Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C17H19NO3.HI.2H2O |
| Molecular Weight | 449.2806 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.I.[H][C@@]12OC3=C(O)C=CC4=C3[C@@]15CCN(C)[C@]([H])(C4)[C@]5([H])C=C[C@@H]2O
InChI
InChIKey=MQIDJXULXRKOFP-JGHDFLKSSA-N
InChI=1S/C17H19NO3.HI.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 | 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 | 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 | HI |
| Molecular Weight | 127.9124 |
| 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 |
|||
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 |
|
| Morphine preconditioning attenuates neutrophil activation in rat models of myocardial infarction. | 1998 Dec |
|
| Epidural analgesia in children with cerebral palsy. | 1998 Dec |
|
| Efficacy and complications of morphine infusions in postoperative paediatric patients. | 1999 |
|
| 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 |
|
| Intra-articular morphine for pain relief after knee arthroscopy. | 1999 Mar |
|
| Sleep impairments in rats implanted with morphine pellets. | 1999 Nov |
|
| 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 |
|
| Nonconvulsive status epilepticus: the role of morphine and its antagonist. | 2000 Apr |
|
| The effect of spinal ibuprofen on opioid withdrawal in the rat. | 2000 Aug |
|
| Apnoea with intrathecal morphine. | 2000 Dec |
|
| Cyclophosphamide-induced cystitis in freely-moving conscious rats: behavioral approach to a new model of visceral pain. | 2000 Jul |
|
| Systemic naloxone enhances cerebral blood flow in anesthetized morphine-dependent rats. | 2000 Nov 24 |
|
| Inhaled morphine to relieve dyspnea in advanced cystic fibrosis lung disease. | 2000 Sep |
|
| mGlu5 receptors and nociceptive function II. mGlu5 receptors functionally expressed on peripheral sensory neurones mediate inflammatory hyperalgesia. | 2001 |
|
| Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor. | 2001 Apr |
|
| Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection. | 2001 Feb |
|
| Multicentre randomised controlled trial of nasal diamorphine for analgesia in children and teenagers with clinical fractures. | 2001 Feb 3 |
|
| Ketorolac reduces postoperative narcotic requirements. | 2001 Jan |
|
| Morphine nerve paste. | 2001 Jan |
|
| Early serial EEG in hypoxic ischaemic encephalopathy. | 2001 Jan |
|
| Buprenorphine substitution ameliorates spontaneous withdrawal in fentanyl-dependent rat pups. | 2001 Jan |
|
| Tonic descending facilitation from the rostral ventromedial medulla mediates opioid-induced abnormal pain and antinociceptive tolerance. | 2001 Jan 1 |
|
| Numerical density of mu opioid receptor expressing neurons in the frontal cortex of drug related fatalities. | 2001 Jan 15 |
|
| 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 |
|
| Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat. | 2001 Jan-Feb |
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 10:13:57 GMT 2023
by
admin
on
Sat Dec 16 10:13:57 GMT 2023
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| Record UNII |
0G2SR6TT4X
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| Record Status |
Validated (UNII)
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| Record Version |
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-
Download
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Common Name | English |
| Code System | Code | Type | Description | ||
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121489439
Created by
admin on Sat Dec 16 10:13:57 GMT 2023 , Edited by admin on Sat Dec 16 10:13:57 GMT 2023
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PRIMARY | |||
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0G2SR6TT4X
Created by
admin on Sat Dec 16 10:13:57 GMT 2023 , Edited by admin on Sat Dec 16 10:13:57 GMT 2023
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PRIMARY |
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |