NP-MRD: Showing NP-Card for pemoline (NP0206181)

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Record Information

Version

2.0

Created at

2022-09-05 02:19:50 UTC

Updated at

2022-09-05 02:19:50 UTC

NP-MRD ID

NP0206181

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pemoline

Description

Pemoline, also known as cylert or azoxodon, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Pemoline is a drug which is used for treatment of attention deficit hyperactivity disorder (adhd). Approximately 1-2% of patients taking the drug show elevated levels of liver transaminase enzymes, a marker for liver toxicity, though serious cases are rare. Pemoline is an extremely weak basic (essentially neutral) compound (based on its pKa). The salts in use are pemoline magnesium (free base conversion ratio.751), Pemoline iron (.578), Pemoline copper (.644), Pemoline nickel (.578), Pemoline rubidium, pemoline calcium, pemoline chromium, and chelates of the above which are identical in weight to the salt mentioned. Pemoline (as Betanamin) continues to be available in Japan, where no liver failure cases have been reported associated with its use, however it is only prescribed for the niche indication of narcolepsy, and at a lower dose than previously used in the USA.In March 2005 Abbott Laboratories and generic manufacturers withdrew pemoline from the American market due to concerns about the liver toxicity risk. Under the names Betanamin, Cylert, Tradon, and Ceractiv it was used as a medication to treat attention-deficit hyperactivity disorder (ADHD) and narcolepsy. pemoline is found in Delphinium barbeyi, Delphinium delavayi and Delphinium occidentale. pemoline was first documented in 1985 (PMID: 4021028). For this reason, and the fact that it has little or no affinity for adrenaline receptors, pemoline has minimal sympathomimetic side effects such as: Dry mouth, reduction in appetite, high blood pressure, increased heart rate, constriction of smooth muscle, cardiac stress, dilated pupils and insomnia (PMID: 11216184) (PMID: 2210262) (PMID: 2303976) (PMID: 2388127).

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1230                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.459   0.971   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   0.495   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.475   2.436   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.030   3.682   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.705   0.066   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.705  -1.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.951   0.971   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.039  -2.244   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.371  -2.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.935   2.436   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.039  -3.784   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.371  -3.784   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.705  -4.554   0.000  0.00  0.00           C+0
CONECT    1    5   10                                                       
CONECT    2    7                                                            
CONECT    3    7   10                                                       
CONECT    4   10                                                            
CONECT    5    1    6    7                                                  
CONECT    6    5    8    9                                                  
CONECT    7    2    3    5                                                  
CONECT    8    6   11                                                       
CONECT    9    6   12                                                       
CONECT   10    1    3    4                                                  
CONECT   11    8   13                                                       
CONECT   12    9   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-5-phenyl-4(5H)-oxazolone	ChEBI
2-Imino-4-keto-5-phenyltetrahydrooxazole	ChEBI
2-Imino-5-phenyl-4-oxazolidinone	ChEBI
5-Phenyl-2-imino-4-oxazolidinone	ChEBI
5-Phenyl-2-imino-4-oxooxazolidine	ChEBI
5-Phenylisohydantion	ChEBI
Azoxodon	ChEBI
Betanamin	ChEBI
Cylert	ChEBI
Dantromin	ChEBI
Deltamine	ChEBI
Hyton	ChEBI
Myamin	ChEBI
Nitan	ChEBI
Notair	ChEBI
Pemolina	ChEBI
Pemolinum	ChEBI
Pheniminooxazolidinone	ChEBI
Phenylisohydantoin	ChEBI
Phenylpseudohydantoin	ChEBI
Abbott brand OF pemoline	MeSH
Lilly brand OF pemoline	MeSH
Compounds, pemoline	MeSH
Pemoline compounds	MeSH
Tradon	MeSH
Magnesium, pemoline	MeSH
Mallinckrodt brand OF pemoline	MeSH
PemADD	MeSH
Pemoline magnesium	MeSH
Phenoxazole	MeSH

Chemical Formula

C₉H₈N₂O₂

Average Mass

176.1720 Da

Monoisotopic Mass

176.05858 Da

IUPAC Name

2-amino-5-phenyl-4,5-dihydro-1,3-oxazol-4-one

Traditional Name

pemoline

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)C(O1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C9H8N2O2/c10-9-11-8(12)7(13-9)6-4-2-1-3-5-6/h1-5,7H,(H2,10,11,12)

InChI Key

NRNCYVBFPDDJNE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Delphinium barbeyi	LOTUS Database	35616633
Delphinium delavayi	LOTUS Database	35616633
Delphinium occidentale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Oxazoline
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-oxazoles (CHEBI:7953 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.52	ALOGPS
logP	0.8	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.95	ChemAxon
pKa (Strongest Basic)	0.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.7 m³·mol⁻¹	ChemAxon
Polarizability	17.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB01230

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C07899

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pemoline

METLIN ID

Not Available

PubChem Compound

4723

PDB ID

Not Available

ChEBI ID

7953

Good Scents ID

Not Available

References

General References

Hogan V: Pemoline (Cylert): market withdrawal. CMAJ. 2000 Jan 11;162(1):106, 110. [PubMed:11216184 ]
Nehra A, Mullick F, Ishak KG, Zimmerman HJ: Pemoline-associated hepatic injury. Gastroenterology. 1990 Nov;99(5):1517-9. doi: 10.1016/0016-5085(90)91186-a. [PubMed:2210262 ]
Pratt DS, Dubois RS: Hepatotoxicity due to pemoline (Cylert): a report of two cases. J Pediatr Gastroenterol Nutr. 1990 Feb;10(2):239-41. doi: 10.1097/00005176-199002000-00016. [PubMed:2303976 ]
Elitsur Y: Pemoline (Cylert)-induced hepatotoxicity. J Pediatr Gastroenterol Nutr. 1990 Jul;11(1):143-4. doi: 10.1097/00005176-199007000-00031. [PubMed:2388127 ]
Polchert SE, Morse RM: Pemoline abuse. JAMA. 1985 Aug 16;254(7):946-7. [PubMed:4021028 ]
LOTUS database [Link]

Showing NP-Card for pemoline (NP0206181)

MOL for NP0206181 (pemoline)

3D MOL for NP0206181 (pemoline)

3D SDF for NP0206181 (pemoline)

3D-SDF for NP0206181 (pemoline)

PDB for NP0206181 (pemoline)

3D PDB for NP0206181 (pemoline)

SMILES for NP0206181 (pemoline)

INCHI for NP0206181 (pemoline)

Structure for NP0206181 (pemoline)

3D Structure for NP0206181 (pemoline)