Identification

Generic Name
Anatibant
DrugBank Accession Number
DB05038
Background

Anatibant is a selective, very potent, small-molecule Bradykinin B2 receptor antagonist. It is developed for the for the treatment of traumatic brain injury (TBI).

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 711.66
Monoisotopic: 710.1844949
Chemical Formula
C34H36Cl2N6O5S
Synonyms
  • Anatibant
External IDs
  • LF16-0687MS

Pharmacology

Indication

Investigated for use/treatment in traumatic brain injuries.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Anatibant is a new potent and selective non-peptide antagonist of the bradyknin B2 receptor. Anatibant crosses the blood brain barrier, reduces brain edema formation and brain damage, and improves neurological function following experimental traumatic brain injury. The underlying mechanisms are still not well understood. So far bradykinin B2 receptor-mediated neuroprotection was mainly explained by the reduction of vascular permeability and subsequent reduction of post-ischemic or post-traumatic brain edema.

TargetActionsOrganism
UB2 bradykinin receptor
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

>97.7%

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline 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
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Quinolines and derivatives / Benzenesulfonamides / Benzamides / Benzenesulfonyl compounds / Pyrrolidinecarboxamides / Benzoyl derivatives / Dichlorobenzenes / Methylpyridines / Alkyl aryl ethers
show 13 more
Substituents
1,3-dichlorobenzene / Alkyl aryl ether / Alpha-amino acid amide / Amidine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzamide / Benzenesulfonamide
show 36 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
CLO4JRD21F
CAS number
209733-45-9
InChI Key
XUHBBTKJWIBQMY-MHZLTWQESA-N
InChI
InChI=1S/C34H36Cl2N6O5S/c1-20-18-21(2)41-31-24(20)6-3-8-28(31)47-19-25-26(35)13-14-29(30(25)36)48(45,46)42-17-4-7-27(42)34(44)40-16-5-15-39-33(43)23-11-9-22(10-12-23)32(37)38/h3,6,8-14,18,27H,4-5,7,15-17,19H2,1-2H3,(H3,37,38)(H,39,43)(H,40,44)/t27-/m0/s1
IUPAC Name
4-carbamimidoyl-N-(3-{[(2S)-1-(2,4-dichloro-3-{[(2,4-dimethylquinolin-8-yl)oxy]methyl}benzenesulfonyl)pyrrolidin-2-yl]formamido}propyl)benzamide
SMILES
CC1=CC(C)=C2C=CC=C(OCC3=C(Cl)C=CC(=C3Cl)S(=O)(=O)N3CCC[C@H]3C(=O)NCCCNC(=O)C3=CC=C(C=C3)C(N)=N)C2=N1

References

General References
  1. Kaplanski J, Pruneau D, Asa I, Artru AA, Azez A, Ivashkova Y, Rudich Z, Shapira Y: LF 16-0687 Ms, a bradykinin B2 receptor antagonist, reduces brain edema and improves long-term neurological function recovery after closed head trauma in rats. J Neurotrauma. 2002 Aug;19(8):953-64. [Article]
  2. Pruneau D, Paquet JL, Luccarini JM, Defrene E, Fouchet C, Franck RM, Loillier B, Robert C, Belichard P, Duclos H, Cremers B, Dodey P: Pharmacological profile of LF 16-0687, a new potent non-peptide bradykinin B2 receptor antagonist. Immunopharmacology. 1999 Sep;43(2-3):187-94. [Article]
PubChem Compound
9831652
PubChem Substance
175426935
ChemSpider
8007384
ChEBI
138828
ChEMBL
CHEMBL2107725
ZINC
ZINC000053261548

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.000654 mg/mLALOGPS
logP4.7ALOGPS
logP3.97ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)10.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area167.57 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity196.94 m3·mol-1ChemAxon
Polarizability73.36 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier-0.7481
Caco-2 permeable-0.6653
P-glycoprotein substrateSubstrate0.7833
P-glycoprotein inhibitor INon-inhibitor0.6492
P-glycoprotein inhibitor IIInhibitor0.6253
Renal organic cation transporterNon-inhibitor0.579
CYP450 2C9 substrateNon-substrate0.5104
CYP450 2D6 substrateNon-substrate0.774
CYP450 3A4 substrateSubstrate0.6293
CYP450 1A2 substrateNon-inhibitor0.7378
CYP450 2C9 inhibitorInhibitor0.5692
CYP450 2D6 inhibitorNon-inhibitor0.8276
CYP450 2C19 inhibitorNon-inhibitor0.5739
CYP450 3A4 inhibitorInhibitor0.8514
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8081
Ames testNon AMES toxic0.5968
CarcinogenicityNon-carcinogens0.6938
BiodegradationNot ready biodegradable0.9898
Rat acute toxicity2.5525 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9513
hERG inhibition (predictor II)Inhibitor0.6874
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

Targets

Drugtargets2
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Details
1. B2 bradykinin receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Type 1 angiotensin receptor binding
Specific Function
Receptor for bradykinin. It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system.
Gene Name
BDKRB2
Uniprot ID
P30411
Uniprot Name
B2 bradykinin receptor
Molecular Weight
44460.15 Da
References
  1. Pruneau D, Paquet JL, Luccarini JM, Defrene E, Fouchet C, Franck RM, Loillier B, Robert C, Belichard P, Duclos H, Cremers B, Dodey P: Pharmacological profile of LF 16-0687, a new potent non-peptide bradykinin B2 receptor antagonist. Immunopharmacology. 1999 Sep;43(2-3):187-94. [Article]

Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51