. | 2001 Jan |
|
Sublingual morphine may be a suitable alternative for pain control in children in the postoperative period. | 2001 Jan |
|
Morphine with or without a local anaesthetic for postoperative intrathecal pain treatment after selective dorsal rhizotomy in children. | 2001 Jan |
|
Antianalgesic action of nociceptin originating in the brain is mediated by spinal prostaglandin E(2) in mice. | 2001 Jan |
|
Augmented accumbal serotonin levels decrease the preference for a morphine associated environment during withdrawal. | 2001 Jan |
|
Heroin-related deaths in Victoria: a review of cases for 1997 and 1998. | 2001 Jan 1 |
|
Acute thermal hyperalgesia elicited by low-dose morphine in normal mice is blocked by ultra-low-dose naltrexone, unmasking potent opioid analgesia. | 2001 Jan 5 |
|
Morphine induces short-lived changes in G-protein gene expression in rat prefrontal cortex. | 2001 Jan 5 |
Patents
Sample Use Guides
Dosage for Intravenous Administration: Adult Dosage: The initial dose of morphine should be 2 mg to 10 mg/70 kg of body weight.
Dosage for Epidural Administration: Adult Dosage: Initial injection of 5 mg in the lumbar region may provide satisfactory pain relief for up to 24 hours. If adequate pain relief is not achieved within one hour, careful administration of incremental doses of 1 to 2 mg at intervals sufficient to assess effectiveness may be given. Do not administer more than 10 mg per 24 hours.
Dosage for Intrathecal Administration: Adult Dosage: Intrathecal dosage is usually 1/10 that of epidural dosage. A single injection of 0.2 to 1 mg may provide satisfactory pain relief for up to 24 hours. (Caution: this is only 0.4 to 2 mL of the 5 mg/10 mL ampul or 0.2 to 1 mL of the 10 mg/10 mL ampul of DURAMORPH). Do not inject intrathecally more than 2 mL of the 5 mg/10 mL ampul or 1 mL of the 10 mg/10 mLampul. Repeated intrathecal injections of DURAMORPH are not recommended. If pain recurs, consider consider alternative routes of administration.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27514308
It was evaluated the effect of morphine on the proangiogenic interaction taking place between macrophages and breast cancer cells in vitro. It was shown, that morphine prevents, in part via modulating VEGF-A expression, the pro-angiogenic interaction between macrophages and breast cancer cells. The conditioned medium (CM) from breast cancer cells co-cultured with macrophages elicited endothelial cell proliferation and tube formation. This effect was inhibited if the co-culture occurred in the presence of morphine (20 uM). Using a mouse antibody array, it was identified several angiogenesis-regulating factors differentially expressed in the CM of co-cultured cells prepared in the presence or absence of morphine (o, 10, 20 uM), amongst which interleukin (IL)-6, tumour necrosis factor (TNF)-α and vascular endothelial growth factor (VEGF)-A. VEGF was induced in both cell types by the co-culture and this was prevented by morphine in a non-naloxone reversible fashion. The effect of CM from co-cultured cells on endothelial tube formation, but not proliferation, was prevented by anti-VEGF neutralizing antibody
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:35:43 GMT 2023
by
admin
on
Fri Dec 15 16:35:43 GMT 2023
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Record UNII |
76I7G6D29C
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ESSENTIAL MEDICINES LIST |
8.4
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CFR |
21 CFR 862.3640
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WHO-ATC |
N02AA51
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WHO-VATC |
QN02AA01
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DEA NO. |
9300
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NDF-RT |
N0000175684
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LIVERTOX |
NBK548230
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WHO-VATC |
QA07DA52
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NDF-RT |
N0000175690
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WHO-ESSENTIAL MEDICINES LIST |
2.2
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WHO-ESSENTIAL MEDICINES LIST |
1.3
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WHO-VATC |
QN02AA51
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WHO-VATC |
QN02AG01
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WHO-ATC |
N02AA01
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WHO-VATC |
QR05DA05
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WHO-ATC |
N02AG01
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WHO-ATC |
R05DA05
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NCI_THESAURUS |
C1657
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WHO-ATC |
A07DA52
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Code System | Code | Type | Description | ||
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CHEMBL70
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1627
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2134
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D009020
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1845
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DB00295
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C62051
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SUB03332MIG
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7052
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PRIMARY | RxNorm | ||
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200-320-2
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57-27-2
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m7631
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PRIMARY | Merck Index | ||
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Morphine
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100000091372
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5288826
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58097
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17303
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SUB121757
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DTXSID9023336
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MORPHINE
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76I7G6D29C
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76I7G6D29C
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
Ki
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DERIVATIVE -> PARENT |
Dihydrodesoxymorphine (derivative of morphine). as per INCB
|
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SALT/SOLVATE -> PARENT |
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SUB_CONCEPT->SUBSTANCE |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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DERIVATIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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DERIVATIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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DERIVATIVE -> PARENT |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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DERIVATIVE -> PARENT |
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TARGET -> AGONIST |
Ki
|
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DERIVATIVE -> PARENT |
Dihydrocodeinone-6-carboxymethyloxime (derivate of morphine). as per INCB
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TRANSPORTER -> SUBSTRATE | |||
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DERIVATIVE -> PARENT |
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DERIVATIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
Ki
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PARENT -> SALT/SOLVATE |
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DERIVATIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
MAJOR
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PRODRUG -> METABOLITE ACTIVE |
MINOR METABOLITE
MINOR
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METABOLITE INACTIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE ACTIVE -> PARENT |
MAJOR
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
ED50-PO(mg/kg) = 0.33, LD50-PO(mg/kg) = 470, Potency ratio to morphine = 1, Potency ratio to fentanyl = 0.02
|