Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H8N4.ClH |
Molecular Weight | 196.637 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NNC1=NN=CC2=C1C=CC=C2
InChI
InChIKey=ZUXNZUWOTSUBMN-UHFFFAOYSA-N
InChI=1S/C8H8N4.ClH/c9-11-8-7-4-2-1-3-6(7)5-10-12-8;/h1-5H,9H2,(H,11,12);1H
DescriptionSources: http://www.drugbank.ca/drugs/DB01275Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/hydralazine.html
Sources: http://www.drugbank.ca/drugs/DB01275
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/hydralazine.html
Hydralazine is a direct-acting vasodilator that is used as an antihypertensive agent. Hydralazine works by relaxing blood vessels (arterioles more than venules) and increasing the supply of blood and oxygen to the heart while reducing its workload. It also functions as an antioxidant. It inhibits membrane-bound enzymes that form reactive oxygen species, such as superoxides. Excessive superoxide counteracts NO-induced vasodilation. Hydralazine is used for the treatment of essential hypertension, alone or as an adjunct. Also for the management of severe hypertension when the drug cannot be given orally or when blood pressure must be lowered immediately, congestive heart failure (in combination with cardiac glycosides and diuretics and/or with isosorbide dinitrate), and hypertension secondary to pre-eclampsia/eclampsia.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9390968
Curator's Comment: some metabolites of hydralazine are known to cross the blood-brain barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3437 Sources: http://www.drugbank.ca/drugs/DB01275 |
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Target ID: GO:0070471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3354891 |
400.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Hydralazine Hydrochloride Approved UseSevere essential hypertension when the drug cannot be given orally or when there is an urgent need to lower
blood pressure. Launch Date1985 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6653641 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: HYDRALAZINE |
HYDRALAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
407 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6653641 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: HYDRALAZINE |
HYDRALAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6653641 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: HYDRALAZINE |
HYDRALAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13% |
HYDRALAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Co-administed with:: ethanol Sources: |
unhealthy, 27 n = 1 Health Status: unhealthy Condition: Hypertension Age Group: 27 Sex: F Population Size: 1 Sources: |
Disc. AE: Tachycardia... AEs leading to discontinuation/dose reduction: Tachycardia Sources: |
750 mg single, oral Overdose Dose: 750 mg Route: oral Route: single Dose: 750 mg Co-administed with:: clonazepam, p.o(10 mg, single) Sources: Page: p.53, 54 |
unhealthy, 38 n = 1 Health Status: unhealthy Condition: Hypertension Age Group: 38 Sex: F Population Size: 1 Sources: Page: p.53, 54 |
Disc. AE: Lethargy, Hypotension... AEs leading to discontinuation/dose reduction: Lethargy Sources: Page: p.53, 54Hypotension Tachycardia Chest pain |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: |
Disc. AE: Skin rash, Febrile reaction... AEs leading to discontinuation/dose reduction: Skin rash (rare) Sources: Febrile reaction (rare) |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.2 |
Disc. AE: Systemic lupus erythematosus synd, Glomerulonephritis... AEs leading to discontinuation/dose reduction: Systemic lupus erythematosus synd Sources: Page: p.2Glomerulonephritis |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.3 |
Disc. AE: Angina pectoris, Myocardial infarction... AEs leading to discontinuation/dose reduction: Angina pectoris Sources: Page: p.3Myocardial infarction Peripheral neuritis |
40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.1 |
Disc. AE: Systemic lupus erythematosus synd, Glomerulonephritis... AEs leading to discontinuation/dose reduction: Systemic lupus erythematosus synd Sources: Page: p.1Glomerulonephritis |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Tachycardia | Disc. AE | 2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Co-administed with:: ethanol Sources: |
unhealthy, 27 n = 1 Health Status: unhealthy Condition: Hypertension Age Group: 27 Sex: F Population Size: 1 Sources: |
Chest pain | Disc. AE | 750 mg single, oral Overdose Dose: 750 mg Route: oral Route: single Dose: 750 mg Co-administed with:: clonazepam, p.o(10 mg, single) Sources: Page: p.53, 54 |
unhealthy, 38 n = 1 Health Status: unhealthy Condition: Hypertension Age Group: 38 Sex: F Population Size: 1 Sources: Page: p.53, 54 |
Hypotension | Disc. AE | 750 mg single, oral Overdose Dose: 750 mg Route: oral Route: single Dose: 750 mg Co-administed with:: clonazepam, p.o(10 mg, single) Sources: Page: p.53, 54 |
unhealthy, 38 n = 1 Health Status: unhealthy Condition: Hypertension Age Group: 38 Sex: F Population Size: 1 Sources: Page: p.53, 54 |
Lethargy | Disc. AE | 750 mg single, oral Overdose Dose: 750 mg Route: oral Route: single Dose: 750 mg Co-administed with:: clonazepam, p.o(10 mg, single) Sources: Page: p.53, 54 |
unhealthy, 38 n = 1 Health Status: unhealthy Condition: Hypertension Age Group: 38 Sex: F Population Size: 1 Sources: Page: p.53, 54 |
Tachycardia | Disc. AE | 750 mg single, oral Overdose Dose: 750 mg Route: oral Route: single Dose: 750 mg Co-administed with:: clonazepam, p.o(10 mg, single) Sources: Page: p.53, 54 |
unhealthy, 38 n = 1 Health Status: unhealthy Condition: Hypertension Age Group: 38 Sex: F Population Size: 1 Sources: Page: p.53, 54 |
Febrile reaction | rare Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: |
Skin rash | rare Disc. AE |
200 mg 1 times / day multiple, oral (max) Recommended Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: |
Glomerulonephritis | Disc. AE | 300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.2 |
Systemic lupus erythematosus synd | Disc. AE | 300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.2 |
Angina pectoris | Disc. AE | 300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.3 |
Myocardial infarction | Disc. AE | 300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.3 |
Peripheral neuritis | Disc. AE | 300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.3 |
Glomerulonephritis | Disc. AE | 40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.1 |
Systemic lupus erythematosus synd | Disc. AE | 40 mg single, intravenous Recommended Dose: 40 mg Route: intravenous Route: single Dose: 40 mg Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Hypertension 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 |
---|---|---|---|---|
no [IC50 >1000 uM] | ||||
no | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
unlikely | ||||
yes [IC50 197 uM] | ||||
yes [Ki 83 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Clinical consequences of polymorphic acetylation of basic drugs. | 1977 Sep |
|
Immunological side-effects of antihypertensive drugs. | 1979 |
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Acute hemodynamic effects of pinacidil and hydralazine in essential hypertension. | 1985 Mar |
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Therapeutic implications of hypertension-induced glomerular injury. Comparison of enalapril and a combination of hydralazine, reserpine, and hydrochlorothiazide in an experimental model. | 1985 Sep 27 |
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Suppression of ventricular arrhythmias after coronary artery ligation by pinacidil, a vasodilator drug. | 1985 Sep-Oct |
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Drug-associated glomerulopathies. | 1986 |
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Comparative study of endralazine and hydralazine for the treatment of hypertension uncontrolled by a beta-blocker and diuretic. | 1986 |
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Clinical pharmacology and therapeutic role of prazosin and related alpha-adrenoceptor antagonists. | 1986 |
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Therapeutic advantage of converting enzyme inhibitors in arresting progressive renal disease associated with systemic hypertension in the rat. | 1986 Jun |
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Inhibition of sympathoadrenal activity by atrial natriuretic factor in dogs. | 1987 Apr |
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Isolated minimal change nephropathy associated with diclofenac. | 1987 Jul 18 |
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Vasodilators and regression of left ventricular hypertrophy. Hydralazine versus prazosin in hypertensive humans. | 1987 May |
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Hydralazine-induced cholestatic jaundice following liver transplantation. | 1989 Jan |
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Myocardial ischemia during isoflurane anesthesia: the effect of substituting halothane. | 1989 Jun |
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Features of the acute hypotensive action of carvedilol and its ameliorating effect on myocardial ischemia. | 1991 |
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A comparison of enalapril with hydralazine-isosorbide dinitrate in the treatment of chronic congestive heart failure. | 1991 Aug 1 |
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Effects of hydralazine and increased cardiac output on recombinant tissue plasminogen activator-induced thrombolysis in canine pulmonary embolism. | 1991 Mar |
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Phaeochromocytoma: an unusual cause of hypertension in pregnancy. | 2001 Jan |
|
Drugs for treatment of very high blood pressure during pregnancy. | 2002 |
|
Angiotensin II regulation of vascular endothelial growth factor and receptors Flt-1 and KDR/Flk-1 in cyclosporine nephrotoxicity. | 2002 Aug |
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[Pulmonary hypertension and pregnancy]. | 2002 Feb |
|
Nifedipine or hydralazine as a first-line agent to control hypertension in severe preeclampsia. | 2002 Jan |
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High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter. | 2002 Jun |
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Analyses of differential gene expression in genetic hypertensive rats by microarray. | 2002 Mar |
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Tight blood pressure control decreases apoptosis during renal damage. | 2004 Mar |
|
Calcium channel blockades exhibit anti-inflammatory and antioxidative effects by augmentation of endothelial nitric oxide synthase and the inhibition of angiotensin converting enzyme in the N(G)-nitro-L-arginine methyl ester-induced hypertensive rat aorta: vasoprotective effects beyond the blood pressure-lowering effects of amlodipine and manidipine. | 2005 Aug |
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Effect of AT1 receptor antagonism on vascular and circulating inflammatory mediators in SHR: role of NF-kappaB/IkappaB system. | 2005 Jan |
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Global DNA hypermethylation-associated cancer chemotherapy resistance and its reversion with the demethylating agent hydralazine. | 2006 Aug 7 |
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Role of connective tissue growth factor in vascular and renal damage associated with hypertension in rats. Interactions with angiotensin II. | 2006 Dec |
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Peroxisome proliferator-activated receptor gamma regulates angiotensin II-stimulated phosphatidylinositol 3-kinase and mitogen-activated protein kinase in blood vessels in vivo. | 2006 Jan |
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Hydralazine inhibits rapid acrolein-induced protein oligomerization: role of aldehyde scavenging and adduct trapping in cross-link blocking and cytoprotection. | 2006 Mar |
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Differential expression of components of the cardiomyocyte adrenomedullin/intermedin receptor system following blood pressure reduction in nitric oxide-deficient hypertension. | 2006 Mar |
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Antihypertensive drugs clonidine, diazoxide, hydralazine and furosemide regulate the production of cytokines by placentas and peripheral blood mononuclear cells in normal pregnancy. | 2006 May |
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Persistent hypertension and progressive renal injury induced by salt overload after short term nitric oxide inhibition. | 2007 Dec |
|
The effects of DNA methylation and histone deacetylase inhibitors on human papillomavirus early gene expression in cervical cancer, an in vitro and clinical study. | 2007 Feb 26 |
|
D-Penicillamine-induced ANCA-associated crescentic glomerulonephritis in Wilson disease. | 2007 Nov |
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Beneficial effects of the Rho kinase inhibitor Y27632 in murine puromycin aminonucleoside nephrosis. | 2008 |
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Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008 Dec |
|
The prince and the pauper. A tale of anticancer targeted agents. | 2008 Oct 23 |
|
Simultaneous posterior ischemic optic neuropathy, cerebral border zone infarction, and spinal cord infarction after correction of malignant hypertension. | 2008 Sep |
|
Administration of angiotensin II, but not catecholamines, induces accumulation of lipids in the rat heart. | 2009 Feb 14 |
|
"Pulse" treatment with high-dose angiotensin blocker reverses renal arteriolar hypertrophy and regresses hypertension. | 2009 Jan |
|
Epigenetic regulation of Foxp3 expression in regulatory T cells by DNA methylation. | 2009 Jan 1 |
|
Hydralazine-induced cholestatic hepatitis. | 2009 Jul-Aug |
|
Resveratrol attenuates angiotensin II-induced interleukin-6 expression and perivascular fibrosis. | 2009 Jun |
|
D-penicillamine-induced autoimmunity: relationship to macrophage activation. | 2009 Sep |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
Angiotensin II-induced vascular endothelial dysfunction through RhoA/Rho kinase/p38 mitogen-activated protein kinase/arginase pathway. | 2011 May |
|
Diesel exhaust induced pulmonary and cardiovascular impairment: the role of hypertension intervention. | 2013 Apr 15 |
|
Acrolein and chloroacetaldehyde: an examination of the cell and cell-free biomarkers of toxicity. | 2013 Feb 25 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/hydralazine.html
Curator's Comment: can also be used intramuscularly or as a rapid intravenous bolus injection directly into the vein. http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/040136s005lbl.pdf
Initial dose: 10 mg orally 4 times a day for the first 2 to 4 days. Increase to 25 mg orally 4 times a day for the balance of the first week.
For the second and subsequent weeks, increase dosage to 50 mg orally 4 times a day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7660828
Hydralazine (0.03-10 mmol.L(-1)) inhibited the activities of both PKA and PKG with IC50 of 1.2 and 2.5 mmol.L(-1), respectively
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C270
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Code System | Code | Type | Description | ||
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HYDRALAZINE HYDROCHLORIDE
Created by
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Soluble in 25 parts of water; slightly soluble in ethanol (~750 g/l) TS; very slightly soluble in ether R. Category: Antihypertensive drug. Storage: Hydralazine hydrochloride should be kept in a well-closed container, protected from light. Additional information: Hydralazine hydrochloride melts at about 275 ?C with decomposition. Even in the absence of light, it is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Definition: Hydralazine hydrochloride contains not less than 98.0% and not more than 101.0% of C8H8N4,HCl, calculated with reference to the dried substance. | ||
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FD171B778Y
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CHEMBL276832
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206-151-0
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82027
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DTXSID1044645
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434
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m6072
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C551
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SUB02553MIG
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304-20-1
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31672
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FD171B778Y
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9351
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DBSALT000792
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1313006
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ACTIVE MOIETY
SUBSTANCE RECORD