Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H19NO3.BrH.2H2O |
| Molecular Weight | 402.28 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.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=VIBALKJNEFEVTA-JGHDFLKSSA-N
InChI=1S/C17H19NO3.BrH.2H2O/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;2*1H2/t10-,11+,13-,16-,17-;;;/m0.../s1
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
| 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 |
|||
Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) |
|||
Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) |
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 |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [Km 10100 uM] | ||||
Page: - |
yes [Km 12600 uM] | |||
| yes [Km 14150 uM] | ||||
Page: - |
yes [Km 18000 uM] | |||
Page: - |
yes [Km 18700 uM] | |||
| yes [Km 25400 uM] | ||||
Page: - |
yes [Km 2600 uM] | |||
| yes [Km 3.4 uM] | ||||
Page: - |
yes [Km 3200 uM] | |||
Page: - |
yes [Km 37400 uM] | |||
| yes [Km 380 uM] | ||||
| yes [Km 4800 uM] | ||||
| yes [Km 6400 uM] | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs. | 1976 Aug |
|
| Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product atherosperminine. | 1978 Sep 15 |
|
| Side-effects of epidural infusions of opioid bupivacaine mixtures. | 1998 Dec |
|
| Morphine preconditioning attenuates neutrophil activation in rat models of myocardial infarction. | 1998 Dec |
|
| Epidural analgesia in children with cerebral palsy. | 1998 Dec |
|
| 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 |
|
| [Transverse myelopathy as a complication following long-term intrathecal application of morphine in chronic back pain]. | 1999 Aug |
|
| Cardiovascular changes during morphine administration and spontaneous withdrawal in the rat. | 1999 Feb 26 |
|
| [The discriminative stimulus properties of naloxone during dissociative learning in a Y maze in morphine-dependent rats]. | 1999 Jan-Feb |
|
| 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 |
|
| Intra-articular morphine for pain relief after knee arthroscopy. | 1999 Mar |
|
| Effect of intrathecal agmatine on inflammation-induced thermal hyperalgesia in rats. | 1999 Mar 5 |
|
| 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 |
|
| Morphine promotes apoptosis in Jurkat cells. | 1999 Oct |
|
| 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 |
|
| A comparison of continuous epidural infusion and intermittent intravenous bolus doses of morphine in children undergoing selective dorsal rhizotomy. | 1999 Sep-Oct |
|
| 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 |
|
| Apnoea with intrathecal morphine. | 2000 Dec |
|
| Prenatal morphine exposure alters N-methyl-D-aspartate- and kainate-induced seizures in adult male rats. | 2000 Jan 1 |
|
| Lack of specific effects of selective D(1) and D(2) dopamine antagonists vs. risperidone on morphine-induced hyperactivity. | 2000 May |
|
| Large-dose oral dextromethorphan as an adjunct to patient-controlled analgesia with morphine after knee surgery. | 2001 Feb |
|
| 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 |
|
| Contralateral but not systemic administration of the kappa-opioid agonist U-50,488H induces anti-nociception in acute hindpaw inflammation in rats. | 2001 Jan |
|
| Randomized clinical trial of diathermy versus scalpel incision in elective midline laparotomy. | 2001 Jan |
|
| Opiates, intracranial pressure, and autoregulation. | 2001 Jan |
|
| A prospective survey of patients after cessation of patient-controlled analgesia. | 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 |
|
| Heroin-related deaths in Victoria: a review of cases for 1997 and 1998. | 2001 Jan 1 |
|
| Numerical density of mu opioid receptor expressing neurons in the frontal cortex of drug related fatalities. | 2001 Jan 15 |
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
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 18:51:16 GMT 2023
by
admin
on
Sat Dec 16 18:51:16 GMT 2023
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| Record UNII |
87LP9D5J54
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| Record Status |
Validated (UNII)
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| Record Version |
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87LP9D5J54
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5974-16-3
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129654895
Created by
admin on Sat Dec 16 18:51:17 GMT 2023 , Edited by admin on Sat Dec 16 18:51:17 GMT 2023
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE |
