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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H23NO5
Molecular Weight 369.411
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIAMORPHINE

SMILES

[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2OC(C)=O)=CC=C3OC(C)=O

InChI

InChIKey=GVGLGOZIDCSQPN-PVHGPHFFSA-N
InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H23NO5
Molecular Weight 369.411
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.

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
[Regulation of the central opioidergic nervous system on the emotional state of anxiety and its possible mechanisms].
1997 Jan
Butorphanol agonist effects and acute physical dependence in opioid abusers: comparison with morphine.
1998 Dec 1
Reduction of dyskinesia and induction of akinesia induced by morphine in two parkinsonian patients with severe sciatica.
1999
Efficacy and complications of morphine infusions in postoperative paediatric patients.
1999
[The discriminative stimulus properties of naloxone during dissociative learning in a Y maze in morphine-dependent rats].
1999 Jan-Feb
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
Morphine promotes apoptosis in Jurkat cells.
1999 Oct
Patient-controlled analgesia with morphine plus lysine acetyl salicylate.
1999 Oct
Morphine induced allodynia in a child with brain tumour.
1999 Sep 4
Prenatal morphine exposure alters N-methyl-D-aspartate- and kainate-induced seizures in adult male rats.
2000 Jan 1
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
Pethidine reverses morphine-induced delirium.
2000 Jun
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
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
Contralateral but not systemic administration of the kappa-opioid agonist U-50,488H induces anti-nociception in acute hindpaw inflammation in rats.
2001 Jan
Comparison of three methods to find the vapor activity of a hydration step.
2001 Jan
Ketorolac reduces postoperative narcotic requirements.
2001 Jan
Randomized clinical trial of diathermy versus scalpel incision in elective midline laparotomy.
2001 Jan
A prospective survey of patients after cessation of patient-controlled analgesia.
2001 Jan
Antianalgesic action of nociceptin originating in the brain is mediated by spinal prostaglandin E(2) in mice.
2001 Jan
Tonic descending facilitation from the rostral ventromedial medulla mediates opioid-induced abnormal pain and antinociceptive tolerance.
2001 Jan 1
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:59:58 GMT 2023
Edited
by admin
on Fri Dec 15 14:59:58 GMT 2023
Record UNII
70D95007SX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIAMORPHINE
WHO-DD  
Common Name English
DIAPHORM
Common Name English
DIAMORPHINE-
Common Name English
DIACETYLMORPHINE
MI  
Common Name English
DIACETYLMORPHINE [MI]
Common Name English
IDS-NH-001(SECT.3)
Code English
ECLORION
Common Name English
HEROIN [HSDB]
Common Name English
Diamorphine [WHO-DD]
Common Name English
(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-17-METHYLMORPHINAN-3,6-DIOL DIACETATE (ESTER)
Common Name English
CHINA WHITE
Common Name English
HEROIN
HSDB  
Common Name English
IDS-NH-001
Code English
J6.494G
Code English
ACETOMORPHINE
Common Name English
MORPHACETIN
Common Name English
Classification Tree Code System Code
WHO-ATC N07BC06
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
NCI_THESAURUS C1657
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
WHO-VATC QN07BC06
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
DEA NO. 9200
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
WHO-ATC N02AA09
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
Code System Code Type Description
FDA UNII
70D95007SX
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
EVMPD
SUB13556MIG
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
DRUG CENTRAL
4412
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
NCI_THESAURUS
C424
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
RXCUI
3304
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m4241
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB01452
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
ChEMBL
CHEMBL459324
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
WIKIPEDIA
HEROIN
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
209-217-7
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
PUBCHEM
5462328
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
CAS
561-27-3
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
CHEBI
27808
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
MESH
D003932
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
HSDB
6473
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID6046761
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
SMS_ID
100000079547
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
LACTMED
Heroin
Created by admin on Fri Dec 15 14:59:58 GMT 2023 , Edited by admin on Fri Dec 15 14:59:58 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
Reported not to bind to serum proteins
BINDING
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE ACTIVE -> PRODRUG
6-MAM is a metabolite unique to heroin
METABOLITE -> PARENT
METABOLITE LESS ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY