Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H19ClN2 |
Molecular Weight | 274.788 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC(C1=CC=C(Cl)C=C1)C2=CC=CC=N2
InChI
InChIKey=SOYKEARSMXGVTM-UHFFFAOYSA-N
InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
Molecular Formula | C16H19ClN2 |
Molecular Weight | 274.788 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Chlorpheniramine is an antihistamine. Chlorpheniramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. Chlorpheniramine is used for relieving symptoms of sinus congestion, sinus pressure, runny nose, watery eyes, itching of the nose and throat, and sneezing due to upper respiratory infections (eg, colds), allergies, and hay fever. In addition to being a histamine H1 receptor (HRH1) antagonist, chlorphenamine has been shown to work as a serotonin-norepinephrine reuptake inhibitor or SNRI.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL612856 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750932 |
136.0 µM [IC50] | ||
Target ID: CHEMBL231 |
12.0 nM [IC50] | ||
Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) |
15.2 nM [Kd] | ||
Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) |
203.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Chlor-Trimeton Approved UseUses
temporarily relieves the following symptoms due to hay fever or other upper respiratory allergies:
sneezing
runny nose
itchy, watery eyes
itching of the nose or throat Launch Date-6.116256E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
8 mg 2 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
32.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
4 mg 4 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
25.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
8 mg 2 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7069073/ |
0.12 mg/kg bw single, oral dose: 0.12 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1075.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
8 mg 2 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1202.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
4 mg 4 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
961 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
8 mg 2 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
246.16 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7069073/ |
0.12 mg/kg bw single, oral dose: 0.12 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
24.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
8 mg 2 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
25.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
4 mg 4 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
25.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/ |
8 mg 2 times / day steady-state, oral dose: 8 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7069073/ |
0.12 mg/kg bw single, oral dose: 0.12 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
CHLORPHENIRAMINE serum | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
5 mg single, intravenous |
healthy, 27-40 years n = 2 Health Status: healthy Age Group: 27-40 years Sex: M+F Population Size: 2 Sources: |
|
48 mg 1 times / day multiple, oral Studied dose Dose: 48 mg, 1 times / day Route: oral Route: multiple Dose: 48 mg, 1 times / day Sources: |
unhealthy, 34 years (range: 13-52 years) n = 10 Health Status: unhealthy Age Group: 34 years (range: 13-52 years) Sex: M+F Population Size: 10 Sources: |
|
4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: |
unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: |
Other AEs: Tryptase increased, Urticaria... Other AEs: Tryptase increased (1 patient) Sources: Urticaria (2 patients) Abdominal cramp (1 patient) Nausea (1 patient) Diarrhea (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abdominal cramp | 1 patient | 4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: |
unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: |
Diarrhea | 1 patient | 4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: |
unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: |
Nausea | 1 patient | 4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: |
unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: |
Tryptase increased | 1 patient | 4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: |
unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: |
Urticaria | 2 patients | 4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: |
unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
weak [Ki 11 uM] | ||||
yes [Ki 191.2 uM] | ||||
yes [Ki 87.6 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/11284026/ Page: 6.0 |
no | |||
yes | likely (co-administration study) Comment: The two poor metabolizers with respect to CYP2D6 were included as controls in the present study, as quinidine would not be expected to produce any further inhibition of CYP2D6 in those subjects. However, a slight decrease in AUC(0,∞) and a slight increase in CLoral was observed for both the (R)-(−)- and the (S)-(+)-enantiomers following administration of quinidine, although it is not possible to draw a firm conclusion from such a small number of subjects |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Toxic epidermal necrolysis associated with pentazocine therapy and severe reversible renal failure. | 1973 Mar |
|
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity. | 1975 Feb |
|
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants. | 1975 Sep 4 |
|
Skeletal muscle necrosis following membrane-active drugs plus serotonin. | 1976 May |
|
Aplastic anaemia after prolonged treatment with chlorpheniramine. | 1977 Mar 5 |
|
Jaundice during cyproheptadine treatment. | 1978 Mar 25 |
|
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule. | 1978 Oct 7 |
|
The I antigen as an immune complex receptor in a case of haemolytic anaemia induced by an antihistaminic agent. | 1981 Sep |
|
Enhancement of morphine-induced hyperactivity by antihistaminic drugs in mice. | 1986 Dec |
|
Antagonism of drug-induced yawning and penile erections in rats. | 1986 Mar 18 |
|
Antihistaminics enhance morphine-, but not amphetamine- and scopolamine-induced hyperactivity in mice. | 1987 |
|
Antihistaminic-opioid combination: effect on locomotor activity in mice. | 1988 Sep-Oct |
|
A comparison of acrivastine versus chlorpheniramine in the treatment of chronic idiopathic urticaria. | 1989 |
|
[Antimycobacterial antihistaminics]. | 1989 Aug |
|
Drug-induced acute pulmonary edema--sequential changes in CT images. | 1991 Nov-Dec |
|
Proconvulsant effect of ketotifen, a histamine H1 antagonist, confirmed by the use of d-chlorpheniramine with monitoring electroencephalography. | 1993 Apr |
|
Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema. | 1993 Dec |
|
Role of cysteinyl-leukotrienes and histamine in mediating intrinsic tone in isolated human bronchi. | 1994 Jan |
|
Benefit/risk ratio of the antihistamines (H1-receptor antagonists) terfenadine and chlorpheniramine in children. | 1994 Jun |
|
In vivo and in vitro interaction of the novel selective histamine H1 receptor antagonist mizolastine with H1 receptors in the rodent. | 1995 May |
|
Combining event rates from clinical trials: comparison of Bayesian and classical methods. | 1996 May |
|
The role of histaminergic-noradrenergic axis in naloxone-induced withdrawal symptoms in mice. | 1996 Sep |
|
[Dexchlorpheniramine-induced acute hepatitis: a case with positive rechallenge]. | 1998 Oct |
|
2-O-(2-hydroxybutyl)-beta-cyclodextrin as a chiral selector for the capillary electrophoretic separation of chiral drugs. | 2005 Aug |
|
Synergistic action of famotidine and chlorpheniramine on acetic acid-induced chronic gastric ulcer in rats. | 2005 Dec 7 |
|
Cutaneous adverse drug reaction to oral chlorphenamine detected with patch testing. | 2005 Jan |
|
Impact of CYP2D6*10 on H1-antihistamine-induced hypersomnia. | 2006 Dec |
|
Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs. | 2006 Mar |
|
Phase II study of gemcitabine, doxorubicin and paclitaxel (GAT) as first-line chemotherapy for metastatic breast cancer: a translational research experience. | 2006 Mar 21 |
|
Histamine induces MUC5AC expression via a hCLCA1 pathway. | 2007 |
|
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish. | 2007 Apr |
|
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats. | 2008 Mar |
|
Allergic hemiglossitis as a unique case of food allergy: a case report. | 2008 Mar 6 |
|
Ultra-fast chromatographic micro-assay for quantification of diphenidol in plasma: application in an oral multi-dose switchability trial. | 2008 Oct |
|
Rare case of "red man" syndrome in a female patient treated with oral vancomycin for Clostridium difficile diarrhoea. | 2009 |
|
Investigation of enantiomeric separation of basic drugs by capillary electrophoresis using clindamycin phosphate as a novel chiral selector. | 2009 Aug |
|
Suspected anaphylactic reactions associated with anaesthesia. | 2009 Feb |
|
Toxicity associated with combination oxaliplatin plus fluoropyrimidine with or without cetuximab in the MRC COIN trial experience. | 2009 Jan 27 |
|
A computational approach to studying monomer selectivity towards the template in an imprinted polymer. | 2009 Jul |
|
Block of HERG k channel by classic histamine h(1) receptor antagonist chlorpheniramine. | 2009 Jun |
|
[Stevens-Johnson syndrome plus intrahepatic cholestasis caused by clindamycin or chlorpheniramine]. | 2009 May 15 |
|
Continuous quinacrine treatment results in the formation of drug-resistant prions. | 2009 Nov |
|
Hepatotoxicity induced by methimazole in a previously healthy patient. | 2009 Sep |
|
Retro-orbital oedema and transient blindness following endoscopic oesophagogastroduodenoscopy: a case report. | 2009 Sep 2 |
|
Dextromethorphan, chlorphenamine and serotonin toxicity: case report and systematic literature review. | 2010 Dec |
|
Differential responding of autonomic function to histamine H₁ antagonism in irritable bowel syndrome. | 2010 Dec |
|
Transport of phenylethylamine at intestinal epithelial (Caco-2) cells: mechanism and substrate specificity. | 2010 Feb |
|
Randomised controlled double-blind non-inferiority trial of two antivenoms for saw-scaled or carpet viper (Echis ocellatus) envenoming in Nigeria. | 2010 Jul 27 |
|
Simultaneous determination of paracetamol, pseudoephedrine, dextrophan and chlorpheniramine in human plasma by liquid chromatography-tandem mass spectrometry. | 2010 Mar 1 |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/chlorpheniramine.html
Tablets or syrup: 4 mg orally every 4 to 6 hours.
Sustained-release: 8 to 16 mg orally every 8 to 12 hours as needed or 16 mg orally once a day as needed.
Maximum dose 32 mg/day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1673158
Chlorpheniramine inhibits the [3H]mepyramine binding to the histamine H1 receptor in guinea pig cortex with IC50 of 8.8 nM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:34:09 UTC 2023
by
admin
on
Thu Jul 06 22:34:09 UTC 2023
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Record UNII |
3U6IO1965U
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
R06AB04
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NDF-RT |
N0000175587
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NDF-RT |
N0000000190
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WHO-VATC |
QR06AB04
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LIVERTOX |
195
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WHO-ESSENTIAL MEDICINES LIST |
03
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WHO-ATC |
R06AB54
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NCI_THESAURUS |
C29578
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WHO-VATC |
QR06AB54
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616
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DTXSID0022804
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C61672
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2725
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2400
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3032
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DB01114
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205-054-0
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Chlorpheniramine
Created by
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132-22-9
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3U6IO1965U
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104
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CHLORPHENAMINE
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SUB06201MIG
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D002744
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100000090540
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M3456
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6976
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3U6IO1965U
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CHEMBL505
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52010
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR | |||
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SUB_CONCEPT->SUBSTANCE | |||
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TRANSPORTER -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |