U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO3
Molecular Weight 285.3377
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MORPHINE

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]15CCN(C)[C@]([H])(C4)[C@]5([H])C=C[C@@H]2O

InChI

InChIKey=BQJCRHHNABKAKU-KBQPJGBKSA-N
InChI=1S/C17H19NO3/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/t10-,11+,13-,16-,17-/m0/s1

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DURAMORPH PF

Approved Use

DURAMORPH 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 Date

4.64313614E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
yes [Km 10100 uM]
yes [Km 12600 uM]
yes [Km 14150 uM]
yes [Km 18000 uM]
yes [Km 18700 uM]
yes [Km 25400 uM]
yes [Km 2600 uM]
yes [Km 3.4 uM]
yes [Km 3200 uM]
yes [Km 37400 uM]
yes [Km 380 uM]
yes [Km 4800 uM]
yes [Km 6400 uM]
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
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
[Regulation of the central opioidergic nervous system on the emotional state of anxiety and its possible mechanisms].
1997 Jan
Morphine preconditioning attenuates neutrophil activation in rat models of myocardial infarction.
1998 Dec
Epidural analgesia in children with cerebral palsy.
1998 Dec
Reduction of dyskinesia and induction of akinesia induced by morphine in two parkinsonian patients with severe sciatica.
1999
[Transverse myelopathy as a complication following long-term intrathecal application of morphine in chronic back pain].
1999 Aug
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
[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 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
The effects of quinine and 4-aminopyridine on conditioned place preference and changes in motor activity induced by morphine in rats.
1999 May
Controlling myoclonus after high-dosage morphine infusions.
1999 May 15
Sleep impairments in rats implanted with morphine pellets.
1999 Nov
Patient-controlled analgesia with morphine plus lysine acetyl salicylate.
1999 Oct
A comparison of continuous epidural infusion and intermittent intravenous bolus doses of morphine in children undergoing selective dorsal rhizotomy.
1999 Sep-Oct
Morphine inhibits human microglial cell production of, and migration towards, RANTES.
2000
Peroperative titration of morphine improves immediate postoperative analgesia after total hip arthroplasty.
2000 Apr
Intrathecal morphine suppresses NK cell activity following abdominal surgery.
2000 Apr
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
Preemptive intravenous morphine-6-glucuronide is ineffective for postoperative pain relief.
2000 Feb
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
Prenatal morphine exposure enhances seizure susceptibility but suppresses long-term potentiation in the limbic system of adult male rats.
2000 Jun 30
Lack of specific effects of selective D(1) and D(2) dopamine antagonists vs. risperidone on morphine-induced hyperactivity.
2000 May
Morphine-induced macrophage apoptosis: the role of transforming growth factor-beta.
2000 May
Advantages of intrathecal nalbuphine, compared with intrathecal morphine, after cesarean delivery: an evaluation of postoperative analgesia and adverse effects.
2000 Sep
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
Multicentre randomised controlled trial of nasal diamorphine for analgesia in children and teenagers with clinical fractures.
2001 Feb 3
Knockdown of spinal metabotropic glutamate receptor 1 (mGluR(1)) alleviates pain and restores opioid efficacy after nerve injury in rats.
2001 Jan
Circuitry underlying antiopioid actions of cholecystokinin within the rostral ventromedial medulla.
2001 Jan
Early serial EEG in hypoxic ischaemic encephalopathy.
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
A prospective survey of patients after cessation of patient-controlled analgesia.
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
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
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
Name Type Language
MORPHINE
HSDB   MART.   MI   VANDF   WHO-DD  
Common Name English
NEPENTHE
Common Name English
CODEINE PHOSPHATE SESQUIHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
CODEINE MONOHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY A [EP IMPURITY]
Common Name English
MORPHIUM
Common Name English
MORPHINE [MART.]
Common Name English
DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY B [EP IMPURITY]
Common Name English
MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL, (5.ALPHA.,6.ALPHA.)-
Common Name English
MORPHINE [VANDF]
Common Name English
MORPHIA
Common Name English
DUROMORPH
Common Name English
ANHYDROUS MORPHINE
Common Name English
MORPHINE [HSDB]
Common Name English
MORPHINE EXTENDED RELEASE
Common Name English
OSPALIVINA
Common Name English
MORPHINE [MI]
Common Name English
N02AA01
Code English
4,5.ALPHA.-EPOXY-17-METHYL-7,8-DIDEHYDROMORPHINAN-3,6.ALPHA.-DIO
Systematic Name English
(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-17-METHYLMORPHINAN-3,6-DIOL
Systematic Name English
7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-17-METHYLMORPHINAN-3,6.ALPHA.-DIOL
Systematic Name English
APOMORPHINE HYDROCHLORIDE HEMIHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
HYDROMORPHONE HYDROCHLORIDE IMPURITY, MORPHINE- [USP IMPURITY]
Common Name English
CODEINE PHOSPHATE HEMIHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
CODEINE HYDROCHLORIDE DIHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
MORPHINE (ANHYDROUS) [VANDF]
Common Name English
Morphine [WHO-DD]
Common Name English
IDS-NM-009
Code English
HYDROMORPHONE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
MORPHINE (ANHYDROUS)
VANDF  
Common Name English
MORPHINE ANHYDROUS
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
CFR 21 CFR 862.3640
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-ATC N02AA51
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-VATC QN02AA01
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
DEA NO. 9300
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
NDF-RT N0000175684
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
LIVERTOX NBK548230
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-VATC QA07DA52
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
NDF-RT N0000175690
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 2.2
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 1.3
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-VATC QN02AA51
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-VATC QN02AG01
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-ATC N02AA01
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-VATC QR05DA05
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-ATC N02AG01
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-ATC R05DA05
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
NCI_THESAURUS C1657
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
WHO-ATC A07DA52
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
Code System Code Type Description
ChEMBL
CHEMBL70
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
IUPHAR
1627
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
HSDB
2134
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
MESH
D009020
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
DRUG CENTRAL
1845
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
DRUG BANK
DB00295
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
NCI_THESAURUS
C62051
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
EVMPD
SUB03332MIG
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
RXCUI
7052
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY RxNorm
ECHA (EC/EINECS)
200-320-2
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
CAS
57-27-2
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
MERCK INDEX
M7631
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY Merck Index
LACTMED
Morphine
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
PUBCHEM
5288826
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
CHEBI
58097
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
CHEBI
17303
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
EVMPD
SUB121757
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
EPA CompTox
DTXSID9023336
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
WIKIPEDIA
MORPHINE
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
FDA UNII
76I7G6D29C
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY
DAILYMED
76I7G6D29C
Created by admin on Fri Dec 16 20:34:22 UTC 2022 , Edited by admin on Fri Dec 16 20:34:22 UTC 2022
PRIMARY