desoxyepothilone B: microtubule-targeted antitumor agent; lacking the epoxide of epothilone B; may be equiv to epothilone D
epothilone D : An epithilone that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group.
ID Source | ID |
---|---|
PubMed CID | 447865 |
CHEMBL ID | 96172 |
CHEBI ID | 29579 |
SCHEMBL ID | 4415 |
MeSH ID | M0294240 |
Synonym |
---|
chebi:29579 , |
12,13-desoxyepothilone b, cis |
R1492 , |
CHEMBL96172 |
HY-15278 |
(4s-(4r*,8r*,9r*,13z,16r*(e)))-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)oxacyclohexadec-13-ene-2,6-dione |
nsc-703147 |
12,13-desoxy-epothilone b |
kos-862 |
(-)-desoxyepothilone b |
depob |
nsc-721085 |
biologically synthesized epothilone d |
z-12,13-desoxyepothilone b |
nsc721085 |
(-)-epothilone d |
12,13-deoxyepothilone b |
oxacyclohexadec-13-ene-2,6-dione, 4,6-dihydroxy-5,5,7,9,13-pentamethyl-16-((1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4s,7r,8s,9s,13z,16s)- |
nsc 703147 |
oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4s-(4r*,7s,8r*,9r*,13z,16r*(e)))- |
EPD , |
epothilone d |
desoxyepothilone b |
189453-10-9 |
DB01873 |
12,13-desoxyepothilone b |
kos 862 |
nsc703147 |
LMPK04000001 |
(4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione |
epothiolone d |
unii-t0358e0yuf |
epothilone b, desoxy |
kos862 |
t0358e0yuf , |
depob cpd |
epothilon d |
CS-0655 |
epo d |
AM81237 |
oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4s,7r,8s,9s,13z,16s)- |
SCHEMBL4415 |
oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (4s,7r,8s,9s,13z,16s)- |
epothilone d [who-dd] |
epothilone d [mi] |
(4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(e)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]-1-oxacyclohexadec-13-ene-2,6-dione |
XOZIUKBZLSUILX-GIQCAXHBSA-N |
(4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]oxacyclohexadec-13-ene-2,6-dione |
(4s,7r,8s,9s,16s,z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((e)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadec-13-ene-2,6-dione |
AC-22616 |
AKOS025401598 |
EX-A495 |
(4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1e)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-oxacyclohexadec-13-ene-2,6-dione |
mfcd27976357 |
(4s,7r,8s,9s,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione |
DTXSID70880053 |
epothilone-d |
desoxyepothilone b; (3s,7s,14s,15s,16r)-3,15-dihydroxy-2,2,10,14,16-pentamethyl-7-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-6-oxacyclohexadec-9-ene-1,5-dione |
A880448 |
Role | Description |
---|---|
microtubule-stabilising agent | Any substance that interacts with tubulin to promote polymerisation of microtubules. |
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Class | Description |
---|---|
epothilone | Any member of the class of 16-membered macrolide natural products, or their analogues, normally containing a double bond or its epoxide at positions 12-13 and bearing hydroxy groups at positions 4 and 8, methyl groups at positions 5, 5, 7, and 9, an oxo group at position 6, and a 1-(2-substituted-1,3-thiazol-4-yl)prop-1-en-2-yl substituent at position 15. |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
PPM1D protein | Homo sapiens (human) | Potency | 0.0131 | 0.0052 | 9.4661 | 32.9993 | AID1347411 |
Interferon beta | Homo sapiens (human) | Potency | 0.0131 | 0.0033 | 9.1582 | 39.8107 | AID1347411 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Process | via Protein(s) | Taxonomy |
---|---|---|
cytokine activity | Interferon beta | Homo sapiens (human) |
cytokine receptor binding | Interferon beta | Homo sapiens (human) |
type I interferon receptor binding | Interferon beta | Homo sapiens (human) |
protein binding | Interferon beta | Homo sapiens (human) |
chloramphenicol O-acetyltransferase activity | Interferon beta | Homo sapiens (human) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Process | via Protein(s) | Taxonomy |
---|---|---|
extracellular space | Interferon beta | Homo sapiens (human) |
extracellular region | Interferon beta | Homo sapiens (human) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1347412 | qHTS assay to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: Counter screen cell viability and HiBit confirmation | 2020 | ACS chemical biology, 07-17, Volume: 15, Issue:7 | High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle. |
AID1347414 | qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: Secondary screen by immunofluorescence | 2020 | ACS chemical biology, 07-17, Volume: 15, Issue:7 | High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle. |
AID1347411 | qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary | 2020 | ACS chemical biology, 07-17, Volume: 15, Issue:7 | High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle. |
AID772394 | Stabilization of microtubule in HEK293 cells assessed as increase in acetylated alpha-tubulin at 100 nM after 4 hrs by ELISA | 2013 | ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9 | MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications. |
AID361147 | Cytotoxicity against camptothecin-resistant human CCRF-CEM cells after 3 days by SRB assay | 2002 | Journal of natural products, Jul, Volume: 65, Issue:7 | A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. |
AID356491 | Cytotoxicity against human NCI/ADR cells after 3 days by SRB assay | 2003 | Journal of natural products, Oct, Volume: 66, Issue:10 | Isolation and characterization of new epothilone analogues from recombinant Myxococcus xanthus fermentations. |
AID771385 | Cytotoxicity against human MCF7 cells after 72 hrs | 2013 | European journal of medicinal chemistry, Oct, Volume: 68 | Epothilone D and its 9-Methyl analogues: combinatorial syntheses, conformation, and biological activities. |
AID361142 | Cytotoxicity against human SF268 cells after 3 days by SRB assay | 2002 | Journal of natural products, Jul, Volume: 65, Issue:7 | A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. |
AID361144 | Cytotoxicity against human HL60 cells after 3 days by SRB assay | 2002 | Journal of natural products, Jul, Volume: 65, Issue:7 | A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. |
AID159565 | Induction of polymerization of porcine brain-derived microtubule protein by 2 uM epothilone B | 2000 | Bioorganic & medicinal chemistry letters, Dec-18, Volume: 10, Issue:24 | Synthesis and biological evaluation of highly potent analogues of epothilones B and D. |
AID94006 | Concentration required to inhibit the growth of paclitaxel-sensitive human epidermoid carcinoma cells KB-31 by 50 percent (72 hr exposure) | 2000 | Bioorganic & medicinal chemistry letters, Dec-18, Volume: 10, Issue:24 | Synthesis and biological evaluation of highly potent analogues of epothilones B and D. |
AID361145 | Cytotoxicity against mitoxantrone-resistant human HL60 cells after 3 days by SRB assay | 2002 | Journal of natural products, Jul, Volume: 65, Issue:7 | A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. |
AID771383 | Inhibition of tubulin polymerization (unknown origin) at 5 uM | 2013 | European journal of medicinal chemistry, Oct, Volume: 68 | Epothilone D and its 9-Methyl analogues: combinatorial syntheses, conformation, and biological activities. |
AID772388 | Plasma concentration in CD1 mouse at 5 mg/kg, ip administered as single dose at 16 hrs | 2013 | ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9 | MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications. |
AID356493 | Cytotoxicity against human NCI-H460 cells after 3 days by SRB assay | 2003 | Journal of natural products, Oct, Volume: 66, Issue:10 | Isolation and characterization of new epothilone analogues from recombinant Myxococcus xanthus fermentations. |
AID1182022 | Inhibition of human P-glycoprotein expressed in NCI/ADR-RES cells assessed as reduction of calcein-AM transport after 20 mins by fluorescence assay | 2014 | Journal of medicinal chemistry, Jul-24, Volume: 57, Issue:14 | Brain-penetrant, orally bioavailable microtubule-stabilizing small molecules are potential candidate therapeutics for Alzheimer's disease and related tauopathies. |
AID361141 | Cytotoxicity against human NCI/ADR-RES cells after 3 days by SRB assay | 2002 | Journal of natural products, Jul, Volume: 65, Issue:7 | A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. |
AID361140 | Cytotoxicity against human MCF7 cells after 3 days by SRB assay | 2002 | Journal of natural products, Jul, Volume: 65, Issue:7 | A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. |
AID159417 | Concentrations required to induce 50 percent polymerization of porcine brain-derived micro-tubule protein | 2000 | Bioorganic & medicinal chemistry letters, Dec-18, Volume: 10, Issue:24 | Synthesis and biological evaluation of highly potent analogues of epothilones B and D. |
AID361143 | Cytotoxicity against human NCI-H460 cells after 3 days by SRB assay | 2002 | Journal of natural products, Jul, Volume: 65, Issue:7 | A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. |
AID361146 | Cytotoxicity against human CCRF-CEM cells after 3 days by SRB assay | 2002 | Journal of natural products, Jul, Volume: 65, Issue:7 | A new cytotoxic epothilone from modified polyketide synthases heterologously expressed in Myxococcus xanthus. |
AID1182021 | Induction of microtubule stabilization in human QBI293 cells assessed as increase in acetylated alpha-tubulin at 100 nM after 4 hrs by immunofluorescence assay relative to control | 2014 | Journal of medicinal chemistry, Jul-24, Volume: 57, Issue:14 | Brain-penetrant, orally bioavailable microtubule-stabilizing small molecules are potential candidate therapeutics for Alzheimer's disease and related tauopathies. |
AID356712 | Cytotoxicity against mouse L929 cells | 2001 | Journal of natural products, Jul, Volume: 64, Issue:7 | New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies. |
AID772387 | Drug uptake in CD1 mouse brain at 5 mg/kg, ip administered as single dose at 16 hrs | 2013 | ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9 | MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications. |
AID356490 | Cytotoxicity against human MCF7 cells after 3 days by SRB assay | 2003 | Journal of natural products, Oct, Volume: 66, Issue:10 | Isolation and characterization of new epothilone analogues from recombinant Myxococcus xanthus fermentations. |
AID772391 | Plasma concentration in CD1 mouse at 5 mg/kg, ip administered as single dose at 4 hrs | 2013 | ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9 | MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications. |
AID356492 | Cytotoxicity against human SF268 cells after 3 days by SRB assay | 2003 | Journal of natural products, Oct, Volume: 66, Issue:10 | Isolation and characterization of new epothilone analogues from recombinant Myxococcus xanthus fermentations. |
AID772395 | Stabilization of microtubule in HEK293 cells assessed as increase in acetylated alpha-tubulin after 4 hrs by ELISA | 2013 | ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9 | MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications. |
AID772386 | Drug uptake in CD1 mouse brain at 5 mg/kg, ip administered as single dose at 4 hrs | 2013 | ACS medicinal chemistry letters, Sep-12, Volume: 4, Issue:9 | MT-Stabilizer, Dictyostatin, Exhibits Prolonged Brain Retention and Activity: Potential Therapeutic Implications. |
AID94043 | Concentration required to inhibit the growth of paclitaxel-resistant human epidermoid carcinoma cells KB-8511 by 50 percent (72 hr exposure) | 2000 | Bioorganic & medicinal chemistry letters, Dec-18, Volume: 10, Issue:24 | Synthesis and biological evaluation of highly potent analogues of epothilones B and D. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 2 (2.04) | 18.2507 |
2000's | 52 (53.06) | 29.6817 |
2010's | 35 (35.71) | 24.3611 |
