U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of MITOLACTOL

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-

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
81.9 μM
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

AUC

ValueDoseCo-administeredAnalytePopulation
24.7 nM × min
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

T1/2

ValueDoseCo-administeredAnalytePopulation
92.4 min
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

Doses

DosePopulationAdverse 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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
DLT: Myelosuppression...
Disc. AE: Hepatic failure, Sepsis...
Dose limiting toxicities:
Myelosuppression (grade 5, 20%)
AEs leading to
discontinuation/dose reduction:
Hepatic failure (grade 5, 20%)
Sepsis (grade 5, 20%)
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
DLT: Thrombocytopenia, Thrombocytopenia...
Disc. AE: Leukopenia, Sepsis...
Other AEs: Leukopenia...
Dose limiting toxicities:
Thrombocytopenia (grade 4, 20%)
Thrombocytopenia (grade 4, 5%)
AEs leading to
discontinuation/dose reduction:
Leukopenia (grade 4, 1.7%)
Sepsis (grade 5, 1.7%)
Other AEs:
Leukopenia (grade 4, 11.7%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
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:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Induction chemotherapy response and recurrence rates in correlation with N0 or N+ stage in oral squamous cell cancer (OSCC).
2010-12
Phase II TPDCV protocol for pediatric low-grade hypothalamic/chiasmatic gliomas: 15-year update.
2010-10
Neoadjuvant chemotherapy: does it have benefits for the surgeon in the treatment of advanced squamous cell cancer of the oral cavity?
2010-06
Down-regulation of lung resistance related protein by RNA interference targeting survivin induces the reversal of chemoresistances in hepatocellular carcinoma.
2009-11-05
Evaluation of the paclitaxel-ifosfamide-cisplatin (TIP) combination in relapsed and/or metastatic cervical cancer.
2009-10-06
Association between serotonin transporter availability and overall rating scores of quality of life in healthy volunteers.
2009-06-15
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).
2008-06
A review of topotecan in combination chemotherapy for advanced cervical cancer.
2008-02
[Expression of MDR1 and GST-pi in osteosarcoma and soft tissue sarcoma and their correlation with chemotherapy resistance].
2006-06
Randomized use of cyclosporin A (CsA) to modulate P-glycoprotein in children with AML in remission: Pediatric Oncology Group Study 9421.
2006-02-15
Treatments for astrocytic tumors in children: current and emerging strategies.
2006
Phase I-II study of irinotecan (CPT-11) plus nedaplatin (254-S) with recombinant human granulocyte colony-stimulating factor support in patients with advanced or recurrent cervical cancer.
2004-09-13
Failure of alkylating agents to improve induction chemotherapy of oropharyngeal squamous cell cancer.
2004-08-28
E-cadherin-dependent intercellular adhesion enhances chemoresistance.
2003-11
[Chemotherapy of recurrent supratentorial malignant gliomas (phase II study)].
2002-01-20
BCNU-DBD (Dibromodulcitol) chemotherapy of recurrent supratentorial anaplastic astrocytomas and glioblastomas.
2002
Reversal of multidrug resistance by novel nitrophenyl pyrones, SNF4435C and D.
2001-11
Apoptotic and mitotic activity in squamous cell carcinoma cells after combined modality treatment with gamma-irradiation and dibromodulcitol.
2001
Patents

Sample Use Guides

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
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.
Name Type Language
MITOLACTOL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
NCI-C04795
Preferred Name English
NSC-104800
Code English
MITOLACTOL [MI]
Common Name English
DIBROMODULCITOL
Common Name English
DIBROMDULCIT
Common Name English
1,6-DIBROMO-1,6-DIDEOXY-D-GALACTITOL
Common Name English
Mitolactol [WHO-DD]
Common Name English
GALACTITOL, 1,6-DIBROMO-1,6-DIDEOXY-
Systematic Name English
MITOLACTOL [MART.]
Common Name English
mitolactol [INN]
Common Name English
ELOBROMOL
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 90295
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
NCI_THESAURUS C475
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
FDA ORPHAN DRUG 33188
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
NCI_THESAURUS C798
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C662
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
INN
3143
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
EVMPD
SUB09005MIG
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID8020414
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
MESH
D008936
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
MERCK INDEX
m7569
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL2104612
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
NSC
104800
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
CAS
10318-26-0
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
DRUG BANK
DB12916
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
SMS_ID
100000080878
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
PUBCHEM
5284380
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
DRUG CENTRAL
857
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY
FDA UNII
LJ2P1SIK8Y
Created by admin on Mon Mar 31 19:25:41 GMT 2025 , Edited by admin on Mon Mar 31 19:25:41 GMT 2025
PRIMARY