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Identification
NameBatimastat
Accession NumberDB03880  (EXPT00627)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers
  • BB-94
  • BB94
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIBK349F52C9
CAS number130370-60-4
WeightAverage: 477.64
Monoisotopic: 477.175597875
Chemical FormulaC23H31N3O4S2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Phenylpropylamine
  • Amphetamine or derivatives
  • Alkylarylthioether
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Thiophene
  • Secondary carboxylic acid amide
  • Hydroxamic acid
  • Carboxamide group
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsAn anticancer drug that belongs to the family of drugs called angiogenesis inhibitors. Batimastat is a matrix metalloproteinase inhibitor.
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Batimastat.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Batimastat.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Batimastat.
AlprazolamThe serum concentration of Alprazolam can be increased 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.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Batimastat.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Batimastat.
BevacizumabBevacizumab may increase the cardiotoxic activities of Batimastat.
BoceprevirThe serum concentration of Batimastat can be decreased when it is combined with Boceprevir.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Batimastat.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Batimastat.
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Batimastat.
CarbamazepineThe metabolism of Batimastat can be increased when combined with Carbamazepine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Batimastat.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Batimastat.
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Batimastat.
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be increased when it is combined with Batimastat.
CyclophosphamideThe risk or severity of adverse effects can be increased when Batimastat is combined with Cyclophosphamide.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Batimastat.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Batimastat.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Batimastat.
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Batimastat.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Batimastat.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Batimastat.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Batimastat.
DigoxinDigoxin may decrease the cardiotoxic activities of Batimastat.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Batimastat.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Batimastat.
DosulepinThe serum concentration of Dosulepin can be increased when it is combined with Batimastat.
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Batimastat.
DyphyllineThe serum concentration of Dyphylline can be decreased when it is combined with Batimastat.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Batimastat.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Batimastat.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Batimastat.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Batimastat.
EsmirtazapineThe serum concentration of Esmirtazapine can be increased when it is combined with Batimastat.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Batimastat.
GarlicThe serum concentration of Batimastat can be decreased when it is combined with Garlic.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Batimastat.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Batimastat.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Batimastat.
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Batimastat.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Batimastat.
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Batimastat.
OuabainOuabain may decrease the cardiotoxic activities of Batimastat.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Batimastat.
PethidineThe risk or severity of adverse effects can be increased when Batimastat is combined with Pethidine.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Batimastat.
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Batimastat.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Batimastat.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Batimastat.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Batimastat.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Batimastat.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Batimastat.
St. John's WortThe metabolism of Batimastat can be increased when combined with St. John's Wort.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Batimastat.
TemsirolimusThe risk or severity of adverse effects can be increased when Batimastat is combined with Temsirolimus.
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Batimastat.
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Batimastat.
TipranavirThe serum concentration of Batimastat can be decreased when it is combined with Tipranavir.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Batimastat.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Batimastat.
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Batimastat.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Batimastat.
Food InteractionsNot 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
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 hydrophobic residues are preferred at the P1 site, with small hydrophobic residues (preferably alanine) occupying P3.
Gene Name:
MMP12
Uniprot ID:
P39900
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. Isoform short cleaves fibronectin and also collagen type III, but at lower rate. It has no effect on type I, II, IV and V collagen. However, upon interaction with CSPG4, it may be involved in degrada...
Gene Name:
MMP16
Uniprot ID:
P51512
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. May be involved in sperm maturation.
Gene Name:
ADAM28
Uniprot ID:
Q9UKQ2
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 processing mostly during the peri-implantation period.
Gene Name:
ADAMTS5
Uniprot ID:
Q9UNA0
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23