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Details

Stereochemistry ACHIRAL
Molecular Formula C33H31Cl2F3N6O3S2
Molecular Weight 751.669
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CB1-IN-1

SMILES

FC(F)(F)C1=CC=C(C=C1)C#CC2=CC=C(S2)C3=C(CNS(=O)(=O)N4CCCC4)C(=NN3C5=C(Cl)C=C(Cl)C=C5)C(=O)NN6CCCCC6

InChI

InChIKey=KAIYFJUWIBTYPK-UHFFFAOYSA-N
InChI=1S/C33H31Cl2F3N6O3S2/c34-24-11-14-28(27(35)20-24)44-31(29-15-13-25(48-29)12-8-22-6-9-23(10-7-22)33(36,37)38)26(21-39-49(46,47)43-18-4-5-19-43)30(40-44)32(45)41-42-16-2-1-3-17-42/h6-7,9-11,13-15,20,39H,1-5,16-19,21H2,(H,41,45)

HIDE SMILES / InChI
Molecular Formula C33H31Cl2F3N6O3S2
Molecular Weight 751.669
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

CB1-IN-1 is a peripas a peripherally restricted CB1R antagonist. It cause weight-loss in diet-induced obese mice.

CNS Activity

CNS Non-penetrant
1014
Curator's Comment: Known to be CNS-nonpenetrant in mice. Human data not available.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Cannabinoid receptor 1
30
Target ID: P21554|||Q5UB37
Gene ID: 1268.0
Gene Symbol: CNR1
Target Organism: Homo sapiens (Human)
Inverse Agonist
80
 0.3 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Discovery of 1-(2,4-dichlorophenyl)-N-(piperidin-1-yl)-4-((pyrrolidine-1-sulfonamido)methyl)-5-(5-((4-(trifluoromethyl)phenyl)ethynyl)thiophene-2-yl)-1H-pyrazole-3-carboxamide as a novel peripherally restricted cannabinoid-1 receptor antagonist with significant weight-loss efficacy in diet-induced obese mice.
2013 Dec 27
Patents

Patents

WO 2013048989 A2
1

Sample Use Guides

In Vivo Use Guide
In a mice study CB1-IN-1 was administered orally at doses 10 and 20 mg/kg.
Route of Administration: Oral
In Vitro Use Guide
Binding affinity was determined by inhibition of [3H]-CP-55940 binding to hCB1R-transfected HEK 293 membrane.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:41:28 GMT 2023
Edited
by admin
on Sat Dec 16 10:41:28 GMT 2023
Record UNII
HM6U9H369B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CB1-IN-1
Code English
DBPR-211
Code English
1H-PYRAZOLE-3-CARBOXAMIDE, 1-(2,4-DICHLOROPHENYL)-N-1-PIPERIDINYL-4-(((1-PYRROLIDINYLSULFONYL)AMINO)METHYL)-5-(5-(2-(4-(TRIFLUOROMETHYL)PHENYL)ETHYNYL)-2-THIENYL)-
Systematic Name English
1-(2,4-DICHLOROPHENYL)-N-1-PIPERIDINYL-4-(((1-PYRROLIDINYLSULFONYL)AMINO)METHYL)-5-(5-(2-(4-(TRIFLUOROMETHYL)PHENYL)ETHYNYL)-2-THIENYL)-1H-PYRAZOLE-3-CARBOXAMIDE
Systematic Name English
Code System Code Type Description
PUBCHEM
71515460
Created by admin on Sat Dec 16 10:41:28 GMT 2023 , Edited by admin on Sat Dec 16 10:41:28 GMT 2023
PRIMARY
FDA UNII
HM6U9H369B
Created by admin on Sat Dec 16 10:41:28 GMT 2023 , Edited by admin on Sat Dec 16 10:41:28 GMT 2023
PRIMARY
CAS
1429239-98-4
Created by admin on Sat Dec 16 10:41:28 GMT 2023 , Edited by admin on Sat Dec 16 10:41:28 GMT 2023
PRIMARY
NIH
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