quinine sulfate

ID: ALA2359966

Cas Number: 6119-70-6

PubChem CID: 16211610

Product Number: Q117567, Order Now?

Max Phase: Approved

First Approval: 2005

Molecular Formula: C40H54N4O10S

Molecular Weight: 324.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Anhydrous quinine sulfate | Chininum sulphuricum | Gls 1200 | Gls-1200 | Quinamm | Quinine hemisulfate anhydrous | Quinine sulfate | Quinine sulfate (2:1) | Quinine sulfate hydrate | Quinine sulphate | Quinine, sulfate (2:1) (salt) | FEMA NO. 2977 | GLS1200 | NSC-5362 | NSC-757298 | 207671-44-1|QUININE SULFATE DIHYDRATE|quinine sulfate|Chininum sulphuricum|Quinamm|Quinine hemisulfate salt monohydrate|6119-70-6|Quinine sulfate hydrate|FEMA No. 2977|Qualaquin|Quinine sulfate (2:1) (salt) dihydrateShow More⌵

Trade Names(3): Qualaquin | Quinate | Quinine sulfate

Canonical SMILES:  C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12.C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12.O.O.O=S(=O)(O)O

Standard InChI:  InChI=1S/2C20H24N2O2.H2O4S.2H2O/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;1-5(2,3)4;;/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4);2*1H2/t2*13-,14-,19-,20+;;;/m00.../s1

Standard InChI Key:  ZHNFLHYOFXQIOW-LPYZJUEESA-N

Molfile:  

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M  END

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 324.42

Molecular Weight (Monoisotopic): 324.1838

AlogP: 3.17

#Rotatable Bonds: 4

Polar Surface Area: 45.59

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 9.05

CX LogP: 2.51

CX LogD: 0.86

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.88

Np Likeness Score: 0.83

References

1. Huy NT, Uyen DT, Maeda A, Trang DT, Oida T, Harada S, Kamei K..  (2007)  Simple colorimetric inhibition assay of heme crystallization for high-throughput screening of antimalarial compounds.,  51  (1): [PMID:17088494] [10.1128/aac.00985-06]

2. Williams A, Sarkar S, Cuddon P, Ttofi EK, Saiki S, Siddiqi FH, Jahreiss L, Fleming A, Pask D, Goldsmith P, O'Kane CJ, Floto RA, Rubinsztein DC..  (2008)  Novel targets for Huntington's disease in an mTOR-independent autophagy pathway.,  4  (5): [PMID:18391949] [10.1038/nchembio.79]

3. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

4. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

5. Lucumi E, Darling C, Jo H, Napper AD, Chandramohanadas R, Fisher N, Shone AE, Jing H, Ward SA, Biagini GA, DeGrado WF, Diamond SL, Greenbaum DC..  (2010)  Discovery of potent small-molecule inhibitors of multidrug-resistant Plasmodium falciparum using a novel miniaturized high-throughput luciferase-based assay.,  54  (9): [PMID:20547797] [10.1128/aac.00431-10]

6. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

7. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

8. Unpublished dataset, 

9. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

10. PubChem BioAssay data set, 

11. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

12. Montoia A, Rocha E Silva LF, Torres ZE, Costa DS, Henrique MC, Lima ES, Vasconcellos MC, Souza RC, Costa MR, Grafov A, Grafova I, Eberlin MN, Tadei WP, Amorim RC, Pohlit AM..  (2014)  Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog.,  24  (12): [PMID:24813729] [10.1016/j.bmcl.2014.04.070]

13. Russo CM, Adhikari AA, Wallach DR, Fernandes S, Balch AN, Kerr WG, Chisholm JD..  (2015)  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5'-phosphatase (SHIP).,  25  (22): [PMID:26453006] [10.1016/j.bmcl.2015.09.034]

14. British National Formulary (72nd edition), 

15. Unpublished dataset, 

Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• British National Formulary