ODAPIPAM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H20ClNO2
Molecular Weight	329.821
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC2=CC(Cl)=C(O)C=C2[C@H](C1)C3=C4OCCC4=CC=C3

InChI

InChIKey=SKMVRXPBCSTNKE-MRXNPFEDSA-N

InChI=1S/C19H20ClNO2/c1-21-7-5-13-9-17(20)18(22)10-15(13)16(11-21)14-4-2-3-12-6-8-23-19(12)14/h2-4,9-10,16,22H,5-8,11H2,1H3/t16-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1352206
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10231129

Odapipam is a benzazepine with high affinity and selectivity for D1-dopamine receptors. Labeled with C-11, it has been used as a PET radiotracer to visualize D1 receptors both in striatal and extrastriatal areas, such as the prefrontal cortex. Odapipam inhibits dopamine D1 receptor binding in vitro with low nanomolar to picomolar dissociation constants. The affinity of [11C]NNC 756 for D1 receptors is 0.18 nM. Odapipam was tested in phase I of clinical trials for the treatment of psychotic disorders, but failed.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D1 receptor 101 Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7855175	Antagonist 2778		0.18 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Psychotic disorder 26 Sources: http://adisinsight.springer.com/drugs/800006052	Primary		Phase I 428	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGTs 13 P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=363680321	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363680321	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=363680321	yes [IC50 0.4772 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363680321	no
UGTs 13	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/7483661/	yes

Sourcing

Vendor/Aggregator	ID	URL
Axon MedChem	1405	https://www.axonmedchem.com/product/1405
Chem Scene	CS-0103418	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0103418
MolPort	MolPort-035-681-200	https://www.molport.com/shop/molecule-link/MolPort-035-681-200
Tetrahedron	TS77836	http://www.thsci.com/search.do?q=TS77836
eMolecules	275115748	https://orderbb.emolecules.com/search/#?query=275115748
eMolecules	300544468	https://orderbb.emolecules.com/search/#?query=300544468
eMolecules	36367066	https://orderbb.emolecules.com/search/#?query=36367066

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

The drug is given as a single oral dose of 80 mg.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

ODAPIPAM

Official Name

English

(+)-(S)-8-CHLORO-5-(2,3-DIHYDRO-7-BENZOFURANYL)-2,3,4,5-TETRAHYDRO-3-METHYL-1H-3-BENZAZEPIN-7-OL

Systematic Name

English

odapipam [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66883