Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C56H71N9O23S |
Molecular Weight | 1270.274 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 15 / 15 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@H](O)CN1C(=O)[C@@]([H])(NC(=O)[C@H](C[C@@H](O)[C@@H](O)NC(=O)[C@]3([H])[C@@H](O)[C@@H](C)CN3C(=O)[C@@]([H])(NC(=O)[C@@]([H])(NC2=O)[C@H](O)[C@@H](O)C4=CC(OS(O)(=O)=O)=C(O)C=C4)[C@H](O)CC(N)=O)NC(=O)C5=CC=C(C=C5)C6=NOC(=C6)C7=CC=C(OCCCCC)C=C7)[C@@H](C)O
InChI
InChIKey=PIEUQSKUWLMALL-YABMTYFHSA-N
InChI=1S/C56H71N9O23S/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85)/t25-,26+,31+,34-,35-,37+,38+,42-,43-,44-,45-,46-,47-,48-,52+/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/19933794Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/ppa/micafungin.html | https://en.wikipedia.org/wiki/Micafungin
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19933794
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/ppa/micafungin.html | https://en.wikipedia.org/wiki/Micafungin
Micafungin (trade name Mycamine) is an echinocandin antifungal drug. Micafungin, the active ingredient in Mycamine, inhibits the synthesis of 1,3-β-D-glucan, an essential component of fungal cell walls, which is not present in mammalian cells. Micafungin is indicated for the treatment of candidemia, acute disseminated candidiasis, Candida peritonitis, abscesses and esophageal candidiasis. Possible histamine-mediated symptoms have been reported with Mycamine, including rash, pruritus, facial swelling and vasodilatation.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17381184 | https://www.ncbi.nlm.nih.gov/pubmed/17696807
Curator's Comment: Micafungin was present in low levels at brain tissue, indicating limited penetration into central nervous system (CNS) tissue.
https://www.ncbi.nlm.nih.gov/pubmed/19933794
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364673 |
0.208 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | MYCAMINE Approved UseMycamine® is indicated in adult and pediatric patients 4 months and older for: Mycamine is an echinocandin indicated in adult and pediatric patients 4 months and older for: •Treatment of Patients with Candidemia, Acute Disseminated Candidiasis, Candida Peritonitis and Abscesses (1.1) •Treatment of Patients with Esophageal Candidiasis (1.2) •Prophylaxis of Candida Infections in Patients Undergoing Hematopoietic Stem Cell Transplantation (1.3) 1.1 Treatment of Patients with Candidemia, Acute Disseminated Candidiasis, Candida Peritonitis and Abscesses [see Clinical Studies (14.1) Launch Date2005 |
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Preventing | MYCAMINE Approved UseMycamine® is indicated in adult and pediatric patients 4 months and older for: Mycamine is an echinocandin indicated in adult and pediatric patients 4 months and older for: •Treatment of Patients with Candidemia, Acute Disseminated Candidiasis, Candida Peritonitis and Abscesses (1.1) •Treatment of Patients with Esophageal Candidiasis (1.2) •Prophylaxis of Candida Infections in Patients Undergoing Hematopoietic Stem Cell Transplantation (1.3) 1.1 Treatment of Patients with Candidemia, Acute Disseminated Candidiasis, Candida Peritonitis and Abscesses [see Clinical Studies (14.1) Launch Date2005 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.4 μg/mL |
150 mg 1 times / day multiple, intravenous dose: 150 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
60.8 μg/mL |
8 mg/kg bw 1 times / day multiple, intravenous dose: 8 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
10.1 μg/mL |
100 mg 1 times / day steady-state, intravenous dose: 100 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
167 μg × h/mL |
150 mg 1 times / day multiple, intravenous dose: 150 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
663 μg × h/mL |
8 mg/kg bw 1 times / day multiple, intravenous dose: 8 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
97 μg × h/mL |
100 mg 1 times / day steady-state, intravenous dose: 100 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.2 h |
150 mg 1 times / day multiple, intravenous dose: 150 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
17.2 h |
8 mg/kg bw 1 times / day multiple, intravenous dose: 8 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
13.4 h |
100 mg 1 times / day steady-state, intravenous dose: 100 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
100 mg 1 times / day steady-state, intravenous dose: 100 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
MICAFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
8 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 8 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 8 mg/kg, 1 times / day Sources: Page: p.48 |
unhealthy, 19 - 62 n = 8 Health Status: unhealthy Condition: Haematopoietic stem cell transplantation Age Group: 19 - 62 Sex: M+F Population Size: 8 Sources: Page: p.48 |
|
200 mg single, intravenous Highest studied dose Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Co-administed with:: prednisolone, iv, single(20 mg) Sources: Page: p.1, p.4 |
healthy Health Status: healthy Condition: Candidiasis Sources: Page: p.1, p.4 |
Disc. AE: Intravascular hemolysis... AEs leading to discontinuation/dose reduction: Intravascular hemolysis (acute) Sources: Page: p.1, p.4 |
16 mg/kg single, intravenous Overdose Dose: 16 mg/kg Route: intravenous Route: single Dose: 16 mg/kg Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.9 |
|
150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1 |
Disc. AE: Anaphylaxis, Anaphylactoid reaction... AEs leading to discontinuation/dose reduction: Anaphylaxis Sources: Page: p.1Anaphylactoid reaction |
150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Disc. AE: Hemolysis, Hemolytic anemia... AEs leading to discontinuation/dose reduction: Hemolysis (significant) Sources: Page: p.1, p.4Hemolytic anemia Abnormal liver function tests Hepatic impairment Hepatitis Hepatic failure Blood urea increased Creatinine increased Renal impairment Renal failure (acute) |
150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.5 |
Disc. AE: Exfoliative conditions, Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Exfoliative conditions Sources: Page: p.5Stevens-Johnson syndrome Toxic epidermal necrolysis Rash |
150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.8 |
Disc. AE: Hepatic and hepatobiliary disorders, Hepatic and hepatobiliary disorders... AEs leading to discontinuation/dose reduction: Hepatic and hepatobiliary disorders (1.1%) Sources: Page: p.8Hepatic and hepatobiliary disorders (serious, 0.4%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Intravascular hemolysis | acute Disc. AE |
200 mg single, intravenous Highest studied dose Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Co-administed with:: prednisolone, iv, single(20 mg) Sources: Page: p.1, p.4 |
healthy Health Status: healthy Condition: Candidiasis Sources: Page: p.1, p.4 |
Anaphylactoid reaction | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1 |
Anaphylaxis | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1 |
Abnormal liver function tests | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Blood urea increased | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Creatinine increased | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Hemolytic anemia | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Hepatic failure | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Hepatic impairment | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Hepatitis | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Renal impairment | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Renal failure | acute Disc. AE |
150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Hemolysis | significant Disc. AE |
150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.1, p.4 |
unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: Page: p.1, p.4 |
Exfoliative conditions | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.5 |
Rash | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.5 |
Stevens-Johnson syndrome | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.5 |
Toxic epidermal necrolysis | Disc. AE | 150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.5 |
Hepatic and hepatobiliary disorders | 1.1% Disc. AE |
150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.8 |
Hepatic and hepatobiliary disorders | serious, 0.4% Disc. AE |
150 mg 1 times / day multiple, intravenous Recommended Dose: 150 mg, 1 times / day Route: intravenous Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Candidiasis Sources: Page: p.8 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 77.0 |
no | |||
Page: 75.0 |
yes [Inhibition 50 uM] | |||
Page: 75.0 |
yes [Inhibition 50 uM] | |||
Page: 75.0 |
yes [Inhibition 50 uM] | |||
Page: 75.0 |
yes [Inhibition 50 uM] | |||
Page: 75.0 |
yes [Inhibition 50 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 78.0 |
inconclusive | |||
Page: 76.0 |
likely | |||
yes | ||||
yes | ||||
Page: 56.0 |
yes | |||
Page: 56.0 |
yes | |||
Page: 56.0 |
yes | |||
Page: 56.0 |
yes | |||
Page: 56.0 |
yes | |||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 24, 25 |
PubMed
Title | Date | PubMed |
---|---|---|
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of pulmonary aspergillosis. | 2000 Mar |
|
In vitro antifungal activity of FK463, a new water-soluble echinocandin-like lipopeptide. | 2000 Sep |
|
Prophylactic effect of FK463, a novel antifungal lipopeptide, against Pneumocystis carinii infection in mice. | 2000 Sep |
|
In vitro activity of micafungin (FK-463) against Candida spp.: microdilution, time-kill, and postantifungal-effect studies. | 2002 Dec |
|
Micafungin: pharmacology, experimental therapeutics and clinical applications. | 2005 Apr |
|
Echinocandins in the management of invasive fungal infections, Part 2. | 2006 Oct 1 |
|
The echinocandin micafungin: a review of the pharmacology, spectrum of activity, clinical efficacy and safety. | 2007 Jun |
|
In vitro and in vivo antifungal activities of T-2307, a novel arylamidine. | 2008 Apr |
|
Multilaboratory testing of two-drug combinations of antifungals against Candida albicans, Candida glabrata, and Candida parapsilosis. | 2011 Apr |
|
Identification and characterization of the echinocandin B biosynthetic gene cluster from Emericella rugulosa NRRL 11440. | 2012 Oct 10 |
|
Synergistic antifungal activity of KB425796-C in combination with micafungin against Aspergillus fumigatus and its efficacy in murine infection models. | 2013 Aug |
Patents
Sample Use Guides
Esophageal Candidiasis - 150 mg per day
Prophylaxis of Candida Infections in HSCT Recipients - 50 mg per day
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12003006
The IC50 value of FK463 for mannan inhibition was over 100 ug/ml.
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Classification Tree | Code System | Code | ||
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LIVERTOX |
634
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WHO-ATC |
J02AX05
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NDF-RT |
N0000175508
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WHO-VATC |
QJ02AX05
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NCI_THESAURUS |
C514
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NDF-RT |
N0000175508
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NDF-RT |
N0000175507
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R10H71BSWG
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C121905
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100000091615
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CHEMBL457547
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235114-32-6
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1798
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600520
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m7524
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8069
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325887
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DB01141
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DTXSID90873341
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C1850
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R10H71BSWG
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477468
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MICAFUNGIN
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SUB16444MIG
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)