Mitobronitol

Mitobronitol
Names

Preferred IUPAC name 1,6-Dibromo-1,6-dideoxy-D-mannitol
Systematic IUPAC name 1,6-Dibromohexane-2,3,4,5-tetrol^[1]
Identifiers
CAS Number	488-41-5 (2S,3S,4S,5S)-2,3,4,5-tetrol^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL161657^Y ChEMBL447629^Y
ChemSpider	4063^Y 5145112 (2S,3S,5R)-2,3,5-triol^Y 5145112 (2R,3R,4R,5R)-2,3,4,5-tetrol^Y
ECHA InfoCard	100.006.979
EC Number	207-676-8
KEGG	D02020^Y
MeSH	Mitobronitol
PubChem	4208 44119013 (2R,3R)-2,3-diol 6713087 (2S,3S,5R)-2,3,5-triol 2794952 (2R,3R,4R,5R)-2,3,4,5-tetrol 656655 (2S,3S,4S,5S)-2,3,4,5-tetrol
RTECS number	OP2800000 (2RS,3RS,4RS,5RS)-2,3,4,5-tetrol
UNII	5UP30YED7N^Y
InChI InChI=1S/C6H12Br2O4/c7-1-3(9)5(11)6(12)4(10)2-8/h3-6,9-12H,1-2H2^Y Key: VFKZTMPDYBFSTM-UHFFFAOYSA-N^Y
SMILES OC(CBr)C(O)C(O)C(O)CBr
Properties
Chemical formula	C₆H₁₂Br₂O₄
Molar mass	307.97 g·mol⁻¹
Appearance	Colourless crystals
log P	−0.226 (2RS,3RS,4RS,5RS)-2,3,4,5-tetrol
Acidity (pK_a)	12.609 (2RS,3RS,4RS,5RS)-2,3,4,5-tetrol
Basicity (pK_b)	1.388 (2RS,3RS,4RS,5RS)-2,3,4,5-tetrol
Pharmacology
ATC code	L01AX01 (WHO)
Related compounds
Related compounds	1,2-Dibromopropane 1,3-Dibromopropane 1,2,3-Tribromopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Mitobronitol (1,6-dibromo-1,6-dideoxy-D-mannitol) is a brominated analog of mannitol. It is an anticancer drug that is classified as an alkylating agent.^[2]

References

↑ "Mitolactol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 22 June 2012.
↑ Mitobronitol, The Centre for Cancer Education

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vinflunine^§ Vindesine Vinorelbine)

Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Raltitrexed Pemetrexed)

Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Thioguanine^# Mercaptopurine^#)

Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil^# Capecitabine Tegafur (+gimeracil/oteracil) Carmofur Floxuridine) DNA polymerase inhibitor (Cytarabine^#) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)

Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Camptothecin Cositecan^† Belotecan Gimatecan Exatecan Irinotecan Lurtotecan^‡ Silatecan^§ Topotecan Rubitecan^‡)

II	Podophyllum (Etoposide^# Teniposide)

II+Intercalation	Anthracyclines (Aclarubicin Daunorubicin^# Doxorubicin^# Epirubicin Idarubicin Amrubicin^† Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Mechlorethamine Cyclophosphamide^# (Ifosfamide Trofosfamide) Chlorambucil^# (Melphalan Prednimustine) Bendamustine Uramustine Estramustine Nitrosoureas: Carmustine Lomustine (Semustine) Fotemustine Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone ThioTEPA Triaziquone Triethylenemelamine

Platinum-based	Carboplatin Cisplatin Dicycloplatin Nedaplatin Oxaliplatin Satraplatin

Nonclassical	Hydrazines (Procarbazine^#) Triazenes (Dacarbazine^# Temozolomide) Altretamine Mitobronitol Pipobroman

Intercalation	Streptomyces (Actinomycin^# Bleomycin^# Mitomycin Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Alvocidib^† Seliciclib^† Palbociclib) PrI Bortezomib Carfilzomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Olaparib) HDAC (Belinostat Panobinostat Romidepsin Vorinostat) PIKI (Idelalisib)

Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)

Other/ungrouped	Amsacrine Trabectedin Retinoids (Alitretinoin Tretinoin) Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Celecoxib Demecolcine Elesclomol^§ Elsamitrucin Etoglucid Lonidamine Lucanthone Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Eribulin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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