Details
Stereochemistry | ACHIRAL |
Molecular Formula | 3C8H15O2.Bi |
Molecular Weight | 638.5909 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Bi+3].CCCC(CCC)C([O-])=O.CCCC(CCC)C([O-])=O.CCCC(CCC)C([O-])=O
InChI
InChIKey=YZDVVHSLIPLZLO-UHFFFAOYSA-K
InChI=1S/3C8H16O2.Bi/c3*1-3-5-7(6-4-2)8(9)10;/h3*7H,3-6H2,1-2H3,(H,9,10);/q;;;+3/p-3
Molecular Formula | C8H15O2 |
Molecular Weight | 143.2035 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Bi |
Molecular Weight | 208.9804 |
Charge | 3 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
http://psychopharmacologyinstitute.com/mood-stabilizers/valproate-in-psychiatry-approved-indications-and-off-label-uses/ | https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022152s002lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/12847559 | https://www.ncbi.nlm.nih.gov/pubmed/11742974 | https://www.ncbi.nlm.nih.gov/pubmed/11473107
Curator's Comment: Description was created based on several sources, including
http://psychopharmacologyinstitute.com/mood-stabilizers/valproate-in-psychiatry-approved-indications-and-off-label-uses/ | https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022152s002lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/12847559 | https://www.ncbi.nlm.nih.gov/pubmed/11742974 | https://www.ncbi.nlm.nih.gov/pubmed/11473107
Valproic acid (VPA; valproate; di-n-propylacetic acid, DPA; 2-propylpentanoic acid, or 2-propylvaleric acid) was first synthesized in 1882, by Burton. FDA approved valproic acid for the treatment of manic episodes associated with bipolar disorder, for the monotherapy and adjunctive therapy of complex partial seizures and simple and complex absence seizures and adjunctive therapy in patients with multiple seizure types that include absence seizures and for the prophylaxis of migraine headaches.
The mechanisms of VPA which seem to be of clinical importance in the treatment of epilepsy include increased gamma-aminobutyric acid (GABA)-ergic activity, reduction in excitatory neurotransmission, and modification of monoamines. Recently, it was discovered that the VPA is a class I selective histone deacetylase inhibitor. This activity can be distinguished from its therapeutically exploited antiepileptic activity.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11473107 |
0.4 mM [IC50] | ||
Target ID: CHEMBL1937 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11742974/ |
0.54 mM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DEPAKENE Approved UseDepakene (valproic acid) is indicated as monotherapy and adjunctive therapy in the treatment of patients with complex partial seizures that occur either in isolation or in association with other types of seizures. Depakene (valproic acid) is indicated for use as sole and adjunctive therapy in the treatment of simple and complex absence seizures, and adjunctively in patients with multiple seizure types which include absence seizures.
Simple absence is defined as very brief clouding of the sensorium or loss of consciousness accompanied by certain generalized epileptic discharges without other detectable clinical signs. Complex absence is the term used when other signs are also present. |
|||
Preventing | STAVZOR Approved UseStavzor (valproic acid) delayed release capsules is indicated for:
• Acute treatment of manic episodes associated with bipolar disorder
• Monotherapy and adjunctive therapy of complex partial seizures and simple and complex absence seizures; adjunctive therapy in patients with multiple seizure types that include absence seizures
• Prophylaxis of migraine headaches Launch Date2008 |
|||
Primary | STAVZOR Approved UseStavzor (valproic acid) delayed release capsules is indicated for:
• Acute treatment of manic episodes associated with bipolar disorder
• Monotherapy and adjunctive therapy of complex partial seizures and simple and complex absence seizures; adjunctive therapy in patients with multiple seizure types that include absence seizures
• Prophylaxis of migraine headaches Launch Date2008 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
107.2 mg/L |
500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
VALPROIC ACID plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1951 mg × h/L |
500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
VALPROIC ACID plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16 h |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALPROIC ACID unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
150 mg/kg single, intravenous Highest studied dose Dose: 150 mg/kg Route: intravenous Route: single Dose: 150 mg/kg Sources: Page: p.6 |
healthy, 30.2 ± 11.7 n = 3 Health Status: healthy Age Group: 30.2 ± 11.7 Sex: M+F Population Size: 3 Sources: Page: p.6 |
DLT: Headache, Nausea... |
140 mg/kg single, intravenous MTD Dose: 140 mg/kg Route: intravenous Route: single Dose: 140 mg/kg Sources: Page: p.6 |
healthy, 30.2 ± 11.7 n = 6 Health Status: healthy Age Group: 30.2 ± 11.7 Sex: M+F Population Size: 6 Sources: Page: p.6 |
|
25 g single, oral Overdose Dose: 25 g Route: oral Route: single Dose: 25 g Sources: Page: p.1 |
unhealthy, 37 n = 1 Health Status: unhealthy Condition: Seizures |Bipolar disorder Age Group: 37 Sex: M Population Size: 1 Sources: Page: p.1 |
Disc. AE: Somnolence... AEs leading to discontinuation/dose reduction: Somnolence Sources: Page: p.1 |
100 g single, oral Overdose Dose: 100 g Route: oral Route: single Dose: 100 g Sources: Page: 110000 |
unhealthy, 41 n = 1 Health Status: unhealthy Condition: Epilepsy Age Group: 41 Sex: M Population Size: 1 Sources: Page: 110000 |
Disc. AE: Coma... AEs leading to discontinuation/dose reduction: Coma Sources: Page: 110000 |
120 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 120 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 120 mg/kg, 1 times / day Sources: Page: p.179 |
unhealthy, 62.5 n = 5 Health Status: unhealthy Condition: Cancer Age Group: 62.5 Sex: M+F Population Size: 5 Sources: Page: p.179 |
DLT: Somnolence... Dose limiting toxicities: Somnolence (40%) Sources: Page: p.179 |
60 mg/kg 1 times / day multiple, intravenous MTD Dose: 60 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 60 mg/kg, 1 times / day Sources: Page: p.178 |
unhealthy, 62.5 n = 3 Health Status: unhealthy Condition: Cancer Age Group: 62.5 Sex: M+F Population Size: 3 Sources: Page: p.178 |
|
60 mg/kg 1 times / day multiple, oral Recommended Dose: 60 mg/kg, 1 times / day Route: oral Route: multiple Dose: 60 mg/kg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Seizures Sources: Page: p.1 |
Disc. AE: Hepatotoxicity, Pancreatitis... AEs leading to discontinuation/dose reduction: Hepatotoxicity Sources: Page: p.1Pancreatitis |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Headache | DLT | 150 mg/kg single, intravenous Highest studied dose Dose: 150 mg/kg Route: intravenous Route: single Dose: 150 mg/kg Sources: Page: p.6 |
healthy, 30.2 ± 11.7 n = 3 Health Status: healthy Age Group: 30.2 ± 11.7 Sex: M+F Population Size: 3 Sources: Page: p.6 |
Nausea | DLT | 150 mg/kg single, intravenous Highest studied dose Dose: 150 mg/kg Route: intravenous Route: single Dose: 150 mg/kg Sources: Page: p.6 |
healthy, 30.2 ± 11.7 n = 3 Health Status: healthy Age Group: 30.2 ± 11.7 Sex: M+F Population Size: 3 Sources: Page: p.6 |
Somnolence | Disc. AE | 25 g single, oral Overdose Dose: 25 g Route: oral Route: single Dose: 25 g Sources: Page: p.1 |
unhealthy, 37 n = 1 Health Status: unhealthy Condition: Seizures |Bipolar disorder Age Group: 37 Sex: M Population Size: 1 Sources: Page: p.1 |
Coma | Disc. AE | 100 g single, oral Overdose Dose: 100 g Route: oral Route: single Dose: 100 g Sources: Page: 110000 |
unhealthy, 41 n = 1 Health Status: unhealthy Condition: Epilepsy Age Group: 41 Sex: M Population Size: 1 Sources: Page: 110000 |
Somnolence | 40% DLT |
120 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 120 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 120 mg/kg, 1 times / day Sources: Page: p.179 |
unhealthy, 62.5 n = 5 Health Status: unhealthy Condition: Cancer Age Group: 62.5 Sex: M+F Population Size: 5 Sources: Page: p.179 |
Hepatotoxicity | Disc. AE | 60 mg/kg 1 times / day multiple, oral Recommended Dose: 60 mg/kg, 1 times / day Route: oral Route: multiple Dose: 60 mg/kg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Seizures Sources: Page: p.1 |
Pancreatitis | Disc. AE | 60 mg/kg 1 times / day multiple, oral Recommended Dose: 60 mg/kg, 1 times / day Route: oral Route: multiple Dose: 60 mg/kg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Seizures Sources: Page: p.1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
minimal | ||||
minimal | ||||
minimal | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022152s000_ClinPharmR.pdf#page=17 Page: 17.0 |
no | |||
weak [Ki 7975 uM] | ||||
weak [Ki 8553 uM] | ||||
weak [Ki 9150 uM] | ||||
yes [Ki 600 uM] | likely (co-administration study) Comment: competitive inhibition; risk of pharmacokinetic drug–drug interactions should be taken into account during concomitant use of valproic acid and CYP2C9 substrates |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/9606477/ Page: 3.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/9606477/ Page: 3.0 |
yes | |||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Pathomorphological changes in mouse liver and kidney during prolonged valproate administration. | 2000 |
|
Fatal deterioration of neurological disease after orthotopic liver transplantation for valproic acid-induced liver damage. | 2000 Aug |
|
Nonspecific stimulation of the maternal immune system. I. Effects On teratogen-induced fetal malformations. | 2000 Dec |
|
Valproate and other anticonvulsants for psychiatric disorders. | 2000 Dec 11 |
|
[Lyell syndrome associated with lamotrigine]. | 2000 Dec 16-31 |
|
Phenytoin poisoning after using Chinese proprietary medicines. | 2000 Jul |
|
In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy. | 2000 Nov |
|
A case of pharmacokinetic interference in comedication of clozapine and valproic acid. | 2000 Nov |
|
Renal tubular function in patients receiving anticonvulsant therapy: a long-term study. | 2000 Nov |
|
Valproate-induced tinnitus misinterpreted as psychotic symptoms. | 2000 Oct |
|
Acute hepatitis after lamotrigine administration. | 2000 Sep |
|
Influence of chronic barbiturate administration on sleep apnea after hypersomnia presentation: case study. | 2000 Sep |
|
[Dementia and extrapyramidal problems caused by long-term valproic acid]. | 2000 Sep-Oct |
|
Action of valproic acid on Xenopus laevis development: teratogenic effects on eyes. | 2001 |
|
Benzodiazepines and anticonvulsants for social phobia (social anxiety disorder). | 2001 |
|
Probenecid-associated alterations in valproate glucuronide hepatobiliary disposition: mechanistic assessment using mathematical modeling. | 2001 Apr |
|
Determination of the antiepileptics vigabatrin and gabapentin in dosage forms and biological fluids using Hantzsch reaction. | 2001 Feb |
|
Valproate, but not lamotrigine, induces ovarian morphological changes in Wistar rats. | 2001 Feb |
|
Valproate and the risk of hyperandrogenism. | 2001 Feb |
|
Collaborative study on rat sperm motion analysis using CellSoft Series 4000 semen analyzer. | 2001 Feb |
|
Treatment and management of cluster headache. | 2001 Feb |
|
Antiepileptic drug withdrawal in patients with temporal lobe epilepsy undergoing presurgical video-EEG monitoring. | 2001 Feb |
|
A case of chronic pancreatic insufficiency due to valproic acid in a child. | 2001 Feb |
|
[Treatment of cluster headache]. | 2001 Feb |
|
Glutamate receptor antagonists differentially affect the protective activity of conventional antiepileptics against amygdala-kindled seizures in rats. | 2001 Feb |
|
Treatment of impulsivity and aggression in a patient with vascular dementia. | 2001 Feb |
|
Melt pelletization of a hygroscopic drug in a high shear mixer. Part 3. Effects of binder variation. | 2001 Feb |
|
Effect of coadministered drugs and ethanol on the binding of therapeutic drugs to human serum in vitro. | 2001 Feb |
|
Divalproex sodium augmentation of haloperidol in hospitalized patients with schizophrenia: clinical and economic implications. | 2001 Feb |
|
Rufinamide: a double-blind, placebo-controlled proof of principle trial in patients with epilepsy. | 2001 Feb |
|
Different control of GH secretion by gamma-amino- and gamma-hydroxy-butyric acid in 4-year abstinent alcoholics. | 2001 Feb 1 |
|
Independent short-term variability of spike-like (600 Hz) and postsynaptic (N20) cerebral SEP components. | 2001 Feb 12 |
|
[Febrile convulsions, Treatment and prognosis]. | 2001 Feb 19 |
|
The impact of pharmacogenetics for migraine. | 2001 Feb 9 |
|
Valproic acid has temporal variability in urinary clearance of metabolites. | 2001 Jan |
|
Electrophysiological and pharmacological properties of the human brain type IIA Na+ channel expressed in a stable mammalian cell line. | 2001 Jan |
|
Evaluating the tolerability of the newer mood stabilizers. | 2001 Jan |
|
Contribution of sodium valproate to the syndrome of inappropriate secretion of antidiuretic hormone. | 2001 Jan |
|
Clozapine therapy for a patient with a history of Hodgkin's disease. | 2001 Jan |
|
Effects of antiepileptic drugs on rat platelet aggregation: ex vivo and in vitro study. | 2001 Jan |
|
Occurrence of thrombocytopenia in psychiatric patients taking valproate. | 2001 Jan |
|
Additional educational needs in children born to mothers with epilepsy. | 2001 Jan |
|
Valproic acid embryopathy: report of two siblings with further expansion of the phenotypic abnormalities and a review of the literature. | 2001 Jan 15 |
|
Weight change associated with valproate and lamotrigine monotherapy in patients with epilepsy. | 2001 Jan 23 |
|
Hypothermia and thermoregulatory derangements induced by valproic acid. | 2001 Jan 9 |
|
Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy. | 2001 Jan 9 |
|
Mood stabilizers and ion regulation. | 2001 Jan-Feb |
|
Does genomic imprinting contribute to valproic acid teratogenicity? | 2001 Jan-Feb |
|
Synthesis and intramitochondrial levels of valproyl-coenzyme A metabolites. | 2001 Mar 1 |
|
Placebo-controlled study of divalproex sodium for agitation in dementia. | 2001 Winter |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/valproic-acid.html
Usual Adult Dose for Epilepsy
Complex partial seizures:
Initial dose: 10 to 15 mg/kg orally or intravenously per day as an IV infusion in divided doses, increased by 5 to 10 mg/kg per week if necessary according to clinical response
Maintenance dose: 10 to 60 mg/kg per day in divided doses
Maximum dose: 60 mg/kg per day
Simple and complex absence seizures:
Initial dose: 15 mg/kg orally or intravenously per day as an IV infusion in divided doses, increased at one week intervals by 5 to 10 mg/kg/day according to seizure control and tolerability
Maximum dose: 60 mg/kg per day
Comments:
-If the total daily dose exceeds 250 mg, it should be given in 2 to 3 divided doses.
-Use of IV valproate sodium for periods longer than 14 days has not been studied; patients should be converted to oral valproate as soon as clinically feasible.
-When switching from oral to IV valproate, the total daily dose of IV valproate should be equivalent to the total daily dose of oral valproate, and administered at the same frequency as the oral product.
-Equivalence between IV and oral valproate products at steady state has only been evaluated in a 6-hourly dosing regimen. Trough plasma level monitoring may be required if IV valproate is administered 2 to 3 times a day.
-Complex partial seizures: When converting patients to valproate monotherapy, concomitant antiepileptic drug dosage can generally be reduced by approximately 25% every 2 weeks, commencing either at the start of valproate therapy or delayed by 1 to 2 weeks. Patients should be monitored closely during this period for increased seizure frequency.
Uses: Monotherapy and adjunctive therapy in the treatment of complex partial seizures; sole and adjunctive therapy for simple and complex absence seizures; adjunctive therapy in patients with multiple seizure types that include absence seizures.
Usual Adult Dose for Mania
Delayed-release capsules :
Initial dose: 750 mg orally per day in divided doses
Maximum dose: 60 mg/kg orally per day
Duration: Safety and efficacy beyond 3 weeks has not been established
Comments:
-The dose should be increased as rapidly as possible to achieve the lowest therapeutic dose which produces the desired clinical effect or the desired range of plasma concentrations.
-In placebo-controlled clinical trials of acute mania, patients were dosed to a clinical response with a trough plasma concentration of 50 to 125 mcg/mL.
-Maximum concentrations were generally achieved within 14 days.
-Safety and efficacy for longer term use in the maintenance of the initial response and prevention of new manic episodes has not been systematically evaluated in clinical trials. Use for extended periods should be accompanied by regular review for the long-term usefulness of the drug for the individual patient.
Use: Treatment of manic episodes associated with bipolar disorder.
Usual Adult Dose for Migraine Prophylaxis
Delayed release oral capsules:
Initial dose: 250 mg orally twice a day
Comments:
-Some patients may benefit from doses up to 1000 mg per day.
-In clinical trials, there was no evidence that higher doses led to greater efficacy.
Usual Pediatric Dose for Epilepsy
10 years of age or older:
Complex partial seizures:
Initial dose: 10 to 15 mg/kg orally or intravenously per day as an IV infusion in divided doses, increased by 5 to 10 mg/kg per week if necessary according to clinical response
Maintenance dose: 10 to 60 mg/kg per day in divided doses
Maximum dose: 60 mg/kg per day
Simple and complex absence seizures:
Initial dose: 15 mg/kg orally or intravenously per day as an IV infusion in divided doses, increased at one week intervals by 5 to 10 mg/kg/day according to seizure control and tolerability
Maximum dose: 60 mg/kg per day
Comments:
-If the total daily dose exceeds 250 mg, it should be given in 2 to 3 divided doses.
-Use of IV valproate sodium for periods longer than 14 days has not been studied; patients should be converted to oral valproate as soon as clinically feasible.
-When switching from oral to IV valproate, the total daily dose of IV valproate should be equivalent to the total daily dose of oral valproate, and administered at the same frequency as the oral product.
-Equivalence between IV and oral valproate products at steady state has only been evaluated in a 6-hourly dosing regimen. Trough plasma level monitoring may be required if IV valproate is administered 2 to 3 times a day.
-Complex partial seizures: When converting patients to valproate monotherapy, concomitant antiepileptic drug dosage can generally be reduced by approximately 25% every 2 weeks, commencing either at the start of valproate therapy or delayed by 1 to 2 weeks. Patients should be monitored closely during this period for increased seizure frequency.
Uses: Monotherapy and adjunctive therapy in the treatment of complex partial seizures; sole and adjunctive therapy for simple and complex absence seizures; adjunctive therapy in patients with multiple seizure types that include absence seizures.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28407839
H9C2 cells were cultured and allotted to the blank, vehicle, and valproic acid (VPA)-treated groups: the VPA treated group received VPA exposure at concentrations of 2.0, 4.0 and 8.0 mmol/L. VPA might result in acetylation/deacetylation imbalances by inhibiting HDAC1-3 protein expression and total HDAC activity, leading to the down-regulation of mRNA and protein expression of Vangl2 and Scrib.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:07:04 GMT 2023
by
admin
on
Fri Dec 15 19:07:04 GMT 2023
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Record UNII |
87PTX621FI
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Record Status |
Validated (UNII)
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Record Version |
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DB13910
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |