Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H12Br2O4 |
Molecular Weight | 307.965 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H](CBr)[C@@H](O)[C@@H](O)[C@H](O)CBr
InChI
InChIKey=VFKZTMPDYBFSTM-GUCUJZIJSA-N
InChI=1S/C6H12Br2O4/c7-1-3(9)5(11)6(12)4(10)2-8/h3-6,9-12H,1-2H2/t3-,4+,5+,6-
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2484330Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20842409 | https://www.ncbi.nlm.nih.gov/pubmed/6652807 | https://www.ncbi.nlm.nih.gov/pubmed/8996138 | https://www.ncbi.nlm.nih.gov/pubmed/18142452
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2484330
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20842409 | https://www.ncbi.nlm.nih.gov/pubmed/6652807 | https://www.ncbi.nlm.nih.gov/pubmed/8996138 | https://www.ncbi.nlm.nih.gov/pubmed/18142452
Mitolactol is a synthetic derivative of hexitol with antineoplastic and radiosensitizing properties. Mitolactol alkylates DNA via actual or derived epoxide groups, resulting in inhibition of DNA and RNA synthesis.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6652807 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
81.9 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3517245 |
1800 mg/m² single, oral dose: 1800 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
MITOLACTOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
24.7 nM × min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3517245 |
1800 mg/m² single, oral dose: 1800 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
MITOLACTOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
92.4 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3517245 |
1800 mg/m² single, oral dose: 1800 mg/m² route of administration: Oral experiment type: SINGLE co-administered: |
MITOLACTOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1800 mg/m2 1 times / month multiple, oral MTD Dose: 1800 mg/m2, 1 times / month Route: oral Route: multiple Dose: 1800 mg/m2, 1 times / month Sources: Page: p.756 |
unhealthy, ADULT n = 5 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: FASTED Population Size: 5 Sources: Page: p.756 |
DLT: Myelosuppression... Disc. AE: Hepatic failure, Sepsis... Dose limiting toxicities: Myelosuppression (grade 5, 20%) AEs leading todiscontinuation/dose reduction: Hepatic failure (grade 5, 20%) Sources: Page: p.756Sepsis (grade 5, 20%) |
180 mg/m2 1 times / day multiple, oral Studied dose Dose: 180 mg/m2, 1 times / day Route: oral Route: multiple Dose: 180 mg/m2, 1 times / day Sources: Page: p.1893 |
unhealthy, ADULT n = 60 Health Status: unhealthy Condition: squamous cell carcinoma of the Cervix Uteri Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 60 Sources: Page: p.1893 |
DLT: Thrombocytopenia, Thrombocytopenia... Disc. AE: Leukopenia, Sepsis... Other AEs: Leukopenia... Dose limiting toxicities: Thrombocytopenia (grade 4, 5%) AEs leading toThrombocytopenia (grade 4, 20%) discontinuation/dose reduction: Leukopenia (grade 4, 1.7%) Other AEs:Sepsis (grade 5, 1.7%) Leukopenia (grade 4, 11.7%) Sources: Page: p.1893 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Myelosuppression | grade 5, 20% DLT, Disc. AE |
1800 mg/m2 1 times / month multiple, oral MTD Dose: 1800 mg/m2, 1 times / month Route: oral Route: multiple Dose: 1800 mg/m2, 1 times / month Sources: Page: p.756 |
unhealthy, ADULT n = 5 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: FASTED Population Size: 5 Sources: Page: p.756 |
Hepatic failure | grade 5, 20% Disc. AE |
1800 mg/m2 1 times / month multiple, oral MTD Dose: 1800 mg/m2, 1 times / month Route: oral Route: multiple Dose: 1800 mg/m2, 1 times / month Sources: Page: p.756 |
unhealthy, ADULT n = 5 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: FASTED Population Size: 5 Sources: Page: p.756 |
Sepsis | grade 5, 20% Disc. AE |
1800 mg/m2 1 times / month multiple, oral MTD Dose: 1800 mg/m2, 1 times / month Route: oral Route: multiple Dose: 1800 mg/m2, 1 times / month Sources: Page: p.756 |
unhealthy, ADULT n = 5 Health Status: unhealthy Condition: cancer Age Group: ADULT Sex: M+F Food Status: FASTED Population Size: 5 Sources: Page: p.756 |
Leukopenia | grade 4, 1.7% Disc. AE |
180 mg/m2 1 times / day multiple, oral Studied dose Dose: 180 mg/m2, 1 times / day Route: oral Route: multiple Dose: 180 mg/m2, 1 times / day Sources: Page: p.1893 |
unhealthy, ADULT n = 60 Health Status: unhealthy Condition: squamous cell carcinoma of the Cervix Uteri Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 60 Sources: Page: p.1893 |
Leukopenia | grade 4, 11.7% | 180 mg/m2 1 times / day multiple, oral Studied dose Dose: 180 mg/m2, 1 times / day Route: oral Route: multiple Dose: 180 mg/m2, 1 times / day Sources: Page: p.1893 |
unhealthy, ADULT n = 60 Health Status: unhealthy Condition: squamous cell carcinoma of the Cervix Uteri Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 60 Sources: Page: p.1893 |
Thrombocytopenia | grade 4, 20% DLT, Disc. AE |
180 mg/m2 1 times / day multiple, oral Studied dose Dose: 180 mg/m2, 1 times / day Route: oral Route: multiple Dose: 180 mg/m2, 1 times / day Sources: Page: p.1893 |
unhealthy, ADULT n = 60 Health Status: unhealthy Condition: squamous cell carcinoma of the Cervix Uteri Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 60 Sources: Page: p.1893 |
Thrombocytopenia | grade 4, 5% DLT, Disc. AE |
180 mg/m2 1 times / day multiple, oral Studied dose Dose: 180 mg/m2, 1 times / day Route: oral Route: multiple Dose: 180 mg/m2, 1 times / day Sources: Page: p.1893 |
unhealthy, ADULT n = 60 Health Status: unhealthy Condition: squamous cell carcinoma of the Cervix Uteri Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 60 Sources: Page: p.1893 |
Sepsis | grade 5, 1.7% Disc. AE |
180 mg/m2 1 times / day multiple, oral Studied dose Dose: 180 mg/m2, 1 times / day Route: oral Route: multiple Dose: 180 mg/m2, 1 times / day Sources: Page: p.1893 |
unhealthy, ADULT n = 60 Health Status: unhealthy Condition: squamous cell carcinoma of the Cervix Uteri Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 60 Sources: Page: p.1893 |
PubMed
Title | Date | PubMed |
---|---|---|
Apoptotic and mitotic activity in squamous cell carcinoma cells after combined modality treatment with gamma-irradiation and dibromodulcitol. | 2001 |
|
Randomized use of cyclosporin A (CsA) to modulate P-glycoprotein in children with AML in remission: Pediatric Oncology Group Study 9421. | 2006 Feb 15 |
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A review of topotecan in combination chemotherapy for advanced cervical cancer. | 2008 Feb |
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Adjuvant dibromodulcitol and BCNU chemotherapy in anaplastic astrocytoma: results of a randomised European Organisation for Research and Treatment of Cancer phase III study (EORTC study 26882). | 2008 Jun |
|
Phase II TPDCV protocol for pediatric low-grade hypothalamic/chiasmatic gliomas: 15-year update. | 2010 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8996138
Patients were randomized to receive cisplatin 50 mg/m2 or the same dose of cisplatin plus mitolactol (C + M) 180 mg/m2 orally on days 2 to 6
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6652807
Calf thymus DNA (64mg) in 0.25M sodium cacodylate buffer, pH 7.10 (3 ml) and dibromodulcitol (Mitolactol) (308 mg: 1 mmol) in dimethylsulphoxyde (3.5 ml) were mixed and the reaction was allowed to proceed for 2 days at 37°C. The alkylated DNA was then dialysed against 0.01 M Tris-HC1 (pH 7.0) and 0.01 M NaC1 at 4°C for 48 h and hydrolysed at pH 1 for 30 min at 70°C. The pH of hydrolysate was raised to 10.8 prior to chromatography on a column (2.6 cm × 32 cm) of Sephadex G-10. Elution was performed with aq. NH3 pH 10.8 collecting 6.5ml fractions. Four major UV-absorbing peaks were found of which fractions 10-17 contained oligopyrimidine-nucleotides, fraction 19-21 7-alkylated guanines (A2s0/A26o:l.7), fractions 23-29 guanine (A2s0/A26o:l.1) and fractions 33--44 adenine and 3-alkyladenine together (Aes0/A26o:0.36). 7-Alkylguanine derivatives were separated by rechromatography on a column (17 cm x 1.2 cm) of DowexS0 W (H + form) using 1 M HC1 as eluent, 6.5 ml "fractions were collected.
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FDA ORPHAN DRUG |
90295
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NCI_THESAURUS |
C475
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FDA ORPHAN DRUG |
33188
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NCI_THESAURUS |
C798
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3143
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m7569
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CHEMBL2104612
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ACTIVE MOIETY