Mitobronitol: Difference between revisions

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	{{~~Drugbox~~		{{Chembox
		⚫	\| ImageFile = Mitobronitol.png
	\| Verifiedfields = changed
		⚫	\| ImageFile_Ref = {{chemboximage\|correct\|??}}
	\| Watchedfields = changed
			\| ImageSize = 160
	\| verifiedrevid = 408763068
			\| ImageName = Stereo, skeletal formula of mitobronitol (2S,3S,4S,5S)-2,3,4,5-tetrol
	\| ~~IUPAC_name~~ = 1,6-~~dibromo~~-1,6-dideoxy-<small>D</small>-mannitol		\| PIN = 1,6-Dibromo-1,6-dideoxy-<small>D</small>-mannitol{{Citation needed\|date=June 2012}}
⚫	\| ~~image~~ = Mitobronitol.png
			\| SystematicName = 1,6-Dibromohexane-2,3,4,5-tetrol<ref>{{Cite web\|title=Mitolactol - Compound Summary\|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4208&loc=ec_rcs\|work=PubChem Compound\|publisher=National Center for Biotechnology Information\|access-date=22 June 2012\|location=USA\|date=25 March 2005\|at=Identification}}</ref>

			\|Section1={{Chembox Identifiers
	<!--Clinical data-->
	\| ~~tradename~~ =		\| CASNo = 488-41-5
			\| CASNo_Ref = {{cascite\|correct\|??}}
	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
			\| CASNo_Comment = <small>(2''S'',3''S'',4''S'',5''S'')-2,3,4,5-tetrol</small>
	\| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	\| PubChem = 4208
	\| pregnancy_category =
			\| PubChem1 = 44119013
	\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
			\| PubChem1_Comment = <small>(2''R'',3''R'')-2,3-diol</small>
	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
			\| PubChem2 = 6713087
	\| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
			\| PubChem2_Comment = <small>(2''S'',3''S'',5''R'')-2,3,5-triol</small>
	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
	\| ~~legal_status~~ =		\| PubChem3 = 2794952
			\| PubChem3_Comment = <small>(2''R'',3''R'',4''R'',5''R'')-2,3,4,5-tetrol</small>
	\| routes_of_administration =
			\| PubChem4 = 656655

			\| PubChem4_Comment = <small>(2''S'',3''S'',4''S'',5''S'')-2,3,4,5-tetrol</small>
	<!--Pharmacokinetic data-->
	\| ~~bioavailability~~ =		\| ChemSpiderID = 4063
	\| protein_bound =
	\| metabolism =
	\| elimination_half-life =
	\| excretion =

	<!--Identifiers-->
⚫	\| ~~CAS_number_Ref~~ = {{~~cascite~~\|correct\|??}}
	\| CAS_number = 488-41-5
	\| ATC_prefix = L01
	\| ATC_suffix = AX01
⚫	\| PubChem = ~~656655~~
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank =
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID1 = 5145112
	\| ChemSpiderID = 571004
			\| ChemSpiderID1_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| UNII_Ref = {{fdacite\|~~changed~~\|FDA}}
			\| ChemSpiderID1_Comment = <small>(2''S'',3''S'',5''R'')-2,3,5-triol</small>
			\| ChemSpiderID2 = 5145112
			\| ChemSpiderID2_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID2_Comment = <small>(2''R'',3''R'',4''R'',5''R'')-2,3,4,5-tetrol</small>
	\| UNII = 5UP30YED7N		\| UNII = 5UP30YED7N
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| EINECS = 207-676-8
		⚫	\| KEGG = D02020
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
			\| MeSHName = Mitobronitol
⚫	\| KEGG = D02020
			\| ChEMBL = 161657
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ~~ChEMBL~~ = 447629		\| ChEMBL1 = 447629
			\| ChEMBL1_Ref = {{ebicite\|correct\|EBI}}

			\| RTECS = OP2800000 <small>(2''RS'',3''RS'',4''RS'',5''RS'')-2,3,4,5-tetrol</small>
	<!--Chemical data-->
		⚫	\| SMILES = OC(CBr)C(O)C(O)C(O)CBr
⚫	\| C=6 \| H=12 \| Br=2 \| O=4
		⚫	\| StdInChI = 1S/C6H12Br2O4/c7-1-3(9)5(11)6(12)4(10)2-8/h3-6,9-12H,1-2H2
	\| molecular_weight = 307.97 g/mol
⚫	\| ~~smiles~~ = ~~BrC~~(O)(O)(O)(O)CBr
	\| InChI = 1/C6H12Br2O4/c7-1-3(9)5(11)6(12)4(10)2-8/h3-6,9-12H,1-2H2/t3-,4-,5-,6-/m1/s1
⚫	\| ~~InChIKey~~ = VFKZTMPDYBFSTM-~~KVTDHHQDBB~~
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
		⚫	\| StdInChIKey = VFKZTMPDYBFSTM-UHFFFAOYSA-N
⚫	\| StdInChI = 1S/C6H12Br2O4/c7-1-3(9)5(11)6(12)4(10)2-8/h3-6,9-12H,1-2H2~~/t3-,4-,5-,6-/m1/s1~~
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = VFKZTMPDYBFSTM-KVTDHHQDSA-N
	}}		}}
			\|Section2={{Chembox Properties
⚫	'''Mitobronitol''' (1,6-dibromo-1,6-dideoxy-<small>D</small>-mannitol) is a brominated analog of ]. It is an anticancer drug that is classified as an ].<ref>, The Centre for Cancer Education</ref>
		⚫	\| C=6 \| H=12 \| Br=2 \| O=4
			\| Appearance = Colourless crystals
			\| pKa = 12.609 <small>(2''RS'',3''RS'',4''RS'',5''RS'')-2,3,4,5-tetrol</small>
			\| pKb = 1.388 <small>(2''RS'',3''RS'',4''RS'',5''RS'')-2,3,4,5-tetrol</small>
			\| LogP = −0.226 <small>(2''RS'',3''RS'',4''RS'',5''RS'')-2,3,4,5-tetrol</small>
			}}
			\|Section6={{Chembox Pharmacology
			\| ATCCode_prefix = L01
			\| ATCCode_suffix = AX01
			}}
			\|Section8={{Chembox Related
			\| OtherCompounds = {{Unbulleted list\|]\|]\|]}}
			}}
			}}
		⚫	'''Mitobronitol''' ('''1,6-dibromo-1,6-dideoxy-<small>D</small>-mannitol''') is a brominated analog of ]. It is an anticancer drug that is also classified as an ].<ref>, The Centre for Cancer Education</ref>

	==References==		==References==
	{{~~reflist~~}}		{{Reflist}}

	{{Intracellular chemotherapeutic agents}}		{{Intracellular chemotherapeutic agents}}

			]
	]		]
	]		]
	]		]
			]

		⚫	{{Antineoplastic-drug-stub}}

⚫	{{~~antineoplastic~~-drug-stub}}

Latest revision as of 21:33, 5 January 2024

Mitobronitol
Names

Preferred IUPAC name 1,6-Dibromo-1,6-dideoxy-D-mannitol
Systematic IUPAC name 1,6-Dibromohexane-2,3,4,5-tetrol
Identifiers
CAS Number	488-41-5 (2S,3S,4S,5S)-2,3,4,5-tetrol
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL161657 ChEMBL447629
ChemSpider	4063 5145112 (2S,3S,5R)-2,3,5-triol 5145112 (2R,3R,4R,5R)-2,3,4,5-tetrol
ECHA InfoCard	100.006.979
EC Number	207-676-8
KEGG	D02020
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
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,1-2H2Key: VFKZTMPDYBFSTM-UHFFFAOYSA-N
SMILES OC(CBr)C(O)C(O)C(O)CBr
Properties
Chemical formula	C₆H₁₂Br₂O₄
Molar mass	307.966 g·mol
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 , 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.

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 Rabacfosadine 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 (Losoxantrone Mitoxantrone 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 Inavolisib Umbralisib) IDH (Enasidenib Ivosidenib Olutasidenib Vorasidenib)
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 Eflornithine Elesclomol Elsamitrucin Epacadostat Eribulin Estramustine Glasdegib Idecabtagene vicleucel Imetelstat Lifileucel Lisocabtagene maraleucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Nadofaragene firadenovec Navitoclax Obecabtagene autoleucel Oblimersen Omacetaxine mepesuccinate Plitidepsin Tabelecleucel Retinoids (Alitretinoin Tretinoin) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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