Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H25NO3 |
Molecular Weight | 339.4281 |
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(CC6CC6)CC[C@@]14[C@@]5(O)CCC2=C)=CC=C3O
InChI
InChIKey=WJBLNOPPDWQMCH-MBPVOVBZSA-N
InChI=1S/C21H25NO3/c1-12-6-7-21(24)16-10-14-4-5-15(23)18-17(14)20(21,19(12)25-18)8-9-22(16)11-13-2-3-13/h4-5,13,16,19,23-24H,1-3,6-11H2/t16-,19+,20+,21-/m1/s1
Nalmefene is the first medication approved for alcoholism
with the primary goal of reducing alcohol intake in an as
needed approach. Nalmefene
received a marketing authorization valid throughout the
European Union on February 25, 2013 and is under development
in Asia. Nalmefene is an opioid system modulator with a
distinct μ, δ, and κ receptor profile. In vitro studies have demonstrated
that Nalmefene is a selective opioid receptor ligand
with antagonist activity at the μ and δ receptors and partial
agonist activity at the κ receptor. In vivo studies have demonstrated
that nalmefene reduces alcohol consumption, possibly
by modulating cortico-mesolimbic functions. In the US, immediate-release injectable nalmefene was approved in 1995 as an antidote for opioid overdose. It was sold under the trade name Revex. The product was discontinued by its manufacturer around 2008. Currently Nalmefene is sold under the trade name Selincro. Selincro is indicated for the reduction of alcohol consumption in adult patients with alcohol dependence who have a high drinking-risk level, without physical withdrawal symptoms and who do not require immediate detoxification.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
0.44 nM [Ki] | |||
9.3 nM [Ki] | |||
0.12 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Selincro Approved UseSelincro is indicated for the reduction of alcohol consumption in adult patients with alcohol dependence who have a high drinking-risk level, without physical withdrawal symptoms and who do not require immediate detoxification. Launch Date1.36175039E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
155 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
177 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
24.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
57.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
109 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1320 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
16.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8877019/ |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
16.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1876 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
191 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
12 mg single, intravenous dose: 12 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
274 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
29.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8877019/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
314 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
385 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
24 mg single, intravenous dose: 24 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
647 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8877019/ |
1 mg single, intravenous dose: 1 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
11.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
12 mg single, intravenous dose: 12 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8877019/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
8.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3943269/ |
24 mg single, intravenous dose: 24 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3680580/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NALMEFENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
18 mg 1 times / day steady, oral Recommended Dose: 18 mg, 1 times / day Route: oral Route: steady Dose: 18 mg, 1 times / day Sources: |
unhealthy, 39 years n = 1 Health Status: unhealthy Condition: alcohol dependence and Schizoaffective Disorder Age Group: 39 years Sex: M Population Size: 1 Sources: |
Disc. AE: Psychiatric decompensation... AEs leading to discontinuation/dose reduction: Psychiatric decompensation (1 patient) Sources: |
300 mg 1 times / day multiple, oral Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
healthy, adult n = 4 Health Status: healthy Age Group: adult Sex: M Population Size: 4 Sources: |
|
300 mg single, oral Highest studied dose |
healthy, adult n = 4 Health Status: healthy Age Group: adult Sex: M Population Size: 4 Sources: |
|
0.75 ug/kg single, intravenous Highest studied dose Dose: 0.75 ug/kg Route: intravenous Route: single Dose: 0.75 ug/kg Sources: |
unhealthy, adult n = 3 Health Status: unhealthy Condition: postoperative pain Age Group: adult Sex: M+F Population Size: 3 Sources: |
DLT: Anesthesia reversal... Dose limiting toxicities: Anesthesia reversal (2 patients) Sources: |
0.5 ug/kg single, intravenous MTD Dose: 0.5 ug/kg Route: intravenous Route: single Dose: 0.5 ug/kg Sources: |
unhealthy, adult n = 18 Health Status: unhealthy Condition: postoperative pain Age Group: adult Sex: M+F Population Size: 18 Sources: |
DLT: Anesthesia reversal... Dose limiting toxicities: Anesthesia reversal (3 patients) Sources: |
20 mg 2 times / day steady, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Disc. AE: Dizziness... AEs leading to discontinuation/dose reduction: Dizziness (1 patient) Sources: |
5 mg 2 times / day steady, oral Studied dose Dose: 5 mg, 2 times / day Route: oral Route: steady Dose: 5 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Disc. AE: Dizziness, Rash... AEs leading to discontinuation/dose reduction: Dizziness (1 patient) Sources: Rash (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Psychiatric decompensation | 1 patient Disc. AE |
18 mg 1 times / day steady, oral Recommended Dose: 18 mg, 1 times / day Route: oral Route: steady Dose: 18 mg, 1 times / day Sources: |
unhealthy, 39 years n = 1 Health Status: unhealthy Condition: alcohol dependence and Schizoaffective Disorder Age Group: 39 years Sex: M Population Size: 1 Sources: |
Anesthesia reversal | 2 patients DLT |
0.75 ug/kg single, intravenous Highest studied dose Dose: 0.75 ug/kg Route: intravenous Route: single Dose: 0.75 ug/kg Sources: |
unhealthy, adult n = 3 Health Status: unhealthy Condition: postoperative pain Age Group: adult Sex: M+F Population Size: 3 Sources: |
Anesthesia reversal | 3 patients DLT |
0.5 ug/kg single, intravenous MTD Dose: 0.5 ug/kg Route: intravenous Route: single Dose: 0.5 ug/kg Sources: |
unhealthy, adult n = 18 Health Status: unhealthy Condition: postoperative pain Age Group: adult Sex: M+F Population Size: 18 Sources: |
Dizziness | 1 patient Disc. AE |
20 mg 2 times / day steady, oral Recommended Dose: 20 mg, 2 times / day Route: oral Route: steady Dose: 20 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Dizziness | 1 patient Disc. AE |
5 mg 2 times / day steady, oral Studied dose Dose: 5 mg, 2 times / day Route: oral Route: steady Dose: 5 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Rash | 1 patient Disc. AE |
5 mg 2 times / day steady, oral Studied dose Dose: 5 mg, 2 times / day Route: oral Route: steady Dose: 5 mg, 2 times / day Sources: |
unhealthy, adult n = 7 Health Status: unhealthy Condition: alcohol dependence Age Group: adult Sex: M+F Population Size: 7 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
The role of endogenous opioids in congestive heart failure: effects of nalmefene on systemic and regional hemodynamics in dogs. | 1987 Feb |
|
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. | 1998 Mar |
|
Acute effects of nalmefene on LH, prolactin, and testosterone in male rhesus monkeys. | 2000 Jun |
|
New developments in the pharmacotherapy of alcohol dependence. | 2001 |
|
Evidence about the use of naltrexone and for different ways of using it in the treatment of alcoholism. | 2001 Jan-Feb |
|
Pharmacological control of opioid-induced pruritus: a quantitative systematic review of randomized trials. | 2001 Jun |
|
A review of the potential role of methylnaltrexone in opioid bowel dysfunction. | 2001 Nov |
|
Nalmefene for elective reversal of procedural sedation in children. | 2001 Nov |
|
Preclinical models to evaluate potential pharmacotherapeutic agents in treating alcoholism and studying the neuropharmacological bases of ethanol-seeking behaviors in rats. | 2002 Aug |
|
Mesa Grande: a methodological analysis of clinical trials of treatments for alcohol use disorders. | 2002 Mar |
|
[Drug therapy of alcohol dependence--a critical review]. | 2003 |
|
Synergistic effects of cannabinoid inverse agonist AM251 and opioid antagonist nalmefene on food intake in mice. | 2004 Mar 5 |
|
Stimulation of the hypothalamic-pituitary-adrenal axis with the opioid antagonist nalmefene. | 2005 |
|
Determination of nalmefene by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. | 2005 Apr |
|
Prolonged central mu-opioid receptor occupancy after single and repeated nalmefene dosing. | 2005 Dec |
|
Phobic memory and somatic vulnerabilities in anorexia nervosa: a necessary unity? | 2005 Sep 6 |
|
Multicenter investigation of the opioid antagonist nalmefene in the treatment of pathological gambling. | 2006 Feb |
|
Targeted nalmefene with simple medical management in the treatment of heavy drinkers: a randomized double-blind placebo-controlled multicenter study. | 2007 Jul |
|
Emerging pharmacologic options for treating postoperative ileus. | 2007 Oct 15 |
|
Evidence of accelerated ageing in clinical drug addiction from immune, hepatic and metabolic biomarkers. | 2007 Sep 24 |
|
Cholestatic hepatitis as a possible new side-effect of oxycodone: a case report. | 2008 May 1 |
|
Predicting response to opiate antagonists and placebo in the treatment of pathological gambling. | 2008 Nov |
|
Pediatric sedation: a global challenge. | 2010 |
|
Nalmefene in the treatment of pathological gambling: multicentre, double-blind, placebo-controlled study. | 2010 Oct |
|
Brain imaging studies in pathological gambling. | 2010 Oct |
|
Treatment of Gambling Disorders. | 2014 Jun 1 |
Patents
Sample Use Guides
How much to take
- The recommended dose is one tablet on days when you think there is a risk you will drink alcohol
- The maximum dose is one tablet per day.
How and when to take
- You should take the tablet 1-2 hours before you start drinking alcohol.
- Swallow the tablet whole, do not crush or divide the tablet.
- You can take Selincro (Nalmefene) with or without food.
Each film-coated tablet contains 18.06 mg nalmefene (as hydrochloride dihydrate).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2991678
Nalmefene antagonized the bindings of [3H]-dihydromorphine, [3H]-ethylketocyclazocine and [3H]-D-ala-D-leu enkephalin with IC50's in the low nanomolar range in rat brain membranes.. At the central mu receptor, nalmefene bound with an IC50 of 1.0 nM
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C681
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NDF-RT |
N0000000154
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WHO-VATC |
QN07BB05
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WHO-ATC |
N07BB05
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NDF-RT |
N0000175691
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LIVERTOX |
NBK548295
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C038981
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5189
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SUB09139MIG
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NALMEFENE
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C61855
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T-2
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1628
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TOV02TDP9I
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CHEMBL982
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TOV02TDP9I
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1876
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55096-26-9
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DB06230
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5284594
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6761
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100000084441
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31479
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m7715
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PRIMARY | Merck Index |
ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)