COTININE FUMARATE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C10H12N2O.C4H4O4
Molecular Weight	468.5023
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CN1[C@@H](CCC1=O)C2=CN=CC=C2.CN3[C@@H](CCC3=O)C4=CN=CC=C4

InChI

InChIKey=NXHGVNVRWLOZDF-SZYUIZJOSA-N

InChI=1S/2C10H12N2O.C4H4O4/c2*1-12-9(4-5-10(12)13)8-3-2-6-11-7-8;5-3(6)1-2-4(7)8/h2*2-3,6-7,9H,4-5H2,1H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*9-;/m00./s1

HIDE SMILES / InChI

Molecular Formula	C10H12N2O
Molecular Weight	176.2151
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.cdc.gov/biomonitoring/pdf/Cotinine_FactSheet.pdf
Curator's Comment: description was created based on several sources, including: https://cancercontrol.cancer.gov/brp/tcrb/monographs/7/m7_7.pdf | https://www.ncbi.nlm.nih.gov/pubmed/26972290

Cotinine is a product formed after the chemical nicotine enters the body. Measuring cotinine in people’s blood is the most reliable way to determine exposure to nicotine for both smokers and nonsmokers exposed to environmental tobacco smoke. Cotinine is safe, non-addictive and has pharmacokinetic properties adequate for therapeutic use. Research has shown that cotinine has antipsychotic, anxiolytic, and antidepressant properties and modulates the serotonergic, cholinergic and dopaminergic systems. Cotinine behaves as a positive allosteric modulator of the nicotinic acetylcholine receptors and has anti-inflammatory effects. Cotinine is under investigation as an agent for the treatment of depression, PTSD, schizophrenia, Alzheimer's disease and Parkinson's disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Nicotinic acetylcholine receptors alpha3/alpha6/beta2 (Saimiri sciureus) 3 Target ID: Nicotinic acetylcholine receptors alpha3/alpha6/beta2 (Saimiri sciureus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18305015	Agonist 2678	236.0 µM [EC50]
Nicotinic acetylcholine receptors alpha4/beta2 (Saimiri sciureus) 3 Target ID: Nicotinic acetylcholine receptors alpha4/beta2 (Saimiri sciureus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18305015	Agonist 2678	495.0 µM [EC50]
Neuronal acetylcholine receptor protein alpha-7 subunit 77 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23087643	Agonist 2678	175.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Chronic stress 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24713149	Palliative	Preclinical	Unknown Approved Use Unknown
Nicotine dependence 32 Sources: https://www.ncbi.nlm.nih.gov/pubmed/998055 https://www.ncbi.nlm.nih.gov/pubmed/832462 https://www.ncbi.nlm.nih.gov/pubmed/1780420 https://cancercontrol.cancer.gov/brp/tcrb/monographs/7/m7_7.pdf	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Post-traumatic stress disorder 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22137886 https://www.ncbi.nlm.nih.gov/pubmed/26166610	Palliative	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Urine test for the assessment of smoking status.	2001	11440208
The concentration of three anti-seizure medications in hair: the effects of hair color, controlling for dose and age.	2001	11339881
[Prevalence of cannabis and tobacco use in patients attending a methadone center. Evaluation by urinary biomarkers].	2001 Apr	11435993
Accuracy of self-reported cigarette smoking among pregnant women in the 1990s.	2001 Apr	11383579
Infant exposure to environmental tobacco smoke: a prevalence study in Australia.	2001 Apr	11357908
[An appreciation of maternal smoking with high-performance liquid chromatographic determination of maternal and neonatal urinary cotinine].	2001 Apr	11319469
Cigarette smoking, salivary/gingival crevicular fluid cotinine and periodontal status. A 10-year longitudinal study.	2001 Apr	11314889
Smoking status, reading level, and knowledge of tobacco effects among low-income pregnant women.	2001 Apr	11304092
Osteogenic protein-1 overcomes the inhibitory effect of nicotine on posterolateral lumbar fusion.	2001 Aug 1	11474350
Smoking reduction in smokers compliant to a smoking cessation trial with nicotine patch.	2001 Feb	11407211
High-performance liquid chromatographic determination of pyridostigmine bromide, nicotine, and their metabolites in rat plasma and urine.	2001 Jul	11471991
A simple high-pressure liquid chromatography cotinine assay: validation of smoking status in pregnant women.	2001 Jul	11471874
Single-dose pharmacokinetics of bupropion in adolescents: effects of smoking status and gender.	2001 Jul	11452710
Oltipraz chemoprevention trial in Qidong, People's Republic of China: results of urine genotoxicity assays as related to smoking habits.	2001 Jul	11440963
Saliva cotinine as indicator of cigarette smoking in pregnant women.	2001 Jul	11440610
Trends in the smoking habits of young adults with diabetes.	2001 Jul	11423599
Correlation between nicotine-induced inhibition of hematopoiesis and decreased CD44 expression on bone marrow stromal cells.	2001 Jul 15	11435297
Prevalence of nicotine consumption in drug deaths.	2001 Jul 15	11390141
The effect of tobacco smoke, nicotine, and cotinine on the mutagenicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL).	2001 Jul 25	11423342
Nicotine produces selective degeneration in the medial habenula and fasciculus retroflexus.	2001 Jul 6	11430869
An integrated approach to prenatal smoking cessation interventions.	2001 Jul-Aug	11452662
Nicotine metabolism and CYP2A6 allele frequencies in Koreans.	2001 Jun	11434509
Individual differences in urinary cotinine levels in Japanese smokers: relation to genetic polymorphism of drug-metabolizing enzymes.	2001 Jun	11401907
Biomarkers of polycyclic aromatic hydrocarbon-DNA damage and cigarette smoke exposures in paired maternal and newborn blood samples as a measure of differential susceptibility.	2001 Jun	11401906
Heavily smoking women who cannot quit in pregnancy: evidence of pharmacokinetic predisposition.	2001 Jun	11360023
CYP1B1 expression in human lung.	2001 Jun	11353763
Effect of cigarette smoking on levels of bioavailable testosterone in healthy men.	2001 Jun	11352783
Regional cerebral blood flow effects of nicotine in overnight abstinent smokers.	2001 Jun 1	11377408
Quantification of nicotine, chlorpyrifos and their metabolites in rat plasma and urine using high-performance liquid chromatography.	2001 Jun 15	11417874
A prospective study of insulin-like growth factor-I, IGF-binding proteins-1, -2 and -3 and lung cancer risk in women.	2001 Jun 15	11351312
Cluster randomised controlled trial to compare three methods of promoting secondary prevention of coronary heart disease in primary care.	2001 Jun 2	11387182
Cost effectiveness of computer tailored and non-tailored smoking cessation letters in general practice: randomised controlled trial.	2001 Jun 9	11397745
Exposure to ethanol and nicotine during the brain growth spurt: spatial DMP performance in male rats.	2001 Mar	11325407
Nicotine metabolism and CYP2D6 phenotype in smokers.	2001 Mar	11303596
Red wine polyphenols, in the absence of alcohol, reduce lipid peroxidative stress in smoking subjects.	2001 Mar 15	11295361
Cotinine binding to nicotinic acetylcholine receptors in bovine chromaffin cell and rat brain membranes.	2001 May	11403732
CDC unveils body burden.	2001 May	11401773
Lung cancer due to passive smoking--a review.	2001 May	11401014
Household smoking and bronchial hyperresponsiveness in children with asthma.	2001 May	11392364
Effects of smoking cessation and nicotine substitution on systemic eicosanoid production in man.	2001 May	11383717
Preparation of pyridine-N-glucuronides of tobacco-specific nitrosamines.	2001 May	11368554
Science is changing! 300 chemicals and each chemical will have a fingerprint.	2001 May	11368053
Metropolitan home living conditions associated with indoor endotoxin levels.	2001 May	11344344
Adaptation of an enzyme immunoassay to assess urinary cotinine in nonsmokers exposed to tobacco smoke.	2001 May	11325906
Accumulation of nicotine and its metabolites in rat brain after intermittent or continuous peripheral administration of [2'-(14)C]nicotine.	2001 May	11302929
Measures of maternal tobacco exposure and infant birth weight at term.	2001 May 15	11384951
Bacterial mutagenicity of some tobacco aromatic nitrogen bases and their mixtures.	2001 May 31	11377240
In vitro effects of nicotine on mitochondrial respiration and superoxide anion generation.	2001 May 4	11325348
Systemic nicotine exposure in tobacco harvesters.	2001 May-Jun	11480503
Personal exposures to PM(2.5) and polycyclic aromatic hydrocarbons and their relationship to environmental tobacco smoke at two locations in Greece.	2001 May-Jun	11477515

Patents

Sample Use Guides

In Vivo Use Guide

Mouse: 5 mg/kg during 37 days

Route of Administration: Oral

In Vitro Use Guide

High (190 ug/ml) concentration of Cotinine significantly altered all the sperm kinetic variables in relation to the time of incubation (forward motility, velocity, linearity and beat cross-frequency). Despite the impact seen on these parameters, there was still 30% forward motility after 24 h of incubation.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:10:36 GMT 2023` Edited by `admin` on `Fri Dec 15 15:10:36 GMT 2023`
Record UNII	6ZAF060BHS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COTININE FUMARATE

Official Name

English

COTININE FUMARATE [MI]

Common Name

English

COTININE FUMARATE [USAN]

Common Name

English

1-METHYL-5-(3-PYRIDINYL)-2-PYRROLIDINONE FUMARATE

Systematic Name

English

N-METHYL-2-(3-PYRIDYL)-5-PYRROLIDONE FUMARATE

Systematic Name

English

(-)-1-METHYL-5-(3-PYRIDYL)-2-PYRROLIDINONE FUMARATE (2:1)

Systematic Name

English

2-PYRROLIDINONE, 1-METHYL-5-(3-PYRIDINYL)-, (S)-, (E)-2-BUTENEDIOATE (2:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C73579