Batimastat

Identification

Name
Batimastat
Accession Number
DB03880  (EXPT00627)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
BB-94 / BB94
Categories
UNII
BK349F52C9
CAS number
130370-60-4
Weight
Average: 477.64
Monoisotopic: 477.175597875
Chemical Formula
C23H31N3O4S2
InChI Key
XFILPEOLDIKJHX-QYZOEREBSA-N
InChI
InChI=1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1
IUPAC Name
(2R,3S)-N'-hydroxy-N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]-2-(2-methylpropyl)-3-[(thiophen-2-ylsulfanyl)methyl]butanediamide
SMILES
[H][C@@](CC1=CC=CC=C1)(NC(=O)[C@]([H])(CC(C)C)[C@]([H])(CSC1=CC=CS1)C(=O)NO)C(=O)NC

Pharmacology

Indication
Not Available
Pharmacodynamics

An anticancer drug that belongs to the family of drugs called angiogenesis inhibitors. Batimastat is a matrix metalloproteinase inhibitor.

Mechanism of action
TargetActionsOrganism
UNeutrophil collagenaseNot AvailableHuman
UMacrophage metalloelastaseNot AvailableHuman
UMatrix metalloproteinase-16Not AvailableHuman
UDisintegrin and metalloproteinase domain-containing protein 28Not AvailableHuman
UA disintegrin and metalloproteinase with thrombospondin motifs 5Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Batimastat.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Batimastat.
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Batimastat.
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be decreased when it is combined with Batimastat.
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Batimastat.
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Batimastat.
AmitriptylinoxideThe serum concentration of Amitriptylinoxide can be increased when it is combined with Batimastat.
AmoxapineThe serum concentration of Amoxapine can be increased when it is combined with Batimastat.
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Batimastat.
BoceprevirThe serum concentration of Batimastat can be decreased when it is combined with Boceprevir.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D03061
PubChem Compound
5362422
PubChem Substance
46505727
ChemSpider
4515033
BindingDB
50063918
ChEMBL
CHEMBL279786
Therapeutic Targets Database
DNC000274
HET
BAT
Wikipedia
Batimastat
PDB Entries
1dth / 1jk3 / 1mmb / 1rm8 / 2j83 / 2rjq / 4dd8

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.00173 mg/mLALOGPS
logP3.23ALOGPS
logP3.27ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)8.86ChemAxon
pKa (Strongest Basic)-0.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.53 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity127.3 m3·mol-1ChemAxon
Polarizability49.79 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6139
Blood Brain Barrier-0.5657
Caco-2 permeable-0.6506
P-glycoprotein substrateSubstrate0.6881
P-glycoprotein inhibitor INon-inhibitor0.8205
P-glycoprotein inhibitor IINon-inhibitor0.7536
Renal organic cation transporterNon-inhibitor0.9377
CYP450 2C9 substrateNon-substrate0.7476
CYP450 2D6 substrateNon-substrate0.7916
CYP450 3A4 substrateSubstrate0.5052
CYP450 1A2 substrateNon-inhibitor0.7714
CYP450 2C9 inhibitorNon-inhibitor0.7265
CYP450 2D6 inhibitorNon-inhibitor0.8469
CYP450 2C19 inhibitorNon-inhibitor0.6135
CYP450 3A4 inhibitorInhibitor0.7339
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8746
Ames testNon AMES toxic0.5887
CarcinogenicityNon-carcinogens0.7752
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.5464 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9988
hERG inhibition (predictor II)Non-inhibitor0.8582
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Phenylalanine and derivatives
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Alkylarylthioethers / N-acyl amines / Thiophenes / Heteroaromatic compounds / Secondary carboxylic acid amides / Hydroxamic acids / Sulfenyl compounds
show 5 more
Substituents
Phenylalanine or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Amphetamine or derivatives / Aryl thioether / Alkylarylthioether / Monocyclic benzene moiety / Fatty amide / N-acyl-amine / Fatty acyl
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Can degrade fibrillar type I, II, and III collagens.
Gene Name
MMP8
Uniprot ID
P22894
Uniprot Name
Neutrophil collagenase
Molecular Weight
53411.72 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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
May be involved in tissue injury and remodeling. Has significant elastolytic activity. Can accept large and small amino acids at the P1' site, but has a preference for leucine. Aromatic or hydropho...
Gene Name
MMP12
Uniprot ID
P39900
Uniprot Name
Macrophage metalloelastase
Molecular Weight
54001.175 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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Endopeptidase that degrades various components of the extracellular matrix, such as collagen type III and fibronectin. Activates progelatinase A. Involved in the matrix remodeling of blood vessels....
Gene Name
MMP16
Uniprot ID
P51512
Uniprot Name
Matrix metalloproteinase-16
Molecular Weight
69521.03 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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
May play a role in the adhesive and proteolytic events that occur during lymphocyte emigration or may function in ectodomain shedding of lymphocyte surface target proteins, such as FASL and CD40L. ...
Gene Name
ADAM28
Uniprot ID
Q9UKQ2
Uniprot Name
Disintegrin and metalloproteinase domain-containing protein 28
Molecular Weight
87147.04 Da
References
  1. 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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Cleaves aggrecan, a cartilage proteoglycan, and may be involved in its turnover. May play an important role in the destruction of aggrecan in arthritic diseases. May play a role in proteolytic proc...
Gene Name
ADAMTS5
Uniprot ID
Q9UNA0
Uniprot Name
A disintegrin and metalloproteinase with thrombospondin motifs 5
Molecular Weight
101716.955 Da
References
  1. 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 05:13