Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H21NO4 |
Molecular Weight | 327.3743 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12OC3=C4C(C[C@H]5N(CC=C)CC[C@@]14[C@@]5(O)CCC2=O)=CC=C3O
InChI
InChIKey=UZHSEJADLWPNLE-GRGSLBFTSA-N
InChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1
Naloxone, sold under the brand name Narcan among others, is a medication used to block the effects of opioids, especially in overdose. Naloxone has an extremely high affinity for μ-opioid receptors in the central nervous system (CNS). Naloxone is a μ-opioid receptor (MOR) inverse agonist, and its rapid blockade of those receptors often produces rapid onset of withdrawal symptoms. Naloxone also has an antagonist action, though with a lower affinity, at κ- (KOR) and δ-opioid receptors (DOR). If administered in the absence of concomitant opioid use, no functional pharmacological activity occurs (except the inability for the body to combat pain naturally). In contrast to direct opiate agonists, which elicit opiate withdrawal symptoms when discontinued in opiate-tolerant people, no evidence indicates the development of tolerance or dependence on naloxone. The mechanism of action is not completely understood, but studies suggest it functions to produce withdrawal symptoms by competing for opiate receptor sites within the CNS (a competitive antagonist, not a direct agonist), thereby preventing the action of both endogenous and xenobiotic opiates on these receptors without directly producing any effects itself. When administered parenterally (e.g. intravenously or by injection), as is most common, naloxone has a rapid distribution throughout the body. The mean serum half-life has been shown to range from 30 to 81 minutes, shorter than the average half-life of some opiates, necessitating repeat dosing if opioid receptors must be stopped from triggering for an extended period. Naloxone is primarily metabolized by the liver. Its major metabolite is naloxone-3-glucuronide, which is excreted in the urine. Naloxone is useful both in acute opioid overdose and in reducing respiratory or mental depression due to opioids. Whether it is useful in those in cardiac arrest due to an opioid overdose is unclear. Naloxone is poorly absorbed when taken by mouth, so it is commonly combined with a number of oral opioid preparations, including buprenorphine and pentazocine, so that when taken orally, just the opioid has an effect, but if misused by injecting, the naloxone blocks the effect of the opioid. In a meta-analysis of people with shock, including septic, cardiogenic, hemorrhagic, or spinal shock, those who received naloxone had improved blood flow. Naloxone is also experimentally used in the treatment for congenital insensitivity to pain with anhidrosis, an extremely rare disorder (one in 125 million) that renders one unable to feel pain or differentiate temperatures. Naloxone can also be used as an antidote in overdose of clonidine, a medication that lowers blood pressure.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17149859 |
7.3 nM [IC50] | ||
Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12747782 |
49.8 nM [IC50] | ||
Target ID: CHEMBL236 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17388627 |
138.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | NARCAN Approved UsePentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only. Launch Date1971 |
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Primary | NARCAN Approved UsePentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only. Launch Date1971 |
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Primary | NARCAN Approved UsePentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only. Launch Date1971 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.09 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28444856/ |
10 mg/kg single, nasal dose: 10 mg/kg route of administration: Nasal experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.87 ng/mL DRUG LABEL https://www.fda.gov/media/95283/download |
0.4 mg single, intramuscular dose: 0.4 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9.62 ng/mL DRUG LABEL https://www.fda.gov/media/95283/download |
8 mg single, nasal dose: 8 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4.83 ng/mL DRUG LABEL https://www.fda.gov/media/95283/download |
4 mg single, nasal dose: 4 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
37.1 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28444856/ |
10 mg/kg single, nasal dose: 10 mg/kg route of administration: Nasal experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.68 ng × h/mL DRUG LABEL https://www.fda.gov/media/95283/download |
0.4 mg single, intramuscular dose: 0.4 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
15 ng × h/mL DRUG LABEL https://www.fda.gov/media/95283/download |
8 mg single, nasal dose: 8 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.9 ng × h/mL DRUG LABEL https://www.fda.gov/media/95283/download |
4 mg single, nasal dose: 4 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
28.2 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28444856/ |
10 mg/kg single, nasal dose: 10 mg/kg route of administration: Nasal experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.2 h DRUG LABEL https://www.fda.gov/media/95283/download |
0.4 mg single, intramuscular dose: 0.4 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.1 h DRUG LABEL https://www.fda.gov/media/95283/download |
8 mg single, nasal dose: 8 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NALOXONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.8 mg single, intramuscular Dose: 0.8 mg Route: intramuscular Route: single Dose: 0.8 mg Sources: |
healthy, 23.8 years (range: 22.6–25 years) n = 12 Health Status: healthy Age Group: 23.8 years (range: 22.6–25 years) Sex: M+F Population Size: 12 Sources: |
|
160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Disc. AE: Hypotension, Bradycardia... Other AEs: Nausea, Emesis... AEs leading to discontinuation/dose reduction: Hypotension (3 patients) Other AEs:Bradycardia (2 patients) Myoclonus (1 patient) Hypertension (1 patient) Nausea (32%) Sources: Emesis (5%) Seizures (5%) Headache (5%) Confusion (5%) Agitation (3%) |
8 mg single, intranasal Dose: 8 mg Route: intranasal Route: single Dose: 8 mg Sources: |
healthy, adult n = 28 Health Status: healthy Age Group: adult Population Size: 28 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypertension | 1 patient Disc. AE |
160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Myoclonus | 1 patient Disc. AE |
160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Bradycardia | 2 patients Disc. AE |
160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Hypotension | 3 patients Disc. AE |
160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Agitation | 3% | 160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Nausea | 32% | 160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Confusion | 5% | 160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Emesis | 5% | 160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Headache | 5% | 160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Seizures | 5% | 160 mg/m2 single, intravenous (starting) Highest studied dose Dose: 160 mg/m2 Route: intravenous Route: single Dose: 160 mg/m2 Sources: |
unhealthy, 35-85 years n = 38 Health Status: unhealthy Condition: acute ischemic stroke Age Group: 35-85 years Population Size: 38 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
likely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/19874646/ Page: 7,8 |
yes | |||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Prevention by morphine of apomorphine- and oxytocin-induced penile erection and yawning: site of action in the brain. | 1992 Jan |
|
Modification of naloxone-induced withdrawal signs by dextromethorphan in morphine-dependent mice. | 1999 Jul 14 |
|
Seizure and electroencephalographic changes in the newborn period induced by opiates and corrected by naloxone infusion. | 1999 Mar |
|
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice. | 1999 Sep |
|
Morphine inhibits human microglial cell production of, and migration towards, RANTES. | 2000 |
|
Acute detoxification of opioid-addicted patients with naloxone during propofol or methohexital anesthesia: a comparison of withdrawal symptoms, neuroendocrine, metabolic, and cardiovascular patterns. | 2000 Apr |
|
The effect of spinal ibuprofen on opioid withdrawal in the rat. | 2000 Aug |
|
Phenytoin, midazolam, and naloxone protect against fentanyl-induced brain damage in rats. | 2000 Dec |
|
Fentanyl-induced chest wall rigidity and laryngospasm in preterm and term infants. | 2000 Mar |
|
Differential cardiorespiratory effects of endomorphin 1, endomorphin 2, DAMGO, and morphine. | 2000 Sep |
|
Opioid-induced hyperalgesia and incisional pain. | 2001 Jul |
|
Inverse agonists and neutral antagonists at mu opioid receptor (MOR): possible role of basal receptor signaling in narcotic dependence. | 2001 Jun |
|
Naloxone improves arterial blood pressure and hypoxic ventilatory depression, but not survival, of rats during acute hypoxia. | 2001 Mar |
|
Effects of Ferula gummosa Boiss. fractions on morphine dependence in mice. | 2001 Sep |
|
Environment associated with morphine and experience of aggression modulate behaviors of postdependent mice. | 2002 Jan 15 |
|
Safety of enteral naloxone and i.v. neostigmine when used to relieve constipation. | 2003 Jun 15 |
|
Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. | 2003 May |
|
Systemic morphine-induced release of serotonin in the rostroventral medulla is not mimicked by morphine microinjection into the periaqueductal gray. | 2003 Sep |
|
Influence of sweet tasting solutions on opioid withdrawal. | 2004 Dec 15 |
|
Magnesium influence on morphine--induced pharmacodependence in rats. | 2004 Mar |
|
[Effect of nitric oxide synthase inhibitor on the testis cell apoptosis in morphine-dependent rats]. | 2004 Nov |
|
Testosterone and luteinizing hormone responses to naloxone help predict sexual performance in rams. | 2004 Nov |
|
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance. | 2004 Nov |
|
Potentiated startle and hyperalgesia during withdrawal from acute morphine: effects of multiple opiate exposures. | 2004 Nov |
|
Effect of agmatine on the development of morphine dependence in rats: potential role of cAMP system. | 2004 Nov 19 |
|
Effects of L-745,870, a dopamine D4 receptor antagonist, on naloxone-induced morphine dependence in mice. | 2004 Oct |
|
Rapid, transient, and dose-dependent expression of hsp70 messenger RNA in the rat brain after morphine treatment. | 2004 Summer |
|
Calcitonin gene-related peptide-induced suppression of luteinizing hormone pulses in the rat: the role of endogenous opioid peptides. | 2005 Aug 1 |
|
Effect of fentanyl on lidocaine-induced convulsions in mice. | 2005 Dec |
|
Morphine-induced chemotaxis and brain-derived neurotrophic factor expression in microglia. | 2005 Jan 12 |
