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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H36Cl2N6O5S.2CH4O3S
Molecular Weight 903.869
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANATIBANT DIMESYLATE

SMILES

CS(O)(=O)=O.CS(O)(=O)=O.CC1=NC2=C(C=CC=C2OCC3=C(Cl)C(=CC=C3Cl)S(=O)(=O)N4CCC[C@H]4C(=O)NCCCNC(=O)C5=CC=C(C=C5)C(N)=N)C(C)=C1

InChI

InChIKey=YTTYYRCGZDOABP-LPCSYZHESA-N
InChI=1S/C34H36Cl2N6O5S.2CH4O3S/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;2*1-5(2,3)4/h3,6,8-14,18,27H,4-5,7,15-17,19H2,1-2H3,(H3,37,38)(H,39,43)(H,40,44);2*1H3,(H,2,3,4)/t27-;;/m0../s1

HIDE SMILES / InChI
Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C34H36Cl2N6O5S
Molecular Weight 711.658
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Anatibant was a selective small-molecule antagonist of the bradykinin B2 receptor that was undergoing clinical development with Xytis and Fournier for the treatment of brain injuries. Anatibant reduces brain oedema in animal TBI models. Noserious toxicity was found in Phase 1 clinical trials. Following subcutaneous administration of clinically relevant doses, there were no systemic effects but there was pain, inflammation and nodule formation at the injection site. Anatibant inhibits the binding of BK to the B2 receptor. After subcutaneous injection Anatibant is bio-available and crosses the BBB.

CNS Activity

Originator

Approval Year

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Pharmacological profile of LF 16-0687, a new potent non-peptide bradykinin B2 receptor antagonist.
1999 Sep
The N-terminal of icatibant and bradykinin interact with the same Asp residues in the human B2 receptor.
2004 May 3
A single dose, three-arm, placebo-controlled, phase I study of the bradykinin B2 receptor antagonist Anatibant (LF16-0687Ms) in patients with severe traumatic brain injury.
2005 Dec
Autoradiographic analysis of mouse brain kinin B1 and B2 receptors after closed head trauma and ability of Anatibant mesylate to cross the blood-brain barrier.
2006 May
Anatibant, a selective non-peptide bradykinin B2 receptor antagonist, reduces intracranial hypertension and histopathological damage after experimental traumatic brain injury.
2009 Apr 24
Response to: The BRAIN TRIAL: a randomised, placebo controlled trial of a Bradykinin B2 receptor antagonist (Anatibant) in patients with traumatic brain injury.
2009 Dec 3
The BRAIN TRIAL: a randomised, placebo controlled trial of a Bradykinin B2 receptor antagonist (Anatibant) in patients with traumatic brain injury.
2009 Dec 3
Inhibition of bradykinin B2 receptors before, not after onset of experimental subarachnoid hemorrhage prevents brain edema formation and improves functional outcome.
2009 Jul
Patents

Patents

20070116729
157
20080220003
3

Sample Use Guides

In Vivo Use Guide
At 8-12 h after traumatic brain injury (9.9 +/- 2.8 h), patients received a single subcutaneous injection of Anatibant (3.75 mg or 22.5 mg, n = 10 each)
Route of Administration: Other
In Vitro Use Guide
Anatibant (LF 16-0687) bound to the human, rat and guinea-pig recombinant B2 receptor expressed in CHO cells giving K(i) values of 0.67 nM, 1.74 nM and 1.37 nM, respectively. It also bound to the native BK B2 receptor from human umbilical vein (HUV), rat uterus (RU) and guinea-pig ileum (GPI) giving K(i) values of 0.89 nM, 0.28 nM and 0.98 nM, respectively. It inhibited BK-induced IP1, IP2 and IP3 formation in INT407 cells yielding pK(B) values of 8.5, 8.6 and 8.7, respectively. In isolated organs experiments, LF 16-0687 behaved as a competitive antagonist of BK-mediated contractions giving pA2 values of 9.1 in HUV, 7.7 in RU and 9.1 in GPI.
Substance Class Chemical
Created
by admin
on Sat Dec 16 13:48:34 GMT 2023
Edited
by admin
on Sat Dec 16 13:48:34 GMT 2023
Record UNII
16I7ZY06ZY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANATIBANT DIMESYLATE
Common Name English
ANATIBANT DIMESILATE
Common Name English
2-PYRROLIDINECARBOXAMIDE, N-(3-((4-(AMINOIMINOMETHYL)BENZOYL)AMINO)PROPYL)-1-((2,4-DICHLORO-3-(((2,4-DIMETHYL-8-QUINOLINYL)OXY)METHYL)PHENYL)SULFONYL)-, (2S)-, METHANESULFONATE (1:2)
Systematic Name English
Code System Code Type Description
CAS
1332585-65-5
Created by admin on Sat Dec 16 13:48:34 GMT 2023 , Edited by admin on Sat Dec 16 13:48:34 GMT 2023
PRIMARY
FDA UNII
16I7ZY06ZY
Created by admin on Sat Dec 16 13:48:34 GMT 2023 , Edited by admin on Sat Dec 16 13:48:34 GMT 2023
PRIMARY
SMS_ID
100000183822
Created by admin on Sat Dec 16 13:48:34 GMT 2023 , Edited by admin on Sat Dec 16 13:48:34 GMT 2023
PRIMARY
PUBCHEM
21968583
Created by admin on Sat Dec 16 13:48:34 GMT 2023 , Edited by admin on Sat Dec 16 13:48:34 GMT 2023
PRIMARY
Related Record Type Details
Structure of ANATIBANT
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ANATIBANT
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