Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H13NO4 |
Molecular Weight | 211.2145 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@](N)(CC1=CC(O)=C(O)C=C1)C(O)=O
InChI
InChIKey=CJCSPKMFHVPWAR-JTQLQIEISA-N
InChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m0/s1
Molecular Formula | C10H13NO4 |
Molecular Weight | 211.2145 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/13400s086lbl.pdfhttps://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f5f25053-a9f3-48b9-a412-078f5ee942fd&type=displayCurator's Comment: Description was created based on several sources, including
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/13400s086lbl.pdfhttps://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f5f25053-a9f3-48b9-a412-078f5ee942fd&type=display
Curator's Comment: Description was created based on several sources, including
Methyldopate hydrochloride [levo-3-(3,4-dihydroxyphenyl)-2-methylalanine, ethyl ester hydrochloride] is the ethyl ester of methyldopa, supplied as the hydrochloride salt with a molecular weight of 275.73. Methyldopate hydrochloride is more soluble and stable in solution than methyldopa and is the preferred form for intravenous use. Methyldopate hydrochloride is an alpha adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.
CNS Activity
Sources: https://www.drugs.com/monograph/methyldopa.htmlhttps://www.drugs.com/ppa/methyldopa-and-methyldopate-hcl.html
Curator's Comment: Methyldopa and methyldopate cross the blood-brain
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1843 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7136732 |
60.0 µM [IC50] | ||
Target ID: CHEMBL2095203 |
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Target ID: CHEMBL2094111 Sources: https://www.drugs.com/pro/methyldopa.html |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ALDOMET Approved UseINDICATION AND USAGE: Hypertension. Launch Date-2.21961601E11 |
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Primary | ALDOMET Approved UseINDICATION AND USAGE: Hypertension. Launch Date-2.21961601E11 |
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Primary | ALDOMET Approved UseINDICATION AND USAGE: Hypertension. Launch Date-2.21961601E11 |
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Primary | Methyldopate hydrochloride Approved UseHypertension, when parenteral medication is indicated. The treatment of hypertensive crises may be initiated with Methyldopate HCl Injection. Launch Date8.1233281E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
771.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21125810 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHYLDOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.54 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7047042 |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLDOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5352.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21125810 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHYLDOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.28 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7047042 |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLDOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
12.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21125810 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHYLDOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
85% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7047042 |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHYLDOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2.5 g single, oral |
unknown, 19 n = 1 Health Status: unknown Age Group: 19 Sex: M Population Size: 1 Sources: |
Other AEs: Coma... |
2326 mg multiple, oral (mean) Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 n = 30 Health Status: unhealthy Condition: hypertension Age Group: 36-68 Sex: M+F Population Size: 30 Sources: |
Disc. AE: Depression, Tiredness... AEs leading to discontinuation/dose reduction: Depression (2 patients) Sources: Tiredness (2 patients) Diarrhoea (1 patient) Rash (1 patient) Blackout (1 patient) |
250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Other AEs: Somnolence, Dry mouth... Other AEs: Somnolence (15 patients) Sources: Dry mouth (12 patients) Malaise (6 patients) Constipation (5 patients) Anorexia (5 patients) Diarrhoea (3 patients) Depression (2 patients) Weight gain (2 patients) Mental confusion (1 patient) Postural hypotension (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Coma | grade 1 | 2.5 g single, oral |
unknown, 19 n = 1 Health Status: unknown Age Group: 19 Sex: M Population Size: 1 Sources: |
Blackout | 1 patient Disc. AE |
2326 mg multiple, oral (mean) Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 n = 30 Health Status: unhealthy Condition: hypertension Age Group: 36-68 Sex: M+F Population Size: 30 Sources: |
Diarrhoea | 1 patient Disc. AE |
2326 mg multiple, oral (mean) Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 n = 30 Health Status: unhealthy Condition: hypertension Age Group: 36-68 Sex: M+F Population Size: 30 Sources: |
Rash | 1 patient Disc. AE |
2326 mg multiple, oral (mean) Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 n = 30 Health Status: unhealthy Condition: hypertension Age Group: 36-68 Sex: M+F Population Size: 30 Sources: |
Depression | 2 patients Disc. AE |
2326 mg multiple, oral (mean) Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 n = 30 Health Status: unhealthy Condition: hypertension Age Group: 36-68 Sex: M+F Population Size: 30 Sources: |
Tiredness | 2 patients Disc. AE |
2326 mg multiple, oral (mean) Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 n = 30 Health Status: unhealthy Condition: hypertension Age Group: 36-68 Sex: M+F Population Size: 30 Sources: |
Mental confusion | 1 patient | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Postural hypotension | 1 patient | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Dry mouth | 12 patients | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Somnolence | 15 patients | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Depression | 2 patients | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Weight gain | 2 patients | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Diarrhoea | 3 patients | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Anorexia | 5 patients | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Constipation | 5 patients | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Malaise | 6 patients | 250 mg 4 times / day multiple, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: |
unhealthy n = 39 Health Status: unhealthy Condition: hypertension Sex: M+F Population Size: 39 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://molpharm.aspetjournals.org/content/12/6/911 Page: abstract |
likely |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.scirp.org/pdf/JBiSE_2017112915210255.pdf Page: 10.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Dementia induced by methyldopa with haloperidol. | 1976 May 27 |
|
The effect of methyldopa on retinal artery circulation in pre-eclamptic gravidae. | 2000 Jun |
|
Treating hypertension in women of child-bearing age and during pregnancy. | 2001 |
|
Ddc and amd sequences resolve phylogenetic relationships of Drosophila. | 2001 Aug |
|
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes. | 2001 Jan-Feb |
|
NHBPEP report on high blood pressure in pregnancy: a summary for family physicians. | 2001 Jul 15 |
|
Pharmacokinetic and pharmacodynamic alterations of methyldopa in rats with aortic coarctation. A study using microdialysis. | 2001 Nov |
|
The effects of nitric oxide synthase inhibitors on the sedative effect of clonidine. | 2001 Nov |
|
Catechol-O-methyltransferase (COMT) genetic polymorphism in a Turkish population. | 2001 Sep |
|
Hepatotoxicity of commonly used drugs: nonsteroidal anti-inflammatory drugs, antihypertensives, antidiabetic agents, anticonvulsants, lipid-lowering agents, psychotropic drugs. | 2002 |
|
Liddle syndrome in a newborn infant. | 2002 Aug |
|
Brain catecholamine metabolism in catechol-O-methyltransferase (COMT)-deficient mice. | 2002 Jan |
|
C4 deficiency state in antiphospholipid antibody-related recurrent preeclampsia evolving into systemic lupus erythematosus. | 2002 Jul |
|
Analysis of L-dopa in human serum. | 2002 Nov |
|
Oral beta-blockers for mild to moderate hypertension during pregnancy. | 2003 |
|
Determination of antioxidant activity of some drugs using high-pressure liquid chromatography. | 2003 |
|
Comparative single- and multiple-dose pharmacokinetics of levodopa and 3-O-methyldopa following a new dual-release and a conventional slow-release formulation of levodopa and benserazide in healthy volunteers. | 2003 |
|
Methyldopa supplement for resistant essential hypertension: a prospective randomized placebo control crossover study. | 2003 Dec |
|
Replacement of antipsychotic and antiepileptic medication by L-alpha-methyldopa in a woman with velocardiofacial syndrome. | 2003 Mar |
|
Nocturnal sleep, daytime sleepiness, and quality of life in stable patients on hemodialysis. | 2003 Nov 21 |
|
A survey of Canadian practitioners regarding the management of the hypertensive disorders of pregnancy. | 2004 |
|
Pheochromocytoma during pregnancy: laparoscopic and conventional surgical treatment of two cases. | 2004 Feb |
|
Oral enalapril-hydrochlorothiazide-methyldopa as first line treatment for severe hypertension in Nigerians. | 2004 Jan |
|
Liquid chromatography-tandem mass spectrometry method for the determination of tranexamic acid in human plasma. | 2004 Jun 15 |
|
[Centrally-acting antihypertensive drugs]. | 2004 Mar |
|
[Hypertension in pregnancy]. | 2004 Mar |
|
Drug-induced liver injury. | 2004 Mar 1 |
|
Differential modulation by estrogen of alpha2-adrenergic and I1-imidazoline receptor-mediated hypotension in female rats. | 2004 Oct |
|
Treating high blood pressure in Africans with type 2 diabetes. | 2004 Winter |
|
Inadequate control of blood pressure in Nigerians with diabetes. | 2004 Winter |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: When control has been obtained, oral therapy with tablets may be substituted for intravenous therapy, starting with the same dosage schedule used for the parenteral route. The effectiveness and anticipated responses are described in the circular for tablets.
Initial: 250 mg PO q8-12hr for 2 days, increase q2Days PRN
Maintenance: 250-1000 mg/day divided q6-12hr PO, usually no more than 3 g/day
IV (methyldopate): 250-1000 mg infusion over 30-60 minutes q6-8hr PRN; no more than 4 g/day
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27998008
Human uterine microvascular endothelial cells (UtMVEC) (PromoCell, Heidelberg, Germany) were cultured in EGM-2- MV medium (Lonza, Basel, Switzerland) until about 80% confluent. Cells from passage 4-8 were used in this study. Tissue culture plates (24-wells) were coated with undiluted Matrigel (300 μL/well; In Vitro Technologies, Noble Park, Vic., Australia) and polymerized for 30 minutes at 37°C. UtMVECs (100 000 cells/well) were seeded into each well and endothelial cell tubular networks formed within 4 hours of further incubation at 37°C. HTR-8/ SVneo cells (100 000 cells/well) were then added to each well with or without a low dose of TNF-α (0.5 ng/mL) together with methyldopa (5 μg/ mL), labetalol (0.5 μg/mL), hydralazine (10 μg/mL) or clonidine (1.0 μg/ mL) and co-cultured with the endothelial cellular networks. The control co-cultured cells had neither TNF-α nor medications added. After 24 hours of culture, the cells were retrieved from the cellular networks in Matrigel with Cell Recovery Solution (CRS) (In Vitro Technologies) for RNA extraction
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 18:47:42 UTC 2022
by
admin
on
Fri Dec 16 18:47:42 UTC 2022
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Record UNII |
M4R0H12F6M
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
C02AB01
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NDF-RT |
N0000175554
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WHO-ATC |
C02LB01
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NDF-RT |
N0000009918
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WHO-ATC |
C02AB
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38853
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209-089-2
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1545996
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SUB08867MIG
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1110
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M4R0H12F6M
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218
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DTXSID5023295
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C175729
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SUB26433
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M7397
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555-30-6
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M4R0H12F6M
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DB00968
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169916
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METHYLDOPA
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61058
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Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SUBSTANCE->BASIS OF STRENGTH |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
ACTIVE IN RATS
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METABOLITE -> PARENT |
URINE
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PARENT -> METABOLITE |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
Approximately 70 percent of the drug which is absorbed is excreted in the urine as methyldopa and its mono-0-sulfate conjugate
MAJOR
PLASMA; URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |