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{{Short description|Chemical compound}} |
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{{drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 444558328 |
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| IUPAC_name = 1-(2,4-dichlorobenzyl)-1''H''-indazole-3-carboxylic acid |
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| image = Lonidamine.svg |
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<!--Clinical data--> |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 50264-69-2 |
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| ATC_prefix = L01 |
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| ATC_suffix = XX07 |
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| PubChem = 39562 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = U78804BIDR |
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| UNII = U78804BIDR |
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| ChEBI = 50138 |
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| verifiedrevid = 437201268 |
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| IUPAC_name = 1-(2,4-dichlorobenzyl)-1''H''-indazole-3-carboxylic acid |
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| ⚫ |
| image = Lonidamine.svg |
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| ⚫ |
| CAS_number = 50264-69-2 |
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| ⚫ |
| ATC_prefix = L01 |
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| ATC_suffix = XX07 |
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| PubChem = 39562 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07257 |
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| KEGG = D07257 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| C=15|H=10|Cl=2|N=2|O=2 |
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| ChemSpiderID = 36170 |
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| molecular_weight = 321.158 g/mol |
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| bioavailability = |
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<!--Chemical data--> |
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| protein_bound = |
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| metabolism = |
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| C=15 | H=10 | Cl=2 | N=2 | O=2 |
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| smiles = C1=CC=C2C(=C1)C(=NN2CC3=C(C=C(C=C3)Cl)Cl)C(=O)O |
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| elimination_half-life = |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| excretion = |
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| StdInChI = 1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21) |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| StdInChIKey = WDRYRZXSPDWGEB-UHFFFAOYSA-N |
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| pregnancy_category= |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| ⚫ |
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Lonidamine''' is a derivative of indazole-3-carboxylic acid, which for a long time, has been known to inhibit aerobic ] in cancer cells. Interestingly, it seems to enhance aerobic glycolysis in normal cells, but suppress glycolysis in cancer cells. This is most likely through the inhibition of the mitochondrially bound ]. Later studies in Ehrlich ascites tumor cells showed that lonidamine inhibits both respiration and glycolysis leading to a decrease in cellular ATP.<ref name="pmid16892078">{{cite journal |author=Pelicano H, Martin DS, Xu RH, Huang P |title=Glycolysis inhibition for anticancer treatment |journal=Oncogene |volume=25 |issue=34 |pages=4633–4646 |year=2006 |month=August |pmid=16892078 |doi= 10.1038/sj.onc.1209597|url=http://www.kosen21.org/upload_repository2/community/01230411451209597a.pdf}}</ref> |
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'''Lonidamine''' is a derivative of ], which for a long time, has been known to inhibit aerobic ] in cancer cells. It seems to enhance aerobic glycolysis in normal cells, but suppress glycolysis in cancer cells. This is most likely through the inhibition of the mitochondrially bound ]. Later studies in ] cells showed that lonidamine inhibits both respiration and glycolysis leading to a decrease in cellular ATP.<ref name="pmid16892078">{{cite journal |vauthors=Pelicano H, Martin DS, Xu RH, Huang P |title=Glycolysis inhibition for anticancer treatment |journal=Oncogene |volume=25 |issue=34 |pages=4633–4646 |date=August 2006 |pmid=16892078 |doi=10.1038/sj.onc.1209597 |doi-access=free }}</ref> |
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Clinical trials of lonidamine in combination with other anticancer agents for a variety of cancers has begun. This is due to its proven ability to inhibit energy metabolism in cancer cells, and to enhance the activity of anticancer agents.<ref name="pmid16892078" /> |
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Clinical trials of lonidamine in combination with other anticancer agents for a variety of cancers has begun. This is due to its proven ability to inhibit energy metabolism in cancer cells, and to enhance the activity of anticancer agents.<ref name="pmid16892078" /> |
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Lonidamine has been used in the treatment of brain tumours in combination with radiotherapy and temozolomide. Results showed that a combination of temozolomide and lonidamine at clinically achievable, low plasma concentrations, could inhibit tumour growth, and lonidamine could reduce the dose of temozolomide required for radiosensitization of brain tumours.<ref name="pmid19001677">{{cite journal |author=Prabhakara S, Kalia VK |title=Optimizing radiotherapy of brain tumours by a combination of temozolomide & lonidamine |journal=Indian J. Med. Res. |volume=128 |issue=2 |pages=140–8 |year=2008 |month=August |pmid=19001677 |doi= |url=http://www.icmr.nic.in/ijmr/2008/august/0808.pdf}}</ref> |
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Lonidamine has been used in the treatment of brain tumours in combination with radiotherapy and temozolomide.<ref name="pmid19001677"/> An in-vitro study showed that a combination of temozolomide and lonidamine at clinically achievable, low plasma concentrations, could inhibit tumour growth, and lonidamine could reduce the dose of temozolomide required for radiosensitization of brain tumours.<ref name="pmid19001677">{{cite journal |vauthors=Prabhakara S, Kalia VK |title=Optimizing radiotherapy of brain tumours by a combination of temozolomide & lonidamine |journal=Indian J. Med. Res. |volume=128 |issue=2 |pages=140–8 |date=August 2008 |pmid=19001677 |url=http://www.icmr.nic.in/ijmr/2008/august/0808.pdf}}</ref> |
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A derivative of lonidamine, ], is in testing as a possible male ].<ref name=Tash>{{cite journal|last=Tash|first=Joseph|title=A Novel Potent Indazole Carboxylic Acid Derivative Blocks Spermatogenesis and Is Contraceptive in Rats after a Single Oral Dose|journal=Biology of Reproduction|date=July 2008|volume=78|issue=6|pages=1127–1138|doi=10.1095/biolreprod.106.057810|pmid=18218612|doi-access=free}}</ref> |
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Male contraceptive use: "also in the works is a contraceptive nasal spray for men that combines an anti-cancer derivative, lonidamine, with an isolated hormone precursor from insect cells."<ref>http://www.slate.com/id/2245780/</ref> |
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==References== |
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==References== |