2020's | 9 (9.18) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 3 (3.03%) | 5.53% |
Reviews | 15 (15.15%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 81 (81.82%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Trial | Phase | Enrollment | Study Type | Start Date | Status | ||
---|---|---|---|---|---|---|---|
An Open-label Study to Evaluate the Effect of Combination Therapy With Epothilone D and Herceptin on Tumor Response in Patients With HER-2 Overexpressing Locally Advanced or Metastatic Breast Cancer[NCT00337649] | Phase 1/Phase 2 | 27 participants (Actual) | Interventional | 2004-05-31 | Completed | ||
A Phase II Study Of KOS-862 (Epothilone D), Administered Intravenously Weekly For 3 Weeks Every 4 Weeks, In The Second-Line Treatment Of Patients With Advanced Or Metastatic Colorectal Carcinoma (CRC)[NCT00077259] | Phase 2 | 0 participants | Interventional | 2003-10-31 | Completed | ||
A Phase 2 Study of KOS-862 Administered Intravenously Weekly for 3 Weeks Every 4 Weeks, in Patients With Hormone Resistant Prostate Cancer Who Have Progressed Following Initial Therapy for Metastatic Disease[NCT00104130] | Phase 2 | 53 participants | Interventional | 2004-12-31 | Terminated | ||
A Phase II Study of KOS-862, Administered Intravenously Weekly for 3 Weeks Every 4 Weeks, in Patients With Non-Small Cell Lung Cancer Who Have Progressed Following Initial Therapy for Advanced or Metastatic Disease[NCT00081107] | Phase 2 | 0 participants | Interventional | 2003-12-31 | Completed | ||
A Phase 2 Study of KOS-862, Administered Intravenously Weekly for 3 Weeks Every 4 Weeks, in Patients With Non-Small Cell Lung Cancer Who Have Progressed Following Initial Therapy for Advanced or Metastatic Disease[NCT00080509] | Phase 2 | 85 participants | Interventional | 2003-12-31 | Terminated | ||
A Phase 1, Dose Escalation Trial to Evaluate the Safety, Pharmacokinetics, and Pharmacodynamics of Epothilone D in Patients With Advanced Solid Tumors[NCT00030173] | Phase 1 | 45 participants | Interventional | 2001-10-31 | Completed | ||
[information is prepared from clinicaltrials.gov, extracted Sep-2024] |
Article | Year |
---|---|
The microtubule-stabilizing agent, epothilone D, reduces axonal dysfunction, neurotoxicity, cognitive deficits, and Alzheimer-like pathology in an interventional study with aged tau transgenic mice. The Journal of neuroscience : the official journal of the Society for Neuroscience, Mar-14, Volume: 32, Issue: 11 | 2012 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Article | Year |
---|---|
Phase I clinical, pharmacokinetic, and pharmacodynamic study of KOS-862 (Epothilone D) in patients with advanced solid tumors and lymphoma. Investigational new drugs, Volume: 30, Issue: 6 | 2012 |
Simultaneous determination of epothilone D and its hydrolytic metabolite in human plasma by high performance liquid chromatography-tandem mass spectrometry for pharmacokinetic studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, Nov-01, Volume: 877, Issue: 29 | 2009 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Article | Year |
---|---|
Brain-penetrant, orally bioavailable microtubule-stabilizing small molecules are potential candidate therapeutics for Alzheimer's disease and related tauopathies. Journal of medicinal chemistry, Jul-24, Volume: 57, Issue: 14 | 2014 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Article | Year |
---|---|
Epothilone D alters normal growth, viability and microtubule dependent intracellular functions of cortical neurons in vitro. Scientific reports, 01-22, Volume: 10, Issue: 1 | 2020 |
Brain-penetrant microtubule-stabilizing compounds as potential therapeutic agents for tauopathies. Biochemical Society transactions, Volume: 40, Issue: 4 | 2012 |
Epothilone D affects cell cycle and microtubular pattern in plant cells. Journal of experimental botany, Volume: 56, Issue: 418 | 2005 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |