NAV

Geldanamycin

Identification

Generic Name
Geldanamycin
DrugBank Accession Number
DB02424
Background

Not Available

Type
Small Molecule
Groups
Experimental, Investigational
Structure
3D
Similar Structures
Weight
Average: 560.6359
Monoisotopic: 560.273380888
Chemical Formula
C29H40N2O9
Synonyms
Not Available
External IDs
  • U 29135
  • U-29135
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEndoplasmin
inhibitor
Humans
UHeat shock protein HSP 90-alphaNot AvailableHumans
UHeat shock protein HSP 90-betaNot AvailableHumans
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
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Geldanamycin.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Geldanamycin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Geldanamycin is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Geldanamycin is combined with Benzocaine.
Benzyl alcoholThe 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
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);">
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentHematological Malignancy1

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
PropertyValueSource
Water Solubility0.00634 mg/mLALOGPS
logP2.54ALOGPS
logP2.15Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)12.77Chemaxon
pKa (Strongest Basic)-3.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area163.48 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity152.68 m3·mol-1Chemaxon
Polarizability58.64 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9074
Blood Brain Barrier-0.8313
Caco-2 permeable-0.6156
P-glycoprotein substrateSubstrate0.5807
P-glycoprotein inhibitor IInhibitor0.8562
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterNon-inhibitor0.9493
CYP450 2C9 substrateNon-substrate0.8684
CYP450 2D6 substrateNon-substrate0.8444
CYP450 3A4 substrateSubstrate0.5922
CYP450 1A2 substrateNon-inhibitor0.8116
CYP450 2C9 inhibitorNon-inhibitor0.8498
CYP450 2D6 inhibitorNon-inhibitor0.8999
CYP450 2C19 inhibitorNon-inhibitor0.8016
CYP450 3A4 inhibitorNon-inhibitor0.9134
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9492
Ames testNon AMES toxic0.6172
CarcinogenicityNon-carcinogens0.9569
BiodegradationNot ready biodegradable0.7418
Rat acute toxicity2.3822 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9941
hERG inhibition (predictor II)Non-inhibitor0.9645
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-d0779111a22b8faa2b42
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03ec-5000590000-b3b34c0e9c5f0e28d239
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-0000940000-d7dee95e38cd728c6a37
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-2bcf1232f1fa7e25eceb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000120000-67db1c77b35d104f0496
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000980000-9dd7ce8e8b3dd8b2d0a6
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-229.0925109
predicted
DarkChem Lite v0.1.0
[M-H]-237.4986109
predicted
DarkChem Lite v0.1.0
[M-H]-239.84557
predicted
DeepCCS 1.0 (2019)
[M+H]+227.2435109
predicted
DarkChem Lite v0.1.0
[M+H]+236.8512109
predicted
DarkChem Lite v0.1.0
[M+H]+241.56926
predicted
DeepCCS 1.0 (2019)
[M+Na]+227.0245109
predicted
DarkChem Lite v0.1.0
[M+Na]+247.89824
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Endoplasmin
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
  1. 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]
  2. 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]
Details2. Heat 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
Details3. Heat 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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