Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C9H19ClN3O5P |
| Molecular Weight | 315.691 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O
InChI
InChIKey=YAKWPXVTIGTRJH-UHFFFAOYSA-N
InChI=1S/C9H19ClN3O5P/c1-4-17-19(16,18-5-2)8(3)11-9(14)13(12-15)7-6-10/h8H,4-7H2,1-3H3,(H,11,14)
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.drugs.com/international/fotemustine.html | https://www.ncbi.nlm.nih.gov/pubmed/24213227 | https://clinicaltrials.gov/ct2/show/NCT01960192 | https://www.ncbi.nlm.nih.gov/pubmed/26951379 | https://www.ncbi.nlm.nih.gov/pubmed/25702193
Curator's Comment: The description was created based on several sources, including
https://www.drugs.com/international/fotemustine.html | https://www.ncbi.nlm.nih.gov/pubmed/24213227 | https://clinicaltrials.gov/ct2/show/NCT01960192 | https://www.ncbi.nlm.nih.gov/pubmed/26951379 | https://www.ncbi.nlm.nih.gov/pubmed/25702193
Fotemustine is a novel chloroethylnitrosourea alkylating agent approved for use in the treatment of metastasizing melanoma and Recurrent Malignant Gliomas. The antitumor activity of fotemustine is related to its ability to alkylate DNA. It's in vitro or in vivo pharmacological activity is similar or greater than that of other nitrosoureas. Significant activity has been found in mice xenograft models of human primary cerebral tumors after fotemustine intraperitoneal administration. Fotemustine has been registered for use in two indications: disseminated malignant melanoma, including cerebral metastases, and primary brain tumors. Fotemustine is currently used in Europe, particularly in France and Italy, as a salvage therapy for recurrent malignant gliomas. Myelosuppression, leucopenia, and thrombocytopenia are the most frequent side effects of treatment with fotemustine. The objective response to this treatment is between 26% and 70%, and the reported median survival time is 10 months. New drug combinations containing fotemustine and angiogenesis inhibitors, such as bevacizumab, are currently under development.
CNS Activity
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.26 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1451232/ |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.65 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1451232/ |
100 mg/m² 1 times / day multiple, intra-arterial dose: 100 mg/m² route of administration: Intra-arterial experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.35 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
300 mg/m² 1 times / day multiple, intravenous dose: 300 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6.94 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
350 mg/m² 1 times / day multiple, intravenous dose: 350 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.06 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
400 mg/m² 1 times / day multiple, intravenous dose: 400 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8.19 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
450 mg/m² 1 times / day multiple, intravenous dose: 450 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
18.08 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
500 mg/m² 1 times / day multiple, intravenous dose: 500 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1451232/ |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.98 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1451232/ |
100 mg/m² 1 times / day multiple, intra-arterial dose: 100 mg/m² route of administration: Intra-arterial experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.96 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
300 mg/m² 1 times / day multiple, intravenous dose: 300 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7.38 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
350 mg/m² 1 times / day multiple, intravenous dose: 350 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.17 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
400 mg/m² 1 times / day multiple, intravenous dose: 400 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
9.29 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
450 mg/m² 1 times / day multiple, intravenous dose: 450 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12.22 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
500 mg/m² 1 times / day multiple, intravenous dose: 500 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1451232/ |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1451232/ |
100 mg/m² 1 times / day multiple, intra-arterial dose: 100 mg/m² route of administration: Intra-arterial experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
34.99 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
300 mg/m² 1 times / day multiple, intravenous dose: 300 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
29.11 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
350 mg/m² 1 times / day multiple, intravenous dose: 350 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
25.58 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
400 mg/m² 1 times / day multiple, intravenous dose: 400 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
32.26 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
450 mg/m² 1 times / day multiple, intravenous dose: 450 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
20.25 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8462123/ |
500 mg/m² 1 times / day multiple, intravenous dose: 500 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FOTEMUSTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
125 mg/m2 1 times / week multiple, intravenous MTD Dose: 125 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 125 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
DLT: Thrombocytopenia, Anemia... Dose limiting toxicities: Thrombocytopenia (grade 3, 16.7%) Sources: Anemia (grade 3, 33.3%) Leucopenia (grade 3, 16.7%) Neutropenia (grade 3, 16.7%) |
100 mg/m2 1 times / week multiple, intraarterial Studied dose Dose: 100 mg/m2, 1 times / week Route: intraarterial Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Hematological toxicity, Hepatic disease... AEs leading to discontinuation/dose reduction: Hematological toxicity (8.1%) Sources: Hepatic disease (3.5%) Septic shock (grade 5, 2.3%) Gastric ulcer (1.2%) Arterial thrombosis (grade 5, 1.2%) |
100 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Thrombocytopenia, Cardiac failure... AEs leading to discontinuation/dose reduction: Thrombocytopenia (grade 3-4, 14.3%) Sources: Cardiac failure (grade 2, 9.5%) Neutropenic sepsis (grade 5, 4.8%) |
100 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Hematological toxicity, Fatigue... AEs leading to discontinuation/dose reduction: Hematological toxicity (24.7%) Sources: Fatigue (1.2%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Leucopenia | grade 3, 16.7% DLT |
125 mg/m2 1 times / week multiple, intravenous MTD Dose: 125 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 125 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Neutropenia | grade 3, 16.7% DLT |
125 mg/m2 1 times / week multiple, intravenous MTD Dose: 125 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 125 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Thrombocytopenia | grade 3, 16.7% DLT |
125 mg/m2 1 times / week multiple, intravenous MTD Dose: 125 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 125 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Anemia | grade 3, 33.3% DLT |
125 mg/m2 1 times / week multiple, intravenous MTD Dose: 125 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 125 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Gastric ulcer | 1.2% Disc. AE |
100 mg/m2 1 times / week multiple, intraarterial Studied dose Dose: 100 mg/m2, 1 times / week Route: intraarterial Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Hepatic disease | 3.5% Disc. AE |
100 mg/m2 1 times / week multiple, intraarterial Studied dose Dose: 100 mg/m2, 1 times / week Route: intraarterial Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Hematological toxicity | 8.1% Disc. AE |
100 mg/m2 1 times / week multiple, intraarterial Studied dose Dose: 100 mg/m2, 1 times / week Route: intraarterial Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Arterial thrombosis | grade 5, 1.2% Disc. AE |
100 mg/m2 1 times / week multiple, intraarterial Studied dose Dose: 100 mg/m2, 1 times / week Route: intraarterial Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Septic shock | grade 5, 2.3% Disc. AE |
100 mg/m2 1 times / week multiple, intraarterial Studied dose Dose: 100 mg/m2, 1 times / week Route: intraarterial Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Cardiac failure | grade 2, 9.5% Disc. AE |
100 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Thrombocytopenia | grade 3-4, 14.3% Disc. AE |
100 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Neutropenic sepsis | grade 5, 4.8% Disc. AE |
100 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Fatigue | 1.2% Disc. AE |
100 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Hematological toxicity | 24.7% Disc. AE |
100 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / week Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Human three prime exonuclease TREX1 is induced by genotoxic stress and involved in protection of glioma and melanoma cells to anticancer drugs. | 2013-08 |
|
| Can high-dose fotemustine reverse MGMT resistance in glioblastoma multiforme? | 2010-11 |
|
| Resection in the popliteal fossa for metastatic melanoma. | 2007-01-19 |
|
| O(6)-methylguanine DNA-methyltransferase (MGMT) overexpression in melanoma cells induces resistance to nitrosoureas and temozolomide but sensitizes to mitomycin C. | 2006-03-01 |
|
| Artesunate in the treatment of metastatic uveal melanoma--first experiences. | 2005-12 |
|
| Organ- and treatment-specific local response rates to systemic and local treatment modalities in stage IV melanoma. | 2005-11 |
|
| Isolated limb infusion with fotemustine after dacarbazine chemosensitisation for inoperable loco-regional melanoma recurrence. | 2004-12 |
|
| Fotemustine compared with dacarbazine in patients with disseminated malignant melanoma: a phase III study. | 2004-03-15 |
|
| Cytotoxicity, DNA damage, and apoptosis induced by new fotemustine analogs on human melanoma cells in relation to O6-methylguanine DNA-methyltransferase expression. | 2003-11 |
|
| Second-line chemotherapy with dacarbazine and fotemustine in nitrosourea-pretreated patients with recurrent glioblastoma multiforme. | 2003-07 |
|
| Survival with dacarbazine and fotemustine in newly diagnosed glioblastoma multiforme. | 2003-02-24 |
|
| Evaluation of the efficiency of chemotherapy in in vivo orthotopic models of human glioma cells with and without 1p19q deletions and in C6 rat orthotopic allografts serving for the evaluation of surgery combined with chemotherapy. | 2002-08-01 |
|
| Cisplatin, dacarbazine, and fotemustine plus interferon alpha in patients with advanced malignant melanoma. A multicenter phase II study of the Italian Cooperative Oncology Group. | 2000-12-15 |
Sample Use Guides
Fotemustine was administered weekly for 3 consecutive weeks (days 1, 8, and 15) at 100 mg/m2 as a 60-minute infusion, followed by a 5-week rest period
Route of Administration:
Intravenous
The BRAFV600E A375, Malme-3M, A2058 and RPMI7951 and wild-type SK-Mel537, SK-Mel505, RPMI18332 and SK-Mel187 melanoma cell lines were used for activity evaluation. Cells were treated with the chemotherapeutic (Fotemustine, FM) and the number of cell divisions following 120h incubation was determined using flow cytometry of CFSE stained cells. The cellular division rate was determined using carboxyfluorescein diacetate succinimidyl ester (CFSE) stained cells [39]. One day after labeling the control sample (0h) was harvested and analyzed by flow cytometry (FACS Canto II). On this day cells were treated or not with vemurafenib, TMZ, FM or combinations of the drugs, and 120h later samples were harvested and subjected to flow cytometry analysis. Using the mean 0h fluorescence signal, a standard curve was plotted to determine the number of cell divisions after 120h incubation in treated and untreated cells.
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| Classification Tree | Code System | Code | ||
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WHO-ATC |
L01AD05
Created by
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NCI_THESAURUS |
C699
Created by
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WHO-VATC |
QL01AD05
Created by
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C054368
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1249
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100000080464
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92118-27-9
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SUB07809MIG
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m5559
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5982
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GQ7JL9P5I2
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104799
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DTXSID80869091
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C1106
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FOTEMUSTINE
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CHEMBL549386
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DB04106
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7762
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ACTIVE MOIETY
