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 |
|
| [Regulation of the central opioidergic nervous system on the emotional state of anxiety and its possible mechanisms]. | 1997 Jan |
|
| Side-effects of epidural infusions of opioid bupivacaine mixtures. | 1998 Dec |
|
| Morphine preconditioning attenuates neutrophil activation in rat models of myocardial infarction. | 1998 Dec |
|
| The involvement of noradrenergic transmission in the morphine-induced locomotor hyperactivity in mice withdrawn from repeated morphine treatment. | 1999 Apr |
|
| [Transverse myelopathy as a complication following long-term intrathecal application of morphine in chronic back pain]. | 1999 Aug |
|
| [Opioid receptor knockout mice]. | 1999 Dec |
|
| Preliminary UK experience of dexmedetomidine, a novel agent for postoperative sedation in the intensive care unit. | 1999 Dec |
|
| 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 |
|
| Modification of naloxone-induced withdrawal signs by dextromethorphan in morphine-dependent mice. | 1999 Jul 14 |
|
| Intra-articular morphine for pain relief after knee arthroscopy. | 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 SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice. | 1999 Sep |
|
| Morphine induced allodynia in a child with brain tumour. | 1999 Sep 4 |
|
| 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 |
|
| Apnoea with intrathecal morphine. | 2000 Dec |
|
| The development of pain-related behaviour and opioid tolerance after neuropathy-inducing surgery and sham surgery. | 2000 Dec 1 |
|
| Orphanin FQ/nociceptin inhibits morphine withdrawal. | 2000 Jan 14 |
|
| 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 |
|
| Insidious intoxication after morphine treatment in renal failure: delayed onset of morphine-6-glucuronide action. | 2000 May |
|
| 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 |
|
| Large-dose oral dextromethorphan as an adjunct to patient-controlled analgesia with morphine after knee surgery. | 2001 Feb |
|
| Contralateral but not systemic administration of the kappa-opioid agonist U-50,488H induces anti-nociception in acute hindpaw inflammation in rats. | 2001 Jan |
|
| Ketorolac reduces postoperative narcotic requirements. | 2001 Jan |
|
| Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols. | 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 |
|
| The combined effects of N-type calcium channel blockers and morphine on A delta versus C fiber mediated nociception. | 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 |
|
| 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 |
|
| 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 |
|
| 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
|
| Record UNII |
0G2SR6TT4X
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
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
|
PRIMARY | |||
|
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
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
ANHYDROUS->SOLVATE | |||
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |