Geldanamycin
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Identification
- Generic Name
- Geldanamycin
- DrugBank Accession Number
- DB02424
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
- Weight
- Average: 560.6359
Monoisotopic: 560.273380888 - Chemical Formula
- C29H40N2O9
- Synonyms
- Not Available
- External IDs
- U 29135
- U-29135
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UEndoplasmin inhibitorHumans UHeat shock protein HSP 90-alpha Not Available Humans UHeat shock protein HSP 90-beta Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetaminophen The serum concentration of Acetaminophen can be increased when it is combined with Geldanamycin. Ambroxol The risk or severity of methemoglobinemia can be increased when Geldanamycin is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Geldanamycin is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Geldanamycin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Geldanamycin is combined with Benzyl alcohol. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Macrolactams
- Sub Class
- Not Available
- Direct Parent
- Macrolactams
- Alternative Parents
- Vinylogous esters / Vinylogous amides / Carbamate esters / Secondary carboxylic acid amides / Secondary alcohols / Organic carbonic acids and derivatives / Lactams / Cyclic ketones / Dialkyl ethers / Azacyclic compounds show 4 more
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Azacycle / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cyclic ketone / Dialkyl ether show 16 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- lactam, macrocycle, benzoquinones (CHEBI:5292) / Ansamycins (C11222)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Z3K3VJ16KU
- CAS number
- 30562-34-6
- InChI Key
- QTQAWLPCGQOSGP-KSRBKZBZSA-N
- InChI
- InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1
- IUPAC Name
- (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate
- SMILES
- CO[C@H]1C[C@H](C)CC2=C(OC)C(=O)C=C(NC(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@H]1O)C2=O
References
- Synthesis Reference
Richard Hutchinson, "Recombinant polynucleotides encoding pro-geldanamycin producing polyketide synthase and accessory proteins, and uses thereof." U.S. Patent US20040077058, issued April 22, 2004.
US20040077058- General References
- Not Available
- External Links
- KEGG Compound
- C11222
- PubChem Compound
- 5288382
- PubChem Substance
- 46505674
- ChemSpider
- 10272739
- BindingDB
- 50008059
- ChEBI
- 5292
- ChEMBL
- CHEMBL278315
- ZINC
- ZINC000100064834
- Therapeutic Targets Database
- DCL000325
- PharmGKB
- PA152031327
- PDBe Ligand
- GDM
- Wikipedia
- Geldanamycin
- PDB Entries
- 1a4h / 1yet / 2esa / 2exl / 2weq / 2yga / 2yge / 2ygf / 3c11 / 4xdm
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 1 Terminated Treatment Hematological Malignancy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00634 mg/mL ALOGPS logP 2.54 ALOGPS logP 2.15 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 12.77 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 163.48 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 152.68 m3·mol-1 Chemaxon Polarizability 58.64 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9074 Blood Brain Barrier - 0.8313 Caco-2 permeable - 0.6156 P-glycoprotein substrate Substrate 0.5807 P-glycoprotein inhibitor I Inhibitor 0.8562 P-glycoprotein inhibitor II Inhibitor 0.8387 Renal organic cation transporter Non-inhibitor 0.9493 CYP450 2C9 substrate Non-substrate 0.8684 CYP450 2D6 substrate Non-substrate 0.8444 CYP450 3A4 substrate Substrate 0.5922 CYP450 1A2 substrate Non-inhibitor 0.8116 CYP450 2C9 inhibitor Non-inhibitor 0.8498 CYP450 2D6 inhibitor Non-inhibitor 0.8999 CYP450 2C19 inhibitor Non-inhibitor 0.8016 CYP450 3A4 inhibitor Non-inhibitor 0.9134 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9492 Ames test Non AMES toxic 0.6172 Carcinogenicity Non-carcinogens 0.9569 Biodegradation Not ready biodegradable 0.7418 Rat acute toxicity 2.3822 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9941 hERG inhibition (predictor II) Non-inhibitor 0.9645
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 229.0925109 predictedDarkChem Lite v0.1.0 [M-H]- 237.4986109 predictedDarkChem Lite v0.1.0 [M-H]- 239.84557 predictedDeepCCS 1.0 (2019) [M+H]+ 227.2435109 predictedDarkChem Lite v0.1.0 [M+H]+ 236.8512109 predictedDarkChem Lite v0.1.0 [M+H]+ 241.56926 predictedDeepCCS 1.0 (2019) [M+Na]+ 227.0245109 predictedDarkChem Lite v0.1.0 [M+Na]+ 247.89824 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
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1. DetailsEndoplasmin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Virion binding
- Specific Function
- Molecular chaperone that functions in the processing and transport of secreted proteins. When associated with CNPY3, required for proper folding of Toll-like receptors (By similarity). Functions in...
- Gene Name
- HSP90B1
- Uniprot ID
- P14625
- Uniprot Name
- Endoplasmin
- Molecular Weight
- 92468.06 Da
References
- Grenert JP, Sullivan WP, Fadden P, Haystead TA, Clark J, Mimnaugh E, Krutzsch H, Ochel HJ, Schulte TW, Sausville E, Neckers LM, Toft DO: The amino-terminal domain of heat shock protein 90 (hsp90) that binds geldanamycin is an ATP/ADP switch domain that regulates hsp90 conformation. J Biol Chem. 1997 Sep 19;272(38):23843-50. [Article]
- Carreras CW, Schirmer A, Zhong Z, Santi DV: Filter binding assay for the geldanamycin-heat shock protein 90 interaction. Anal Biochem. 2003 Jun 1;317(1):40-6. [Article]
2. DetailsHeat shock protein HSP 90-alpha
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tpr domain binding
- Specific Function
- Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
- Gene Name
- HSP90AA1
- Uniprot ID
- P07900
- Uniprot Name
- Heat shock protein HSP 90-alpha
- Molecular Weight
- 84659.015 Da
References
3. DetailsHeat shock protein HSP 90-beta
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Utp binding
- Specific Function
- Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
- Gene Name
- HSP90AB1
- Uniprot ID
- P08238
- Uniprot Name
- Heat shock protein HSP 90-beta
- Molecular Weight
- 83263.475 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:16