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
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
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 |
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16580639 |
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Target ID: P41145 Gene ID: 4986.0 Gene Symbol: OPRK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16530171 |
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Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10670411 |
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 Date4.64313614E11 |
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 |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
yes [Km 10100 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 12600 uM] | |||
Page: - |
yes [Km 14150 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 18000 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 18700 uM] | |||
Page: - |
yes [Km 25400 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 2600 uM] | |||
Page: - |
yes [Km 3.4 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 3200 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12920162/ Page: - |
yes [Km 37400 uM] | |||
Page: - |
yes [Km 380 uM] | |||
Page: - |
yes [Km 4800 uM] | |||
Page: - |
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 |
|
The importance of the number of NMDA receptors in the development of supersensitivity or tolerance to and dependence on morphine. | 1999 Apr |
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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 |
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Seizure and electroencephalographic changes in the newborn period induced by opiates and corrected by naloxone infusion. | 1999 Mar |
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Sleep impairments in rats implanted with morphine pellets. | 1999 Nov |
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Patient-controlled analgesia with morphine plus lysine acetyl salicylate. | 1999 Oct |
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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 |
|
Prior experience of morphine application alters the c-fos response to MDMA ('ecstasy') and cocaine in the rat striatum. | 2000 Apr 14 |
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Pethidine reverses morphine-induced delirium. | 2000 Jun |
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Prenatal morphine exposure enhances seizure susceptibility but suppresses long-term potentiation in the limbic system of adult male rats. | 2000 Jun 30 |
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Morphine-induced macrophage apoptosis: the role of transforming growth factor-beta. | 2000 May |
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Advantages of intrathecal nalbuphine, compared with intrathecal morphine, after cesarean delivery: an evaluation of postoperative analgesia and adverse effects. | 2000 Sep |
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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 |
|
Comparison of three methods to find the vapor activity of a hydration step. | 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 |
|
Morphine with or without a local anaesthetic for postoperative intrathecal pain treatment after selective dorsal rhizotomy in children. | 2001 Jan |
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Occurrence of morphine tolerance and dependence in the nucleus paragigantocellularis neurons. | 2001 Jan 5 |
|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27514308
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
Thu Jul 06 00:01:05 UTC 2023
by
admin
on
Thu Jul 06 00:01:05 UTC 2023
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Record UNII |
76I7G6D29C
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
---|---|---|---|---|
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WHO-ESSENTIAL MEDICINES LIST |
8.4
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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CFR |
21 CFR 862.3640
Created by
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WHO-ATC |
N02AA51
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WHO-VATC |
QN02AA01
Created by
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DEA NO. |
9300
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NDF-RT |
N0000175684
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LIVERTOX |
NBK548230
Created by
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WHO-VATC |
QA07DA52
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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NDF-RT |
N0000175690
Created by
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WHO-ESSENTIAL MEDICINES LIST |
2.2
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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WHO-ESSENTIAL MEDICINES LIST |
1.3
Created by
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WHO-VATC |
QN02AA51
Created by
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WHO-VATC |
QN02AG01
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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WHO-ATC |
N02AA01
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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WHO-VATC |
QR05DA05
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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WHO-ATC |
N02AG01
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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WHO-ATC |
R05DA05
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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NCI_THESAURUS |
C1657
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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WHO-ATC |
A07DA52
Created by
admin on Thu Jul 06 00:01:06 UTC 2023 , Edited by admin on Thu Jul 06 00:01:06 UTC 2023
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Code System | Code | Type | Description | ||
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CHEMBL70
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PRIMARY | |||
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1627
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PRIMARY | |||
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2134
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PRIMARY | |||
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D009020
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PRIMARY | |||
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1845
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PRIMARY | |||
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DB00295
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PRIMARY | |||
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C62051
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PRIMARY | |||
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SUB03332MIG
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PRIMARY | |||
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7052
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PRIMARY | RxNorm | ||
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200-320-2
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PRIMARY | |||
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57-27-2
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PRIMARY | |||
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M7631
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PRIMARY | Merck Index | ||
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Morphine
Created by
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PRIMARY | |||
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100000091372
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PRIMARY | |||
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5288826
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58097
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17303
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PRIMARY | |||
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SUB121757
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DTXSID9023336
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MORPHINE
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PRIMARY | |||
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76I7G6D29C
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76I7G6D29C
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PRIMARY |
Related Record | Type | Details | ||
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TARGET -> AGONIST |
Ki
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SALT/SOLVATE -> PARENT |
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SUB_CONCEPT->SUBSTANCE |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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DERIVATIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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DERIVATIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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DERIVATIVE -> PARENT |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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DERIVATIVE -> PARENT |
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TRANSPORTER -> SUBSTRATE | |||
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TARGET -> AGONIST |
Ki
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DERIVATIVE -> PARENT |
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DERIVATIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS |
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DERIVATIVE -> PARENT |
Dihydrocodeinone-6-carboxymethyloxime (derivate of morphine). as per INCB
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DERIVATIVE -> PARENT |
Dihydrodesoxymorphine (derivative of morphine). as per INCB
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
Ki
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PARENT -> SALT/SOLVATE |
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DERIVATIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
MAJOR
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METABOLITE INACTIVE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE ACTIVE -> PARENT |
MAJOR
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PRODRUG -> METABOLITE ACTIVE |
MINOR METABOLITE
MINOR
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
ED50-PO(mg/kg) = 0.33, LD50-PO(mg/kg) = 470, Potency ratio to morphine = 1, Potency ratio to fentanyl = 0.02
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