|
Naloxone increases ketamine-induced hyperactivity in the open field in female rats. | 2005 Jul |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Effective opiate-receptor antagonist therapy of cholestatic pruritus induced by an oral contraceptive. | 2005 May |
Sample Use Guides
Opioid Overdose–Known or Suspected: An initial dose of 0.4 mg to 2 mg of NARCAN may be administered intravenously. If the desired degree of counteraction and improvement in respiratory functions are not obtained, it may be repeated at two- to three-minute intervals. If no response is observed after 10 mg of NARCAN have been administered, the diagnosis of opioid-induced or partial opioid-induced toxicity should be questioned. Intramuscular or subcutaneous administration may be necessary if the intravenous route is not available.
Postoperative Opioid Depression: For the partial reversal of opioid depression following the use of opioids during surgery, smaller doses of NARCAN are usually sufficient. The dose of NARCAN should be titrated according to the patient’s response. For the initial reversal of respiratory depression, NARCAN should be injected in increments of 0.1 to 0.2 mg intravenously at two- to three-minute intervals to the desired degree of reversal, i.e., adequate ventilation and alertness without significant pain or discomfort. Larger than necessary dosage of NARCAN may result in significant reversal of analgesia and increase in blood pressure. Similarly, too rapid reversal may induce nausea, vomiting, sweating or circulatory stress.
Repeat doses of NARCAN may be required within one- to two-hour intervals depending upon the amount, type (i.e., short or long acting) and time interval since last administration of an opioid. Supplemental intramuscular doses have been shown to produce a longer lasting effect.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17624703
MDCKII-MDR1 assay. Stock solutions of Naloxone (20 mM) were prepared in 100% DMSO and then diluted to the final concentration of 10 mkM, in Dulbecco’s PBS. Naloxone were tested in both directions, apicalto-basolateral (A→B) and basolateral-to-apical (B→A), in duplicate. The ratio BA/AB >2 indicates an efflux phenomena. Permeability studies were conducted at 37 ◦C in incubator for 60 min. The monolayer integrity was evaluated by measuring the TransEpithelial Electrical Resistance (TEER) by using the Millicell-ERS system (Millipore Corporation) and it was considered integer if the resistancewas between 200 and 300 cm2. After the transport study the monolayer integrity was measured
in each well by adding a 0.02 mg/mL solution of lucifer yellow (LY); the test was conducted at 37 ◦C for 60 min, and the fluorescence (RFU) was measured at 485/535 nm.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
280209
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WHO-ESSENTIAL MEDICINES LIST |
4.2
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NDF-RT |
N0000000154
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EMA ASSESSMENT REPORTS |
SUBOXONE (AUTHORIZED: OPIOID-RELATED DISEASES)
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WHO-VATC |
QV03AB15
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FDA ORPHAN DRUG |
79093
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WHO-ATC |
V03AB15
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WHO-ATC |
A06AH04
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LIVERTOX |
NBK548244
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NDF-RT |
N0000175691
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WHO-ATC |
N02AA53
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NCI_THESAURUS |
C681
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Code System | Code | Type | Description | ||
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CHEMBL80
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Naloxone
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7459
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5284596
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100000085468
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NALOXONE
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1878
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7242
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PRIMARY | RxNorm | ||
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36B82AMQ7N
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SUB09142MIG
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1526
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DTXSID8023349
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D009270
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36B82AMQ7N
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PRIMARY | |||
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DB01183
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C62054
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1453005
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1638
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3279
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207-365-7
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70413
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m7717
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PRIMARY | Merck Index | ||
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465-65-6
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)