Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H19NO3.BrH |
Molecular Weight | 366.25 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.[H][C@@]12OC3=C(O)C=CC4=C3[C@@]15CCN(C)[C@]([H])(C4)[C@]5([H])C=C[C@@H]2O
InChI
InChIKey=OUOYRIJSFITIHQ-VYKNHSEDSA-N
InChI=1S/C17H19NO3.BrH/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;1H/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 |
Molecular Formula | BrH |
Molecular Weight | 80.912 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
|||
Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16530171 |
|||
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 |
---|---|---|
[Regulation of the central opioidergic nervous system on the emotional state of anxiety and its possible mechanisms]. | 1997 Jan |
|
Butorphanol agonist effects and acute physical dependence in opioid abusers: comparison with morphine. | 1998 Dec 1 |
|
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 |
|
The importance of the number of NMDA receptors in the development of supersensitivity or tolerance to and dependence on morphine. | 1999 Apr |
|
Acute injection of drugs with low addictive potential (delta(9)-tetrahydrocannabinol, 3,4-methylenedioxymethamphetamine, lysergic acid diamide) causes a much higher c-fos expression in limbic brain areas than highly addicting drugs (cocaine and morphine). | 1999 Aug 25 |
|
Prenatal morphine exposure differentially alters seizure susceptibility in developing female rats. | 1999 Aug 5 |
|
[The discriminative stimulus properties of naloxone during dissociative learning in a Y maze in morphine-dependent rats]. | 1999 Jan-Feb |
|
Modification of naloxone-induced withdrawal signs by dextromethorphan in morphine-dependent mice. | 1999 Jul 14 |
|
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 |
|
Controlling myoclonus after high-dosage morphine infusions. | 1999 May 15 |
|
Sleep impairments in rats implanted with morphine pellets. | 1999 Nov |
|
Morphine promotes apoptosis in Jurkat cells. | 1999 Oct |
|
Patient-controlled analgesia with morphine plus lysine acetyl salicylate. | 1999 Oct |
|
Effects of morphine and tramadol on somatic and visceral sensory function and gastrointestinal motility after abdominal surgery. | 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 |
|
Morphine inhibits human microglial cell production of, and migration towards, RANTES. | 2000 |
|
Nonconvulsive status epilepticus: the role of morphine and its antagonist. | 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 effects of intrathecal morphine encapsulated in L- and D-dipalmitoylphosphatidyl choline liposomes on acute nociception in rats. | 2000 Aug |
|
The effect of spinal ibuprofen on opioid withdrawal in the rat. | 2000 Aug |
|
Apnoea with intrathecal morphine. | 2000 Dec |
|
Comparison of intravenous patient-controlled analgesia with tramadol versus morphine after microvascular breast reconstruction. | 2000 Jul |
|
Cyclophosphamide-induced cystitis in freely-moving conscious rats: behavioral approach to a new model of visceral pain. | 2000 Jul |
|
Pethidine reverses morphine-induced delirium. | 2000 Jun |
|
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 |
|
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 |
|
Downbeat nystagmus associated with intravenous patient-controlled administration of morphine. | 2000 Sep |
|
Advantages of intrathecal nalbuphine, compared with intrathecal morphine, after cesarean delivery: an evaluation of postoperative analgesia and adverse effects. | 2000 Sep |
|
Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor. | 2001 Apr |
|
Large-dose oral dextromethorphan as an adjunct to patient-controlled analgesia with morphine after knee surgery. | 2001 Feb |
|
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling. | 2001 Feb 2 |
|
Cellular and synaptic adaptations mediating opioid dependence. | 2001 Jan |
|
Morphine nerve paste. | 2001 Jan |
|
Randomized clinical trial of diathermy versus scalpel incision in elective midline laparotomy. | 2001 Jan |
|
Opiates, intracranial pressure, and autoregulation. | 2001 Jan |
|
Buprenorphine substitution ameliorates spontaneous withdrawal in fentanyl-dependent rat pups. | 2001 Jan |
|
Demographic and therapeutic determinants of pain reactivity in very low birth weight neonates at 32 Weeks' postconceptional Age. | 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 |
|
Sublingual morphine may be a suitable alternative for pain control in children in the postoperative period. | 2001 Jan |
|
Tonic descending facilitation from the rostral ventromedial medulla mediates opioid-induced abnormal pain and antinociceptive tolerance. | 2001 Jan 1 |
|
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 |
|
Occurrence of morphine tolerance and dependence in the nucleus paragigantocellularis neurons. | 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
Sat Dec 16 10:13:59 GMT 2023
by
admin
on
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Record UNII |
X1W88415WG
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Record Status |
Validated (UNII)
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Record Version |
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |