ALTINICLINE MALEATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H14N2.C4H4O4
Molecular Weight	302.3251
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.CN1CCC[C@H]1C2=CN=CC(=C2)C#C

InChI

InChIKey=BCPPKHPWLRPWBJ-OURKGEEVSA-N

InChI=1S/C12H14N2.C4H4O4/c1-3-10-7-11(9-13-8-10)12-5-4-6-14(12)2;5-3(6)1-2-4(7)8/h1,7-9,12H,4-6H2,2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t12-;/m0./s1

HIDE SMILES / InChI

Description
Sources: http://www.prnewswire.com/news-releases/sibia-neurosciences-begins-phase-2-clinical-trial-of-sib-1508y-in-parkinsons-disease-patients-76447552.html
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10812948 https://www.ncbi.nlm.nih.gov/pubmed/18692487

Altinicline (SIB-1508Y, SIB-1765F) is a drug which acts as an agonist at neural nicotinic acetylcholine receptors with high selectivity for the α4β2 subtype. It stimulates release of dopamine and acetylcholine in the brain in both rodent and primate models, and progressed as far as Phase II clinical trials for Parkinson's disease, where "no antiparkinsonian or cognitive-enhancing effects were demonstrated", although its current status is unclear.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nicotinic acetylcholine receptor alpha-4/beta-2 5 Target ID: CHEMBL3301382 Sources: http://jpet.aspetjournals.org/content/280/1/373.full	Agonist 2678		7.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: http://www.prnewswire.com/news-releases/sibia-neurosciences-begins-phase-2-clinical-trial-of-sib-1508y-in-parkinsons-disease-patients-76447552.html	Primary		Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
40 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	unhealthy, ADULT n = 16 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	Other AEs: Nausea and vomiting... Other AEs: Nausea and vomiting Sources: https://pubmed.ncbi.nlm.nih.gov/16476941
10 mg 2 times / day multiple, oral (unknown) MTD Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	unhealthy, ADULT n = 16 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	Other AEs: Lightheadedness, Dizziness... Other AEs: Lightheadedness Dizziness Sources: https://pubmed.ncbi.nlm.nih.gov/16476941
20 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	unhealthy, ADULT n = 16 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	Disc. AE: Thrombocytopenia... AEs leading to discontinuation/dose reduction: Thrombocytopenia (serious, 1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/16476941

AEs

AE	Significance	Dose	Population
Nausea and vomiting		40 mg 2 times / day multiple, oral (unknown) Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	unhealthy, ADULT n = 16 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/16476941
Dizziness		10 mg 2 times / day multiple, oral (unknown) MTD Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	unhealthy, ADULT n = 16 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/16476941
Lightheadedness		10 mg 2 times / day multiple, oral (unknown) MTD Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	unhealthy, ADULT n = 16 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/16476941
Thrombocytopenia	serious, 1 pt Disc. AE	20 mg 2 times / day multiple, oral (unknown) Studied dose Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16476941	unhealthy, ADULT n = 16 Health Status: unhealthy Condition: Parkinson disease Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/16476941

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0027A2	https://www.1pchem.com/search?query=1P0027A2
Alfa Chemistry	179120-92-4	http://www.alfa-chemistry.com/search.aspx?q=179120-92-4
Alfa Chemistry	ACM179120924	http://www.alfa-chemistry.com/search.aspx?q=ACM179120924
Chemspace	CSC009867726	https://chem-space.com/CSC009867726
Chemspace	CSC015398323	https://chem-space.com/CSC015398323
Compound Cloud	11954277
Compound Cloud	3036156
Enamine	BBV-38269655	http://www.enaminestore.com/catalog/BBV-38269655
Enamine	BBV-39756269	http://www.enaminestore.com/catalog/BBV-39756269
MolPort	MolPort-035-765-828	https://www.molport.com/shop/molecule-link/MolPort-035-765-828
MuseChem	I011022	https://www.musechem.com/product/I011022.html
MuseChem	R008808	https://www.musechem.com/product/R008808.html
Tocris	4766	https://www.tocris.com/search.php?Type=QuickSearch&Value=4766
Wonderchem	WD05FUC	http://www.wonder-chem.com/search.html?text=WD05FUC
eMolecules	295589291	https://orderbb.emolecules.com/search/#?query=295589291
eMolecules	31592689	https://orderbb.emolecules.com/search/#?query=31592689

PubMed

Title	Date	PubMed
Evidence that nicotinic alpha(7) receptors are not involved in the hyperlocomotor and rewarding effects of nicotine.	2000 Sep	10945867

Patents

Sample Use Guides

In Vivo Use Guide

10 mg daily

Route of Administration: Oral

In Vitro Use Guide

[3H]-DA uptake in rat striatal synaptosomes was conducted as described before: briefly, 100 μl of crude P2 synaptosomal fraction were preincubated in the presence of varying concentrations of test compounds (SIB-1765F) for 10 min before the addition of [3H]-DA final concentration of 10 nM

Name

Type

Language

ALTINICLINE MALEATE

Official Name

English

(-)-3-ETHYNYL-5-((S)-1-METHYL-2-PYRROLIDINYL)PYRIDINE MALEATE (1:1)

Systematic Name

English

ALTINICLINE MALEATE [USAN]

Common Name

English

(-)-5-ETHYNYLNICOTINE MALEATE (1:1)

Common Name

English

SIB-1508Y

Code

English

(S)-3-ETHYNYL-5-(1-METHYL-2-PYRROLIDINYL)PYRIDINE (Z)-2-BUTENEDIOATE (1:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C73579