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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO3.H2O
Molecular Weight 303.3529
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MORPHINE MONOHYDRATE

SMILES

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

InChI

InChIKey=IYXRQFVHZFEWSY-VYKNHSEDSA-N
InChI=1S/C17H19NO3.H2O/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;1H2/t10-,11+,13-,16-,17-;/m0./s1

HIDE SMILES / InChI

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

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

1984
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
Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product atherosperminine.
1978 Sep 15
Epidural analgesia in children with cerebral palsy.
1998 Dec
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
Prenatal morphine exposure differentially alters seizure susceptibility in developing female rats.
1999 Aug 5
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
Morphine promotes apoptosis in Jurkat cells.
1999 Oct
Potentiation of narcosis after intravenous lidocaine in a patient given spinal opioids.
1999 Sep
Nonconvulsive status epilepticus: the role of morphine and its antagonist.
2000 Apr
Peroperative titration of morphine improves immediate postoperative analgesia after total hip arthroplasty.
2000 Apr
The effect of spinal ibuprofen on opioid withdrawal in the rat.
2000 Aug
Orphanin FQ/nociceptin inhibits morphine withdrawal.
2000 Jan 14
Comparison of intravenous patient-controlled analgesia with tramadol versus morphine after microvascular breast reconstruction.
2000 Jul
Prenatal morphine exposure enhances seizure susceptibility but suppresses long-term potentiation in the limbic system of adult male rats.
2000 Jun 30
Insidious intoxication after morphine treatment in renal failure: delayed onset of morphine-6-glucuronide action.
2000 May
Enhanced spinal nociceptin receptor expression develops morphine tolerance and dependence.
2000 Oct 15
Inhaled morphine to relieve dyspnea in advanced cystic fibrosis lung disease.
2000 Sep
Downbeat nystagmus associated with intravenous patient-controlled administration of morphine.
2000 Sep
Advantages of intrathecal nalbuphine, compared with intrathecal morphine, after cesarean delivery: an evaluation of postoperative analgesia and adverse effects.
2000 Sep
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.
2001 Feb 2
Cellular and synaptic adaptations mediating opioid dependence.
2001 Jan
Morphine nerve paste.
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
Clonidine combined with a long acting local anesthetic does not prolong postoperative analgesia after brachial plexus block but does induce hemodynamic changes.
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
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
Heroin-related deaths in Victoria: a review of cases for 1997 and 1998.
2001 Jan 1
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
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 Fri Dec 15 16:05:44 GMT 2023
Edited
by admin
on Fri Dec 15 16:05:44 GMT 2023
Record UNII
41TQ665R1X
Record Status Validated (UNII)
Record Version
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Name Type Language
MORPHINE MONOHYDRATE
WHO-DD  
Common Name English
MORPHINE MONOHYDRATE [MI]
Common Name English
MORPHINE MONOHYDRATE CII
USP-RS  
Common Name English
Morphine monohydrate [WHO-DD]
Common Name English
MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL- (5-.ALPHA.,6-.ALPHA.)-, MONOHYDRATE
Common Name English
MORPHINE MONOHYDRATE [USP-RS]
Common Name English
MORPHINUM [HPUS]
Common Name English
MORPHINUM
HPUS  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
Code System Code Type Description
CAS
6009-81-0
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
MERCK INDEX
m7631
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
EVMPD
SUB03332MIG
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
RS_ITEM_NUM
1447002
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
FDA UNII
41TQ665R1X
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
CHEBI
17303
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID50975517
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
NCI_THESAURUS
C87362
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
PUBCHEM
21118682
Created by admin on Fri Dec 15 16:05:44 GMT 2023 , Edited by admin on Fri Dec 15 16:05:44 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY