Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H17N3O.C4H6O4.H2O |
Molecular Weight | 379.4076 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OC(=O)CCC(O)=O.CN[C@@H]1CCC2=C(C1)C3=C(N2)C=CC(=C3)C(N)=O
InChI
InChIKey=CUETXFMONOSVJA-KLQYNRQASA-N
InChI=1S/C14H17N3O.C4H6O4.H2O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13;5-3(6)1-2-4(7)8;/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18);1-2H2,(H,5,6)(H,7,8);1H2/t9-;;/m1../s1
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C14H17N3O |
Molecular Weight | 243.3043 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C4H6O4 |
Molecular Weight | 118.088 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Frovatriptan succinate (trade name Frova) is a selective 5-hydroxytryptamine1 (5-HT1B/1D) receptor subtype agonist, and is used for the treatment of migraine attacks with or without aura in adults. Frovatriptan has no significant effects on GABAA mediated channel activity and has no significant affinity for benzodiazepine binding sites. Frovatriptan is believed to act on extracerebral, intracranial arteries and to inhibit excessive dilation of these vessels in migraine. Serious but rare cardiac events have been reported in patients with risk factors predictive of coronary artery disease (CAD). These include coronary artery vasospasm, transient myocardial ischemia, myocardial infarction, ventricular tachycardia and ventricular fibrillation.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
62.0 nM [Ki] | |||
10.3 nM [Ki] | |||
4.4 nM [Ki] | |||
Target ID: CHEMBL1983 |
|||
Target ID: CHEMBL1898 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FROVA Approved UseFROVA is indicated for the acute treatment of migraine attacks with or without aura in adults. FROVA is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine (see CONTRAINDICATIONS). The safety and effectiveness of FROVA have not been established for cluster headache, which is present in an older, predominately male, population. Launch Date1.0051776E12 |
|||
Primary | FROVA Approved UseFROVA is indicated for the acute treatment of migraine attacks with or without aura in adults. FROVA is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine (see CONTRAINDICATIONS). The safety and effectiveness of FROVA have not been established for cluster headache, which is present in an older, predominately male, population. Launch Date1.0051776E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.44 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
29.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25092964 |
2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
FROVATRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
85% |
FROVATRIPTAN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.8 mg single, intravenous Highest studied dose Dose: 0.8 mg Route: intravenous Route: single Dose: 0.8 mg Sources: Page: S56 |
healthy, 21 - 37 n = 12 Health Status: healthy Age Group: 21 - 37 Sex: M+F Population Size: 12 Sources: Page: S56 |
|
40 mg single, oral Highest studied dose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: Page: S56 |
healthy, 21 - 37 n = 12 Health Status: healthy Age Group: 21 - 37 Sex: M+F Population Size: 12 Sources: Page: S56 |
|
40 mg single, oral Highest studied dose Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: Page: S76 |
unhealthy, 40.4 n = 207 Health Status: unhealthy Condition: Migraine Age Group: 40.4 Sex: M+F Population Size: 207 Sources: Page: S76 |
|
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Disc. AE: Arrhythmia, Cerebral hemorrhage... Other AEs: Myocardial ischemia, Myocardial infarction... AEs leading to discontinuation/dose reduction: Arrhythmia Other AEs:Cerebral hemorrhage Subarachnoid hemorrhage Stroke Gastrointestinal ischemia Peripheral vasoconstriction Serotonin syndrome Myocardial ischemia Sources: Page: p.1Myocardial infarction Prinzmetal angina Chest pain Throat pain Neck pain Jaw pain Chest tightness Throat tightness Pressure |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Disc. AE: Splenic infarction, Raynaud's syndrome... AEs leading to discontinuation/dose reduction: Splenic infarction Sources: Page: p.3Raynaud's syndrome Blood pressure high (grade 3) Hypertensive crisis Anaphylactic reaction (grade 4-5) Anaphylactoid reaction (grade 4-5) Angioedema (grade 4-5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Chest pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Chest tightness | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Jaw pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Myocardial infarction | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Myocardial ischemia | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Neck pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Pressure | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Prinzmetal angina | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Throat pain | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Throat tightness | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
|
Arrhythmia | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Cerebral hemorrhage | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Gastrointestinal ischemia | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Peripheral vasoconstriction | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Serotonin syndrome | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Stroke | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Subarachnoid hemorrhage | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.1 |
Hypertensive crisis | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Raynaud's syndrome | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Splenic infarction | Disc. AE | 7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Blood pressure high | grade 3 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Anaphylactic reaction | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Anaphylactoid reaction | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Angioedema | grade 4-5 Disc. AE |
7.5 mg 3 times / day multiple, oral Recommended Dose: 7.5 mg, 3 times / day Route: oral Route: multiple Dose: 7.5 mg, 3 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Migraine Sources: Page: p.3 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 29, 35 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 29, 35 |
no | |||
Page: 35.0 |
no | |||
Page: 29, 35 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 35.0 |
no | |||
Page: 29.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Frovatriptan. | 2001 |
|
Acute treatment of migraine and the role of triptans. | 2001 Mar |
|
Comparative effects of frovatriptan and sumatriptan on coronary and internal carotid vascular haemodynamics in conscious dogs. | 2001 Mar |
|
Advances in pharmacological treatment of migraine. | 2001 Oct |
|
Triptans are all different. | 2001 Sep |
|
Spotlight on rizatriptan in migraine. | 2002 |
|
Clinical efficacy of frovatriptan: placebo-controlled studies. | 2002 Apr |
|
New medications show promise for migraine sufferers. | 2002 Oct |
|
Frovatriptan Vernalis. | 2002 Sep |
|
Newer formulations of the triptans: advances in migraine management. | 2003 |
|
Patent news. | 2003 Dec |
|
New drugs 2003, part I. | 2003 Feb |
|
Frovatriptan: a review. | 2003 Jan |
|
Gateways to clinical trials. | 2004 Apr |
|
Evaluation of Frova, single-use intubation introducer, in a manikin. Comparison with Eschmann multiple-use introducer and Portex single-use introducer. | 2004 Aug |
|
Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. | 2004 Jul |
|
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery. | 2004 Jul |
|
A randomized trial of frovatriptan for the intermittent prevention of menstrual migraine. | 2004 Jul 27 |
|
Menstrual migraine: timing is everything. | 2004 Jul 27 |
|
Cost considerations of acute migraine treatment. | 2004 Mar |
|
Frovatriptan use in migraineurs with or at high risk of coronary artery disease. | 2004 May |
|
[PercuTwist dilational tracheostomy. Prospective evaluation of 54 consecutive patients]. | 2004 May |
|
Randomized, placebo-controlled comparison of early use of frovatriptan in a migraine attack versus dosing after the headache has become moderate or severe. | 2004 Sep |
|
Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs. | 2005 Jan |
|
Gateways to clinical trials. | 2005 Mar |
|
The use of multiattribute decision models in evaluating triptan treatment options in migraine. | 2005 Sep |
|
A comparative study on the cost of new antibiotics and drugs of other therapeutic categories. | 2006 Dec 20 |
|
Frovatriptan review. | 2007 Dec |
|
Latest pain relief a combination of new and old. | 2007 Jan |
|
Triptans in pregnancy. | 2008 Feb |
|
Evaluation of clinical effectiveness of the Frova single-use tracheal tube introducer. | 2008 Feb |
Sample Use Guides
The recommended dose is a single tablet of FROVA (frovatriptan 2.5 mg) taken orally with fluids. If the headache recurs after initial relief, a second tablet may be taken, providing there is an interval of at least 2 hours between doses. The total daily dose of frovatriptan should not exceed 3 tablets (3 x 2.5 mg per day). The safety of treating an average of more than 4 migraine attacks in a 30-day period has not been established.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9700983
Curator's Comment: Frovatriptan was investigated in human isolated basilar and coronary arteries in which the endothelium had been removed. Basilar arteries were obtained post mortem, and coronary arteries were obtained from patients undergoing heart transplant (recipient) or from donor hearts that were not suitable for transplant. Frovatriptan was a potent contractile agent in isolated basilar artery with a -log mean effective concentration (EC50) value of 7.86 +/- 0.07 and intrinsic activity of 1.25 +/- 0.10 relative to 5-HT (n = 4). In coronary arteries, frovatriptan produced contraction with -log EC50 values of 7.38 +/- 0.12 and 7.81 +/- 0.2 in recipient (n = 7) and donor (n = 3) arteries, respectively. The relative degree of contraction of frovatriptan was lower than that of 5-HT, with relative intrinsic activities of 0.42 +/- 0.06 and 0.40 +/- 0.09, respectively.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 18:48:06 UTC 2022
by
admin
on
Fri Dec 16 18:48:06 UTC 2022
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Record UNII |
D28J6W18HY
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47794
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1286413
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322249
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M5571
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C47544
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CHEMBL1279
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KK-26
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D28J6W18HY
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DBSALT001958
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158930-17-7
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Frovatriptan succinate
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152943
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D28J6W18HY
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DTXSID2049056
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SUB22174
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760422
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SUB127149
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |