Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13NO2.C4H6O6 |
Molecular Weight | 317.2919 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.CNC[C@H](O)C1=CC=CC(O)=C1
InChI
InChIKey=NHKOTKKHHYKARN-NDAAPVSOSA-N
InChI=1S/C9H13NO2.C4H6O6/c1-10-6-9(12)7-3-2-4-8(11)5-7;5-1(3(7)8)2(6)4(9)10/h2-5,9-12H,6H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/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 | C4H6O6 |
Molecular Weight | 150.0868 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 Date-5.05007997E11 |
|||
Diagnostic | Phenylephrine Hydrochloride Ophthalmic Solution Approved UseIndicated to dilate the pupil Launch Date-9.7839363E11 |
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 |
---|---|---|
Troglitazone inhibits alpha1-adrenoceptor-induced DNA synthesis in vascular smooth muscle cells. | 1999 Jun 11 |
|
Investigation of the effects of some alkaloidal alpha1-adrenoceptor antagonists on human hyperplastic prostate. | 1999 Jun 25 |
|
Characterization of human recombinant alpha(2A)-adrenoceptors expressed in Chinese hamster lung cells using intracellular Ca(2+) changes: evidence for cross-talk between recombinant alpha(2A)- and native alpha(1)-adrenoceptors. | 2000 Apr |
|
Purinergic and adrenergic agonists synergize in stimulating vasopressin and oxytocin release. | 2000 Dec 1 |
|
Targeted inhibition of calcineurin prevents agonist-induced cardiomyocyte hypertrophy. | 2000 Feb 1 |
|
Roles of tissue transglutaminase in ethanol-induced inhibition of hepatocyte proliferation and alpha 1-adrenergic signal transduction. | 2000 Jul 21 |
|
Presence of NMDA receptor subunits in the male lower urogenital tract. | 2000 Jul-Aug |
|
Requirement of activation of the extracellular signal-regulated kinase cascade in myocardial cell hypertrophy. | 2000 Jun |
|
Effects of salt intake and angiotensin II on vascular reactivity to endothelin-1. | 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 |
|
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 |
|
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 |
|
Catecholamine responses to alpha-adrenergic blockade during exercise in women acutely exposed to altitude. | 2001 Jan |
|
Should the angiotensin II antagonists be discontinued before surgery? | 2001 Jan |
|
[Ca(2+)](i) signaling in renal arterial smooth muscle cells of pregnant rat is enhanced during inhibition of NOS. | 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 |
|
Catecholamine inotropes as growth factors for Staphylococcus epidermidis and other coagulase-negative staphylococci. | 2001 Jan 15 |
|
The dual-specificity phosphatase MKP-1 limits the cardiac hypertrophic response in vitro and in vivo. | 2001 Jan 19 |
|
Pharmacological profile of T-1032, a novel specific phosphodiesterase type 5 inhibitor, in isolated rat aorta and rabbit corpus cavernosum. | 2001 Jan 5 |
|
Insulin-induced relaxation of rat mesenteric artery is mediated by Ca(2+)-activated K(+) channels. | 2001 Jan 5 |
|
Evidence of alpha-adrenoceptor-mediated chronotropic action in children. | 2001 Jan-Feb |
|
In vivo regulation of Na/Ca exchanger expression by adrenergic effectors. | 2001 Mar |
|
Endothelial cell protein kinase G inhibits release of EDHF through a PKG-sensitive cation channel. | 2001 Mar |
|
Endogenous estrogen mediates vascular reactivity and distensibility in pregnant rat mesenteric arteries. | 2001 Mar |
|
Topical phenylephrine increases anal canal resting pressure in patients with faecal incontinence. | 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
Created
by
admin
on
Edited
Sat Dec 16 05:15:32 UTC 2023
by
admin
on
Sat Dec 16 05:15:32 UTC 2023
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Record UNII |
27O3Q5ML57
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C29709
Created by
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CFR |
21 CFR 341.20
Created by
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27O3Q5ML57
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14787-58-7
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NON-SPECIFIC STOICHIOMETRY | |||
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27O3Q5ML57
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91167
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CHEMBL1215
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C66378
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DTXSID901026092
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100000085297
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DBSALT001320
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241-219-3
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SUB03775MIG
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1532950
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17162-39-9
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46174134
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |