Mitobronitol

Mitobronitol
Names

Preferred IUPAC name 1,6-Dibromo-1,6-dideoxy-D-mannitol^{[citation needed]}
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 (JSmol)	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 CID	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
CompTox Dashboard (EPA)	DTXSID3048158 DTXSID7022918, DTXSID3048158
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	307.966 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

Chemical compound

Mitobronitol (1,6-dibromo-1,6-dideoxy-D-mannitol) is a brominated analog of mannitol. It is an anticancer drug that is also 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^# Vindesine Vinflunine^§ 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 (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine^# Tioguanine^#)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine^# Carmofur Doxifluridine Floxuridine Fluorouracil^# Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine^# +daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine^#) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide^#)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Belotecan Camptothecin Cositecan^† Etirinotecan pegol^† Exatecan Gimatecan Irinotecan^# Lurtotecan^‡ Rubitecan^‡ Silatecan^§ Topotecan)
II	Podophyllum (Etoposide^# Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin^† Daunorubicin^# (+cytarabine) Doxorubicin^# Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Losoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril^§

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Bendamustine^# Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas: Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# Mitomycins Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Abemaciclib Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Fuzuloparib) Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib Duvelisib Idelalisib Umbralisib^‡)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Elesclomol^§ Elsamitrucin Enasidenib Epacadostat Eribulin Estramustine phosphate Glasdegib Idecabtagene vicleucel Ivosidenib Lifileucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Plitidepsin Retinoids (Alitretinoin Tretinoin^#) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin