Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H19NO3.HNO3 |
Molecular Weight | 348.3505 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.CN1CC[C@]23[C@H]4OC5=C(O)C=CC(C[C@@H]1[C@@H]2C=C[C@@H]4O)=C35
InChI
InChIKey=VHBDDUMTLJSZDR-VYKNHSEDSA-N
InChI=1S/C17H19NO3.HNO3/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;2-1(3)4/h2-5,10-11,13,16,19-20H,6-8H2,1H3;(H,2,3,4)/t10-,11+,13-,16-,17-;/m0./s1
Molecular Formula | HNO3 |
Molecular Weight | 63.0128 |
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 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 |
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 |
---|---|---|
Side-effects of epidural infusions of opioid bupivacaine mixtures. | 1998 Dec |
|
[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 |
|
Seizure and electroencephalographic changes in the newborn period induced by opiates and corrected by naloxone infusion. | 1999 Mar |
|
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice. | 1999 Sep |
|
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 |
|
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 alters N-methyl-D-aspartate- and kainate-induced seizures in adult male rats. | 2000 Jan 1 |
|
Orphanin FQ/nociceptin inhibits morphine withdrawal. | 2000 Jan 14 |
|
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 |
|
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 |
|
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 |
|
Multicentre randomised controlled trial of nasal diamorphine for analgesia in children and teenagers with clinical fractures. | 2001 Feb 3 |
|
Cellular and synaptic adaptations mediating opioid dependence. | 2001 Jan |
|
Opiates, intracranial pressure, and autoregulation. | 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 |
|
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 |
|
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 |
|
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 |
|
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
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
Mon Mar 31 23:07:07 GMT 2025
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Record UNII |
DV2P23JCWV
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Record Status |
Validated (UNII)
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Record Version |
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209-879-7
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PARENT -> SALT/SOLVATE |