Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13NO2.ClH |
Molecular Weight | 203.666 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CNC[C@H](O)C1=CC(O)=CC=C1
InChI
InChIKey=OCYSGIYOVXAGKQ-FVGYRXGTSA-N
InChI=1S/C9H13NO2.ClH/c1-10-6-9(12)7-3-2-4-8(11)5-7;/h2-5,9-12H,6H2,1H3;1H/t9-;/m0./s1
Molecular Formula | C9H13NO2 |
Molecular Weight | 167.205 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00388Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/204300lbl.pdf and
https://www.drugs.com/pro/phenylephrine-and-chlorpheniramine-tablets.html
Sources: http://www.drugbank.ca/drugs/DB00388
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/204300lbl.pdf and
https://www.drugs.com/pro/phenylephrine-and-chlorpheniramine-tablets.html
Phenylephrine is a powerful vasoconstrictor. It is used as a nasal decongestant and cardiotonic agent. Phenylephrine is a postsynaptic α1-receptor agonist with little effect on β-receptors of the heart. Parenteral administration of phenylephrine causes a rise in systolic and diastolic pressures, a slight decrease in cardiac output, and a considerable increase in peripheral resistance; most vascular beds are constricted, and renal, splanchnic, cutaneous, and limb blood flows are reduced while coronary blood flow is increased. Phenelephrine also causes pulmonary vessel constriction and subsequent increase in pulmonary arterial pressure. Vasoconstriction in the mucosa of the respiratory tract leads to decreased edema and increased drainage of sinus cavities. In general, α1-adrenergic receptors mediate contraction and hypertrophic growth of smooth muscle cells. α1-receptors are 7-transmembrane domain receptors coupled to G proteins, Gq/11. Three α1-receptor subtypes, which share approximately 75% homology in their transmembrane domains, have been identified: α1A (chromosome 8), α1B (chromosome 5), and α1D (chromosome 20). Phenylephrine appears to act similarly on all three receptor subtypes. All three receptor subtypes appear to be involved in maintaining vascular tone. The α1A-receptor maintains basal vascular tone while the α1B-receptor mediates the vasocontrictory effects of exogenous α1-agonists. Activation of the α1-receptor activates Gq-proteins, which results in intracellular stimulation of phospholipases C, A2, and D. This results in mobilization of Ca2+ from intracellular stores, activation of mitogen-activated kinase and PI3 kinase pathways and subsequent vasoconstriction. Phenylephrine produces its local and systemic actions by acting on α1-adrenergic receptors peripheral vascular smooth muscle. Stimulation of the α1-adrenergic receptors results in contraction arteriolar smooth muscle in the periphery. Phenylephrine decreases nasal congestion by acting on α1-adrenergic receptors in the arterioles of the nasal mucosa to produce constriction; this leads to decreased edema and increased drainage of the sinus cavities. Phenylephrine is mainly used to treat nasal congestion, but may also be useful in treating hypotension and shock, hypotension during spinal anaesthesia, prolongation of spinal anaesthesia, paroxysmal supraventricular tachycardia, symptomatic relief of external or internal hemorrhoids, and to increase blood pressure as an aid in the diagnosis of heart murmurs.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22391890
Curator's Comment: Phenylephrine does not cross the blood–brain barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL229 Sources: http://www.drugbank.ca/drugs/DB00388 |
55.0 nM [EC50] | ||
Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25813897 |
5.9 nM [EC50] | ||
Target ID: CHEMBL326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8831777 |
154.88 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VAZCULEP Approved UseVAZCULEP (phenylephrine hydrochloride) is indicated for the treatment of clinically important
hypotension resulting primarily from vasodilation in the setting of anesthesia. Launch Date1953 |
|||
Diagnostic | Phenylephrine Hydrochloride Ophthalmic Solution Approved UseIndicated to dilate the pupil Launch Date1938 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2959 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4492 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1354 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2346 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3900 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
955.8 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.93 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.64 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1.89 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26267590 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYLEPHRINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, 34 years n = 1 Health Status: unhealthy Age Group: 34 years Sex: M Population Size: 1 Sources: |
Disc. AE: Ischemic colitis... AEs leading to discontinuation/dose reduction: Ischemic colitis (acute) Sources: |
40 mg 6 times / day multiple, oral Highest studied dose Dose: 40 mg, 6 times / day Route: oral Route: multiple Dose: 40 mg, 6 times / day Sources: |
unhealthy, 37.5 years (range: 19.0 - 77.0 years) n = 112 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Age Group: 37.5 years (range: 19.0 - 77.0 years) Sex: M+F Population Size: 112 Sources: |
Disc. AE: Chest pain, Jaw pain... Other AEs: Nervous system disorders, Headache... AEs leading to discontinuation/dose reduction: Chest pain (1 patient) Other AEs:Jaw pain (1 patient) Nervous system disorders (3.6%) Sources: Headache (2.7%) Gastrointestinal disorders (8%) Dry mouth (2.7%) Nausea (3.6%) |
10 % 3 times / day multiple, ophthalmic Recommended Dose: 10 %, 3 times / day Route: ophthalmic Route: multiple Dose: 10 %, 3 times / day Sources: |
healthy, > 1 year Health Status: healthy Age Group: > 1 year Sources: |
Other AEs: Eye pain, Blurred vision... Other AEs: Eye pain Sources: Blurred vision Photophobia Allergic conjunctivitis |
250 ug single, intravenous Recommended Dose: 250 ug Route: intravenous Route: single Dose: 250 ug Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Ischemic colitis | acute Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, 34 years n = 1 Health Status: unhealthy Age Group: 34 years Sex: M Population Size: 1 Sources: |
Chest pain | 1 patient Disc. AE |
40 mg 6 times / day multiple, oral Highest studied dose Dose: 40 mg, 6 times / day Route: oral Route: multiple Dose: 40 mg, 6 times / day Sources: |
unhealthy, 37.5 years (range: 19.0 - 77.0 years) n = 112 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Age Group: 37.5 years (range: 19.0 - 77.0 years) Sex: M+F Population Size: 112 Sources: |
Jaw pain | 1 patient Disc. AE |
40 mg 6 times / day multiple, oral Highest studied dose Dose: 40 mg, 6 times / day Route: oral Route: multiple Dose: 40 mg, 6 times / day Sources: |
unhealthy, 37.5 years (range: 19.0 - 77.0 years) n = 112 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Age Group: 37.5 years (range: 19.0 - 77.0 years) Sex: M+F Population Size: 112 Sources: |
Dry mouth | 2.7% | 40 mg 6 times / day multiple, oral Highest studied dose Dose: 40 mg, 6 times / day Route: oral Route: multiple Dose: 40 mg, 6 times / day Sources: |
unhealthy, 37.5 years (range: 19.0 - 77.0 years) n = 112 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Age Group: 37.5 years (range: 19.0 - 77.0 years) Sex: M+F Population Size: 112 Sources: |
Headache | 2.7% | 40 mg 6 times / day multiple, oral Highest studied dose Dose: 40 mg, 6 times / day Route: oral Route: multiple Dose: 40 mg, 6 times / day Sources: |
unhealthy, 37.5 years (range: 19.0 - 77.0 years) n = 112 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Age Group: 37.5 years (range: 19.0 - 77.0 years) Sex: M+F Population Size: 112 Sources: |
Nausea | 3.6% | 40 mg 6 times / day multiple, oral Highest studied dose Dose: 40 mg, 6 times / day Route: oral Route: multiple Dose: 40 mg, 6 times / day Sources: |
unhealthy, 37.5 years (range: 19.0 - 77.0 years) n = 112 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Age Group: 37.5 years (range: 19.0 - 77.0 years) Sex: M+F Population Size: 112 Sources: |
Nervous system disorders | 3.6% | 40 mg 6 times / day multiple, oral Highest studied dose Dose: 40 mg, 6 times / day Route: oral Route: multiple Dose: 40 mg, 6 times / day Sources: |
unhealthy, 37.5 years (range: 19.0 - 77.0 years) n = 112 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Age Group: 37.5 years (range: 19.0 - 77.0 years) Sex: M+F Population Size: 112 Sources: |
Gastrointestinal disorders | 8% | 40 mg 6 times / day multiple, oral Highest studied dose Dose: 40 mg, 6 times / day Route: oral Route: multiple Dose: 40 mg, 6 times / day Sources: |
unhealthy, 37.5 years (range: 19.0 - 77.0 years) n = 112 Health Status: unhealthy Condition: Seasonal Allergic Rhinitis Age Group: 37.5 years (range: 19.0 - 77.0 years) Sex: M+F Population Size: 112 Sources: |
Allergic conjunctivitis | 10 % 3 times / day multiple, ophthalmic Recommended Dose: 10 %, 3 times / day Route: ophthalmic Route: multiple Dose: 10 %, 3 times / day Sources: |
healthy, > 1 year Health Status: healthy Age Group: > 1 year Sources: |
|
Blurred vision | 10 % 3 times / day multiple, ophthalmic Recommended Dose: 10 %, 3 times / day Route: ophthalmic Route: multiple Dose: 10 %, 3 times / day Sources: |
healthy, > 1 year Health Status: healthy Age Group: > 1 year Sources: |
|
Eye pain | 10 % 3 times / day multiple, ophthalmic Recommended Dose: 10 %, 3 times / day Route: ophthalmic Route: multiple Dose: 10 %, 3 times / day Sources: |
healthy, > 1 year Health Status: healthy Age Group: > 1 year Sources: |
|
Photophobia | 10 % 3 times / day multiple, ophthalmic Recommended Dose: 10 %, 3 times / day Route: ophthalmic Route: multiple Dose: 10 %, 3 times / day Sources: |
healthy, > 1 year Health Status: healthy Age Group: > 1 year Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16510159/ Page: 10.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Phosphorylation of elk-1 by MEK/ERK pathway is necessary for c-fos gene activation during cardiac myocyte hypertrophy. | 2000 Aug |
|
Gene transfer of endothelial nitric oxide isoform decreases rat hindlimb vascular resistance in vivo. | 2000 Aug 10 |
|
Purinergic and adrenergic agonists synergize in stimulating vasopressin and oxytocin release. | 2000 Dec 1 |
|
Presence of NMDA receptor subunits in the male lower urogenital tract. | 2000 Jul-Aug |
|
The influence of indomethacin on the acth secretion induced by central stimulation of adrenergic receptors. | 2000 Jun |
|
alpha(1)-Adrenergic stimulation perturbs the left-right asymmetric expression pattern of nodal during rat embryogenesis. | 2000 Nov |
|
The effect of phenylephrine on pain and flare intensity in eyes with uveitis. | 2000 Oct |
|
Phenylephrine protects neonatal rat cardiomyocytes from hypoxia and serum deprivation-induced apoptosis. | 2000 Sep |
|
Intracarotid infusion of the nitric oxide synthase inhibitor, L-NMMA, modestly decreases cerebral blood flow in human subjects. | 2000 Sep |
|
Heparin-mediated hypotension associated with cardiac surgery. | 2000 Sep |
|
Contribution of ryanodine receptor subtype 3 to ca2+ responses in Ca2+-overloaded cultured rat portal vein myocytes. | 2001 Apr 6 |
|
Effects of salt intake and angiotensin II on vascular reactivity to endothelin-1. | 2001 Feb |
|
Reflex cardiovascular responses originating in exercising muscles of mice. | 2001 Feb |
|
Smooth muscle-targeted overexpression of insulin-like growth factor I results in enhanced vascular contractility. | 2001 Feb |
|
Nitric oxide-mediated arteriolar dilation after endothelial deformation. | 2001 Feb |
|
Vascular NAD(P)H oxidase is distinct from the phagocytic enzyme and modulates vascular reactivity control. | 2001 Feb |
|
Regulation of mitogen-activated protein kinases in cardiac myocytes through the small G protein Rac1. | 2001 Feb |
|
Interaction of rapid nongenomic cardiovascular aldosterone effects with the adrenergic system. | 2001 Feb |
|
The transient receptor potential protein homologue TRP6 is the essential component of vascular alpha(1)-adrenoceptor-activated Ca(2+)-permeable cation channel. | 2001 Feb 16 |
|
Ras regulates NFAT3 activity in cardiac myocytes. | 2001 Feb 2 |
|
Depletion of phosphatidylinositol 4,5-bisphosphate by activation of phospholipase C-coupled receptors causes slow inhibition but not desensitization of G protein-gated inward rectifier K+ current in atrial myocytes. | 2001 Feb 23 |
|
Nitric oxide contributes to vascular smooth muscle relaxation in contracting fast-twitch muscles. | 2001 Feb 7 |
|
Extracellular calcium-sensing receptor is expressed in rat hepatocytes. coupling to intracellular calcium mobilization and stimulation of bile flow. | 2001 Feb 9 |
|
Detection and characterization of cholinergic oscillatory control in the forehead microvasculature in response to systemic alpha-agonist infusion in healthy volunteers. | 2001 Jan |
|
A N-terminal PTHrP peptide fragment void of a PTH/PTHrP-receptor binding domain activates cardiac ET(A) receptors. | 2001 Jan |
|
Activity of cardiorespiratory networks revealed by transsynaptic virus expressing GFP. | 2001 Jan |
|
Involvement of Ca2+ -activated K+ channels in ginsenosides-induced aortic relaxation in rats. | 2001 Jan |
|
Effects of LY117018 and the estrogen analogue, 17alpha-ethinylestradiol, on vascular reactivity, platelet aggregation, and lipid metabolism in the insulin-resistant JCR:LA-cp male rat: role of nitric oxide. | 2001 Jan |
|
Effect of dietary vitamin E supplementation on vascular reactivity of thoracic aorta in streptozotocin-diabetic rats. | 2001 Jan |
|
Increased dilator response to heptanol and octanol in aorta from DOCA-salt-hypertensive rats. | 2001 Jan |
|
In vivo measurement of pulsewave velocity in small vessels using intravascular MR. | 2001 Jan |
|
Effects of acute and chronic hypertension on the labyrinthine barriers in rat. | 2001 Jan |
|
Endothelin and nitric oxide mediate reduced myogenic reactivity of small renal arteries from pregnant rats. | 2001 Jan |
|
A metabolic fragment of bradykinin, Arg-Pro-Pro-Gly-Phe, protects against the deleterious effects of lipopolysaccharide in rats. | 2001 Jan |
|
alpha-Adrenoceptor stimulation-mediated negative inotropism and enhanced Na(+)/Ca(2+) exchange in mouse ventricle. | 2001 Jan |
|
Inducible and neuronal nitric oxide synthase involvement in lipopolysaccharide-induced sphincteric dysfunction. | 2001 Jan |
|
Hepatic neovascularization after partial portal vein ligation: novel mechanism of chronic regulation of blood flow. | 2001 Jan |
|
Effect of gamma-melanocyte-stimulating hormones on baroreflex sensitivity and cerebral blood flow autoregulation in rats. | 2001 Jan |
|
Increased alpha(1)- and alpha(2)-adrenoceptor-mediated contractile responses of human skeletal muscle resistance arteries in chronic limb ischemia. | 2001 Jan |
|
Gender-related distinctions in protein kinase C activity in rat vascular smooth muscle. | 2001 Jan |
|
Assessment of baroreflex sensitivity in patients with preserved and impaired left ventricular function by means of the Valsalva manoeuvre and the phenylephrine test. | 2001 Jan |
|
Receptor reserve analysis of the human alpha(2C)-adrenoceptor using. | 2001 Jan 12 |
|
The dual-specificity phosphatase MKP-1 limits the cardiac hypertrophic response in vitro and in vivo. | 2001 Jan 19 |
|
Phosphatidylinositol 4,5-bisphosphate is acting as a signal molecule in alpha(1)-adrenergic pathway via the modulation of acetylcholine-activated K(+) channels in mouse atrial myocytes. | 2001 Jan 5 |
|
Evidence of alpha-adrenoceptor-mediated chronotropic action in children. | 2001 Jan-Feb |
|
Endothelial cell protein kinase G inhibits release of EDHF through a PKG-sensitive cation channel. | 2001 Mar |
|
Reciprocal regulation of cGMP-mediated vasorelaxation by soluble and particulate guanylate cyclases. | 2001 Mar |
|
Endogenous estrogen mediates vascular reactivity and distensibility in pregnant rat mesenteric arteries. | 2001 Mar |
|
EDHF contributes to strain-related differences in pulmonary arterial relaxation in rats. | 2001 Mar |
|
Low temperature prevents potentiation of norepinephrine release by phenylephrine. | 2001 Mar |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Also used as Ophthalmic Solution or oral tablets
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/203510s000lbl.pdf
https://www.drugs.com/dosage/chlorpheniramine-phenylephrine.html
VAZCULEP (phenylephrine hydrochloride) Injection, 10 mg/mL, is injected
intravenously either as a bolus or in a dilute solution as a continuous infusion.
Dilute before administration.
Dosing for treatment of hypotension during anesthesia
Bolus intravenous injection: 40 mcg to 100 mcg every 1-2 minutes as
needed, not to exceed 200 mcg.
Intravenous infusion: 10 mcg/min to 35 mcg/min, titrating to effect, not to
exceed 200 mcg/min.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26406609
The hypertrophic phenotype of neonatal rat cardiomyocyte cultures (cardiomyocyte size, sarcomeric organization, total protein synthesis, c-fos expression) mediated by phenylephrine (10 uM) was counteracted by the selective A1 receptor agonist
Substance Class |
Chemical
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04JA59TNSJ
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 349.18
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CFR |
21 CFR 346.12
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NCI_THESAURUS |
C29709
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EU-Orphan Drug |
EU/3/01/069
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CFR |
21 CFR 341.20
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8094
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CHEMBL1215
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100000090176
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m8668
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C29363
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SUB03777MIG
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441279
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61-76-7
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8164
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04JA59TNSJ
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DTXSID3021142
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757273
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04JA59TNSJ
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200-517-3
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1533002
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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PARENT -> SALT/SOLVATE |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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