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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO3.ClH.3H2O
Molecular Weight 375.844
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MORPHINE HYDROCHLORIDE TRIHYDRATE

SMILES

O.O.O.Cl.[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4O

InChI

InChIKey=XELXKCKNPPSFNN-BJWPBXOKSA-N
InChI=1S/C17H19NO3.ClH.3H2O/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;3*1H2/t10-,11+,13-,16-,17-;;;;/m0..../s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
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

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 involvement of noradrenergic transmission in the morphine-induced locomotor hyperactivity in mice withdrawn from repeated morphine treatment.
1999 Apr
The importance of the number of NMDA receptors in the development of supersensitivity or tolerance to and dependence on morphine.
1999 Apr
[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
Prenatal morphine exposure differentially alters seizure susceptibility in developing female rats.
1999 Aug 5
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
Intra-articular morphine for pain relief after knee arthroscopy.
1999 Mar
Effect of intrathecal agmatine on inflammation-induced thermal hyperalgesia in rats.
1999 Mar 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
Intrathecal morphine suppresses NK cell activity following abdominal surgery.
2000 Apr
The effect of spinal ibuprofen on opioid withdrawal in the rat.
2000 Aug
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
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
Morphine-induced macrophage apoptosis: the role of transforming growth factor-beta.
2000 May
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
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
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
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.
2001 Feb 2
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
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
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
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 15:51:33 GMT 2023
Edited
by admin
on Fri Dec 15 15:51:33 GMT 2023
Record UNII
Q5F3AS69LF
Record Status Validated (UNII)
Record Version
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Name Type Language
MORPHINE HYDROCHLORIDE TRIHYDRATE
WHO-DD  
Common Name English
MORPHINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
MORPHINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL- (5.ALPHA.,6.ALPHA.)-, HYDROCHLORIDE, HYDRATE (1:1:3)
Systematic Name English
MORPHINAN-3,6.ALPHA.-DIOL, 7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-17-METHYL-, HYDROCHLORIDE, TRIHYDRATE
Systematic Name English
MORPHINE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-17-METHYLMORPHINAN-3,6.ALPHA.-DIOL HYDROCHLORIDE (1:1) (SALT) TRIHYDRATE [WHO-IP]
Systematic Name English
MORPHINE HYDROCHLORIDE [WHO-IP]
Common Name English
Morphine hydrochloride trihydrate [WHO-DD]
Common Name English
Code System Code Type Description
SMS_ID
100000091614
Created by admin on Fri Dec 15 15:51:33 GMT 2023 , Edited by admin on Fri Dec 15 15:51:33 GMT 2023
PRIMARY
PUBCHEM
5492889
Created by admin on Fri Dec 15 15:51:33 GMT 2023 , Edited by admin on Fri Dec 15 15:51:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID30904880
Created by admin on Fri Dec 15 15:51:33 GMT 2023 , Edited by admin on Fri Dec 15 15:51:33 GMT 2023
PRIMARY
CAS
6055-06-7
Created by admin on Fri Dec 15 15:51:33 GMT 2023 , Edited by admin on Fri Dec 15 15:51:33 GMT 2023
PRIMARY
FDA UNII
Q5F3AS69LF
Created by admin on Fri Dec 15 15:51:33 GMT 2023 , Edited by admin on Fri Dec 15 15:51:33 GMT 2023
PRIMARY
EVMPD
SUB27294
Created by admin on Fri Dec 15 15:51:33 GMT 2023 , Edited by admin on Fri Dec 15 15:51:33 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
MORPHINE HYDROCHLORIDE TRIHYDRATE
Created by admin on Fri Dec 15 15:51:33 GMT 2023 , Edited by admin on Fri Dec 15 15:51:33 GMT 2023
PRIMARY Description: Colourless, needle-like crystals or a white, crystalline powder; odourless. Solubility: Soluble in 25 parts of water; slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Analgesic. Storage: Morphine hydrochloride should be kept in a tightly closed container, protected from light.Additional information: Even in the absence of light, Morphine hydrochloride is gradually degraded on exposure to a humidatmosphere, the decomposition being faster at higher temperatures. Definition: Morphine hydrochloride contains not less than 98.0% and not more than 101.0% of C17H19NO3,HCl, calculated withreference to the dried substance.
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY